Hack & Hustle

Lean Startup Experiments: Hiring Humans Instead Of Building Technology

Back in the days when we ran our sales consultancy and sales outsourcing company, we did a lot of cold calling for Silicon Valley technology companies. One of our clients was selling software directly to doctors. And the main challenge we had with this was that doctors are really hard to reach. 

So we looked for ways to increase our reach rate. Our clients were spending too much time every day listening to dial tones and then going to voice mail, and not enough time talking to doctors.

That's when we discovered autodialers. 

An autodialer is a neat piece of technology that basically calls several phone numbers at the same time, and drop the numbers which continually ring or go to voice mail. It seemed like autodialers were perfect for us - this technology was made to solve the exact problem we were struggling with.

Because we have brilliant technical co-founders Anthony and Thomas on our team, we were able to build our own autodialer. The question was just: should build our own autodialer or not?

Is It Really Worth It?

But we still weren't exactly sure how much value an autodialer would bring us. Would it be worth spending our engineering time to create the software to be able to dial several numbers simultaneously and only put a call through to a sales rep once an actual human being picked up?

So we hacked together a quick experiment in order to...

Test The Idea

We called a staffing agency and called for more manpower. The next day we had five temps in the office, gave each one a headset and made them dial through a bunch of numbers of clinics and hospitals. Their job was just to dial the numbers, hang up when nobody picked up the phone or when it went to voice mail.

If someone picked up the phone, the temp would say: "Hey, my name is John Smith, I'm calling from XYZ, can I talk to the doctor?" If the person on the other end of the line said yes, the temp would hand over the head set to the sales rep, who would then take the conversation from there.

So our office was filled with temps who were basically doing what an autodialer would normally do: dial a lot of numbers at the same time, and put a call through to a sales rep whenever a human being picked up the phone.

This was indeed as chaotic as you probably imagine it, but it also yielded some very valuable data: our sales reps could speak with 3 to 4 times more doctors per day using this system.

Based on this data we decided to invest engineering time into building our own (non-human) autodialer.


Are You Considering A New Technology?

Imperfect experiments are a lot better than refined theories. Whenever you have an idea that you believe could really move the needle, come up with an experiment that you can run really quick to see if the idea stands a reality check.

Don't spend a lot of time looking at different vendors and comparing things, purchasing and implementing technology. Don't spend hours, days or weeks discussing and pondering different options. Hack together a quick test, look at the data you get and then make an informed decision.

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The Dangers of Pitching Prematurely

A lot of sales people start pitching way too early in a sales call. This almost always shuts down your chances of closing a deal. Want to know how to work your way to the perfect time to pitch? And a failproof method to find out exactly how to customize your pitch for every prospect? 

This method ties in with the most important lesson I ever learned in sales. It's fundamentally about gaining a deep understanding of your prospect, and using it to close the deal.

Remember this scene from Wolf of Wall Street?

You know why all their sales pitches suck? Because each of these sales seminar attendees pitches prematurely. They assume that what they like about this pen is what their buyer likes about the pen. They just show up and throw up all over the prospect, rather than gathering information, engaging the prospect and presenting the solution in response to their fact find.

But rather than talking in abstracts, let's demonstrate this on a specific case.

Example: Pitching a Scheduling App To Doctors

You call up Dr. Smith, and after a quick intro you launch into your pitch, full of enthusiasm.

Sales rep: "Hey Dr. Smith, we've built this scheduling app, and it saves doctors like you a lot of time. Would this be interesting to you?"

Dr. Smith: "No, we don't really have that problem, I don't think this is really for us..."

Sales rep: "Yeah, but our scheduling app can also help you to reduce staff costs because you don't need to have somebody on the phone all the time, going back and forth with potential patients... are you interested in reducing your staffing costs?"

Dr. Smith: "No, I don't think this is something we're interested in..."

Sales rep: "Yeah, but, how about if we could actually increase your revenue a bit?"

... and the sales rep goes on and on like this, without a clear target, without a clear understanding of where to aim at.

Aimlessly Throwing Darts in the Dark

He's just throwing features and value propositions around, hoping something sticks. 

He's just taking stabs in the dark. He's not working, he's guessworking. He's playing value proposition lottery, hoping to get a lucky ticket. That's not selling, that's speculating. It lacks strategy.

Building a No-Street

Every time you throw out another random benefit of your solution, and the prospect says no to that, you are building a no-street. You're conditioning the prospects mind to say "no" to your proposals. The more often the prospect says no to you, the more likely he is going to be to keep saying no, and the bigger the disconnect between you and the prospect.

No -> no -> no -> no -> no -> ... [can you guess what they'll say next?]

Even if you finally get lucky and offer them something they are interested in... if they've just told you no five times in a row, they're much less likely to now change into the yes-lane. They'll just give you another no, because they have mentally tuned out. They feel like you don't really know what they are interested in, you don't really get them, and you don't have anything of value to offer.

How to Work Your Way to Yes - Step #1

What's a better way than random benefit sputtering? You want to gain an understanding of the prospect that is so precise that you can predict in advance where the prospect's sweet spot is. Wouldn't it be awesome to lead the conversation in a direction where you can do just that? Well, there is!

And what's the best way to lead a conversation in sales?

Asking questions!

Specifically open-ended questions (questions which can't be answered with a yes or no). 


Use your questions as satellites which map out the prospects wants and needs. You want to use your satellites to spot the exact coordinates of their sweet spots.

Sales rep: "What's one of the biggest challenges you have in your practice right now, especially when it comes to patients, managing revenue, managing costs, managing your time?"

Dr. Smith: "Figuring out a way to increase revenues is important in todays economy."

Sales rep: "Ok, so increasing revenue is really important for your practice."

Dr. Smith: "Right."

Getting Past Surface Level Understanding

Most people at this point in the conversation would think: 'Great, I got it! I will pitch this doctor our scheduling app as a way to increase revenues!'

But you - the real pro sales rep - aren't satisfied with that. You keep exploring, you take it a step further.

Sales rep: "If increasing revenue is important to you, what have you done in the past to achieve that? And what are you currently considering? Is it about advertising, is it about getting more new patients in? Is it about efficiencies, e.g. having more people show up on time, and reduce the number of no-shows? What kind of measures would you think of that could really make a dent?"

Dr. Smith: "We don't really have a problem with no-shows. The main thing would probably be doing more effective advertising."

Now that piece of information changes the whole dynamic of the conversation dramatically, compared to what the first version of the answer was (and even more so compared to the sales rep shooting darts in the dark).

What's Next? Digging Deeper!


At this point it might seem like there's no way to sell to this doctor - after all, how can your scheduling app help Dr. Smith's advertising?

But this is the point that differentiates mediocre sales reps from great sales reps. Because now you're really getting into consulting. You're not just trying to get the prospects money in exchange for what you've got, you're revealing something of value to your prospect.

Keep asking questions. You try to find out: is advertising is really the thing that would benefit this doctor the most? What's their actual no-show rate? (Maybe there's potential for significant improvement, and Dr. Smith simply isn't aware how big an opportunity for increasing revenues this represents).

Practice The Art Of Listening - Step #2

Don't just listen to what they say, but also listen to how they say it. If you're selling person to person, observe their body language. When does the prospect really light up, when does the energy in his voice get a lot more excited? These are often more important signals to pay attention to than the actual words he speaks.

Test Before You Pitch - Step #3

At this point in the conversation you're probably in a good position to pitch. But again, don't gamble, don't guess, don't hope for luck. Instead, test! 

Don't proclaim: "Dr. Smith, I think I have the perfect solution for you! We can save you cost on scheduling!"

Instead, keep asking, probing, testing:

Sales rep: "Dr. Smith, if there was a way to save on scheduling and staffing, to save on software costs, if you could make significant savings in all the resouces you have to deploy to schedule your day-to-day operations in an effective and efficient manner as possible, would you be interested in a solution like that? Would that be an option for you to save a lot of money, so that you keep your revenues unaffected, but lower the costs, and thus end up with more profits, instead of trying all kinds of new advertising things that have unknown outcomes and aren't predictable?"

And then wait what they say!

Dr. Smith: "Na, I'm not really a saving-money-guy."

That's valuable feedback! It saves you a wasted bullet - now you don't have to pitch what you wanted to pitch, and are still good for another round of interaction and questioning, until you get a clear sense of what would work.

Ultimately, you want to get to a point where Dr. Smith says: "Yes, that would indeed be interesting."


Because now you have a clear target. Now you know which buttons to push and how to frame your solution. Now you can throw and you are certain that you will hit. You have the clarity to know what they care about. Now it's time to actually make that pitch and close the deal. This is how you actually sell the pen.


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Communication For Startup Teams: When Should You Interrupt Someone?

Want to reduce unproductive interruptions in the workplace, and improve the impression you make on others? Just avoid lazy communication, which basically means: think before you speak.

A few days ago someone at worked asked me to email him some numbers from Google Analytics. So I clicked my way around Analytics to collect these numbers, when suddenly it occured to me: "He's got access to this Google Analytics account. He could do that without my help. Why am I doing this work for him?"

So I emailed him and said: "Hey, you have access to GA, you can do this yourself." His response: "Oh shit, yeah, you're right. Ok, I'll do that."

Just be respectful of other people's time.

Can you give me some feedback on this? (And do it for me too)?

Another example. A sales guy asked me to review his sales email. I say sure. I get that email in my inbox, make a few comments, click send.


"Hey Steli, thanks for the comments, how exactly do you want me to shorten the email?"

Well, I described in the email what he should shorten. 

So I respond: "Did you actually read the email? What did I say in that email?"

He responds: "You said the second and third paragraph could be a sentence instead of a paragraph, and I should take out xyz."

I respond: "Well, have you tried doing that?"

He responds: "Hm, no, ok, I will try this now."

Well, why not try it first?

Don't ask other people to do things for you if you could do them yourself, if all it takes for you is to think it through for a moment?

In both cases the person wasn't a lazy person. It was just an impulsive reaction.

It's good to reach out to others if you need help to get something done. But every time you do that, you're withdrawing from an imaginary bank account of favors. You want to spend those favors you withdraw on situations where you really do need help

Should you interrupt someone?

Next time before you interrupt someone's day to help you out about something, pause and mentally go through this process:


Avoid lazy communication. It will make you and your team-mates more a lot more effective, and people will pay more attention and be more willing to help you when you actually need it.

It's little things like this that make or break your personal brand.
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Easiest Negotiation Hack Ever? Postpone!

Imagine you're talking with a prospect that loves your product, and they would be willing to buy if only _______{insert objection X}. Objection X can be anything, but most commonly in sales it's pricing. So let's use that as an example. How can you negotiate your way around _____ {obection X} and close the deal if you can't actually deliver on objection X?

The prospect wants to buy, but only at a steep discount. What usually happens at this point is a long back and forth between seller and prospect. Sometimes that negotiation leads to a deal, sometimes it doesn't.

How to frame price negotiations

You as the seller want to frame this negotiation around the value your product is creating.

The prospect however will most often frame it around the price. They'll tell you that competitor ABC only charges half of what you charge, or that your product really only costs you $50 to deliver, so how dare you charge them $100? If you sell it to them at $55, you're still making a profit, right?


If your product provides thousands of dollars of value to them, it's totally worth for them to pay a couple hundred dollars for it. 


Always sell based on value, not on cost or market.

Customers cherry-picking features?

Sometimes customers will tell you: we really don't need all these features you have, we just want feature number 3 and number 12 and 18. And because they don't use your other 30 features, they'll argue: "Hey, we're only going to use 3 of your 33 features, so we really shouldn't be paying the full price."

Well, yes, they should. Because these three features they want to use are worth more to them than what you charge. And if not, then they're probably not a good customer.

Negotiation not going anywhere?

But what if your your customer doesn't buy into your value-based pricing and insists on a discount? How can you avoid getting stuck in a endless negotation where you're just running in circles, not making progress?

Most sales people will do one of two things:

  • Just keep on pushing and be totally unrelenting? Either win them at your current price point, or lose them as customer. Apply brute force and coerce them to buy.
  • Just accept their discount requests. "Oh, you want a 30% discount? Well, ok, we don't really do this, and I'm actually not earning any commission on this deal, but if that's what it takes to win you as a customer, then I'm willing to do it." (And keep in mind: if you give them the discount they asked for, most of them will think: Hey, if can give me 30%, he can probably give me 50% discount as well.' And they'll ask you for another discount and put pressure on you again.)

Both of these extremes aren't elegant. Negotation is often about creating new options, and this is one of these examples. What you want to do instead is to make them experience the value your product delivers to them.

Propose to postpone

Just propose to postpone the negotiation for a month.

"Mr. Prospect, I think we both agree that our product is perfect for your needs. And I want to get you guys to realize the value of our solution as quickly as possible. It seems like right now, it's hard for us to figure out what the reality is, because we're dealing with hypotheticals.

You haven't used our product in a full-fledged, real environment for a month or two. We can't really know what the value is, how it streamlines your workflow, what it truly delivers to you. And this is why this discussion is so difficult. Our negotiation is based on assumptions, and we don't have any real data to back them up.

So here's what we'll do: Buy our product today. Full price. Use it for one month. In full range, in a real environment, all the features and functions, no limits. And in a month we jump on another call.

Once you've realized how valuable it is, once you know what it can and can not do, once you've really actually used it full-fledged, with the entire team, then we'll figure out what the best price is for you. And I'll guarantee you I'll make you a good deal. But let's have a month full of data before we actually decide what the right pricing is."

Nine out of ten times, the other side will accept this reasonable proposal. You process their payment and do nothing but wait.  


Why is this better for you?

If your product delivers more value than what you charge, you're going to be in a much better position at the end of the month than you are today.

After a month of using your product the customer... 

  1. ... now has experienced all the value of your product.
  2. ... has invested a full month on getting their entire team on board. They are using it day in and day out, they rely more on it.
  3. ... has stored more data in your application, and connected it to more parts of their business.

They've invested all this time into it, and got real value out of it. It's now much harder for them to walk away.

It's now actually harder for them to churn and cancel than it is to buy and just stay a customer, because they're already using your solution, you're already their default modus operandi.

How many people ask for a discount after a month?

Almost nobody. I've had customer tell me: "You know what, I don't want a discount anymore. We love your sales CRM so much, we're happy to pay full price."

But most customers simply won't say anything at all. They just forget about trying to negotiate, or they just don't care anymore. Oftentimes they just asked for a discount because that's how they buy: they always ask for a discount. But once they already bought, they're over it.

Whenever you encounter a seemingly unmanagable objection, see if you can simply hack the negotiation by postponing it. 

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Trust Trumps Transactions

Trust trumps transactions. We really learned this lesson when we were trying to get our first customers for our outsourced sales service.

Nobody will ever buy your product if they don't trust you. Everybody gets that in theory - but few people know how to use that in the sales process to close more deals. When we launched our outsourced sales company we used fake names. We were in stealth mode and didn't want others to know about our new venture yet.

So we had zero credentials, zero credibility, zero references, nothing but hustle. And we wanted other startups to pay us for selling their product in their name. That requires a lot of trust. How did we do it?



How could we build trust?

How could we get a company's CEO to give us the authority to represent their brand to outsiders?

We thought long and hard about this issue, until we came up with a solution:

Technology can solve this problem! We would operate totally transparent. We would record all our communication with outsiders. We would record our calls and emails, so our future customers could listen in and make sure we'd represent them correctly.

(This is the reason why all Business & Enterprise customers or our sales software now have automatic call recording).

So whenever we tried to sell our sales service to a startup, trust was indeed an issue. And boy were we ready to tackle that objection"That's a great point, Mr Prospect! We want to make sure to have your full trust, so we'll operate fully transparent. We'll record every single call, and you can listen to any call recording you want at any time to check that we're doing a good job. Isn't that amazing? Don't you feel a lot better, now that you've heard that all calls are going to be recorded? I'm sure now you can trust us, right?"



They all heard it. They all liked it. Transparency is good. Control is good.

But on an emotional level, it didn't solve the issue they had to begin with. It didn't make them feel any different about our proposal. They still felt apprehensive about it, they still felt like it was too risky to give away their name to an outsourced sales organization to talk to their prospective customers. Even though they knew they could always listen in to these conversations. 

Thousand Questions, One Issue

We had one specific customer - who became our second paying customer, and stayed with us for the longest time, from day one for almost two years.

Our first sales guy pitched them the idea on the phone.

Prospect: "If you could actually deliver on your promise, we'd love it, but... we can't believe that you're actually going to do a good job, and we're afraid of that."

Our sales guy: "We're going to have transparency, you can listen to all the calls, don't worry."

Prospect: "Well, that sounds awesome... but we'll still need time to think about it."


4 calls later... they still couldn't pull the trigger. I was chatting with our sales guy, and he said: "This is crazy! We went through 4000 questions, I answered all of them, they really, really, really want to do it... but they just can't get over it. I don't know what to do. Now they sent us another 30 questions."

We looked at all their objections and questions... and it all boiled down to one thing: trust!

They didn't feel comfortable, they were afraid, they didn't trust us.

So we got them on the phone one more time and said: "Hey, for a moment, let's put aside all these technical questions. If we are honest to each other, you guys are simply not trusting us, and you're afraid that it's going to take too much time to coach, train, check and manage us. You're just afraid of all these things. We can argue this back and forth forever. But words will never make you trust us. Let's do this: Give us one week! We'll study your solution, and in exactly one week, on Tuesday at 9am, we will call you, the CEO, and we will pitch you on your product. We will make a cold call. You'll play a potential customer, we will play your company, and we will pitch you. And your job will be to be the most difficult prospect you could ever think of, ask the most difficult questions ever, and then let our actions speak louder than words. See how we react, see how we respond. See if we can sell you and convince you on buying your product. Because if we can do that, we can do it with anyone else."

There was a moment of silent thinking from the CEOs end of the line, and then he said: "Ok, let's do it."

A week later we cold called him, sold him their solution and asked him: "How did you feel about this call?"

CEO: "Let's get started. Let's do this. I feel really good about you guys."

That's the power of building personal trust. Use your action to create trust, don't just ask for trust with words.

Trust > Transparency

Want to know what's crazy?

These guys, who had such a hard time trusting us in the first place never listened to a single call recording! Not even one single time. We had the logs. We knew exactly what they were looking at. They looked at the dashboards and our performance, but not even one time did they listen to one of the call recordings we shared with them.

Because the moment we created trust... we had it. And we never lost it. They never felt the need to listen in to one of our conversations.

The product had transparency to build trust. But the personal trust we created totally trumped that.

In fact, in all our history with Elastic Sales, we did not even have a single customer who ever listened in to a sales call.

They all liked the idea of transparency. They all liked to have the option to listen in to our calls. But no one ever did. Because they trusted us on a personal level.

The 3 Levels Of Trust

Whenever you are selling a product for a company, you need to build three levels of trust.

You need to make them trust in your product. You need to make them trust in you. And you need to make them trust in your company.

What do you think is the first level of trust you must build in the sales process? 


The personal level! First, they must trust you as a person. That's where you start. With the human being they are interacting with.

Then you create some trust in the product/service/solution you are selling.

And create some trust in the company that is behind the product and the person.

Trust always trumps transactions.

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The Hidden Danger Of Studying Sales Persuasion Techniques

The best sales people I know are those who are life-long learners with a true passion for communication. They read books about the psychology of sales, visit workshops about persuasion techniques, listen to audio recordings about influence strategies, and they utilize the knowledge they acquired in their day-to-day job.

That's great. But there's a hidden danger many aren't aware of, and I see many junior sales reps running into the sales psychology trap. It's hurts them, and it hurts their prospects.

I'm talking about oversimplifying things to a point where it distorts the reality of what's happening in front of them. I'm talking about overeagerly applying labels to people. Don't make generalized assumptions based on isolated signals.

When Overconfidence Leads To Ignorance

Especially because we sales people possess more knowledge about human nature and the psychology of communication, we need to be more attentive to other people. It's too easy to become a victim of our own "good judgment". 

It's great if you're able to read body language. It gives you an advantage over most other people who not only aren't aware of how to read body language, but don't even look at others closely enough to notice their body language. But don't overdo it.

It's great if you can profile whether someone is predominantly processing information visually or auditory or kinestetically... but don't assume that they "are visual" just because they used a couple of visual predicates and speak quickly.

It's great if you are perceptive enough to notice these things. You want to have that kind of awareness which allows you to read between the lines and consciously pick up signals.

All these signals are just the tip of the iceberg. People are more complex than that. Don't assume to understand their deeper feelings because of your superficial observations. 

The danger is that you'll often find your first interpretation to be the right one. And that can make you believe that all your first interpretations are right - which is always wrong. But at that point you're so confident in your own judgment that you're not open-minded enough to notice it.

Acquiring the knowledge is easy. Applying it (correctly) is much more important.

Fortunately there's a simple three step process that you can use to keep your own judgments in check.

1) Observation


Most sales people are pretty good at observing their prospects. They watch their body language, listen to the tone of their voice, pay careful attention to the exact words they use.

Get out of your own head and focus on your prospects.

2) Interpretation


The next step is to interprete what you observed. Ask yourself: what could this mean? (Not what does this mean!

This is where your knowledge of body language, personality types, sales psychology, NLP and influence techniques is helpful. Many of them provide helpful frameworks that help you to quickly classify an observation, and come up with a set of likely explanations.

But just because an observation you made matches something you read in a book doesn't mean that this is the case. So you need to validate your interpretation.

3) Confirmation


Continue observing until you can see a pattern. Don't make assumptions on isolated observations. You can't know whether an individual instance is a reflection of a larger underlying pattern or just an outlier. If you can consistently observe a particular reaction in another person, only then do you have a stronger basis to make an assumption.

Example: "Yes" & Shaking Head

Sometimes people will say "Yes", and at the same time shake their head "no". Now this is a pretty obvious mismatch between their verbal and non-verbal communication. But so far, the observation you made is just this: They said yes, and shook their head "no" at the same time.

Now how do you interpret that?

  • It could be that it was in fact an incincere yes.
  • Maybe they just told you yes because they want to be polite or because they think saying yes is the easiest way to get rid of them. But maybe there's another reason.
  • Maybe they are always shaking their head when they say yes.
  • Maybe they are always shaking their head when they are really excited about something.
  • Maybe they are shaking their head because when you asked them another thought came up, they pondered it for a second and then shook it off (physically shaking their head) and told you yes.
  • Heck, maybe they just have something with their neck!

So now you want to narrow it down to the most likely reason for this mismatch.

One way could be to get them to say yes to something else that you know they are fine with - are they shaking their head there too? If not, then you can conclude that they're not always shaking their head when they say yes.

You can bring up the same topic again and observe how they react.

By process of elimination you can identify the real cause of that mismatch.

Or you could just ask them: "Hey, I noticed you said yes and shook your head at the same time. I just want to confirm if you feel really good about moving forward, of if there's something we should talk about first." The point is that you find an external confirmation for your internal interpretation.

Closed Body Language Or Coffee Stain?

I once gave a seminar where in the front row there was a person who had a totally closed body language: arms crossed, legs crossed. And most body language experts will tell you that this is a strong signal that they're closed to your ideas. 

I noticed that person's body language and thought: 'Wow, this person really hates my talk and probably thinks I'm totally wrong!'

Fortunately the rest of the audience seemed to enjoy my talk, so it didn't throw me off my game. I just kept going with my presentation, all the way until the end when everyone stood up.

And Mister Closed Body Language? He got up, uncrossed his arms and revealed a huge brown coffee stain on his shirt. THAT was the reason for his crossed arms - he just tried to hide the coffee stain, not to close himself to my ideas.


More Observations, Less Judgments

Use your senses more than you use your mind. Be open when you communicate so that you are really aware of what's going on. Don't become the kind of person that's filled with well-informed prejudices.

Next time you catch yourself judging or interpreting someone else, ask yourself: 'Or what could be another explanation for that?'

See a guy with crossed arms and legs? 'Oh, this guy is totally closed to new ideas! ... or what could be another explanation for that?'

See someone using a lot of abstract words, appealing to reason, making logical arguments? 'Oh, this is obviously a left-brain person! .... or what could be another explanation for that?'

Move beyond the easy answers to understand (and influence) people better. You'll experience the depth and richness the world on a deeper level. You'll make more sales and close more deals.

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How NOT to Do Social Sales

Social sales is the hot new thing in the world of B2B sales. And with good reason - most prospects have online profiles that can be a valuable source of insights for sales reps. However, most sales people are using social sales the wrong way - and are missing out on a lot of sales because of that.



I see a lot of sales people using "social sales" as an excuse to do some actual selling. These people will typically spend an excessive amount of time on researching a particular lead or prospect before picking up the phone to call them. 

They seem to think that by spending an hour (or even more!) stalking that person online doing their homework, they'll get valuable insights that will help them close a deal. Which almost never is the case.

How Much Should You Research Your Prospect Before Reaching Out?

About 5 to 10 minutes is enough. More than that is excessive. (There are exceptions to this general rule, but overall up to 10 minutes should be plenty).

You don't need to know all the things they're favoriting on Twitter, liking on Facebook, which pictures they've uploaded on Flickr (I'm old school I know, Instagram!), what they've blogged about and so on.

You can't gain a perfect understanding of a prospect by going all NSA on them.

The Best Way to Learn About Your Prospect?

Talk to them. Ask them questions. That way you'll get relevant information that actually matters. Use the conversation with them to learn more and dig deep. Don't just ask surface level questions. Ask why they find something important, and how they came to that conclusion, and what they're doing about it, what else they've tried before. What's really crucial right now for them? What's a dealbreaker? What's a nice to have?

Listen to the way they say it, listen to the tone of their voice.

Pay attention to context not just content!

If all this "online homework" isn't actually that helpful, why are so many sales people obsessed with it these days?

The Real Reason Why Sales Reps Over-Research Prospects

What's the root cause of this desire to research people online for hours? Why are many modern sales people spending so much time doing it?

rejectionfreezoneBecause it's convenient. Because it's safe. And because they feel insecure about reaching out and interacting with the prospect.

Researching prospects online is risk-free. Nobody will reject you while you're doing online research.

No rejection = No sales.

It's a rejection-free zone. But that's the exact problem. No rejection also means no sales.

There's no selling going on. You're not closing deals. You're not engaging with people. You're just sitting in front of a computer clicking button and taking notes.

When Over-Researching Leads To Over-Confidence

Another mistake that I see a lot of "social sales people" commit is being over-confident. They spend an hour reading all your tweets and Facebook updates, and your last five blog posts... and they think they know you because of that. They think they now have the essence of who you are and what makes you tick, what you like and dislike.

Whenever you walk into a conversation with a human being filled with so many preconceived notions, there's a huge risk that you'll fail to truly interact with that person. It's just the way our brains are wired - we all prefer to have our ideas validated. We all want to be right. But as a sales person, your job is not to be right. Your job is to sell. Let the other person be right and close the deal.

When you're having a sales conversation with a prospect, put your preconceived notions aside. Don't be opinionated, be open-minded. Don't suppose you know what makes them tick. Get out of your own head and really listen to them.

Showing Off Insights

I've seen sales people go as far as bragging about the information they gathered about a prospect. Which is wrong on so many levels. One, it's absolutely boring to the other person, because they know all the things you're telling them about them. They are the ones who shared it online. What's the point of regurgitating that?

And sometimes they make assumptions based on what they read that are just plain wrong. They misinterpret something that person shared online.

Heck, if even the popular Myers-Briggs test doesn't manage to really reveal a person's character in 93 questions, why do these people think they can understand a person because they read a tweet?


Why do they think they can deduct a person's thoughts, feelings, intentions, beliefs and philosophy are, based on a blog comment?

It takes more than that to fully understand somebody.

There Is Value In Social!

I'm not advising you to ignore social. Social can be a powerful tool. But don't buy into the hype. Don't fall prey to wishful thinking that social sales will help you to close more deals without encountering rejection.

You know what you can gain from researching prospects online?

Signals. Tidbits of information. But you need personal interaction and real-time engagement with a person to be able to embed these data points into the right context in order to sell more successfully.

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How to Fire a B2B Customer? (Without Causing Bad Will)

As a B2B startup, there's going to come a time when you have to let go of a customer. It's an ironic role-reversal when you finally are in a position to tell no to someone who wants to pay you money, but firing a customer can be just as hard as winning a customer. Here's how to do it right.

A fellow YCombinator startup recently had an issue with one of their earliest customers. This customer once was very valuable to them: they helped the startup to generate revenues, gain some credibility and validate some of their ideas.

But at the current stage of the startup, this customer wasn't a good fit for the startup anymore. The customer made too many demands which distracted them from their core mission.

It was time to break up with this customer, in order to focus on building their product in a more scalable fashion.

2 Ways To Get Rid Of Them

There are basically two ways to fire a customer.

1) Create A Situation Where They Fire You

The best way to create such a situation is by simply raising your prices to such a ridiculous level that they're surely going to cancel (or if they don't cancel, make the number so high that you'd actually be happy to keep them at that price!).

Get together with the person with whom you have a personal relationship and tell them:

"Listen, our business model has changed and we can't service you successfully anymore at the current price point. The economics make no sense for us anymore. We're forced to increase prices, and your new price is going to be $____________ [insert ridiculous amount]. I totally understand if you're not willing to go along with this, and if you decide that you don't want to pay this new price to keep using our product, we're going to help you transition out in the most successful way, we're going to give you plenty of time and do everything in our power to help you move over in a smooth way. But this is what it is, this is the new price, and I wanted you to know this as soon as possible, so you have a chance to make decisions and choose how to move forward with it."

2) Be Upfront And Honest

Just pick up the phone and tell them about the situation. Tell them that this business relationship doesn't make sense for you anymore. Tell them your business model has changed, your focus as a business has changed, and you can't continue servicing them as a customer anymore, because it would prevent you from growing as a company.

Be proactive, honest and transparent about it. Everybody understands that a business relationship needs to benefitial for both parties, and if it ceases to be, it's time to part ways.

Do It Like A Pro

You don't just want to make them feel like an unwanted customer. Breaking up - even if it's "just" a business relationship - can be emotionally tense. Show them that you really care. Do more than is expected of you, especially in a situation where things are difficult, and you'll discover that people talk highly of you.

Don't let this breakup turn into a dramatic conflict between the two of you - you don't want a disgruntled ex-customer run around and badmouth you. 

Do what's good good for your reputation, good for your brand, and what's the right thing to do anyway.

Be Super-Helpful

Offer them as much help and support to transition to a new solution as you can afford. Provide them with a stellar offboarding experience, so that they have minimum pain moving out from your product into the next. Give them enough time to manage the transition. Even drive to their office and work physically when they need it.

Consult Them On What's Next 

Maybe they'll need help to figure what to do next: build an inhouse solution? Change to one of your competitors? (Which one?)

You know their requirements, and what the market has to offer, and thus are in an excellent position to give them great advice. Do it.


Who should tell the customer that they're being let go? Not some account manager, support staff or some low-level employee. It should be you, or a person with real authority who has been involved in the deal.

Don't Break Up By Email

Ideally meet them in person, look them in the eyes and tell them what's happening. If you can't meet them in person, call them on the phone. But don't send them an email.

Do It Fast

Don't delay the break up. Once you decide that you're going to fire a customer, communicate it with the customer as quickly as possible. Act fast. Don't wait around for week, don't postpone it because it's uncomfortable and you hope that you'll conjure up a better way to deal with this. The more you postpone this decision, the more problems accrue - the more they depend on you, the more money you took from them, the more promises have been made to them...

What's more, as soon as you decide that this is not a good customer, you'll start deprioritizing them, people on your team won't be motivated to serve them well. It's just going to create a lot more bad will, issues, conflicts and challenges until you actually break up with them.

Just get it over with, wo both on you can move on as quickly as possible.

Do It With Friendly Strength

A lot of people feel really bad about breaking up. It's difficult, uncomfortable, and it'll probably upset the other side. It's natural to want to avoid that. And many people execute the break up with weaksauce.


They go in and feel so apologetic, bad and guilty about breaking up, that they'll make a really weak pitch: "Well, we're thinking about this, and I know this sucks, but we also don't know what to do about this..." 

That weakness will just outrage the other side even more. And it can often lead to an abusive reaction from the customer, they'll vent at you more aggressively. They'll often request unreasonable concessions, and they will try to strongarm you into things you shouldn't agree with.

That kind of apologetic approach, can create an environment where they push you to agree to change your mind. They'll coerce you until you give in and say: "Well, you know what, you made some really good points, I'll go back to my team and we'll think about it again, let's see, maybe there is another way."

No, screw that. You made your decision, you stand by that. And when you tell them, tell them in no uncertain terms.

"Listen, here's what's happening, I feel really bad about it, it sucks, but it's the reality: we can't service you anymore, we need to part ways. We'll give you guys two months to transition off, we'll consult you with finding another option, we'll come to your office and help you offboard, we'll do anything in our power, but within the next two months, you guys need to find another solution. We can't service you anymore, it's not going to work."

This Is What's Going To Happen

You're not negotiating with them. You're telling them what's going to happen. Friendly, but strong. It might create temporary discomfort, but they will actually respect you a lot more for it, and it saves both you and them the time that you both might otherwise be wasting on trying to negotiate the case. They'll realize that this is real, there's no way around this, and they'll ask the right question: how do we move on from here?

That's exactly the kind of energy you want to have in this kind of conversation.

FIRING CUSTOMERS: Learning to win new customers and close new customers is important. But learning how to actually fire customers can be just as important. Because bad, toxic customers, customers that derail you into a completely different direction that has no future for your business, can ultimately kill your business.


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Essential Sales Skills For CEOs Webinar

If you're a CEO or founder and want to get a quick introduction to essential sales skills for your startup, this webinar is a good place to start. 34 minutes (or 17 minutes if you watch at double speed) and you'll know the most important fundamentals of sales that truly matter.



Welcome to Essential Sales Skills for CEOs. I'm super excited about this group today, amazing founders and CEOs in the session. We're going to go through the webinar and talk about all the ways that you need to think about sales and the basic sales skills that you have to have if you're a CEO and a founder and somebody who's running a business. And then also how you need to think about all the people in your day-to-day job that you're selling to, and what you're selling them in the first place. So we're going to really go deep in sales focused on the CEO level.

First, let me share a little bit of background. So I've been a founder and CEO my entire life since I dropped out of high school when I was 17, 18. So I'm completely, you know, unqualified for any kind of job. I'm totally unemployable, but I've had at least the title of CEO for a very long time. And I've been selling to CEOs for a very long time.


The latest business that's probably most relevant to you guys is a company that we started called “Elastic Sales”. With Elastic Sales we helped over 200 venture backed startups in Silicon Valley scale their sales efforts. So we coach CEOs and founders in sales. We help them develop a sales process. We help to go out and sell to other businesses mainly in the B2B space. And the majority of those sales were actually to core decision makers, so CXO levels, many, many times to the CEO level. And we, as Elastic Sales, we always sold to the CEO, the final decision maker in basically utilizing Elastic Sales sales force to outsource sales and to get sales consulting and to scale their sales efforts.


We've worked with many, many companies in developing their sales process and scaling that. And in the process, we built a tool. At first we called it our internal “secret sauce” called “Close.io” that our sales people and our sales teams used in order to scale all these sales campaigns and outcompete their competitors. And you know, after a year of holding that piece of software close to our chest and calling it our “secret sauce” and our “secret unfair competitive advantage,” finally we gave in to all the demands from the outside market. We released Close.io, and it's been a tremendous success. Thousands and thousands of companies and sales people, people around the world, are closing more deals and making more sales using our piece of software.

So sales is really near and dear to our heart. It's in our DNA. It's the core thing that drives us and drives our business. And we're talking to CEOs and founders every single week, helping them with their sales strategies, helping them scale their sales forces and overcome their sales challenges.


All right, let's get right to it. So let's start off with Pitchology 101, right, the basics of pitching, the basics of sales. First of all, you need to understand that sales is nothing else than results-driven communication.

It's all about communicating with other people. It doesn't matter if it's in the context of a corporation or an individual buyer. You're always communicating with other human beings. And the goal of the communication is to help them make a decision, to drive a transaction, to drive a result, you know, yes or no. But you are in the results driven communication business.

And when you're managing teams as well as when you're selling yourself, you need to understand and separate communication for communication's sake versus communication for result's sake, right? So when you're in sales mode, and as CEO, you should always be in sales mode. It doesn't matter if you talk to your team to build something, if you talk to the press, if you talk to, you know, co-founders, employees, investors, you're always in sales mode, and talking is not selling. You know, you really need to focus on speaking in a way and communicating in a way that's actually going to drive a result and that has a result at the end of it as the end goal and the core driver of it versus just communicating for the sake of hearing yourself speak. Right?

And that's where sales is the closest to sports, in a way, and why a lot of people that are great at sales are actually people that are very competitive and might have had a background and history in sports because in sales you have a scoreboard. It's not just like, “Oh, I communicated great today, and I think I made some really amazing points.” Nobody gives a shit. Like, “I played really well today, but I didn't score anything.” Nobody gives a shit, right? The only thing that matters is how much, how many results did you drive, how many, you know, scores did you make if you were on the court, if you played basketball, whatever the competitive sport is; and in sales how many deals did you close? Nothing else matters.

And the other thing about that is it doesn't matter what the results were that you drove yesterday. You could be the best of the best, the best of all time. You could have been like Michael Jordan at his prime. When he went on the court for a new game, the score as zero, zero. Nobody said, “Well, this is Michael Jordan. He starts off with, you know, 30 points ahead because he's already worked his ass off for the last couple of years and he's the best of all time.” Nobody gives a shit.

The score he starts is zero. It doesn't matter what your results were last week. You have to perform again. You have to constantly drive results. And that's what it's all about. And as a CEO, you should only communicate to actually drive a result. No other communication should be part of your day-to-day life and the day-to-day where you do things and communicate things.


Because sales is a result driven activity, you know, you're never going to always just get wins. Not every throw is actually going to score. So you're more likely going to get more noes than yeses. You're going to have more failures than successes. If you opted to actually drive a result and get to a yes or no transaction one way or another, you're going to have to live with pain and rejection and failure. So you got to get used to that. And in sales, it's all about figuring out and training your own tolerance for pain and training your own tolerance for rejection. Right?

Most people design their lives around rejection. They design their lives around creating safe spaces where they're going to have to face as little rejection as humanly possible. When you're a CEO and you're selling, you need to get over yourself, which a lot of CEOs – a lot of CEOs have this problem that because they have this “title” for whatever the fuck that's worth, because they have that title, that title is seen as something that's prestigious, they only want to go out and sell when they know they're going to succeed. They don't want to fail in front of their team and staff. They don't want to look stupid. So they always kind of pick and choose what deals and what interaction they should get involved with only when they feel really, really, really confident that they can step in as the CEO and fucking drive the win and make this a big success and close the deal or whatever it is.

You have to get over yourself. You know, if you're only winning as CEO when you're interacting in sales conversations, you're not selling enough. If you're only winning, you're not taking enough risk. You need to fail. You need to show your entire team, organization, the public that it's okay to fail. It's okay to lose when you're playing to win. It's fine. As long as the scoreboard all in all has you ahead, you're fine. It doesn't matter how many times you took a swing, or throw and didn't hit the basket. So it's all about actually figuring out a way to tolerate and manage your emotional household and be okay with rejection. If you're not getting noes, if you're not getting rejected as CEO, you're not selling enough, you're not taking enough risk in sales. You need to be out there and figure out a way to manage your own emotional household and manage the way that rejection will be part of your daily life, hopefully.


Right now a lot of people and a lot of especially inexperienced CEOs – there are two camps: inexperienced CEOs when it comes to sales, people that maybe are very technical or don't have like a long background in sales; and also the other camp, people that love themselves talking, like super outgoing, super gregarious kind of personalities that think talking equates to selling – these two groups of CEOs think that selling is all about hearing yourself speak, selling is all about talking, selling is all about stealing the show and walking to a room and like babbling on forever and, you know, whoever has the most percentage of talk time in a conversation won. Nothing could be further from the truth, right?

In sales, the person who asks leads the conversation. Not in sales, in life, the person who asks the questions is leading the conversation, is focusing and directing and shepherding the conversation IN the direction you want to. You can only sell if you have understanding. You can only have understanding if you ask questions and you actively listen. Sales is all about first qualifying the prospect, qualifying the opportunity before you actually go out there to sell.


Don't throw darts in the dark. Too many people do that. You come into a conversation, you think, “Oh, this could be a potential buyer for a product so let me go on and tell that person everything there is to know about our business, and I'm going to throw as many darts in the dark,” darts representing value propositions, features, functionalities, fun facts. “I'm going to keep on saying, 'Well, our product is this and it does that and we have this and we have that.' I'm going to just throw as many things as possible, and something will surely hit.” Right? That's kind of the most unelegant, brute force, stupid way of selling. And what's going to happen as a results is the person will stop listening to you because you're like this overbearing person that is so self-involved and only in it for yourself. And it's impossible to listen to somebody and actually remember the 25th value proposition of that product. nobody is capable of doing that. And we've all been in these kind of very counterproductive conversations.

You can't just come into a conversation and sell. You come into a conversation to first get to learn and get to understand who it is that you're conversing with, who it is you're communicating with.

  • What are their needs?
  • What are they use cases?
  • What are their goals and challenges and obstacles?
  • Who is this person that I'm selling to and what do they need?

And once you actually get to understanding, not just surface level understanding but deep, real understanding of somebody's situation, then and only then do you have the permission to sell. And then and only then do you have the ammunition to sell because you have real targets.

You know, oh, this person really, really cares about X, Y, Z and I know why they care about it and I know the context, the environment in which they care about this. I really have a deep understanding so when I now start speaking to pitch them on our product, both do I have the authenticity that I believe our product really solves their problem; but I also a have clarity of what I should focus on. Instead of telling them everything our product can do, I'm going to tell them what our product can do that's going to help them and that I know is a priority for them.

So you always want to qualify first before you actually start selling anything. You always want to ask questions before you start assuming you know who they are, what they need and start pitching them on those.

And when you ask questions, make sure that you don't just ask them so it gives you a permission to pitch. Ask them to really understand them. Ask them with the real curiosity and an open mind and actively listen to what they say, the content of their words as well as the context, how they say it. Are they congruent? what's the environment like in which they are interacting and saying these things? Pay attention to not just what they say but how they say it and really drive understanding and qualify them. Yes, they are actually a really good fit for what we do and I understand what they need and why they need it, and I'm going to go and pitch them really effectively, throw in one dart into the target and hitting on the first attempt.


So the other thing that you need to know is that trust comes before any transaction, trust before transaction. Nobody buys anything if they don't believe everything you say, right?

So here's an example. If your phone rings after this webinar, and you pick it up and it's an unknown number, and the other person on the other line goes, “Hey, John. This is Steve. I'm calling from company X, Y and Z. I want to tell you you've won $1 million. Isn't this exciting?”

Are you going to get excited? Are you going to jump up and down from your desk, high-fiving your employees thinking you've just won $1 million? No! Chances are you're going to think about hanging up. You're going to say, “No, no. Not interested,” and you're going to hang up. Why?

Isn't the content of the call amazing? Isn't hearing and learning that you just won $1 million incredible value? Well, the problem is that you have zero trust. The problem is that you believe nothing that was just said. And the more amazing it is, the less you trust it.

It's not only about what you say, it's how you say it and who says it. Credibility and trust before any kind of transaction. You need to establish some level of trust before people can actually buy from you.

You need to understand that trust is being developed on three core levels:

  1. on the company level,
  2. the product level,
  3. and the personal level.

And if you can only establish trust at one level, do it on the personal level because that's the most vivid, active relationship, is you and the person you're selling versus – your product doesn't have a relationship with the person you're selling. Your company, which is this conceptual construct of multiple people and things. A company won't have a relationship. It always comes down to people.

So first, people have to trust you. Then you need to build some trust in your product, whether you're actually going to deliver what you promised.

And you also want to create some trust around your company, right? So why is this company going to be around? Why is this company known for keeping their promises, or fixing their issues. or keeping their words? Why should I believe this company is going to be around for a while? So interacting and getting into a relationship with them is not a waste of time that's going to be worthless in a few months because they're going to be out of business. So you need to build trust and tell people why they should trust your company.

You need to build trust around your product. Why will your product deliver? Why should people trust your product?

And most importantly you need to create trust around you as a person. Why should I want to be business with you? Why should I believe anything you say?


And you can do that explicitly and implicitly. And implicit is always better. Like you can always tell them about things that will make them think, “Oh, this person is trustworthy,” versus saying outright the words, “You should trust me.” Right? I'm always distrustful. The first thing I think when somebody is like, “You should really trust me,” is, “Oh, my God. I will never trust this person.” That's the most obvious thing to think.

So you want to be able to say things like, “Hey, here are the five amazing companies that have bought our product and here's the value they're getting and here's what they're saying about us. Hey, here's my background, here's my personal story, here's the companies that I've built, that I've led as a CEO and the results these companies drove and the legacy I've led them to become. Here's my background and story. Here's where I'm coming from. Here's where I am today. Here's where I'm going next.”

And you want to speak in a way that is authentic so people feel the congruency of your words so every word actually hits and people start believing you and trusting you. And a big benefit that you have as a CEO of a company is that the title alone comes with a lot of trust, right? The title CEO alone comes with a massive bag of goodies, and one of them is trust. People immediately assume you're important. People immediately assume they can trust you a lot more than your sales people or anybody else in your organization. So if you come into that relationship with all these like, you're already coming into this relationship with a lot more trust than normally people would have. And you want to make sure you're taking advantage of that.


Here's a big one about sales. You always – no matter what you do, product, service, I don't care what it is that you're selling – you always sell value. Nobody cares about your features. Nobody cares about how you've built what you've built, the functionality, the features, the buttons, the things. Nobody cares about the things that you're involved with all day long.

All people care about is what is in it for me. What have you done for me lately? What is this going to do for me, for my life?  How is this solving my problems? How is this making my life better? How is this making me more money or saving me money? Like why should I care?

And you have to focus on talking about value versus features. You have to talk about benefits versus functionality. And we all, we all forget this. It doesn't matter how amazing you are as a CEO. It doesn't matter how professional you are as a salesperson. Sooner or later you'll get so self-involved with your product, you're so focused on the features and functionalities and the bolts and bits and little pieces of how everything works that you're going to start talking about these things a lot more than you should be translating these things into value.

It doesn't matter that you're product has X, Y, and Z functionalities. The question is what kind of value does that drive to the other person and why should they care? Is this going to make them more money or save them time? Is this going to make them look good in front of their boss? Or, is this going to save them embarrassment? What is the core value that you could deliver with your product? Only talk about that.

Talk about the value you create. And then later one, as a follow up, you can talk about the vehicle that delivers that value, which in technical products, might be the features and functionalities of your product and the technical background. But the features and functionalities are always the deliverers of value. What people really care first and foremost about is what's in it for me? What is going to be the value of what you're trying to sell me for my life, right? Always sell value. Always do value-based sales. Never do features, functionality-based sales.


The next basic thing you need to know, understand, and master if you're a CEO in sales is the art of managing objections. There is no such thing as no objection sales. If you can pitch somebody, and they just say, “Yes,” and they buy – the most scary prospects for me are the ones that buy without objections. The most scary people that I try to hire for my company are the ones that want to start immediately without having any critical questions. The most scary potential investors are the ones that are immediately talk about investing without having any challenging objections.

Objections mean somebody is real. Objections mean somebody is trying to qualify ifhis is a good fit. Objections mean somebody operates in the real world with real constraints. I like these people. These people actually are the reason I exist. If people just bought left and right and had no objections, challenges and critical questions to ask, there would be no need to do sales anyway. Everybody would just buy. You wouldn't have to sell anything ever.

So objections are a good thing. You shouldn't hide or run from them or be annoyed or inconvenienced by them. You need to learn to manage them, anticipate and then manage. Hard preparation, easy fight.


So here's what you need to do. You should never compute an answer to an objection on the fly and in real time. What that means is if you're selling it doesn't to employees, to investors, to the press, to customers, you're going to get similar questions more often than not. 80% of the time, people want to have very similar objections and questions. There's going to be the, “We don't have any time. This is too expensive, what about security risks?”

Like there's going to be a set of questions, five, ten, 15, 20 questions that you hear again and again and again and again and again. And what surprises me is that people are surprised of hearing these things again and again and again. You know what? The more they hear them, the more annoyed they are that they have to deal with them. How stupid is that?

How about preparing for them and being excited when somebody has that objection because you're prepared to answer it effectively,and you know how to actually answer it in a way that drives your agenda forward and helps them, and helps you move the deal forward.

So what you need to do is once you know what the top five, ten, 15 objections are that you get all the time, sit down, you write these in a piece of paper or a document and you think about an answer that's effective, that only needs one or two sentences, no paragraph, no pages. You want to answer any objection as concise and precise as possible, one or two sentences.

You know what the secret is? It's not even that much about like how amazing is the answer. It's even more about – it's not so much how you answer it, or what you say when answer,but how you're answering it. Whenever you're able to

  • answer an objection in one or two sentences, and
  • keep eye contact, and
  • keep your level of energy and focus and clarity,
what it does is it doesn't just communicate the content of what you're saying, it also – the underlying message to the other party is, “Wow, this guy seems to not be rattled at all by this objection. This person seems to know exactly how to deal with it. This person seems to have a very high a level of clarity on how to manage that objection.”

The underlying message?

You're an expert. You know what you're doing, you've done it before.

That makes people comfortable, and comfort is - more than anything else - what people are looking for when they're bringing up objections. They don't just want to hear you answer and believe it. They want to feel like you are a pro, you've dealt with this before, they're in good hands.

So hard preparation, easy fight, you learn how to embrace objections, manage them, and use them as a tool to sell more effectively.


All right. Now the last of the sales basics for CEOs is the most surprising one. Duh, you have to ask for the close. Every conversation, every communication with somebody, needs to end with an ask for a close. Wow, Steli, you know, this is amazing. I'm so glad I enjoyed this webinar. I've never heard of this before. This is such a groundbreaking concept. Right? This sounds like the most stupid, obvious thing to say, but how is it that every single day I hear sales calls, I participate in sales conversations, where the end is the weakest part of the conversation and the CEO is not going for it? Again, looping that back to the fear of rejection, because they're afraid of hearing a no instead of embracing it.

Ask for the close:

  • Hey, are we in business yet?
  • Hey, what will it take for you and us to get into business?
  • Hey, what would it take for you, now that we've figured out that this is a good fit for you, now that it seems like we're really aligned and I was able to answer all your critical questions to your satisfaction hopefully, I'm curious, what stands in the way of us getting into business?
  • What needs to happen for you to become a customer of our solution?
  • What needs to happen for you to decide to join our team?

Like whatever it is, go for the close. And you know what? More often than not, you're going to get a no, or not yet. That's awesome. Embrace it. Anticipate it. It's a good thing.

What's the most powerful thing you can do when somebody tells you no?

Don't be rattled by it. Keep your smile. Keep your energy and composure. Show the other person that that doesn't affect you, that you anticipated that, and that it's fine for them to not quite be there yet now, but you're going to help them get there. Right?

That's when you come into the conversation, the sales conversation, from a point of friendly strength. Right? You're very friendly to them, but you're also, there's an underlying strength, like a parent interacting with a child that's really upset about something, or throws a tantrum, is coming from a place of knowing, showing the other party, “You know what? I've dealt with this situation before. I know you're not quite there yet. And that's okay. I'm going to help you and guide you through the process until you feel comfortable to make a buying decision.”

Nothing is more powerful than being okay with somebody saying no, and still keeping the conversation moving forward and focusing on servicing them into giving them everything they need to buy your product.

But you have to ask for the close to get the no. You have to ask for the close to get a close. You have to ask for the close to get to a result, a yes or no. You have to make a throw to make a point. You have to take a chance.

Too many times at the end of a conversation, a CEO or a salesperson will not actually really go for it. They will go, “Well, this was a great conversation. I'm really happy about it. Well, let's stay in touch and see how this is going to develop. And then let us know if you have any more questions, and we would love for you guys to buy our product. All right, bye.” Boom. What kind of a shitty close is this?

How about, “Hey, how was this call? Are you happy with all the answers? Are you ready to get in business with us?” Right? “Are you ready to go? Are you ready to rock and roll?”

Ask people for the close to get to a result. Yes or no doesn't matter. A no could be a not yet.

Even if it's a definite no, and there's a real good reason for why they'll never buy your product, you better want to know about it right now than wait for it for weeks. “Oh, are they going to buy or not? I don't know. We're still looking into the account every day and hoping they're going to upgrade or purchase themselves.” That's weak sauce, right? You have to go for it and ask for the close every single time.

The close might be, “Buy our product.” The close might be, “Let's schedule that next meeting.” The close might be, “Introduce me to somebody important.” But you have to ask for it. You can't get what you want if you don't ask for it. Right?


All right. So let's go to the next one. Fortune is in the follow up, and that's really the last step of the Pitchology 101, the Hustling 101, Sales 101 for CEOs, is you know, you know you have to deal with rejection. You have to go out there and pitch people and communicate in a result driven way. You have to qualify them and ask lots of questions to have a real understanding. You have to actually sell in a value focused way. You have to manage objections, and then you have to go for the close. And you know, more often than not, the transaction will not end until you have to do a little bit of follow up. And follow up is really where the fortune is. Follow up is where winning actually happens because nine out of ten times, everybody else will not follow up when a deal falls through.

So here's what happens. You have a sales conversation, you have a meeting, you have a recruiting call, you have an investor meeting or whatever it is, and it goes really well. And then they say, “Hey, let's schedule another call to talk some more,” and then send them an email to schedule the call and crickets, silence. You don't hear from them back.

So you send another email. You don't hear from them back. You wait a little longer, you send another email. You don't hear back. You call, you leave a voice mail. You don't hear back.

At that point, you start assuming, “I've been rejected. They hate me. They probably think I'm horrible and stupid. Oh, my God, I'm going to feel really shitty about this. I don't want to be meeting and keep getting rejected by their silence. So I'm just going to stop and call this a 'loss.'” It's the stupidest idea and the stupidest strategy you could ever apply.

When you have been in a positive interaction with somebody and they fall off the track and they don't communicate with you, you know how many times you should follow up?

Indefinitely! Forever.

You should never stop following up until you get to a result. Again, looping back, result driven communication. Silence is not a result. A no is a result. A yes is a result. But silence isn't.

So here's my simple philosophy. I always follow up indefinitely. I keep following up forever until I hear back. When somebody tells me, “Hey, fuck off dude. I really don't want to hear anything about this anymore,” I'll stop. I totally will stop. But until I hear back, I will never ever stop following up.

You know how many deals we closed, how many investors we got, how many things we've moved forward just by being the only ones that kept following up? A lot more times than you could ever imagine.

I'll give you a quick example, a story that I tell oftentimes. An investor, somebody that's so famous, all of you have used his product, the product that he developed and made billions with I can say with certitude, we got a warm introduction to that investor. Once we were fund raising, that guy replies and says, “Yes, I'm interested. I want to meet up with you guys.” We get all excited, high-five each other. We send an email with some times and dates to meet. Silence. We send another email, silence. We send another email, silence.

You know how many follow ups it took to hear back from him? 48 fucking follow ups, 48 follow ups, where he was totally silent. You know what, when we follow up, we weren't needy about it. I was referring back to the original emails. “Hey, you said 'yes'. What's up? I've followed up with you 12 times. That's not cool. Really, it would be – I really appreciate it if you” – like no!

Every single email, I was clear and to the point, short, precise and concise:

“Hey, another beautiful day in paradise. Here's a little tidbit of good news about our company. How about a quick call on Tuesday or Thursday at this or this time?”

I send another follow up:

“Hey, how about we should try to meet on Wednesday or Saturday.” Nothing.

Another follow up: “Hey, you know, here's another cool news. We just hit this milestone. Would it be possible to meet this week, either this time or that time?”

I just kept following up, professional, clear cut, one or two sentences, precise. After 48 follow ups, the guy replies and says, “Oh, my God. I'm so glad you kept following up. I'm so sorry. I suck. We had this big crisis. I had to fly around the world. I had to do this and that. Yes, can you come tomorrow to my office at 11 a.m.” We went there. We closed the deal. We got the investment.

That's how you win. Follow up when nobody else is following up, because everybody feels rejected and needy and doesn't want to be inconveniencing somebody. This is business. When you're in a relationship with somebody and you interacted with them and they give you positive feedback and said, “Yes, let's move forward,” they've given you permission to follow up. And it's not just rude to follow up. It's rude to be silent. Don't assume people are rejecting you. Assume people are busy. People have other things to do than to answer you. Something came up so keep follow up until you hear from them.

If you only do one follow thing as a CEO is instilling a culture of follow up in your organization, and you have to go first. Lead by example. Show your employees, your team, your investors that you always follow up and follow through to get shit done. Right?


All right. A last little tidbit on the sales side, pulling the CEO card. Like being – just by having the title of CEO, deals will happen faster and better because people assume a lot of stuff with, “Oh, the CEO has stepped in to talk to us.” Right? You could give a junior salesperson the CEO title, and that person will probably close more deals next week just because they come into a conversation with like, “Oh, this is the CEO of our company.”

People assume importance, people assume authority, people assume intelligence, all kinds of amazing shit with the title CEO. So just by having that title, just by giving yourself the title of CEO of your two-person company, right, I'm the chairman and CEO, just by that, people will take you more seriously, people will listen to you more carefully, and people will resonate and respond to your message a lot more powerfully.

So you have to help your team. If you have a sales team already or team that sells, that goes out there, you have to get down and dirty. You have to step in and help your team close deals especially the important ones. Help step into your HR recruiting team to hire people. Step into, you know, the industry and fund raising side. You have to be in the front lines using your title, and using the authority and the magic and the unicorn sprinkling, all the cool goodies that come with that title to get shit done and make transactions happen. So support your team and utilize that title to make stuff happen.

And then one quick other tip is that one of the more core important things about the CEO title is that people assume that you are busy, that you are important. Being busy and important assumes that you don't have time to waste. So when you go into sales conversations, one easy hack to make the other person really feel implicitly that you're important is to have time constraints. If you go into sales calls as a CEO and you take two hours for like a $100 a month deal, you know what the other person will think? Even if they appreciate that you take all the time in the world for them, they will assume you're not important. They will assume you have nothing better to do than to take two hours to close a $19.99 monthly subscription deal with them, all right?

So here's a simple hack. As a CEO, everything you do should have a short and precise time line. You do 15-minute sales calls. You don't do one-hour sales calls. You come into the conversations with having real time constraints. “Hey, my name is Steli. I'm the CEO of Close.io. I'm super excited to talk to you today. I'm going to highlight to be respectful of your time that I'm going to have another call in about 15 minutes. My day-to-day is a little crazy. I apologize for that, but I think that if we both focus, we're going to be able to accomplish our objectives and get really a lot of things done. Why don't you start and tell me the three things that you want to focus on? And then we'll go ahead, and we'll try to make it happen.” Right?

Just by saying, “Hey, I have a real time constraint. I have another call in 15 minutes or 30 minutes, but I think that amount of time, if we focus, will help us get everything done,” just by that and having that kind of energy of like, “I need to get you done. I don't have time to babble on for or talk about the weather and everything. I'm here. I'm focused. I'm going to give you all my attention. Then I have to move on to something else,” just by doing that, you're going to have real impact, and you're going to implicitly communicate to the other party that you're important and busy.

And people love to buy from people that are busy and that are important. Right? It makes them feel comfortable. It makes them feel like this is somebody that's important for a reason. Probably they're very intelligent and successful. So doing business with them is probably going to be a good idea. Right? Use that. 

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Inbound Or Outbound Sales - Which One Should You Focus On?

I share a lot of advice about outbound sales - thus many people naturally assume I'm an outbound advocate. I'm not. It's just one of the things I do, outbound is a part of the puzzle of success in business to me. But I don't think every startup should do outbound sales.

When it comes to inbound versus outbound, I'm not dogmatic - I'm pragmatic!

Fun fact: Close.io is doing zero outbound sales. All our growth is 100% inbound generated! There will come a time when we get outbound sales going, but right now we're too focused optimizing and scaling the inbound part of the business.

Cons of Outbound Sales

Outbound sales has taken a lot of flak - for several reasons...

Public Enemy Number One


Nobody wants to be cold called, even sales reps who cold call don't want to be cold called. I'm more receptive than most to cold calls because I'm a sales aficionado, I appreciate good salesmanship - but even I don't look forward to being pitched.



When you're doing outbound sales, you're interrupting people. Everybody is an expert nowadays on filtering out interruptions. The average US citizen is bombarded with more than 2000 marketing and sales messages every single day (number varies depending on methods used to measure, but 2000 is actually the low end). It's like our brains have a subconscious TiVo or adware program running in our brain that immediately blocks anything that triggers the sales pitch alarm. You basically have to buy, beg or bug your way in.

High-pressure Sales Tactics


These are still commonly used and encouraged in outbound sales organizations - but you can (and should) be a smooth operator rather than a sales bully.

Time Inefficiency


Outbound sales reps waste a lot of time on mind-numbing tasks. They spend only a small part of their workday practicing their core skill: closing deals. (Which is something we're mitigating with our outbound sales software, but it's still a major pain point).



Outbound sales stops working as soon as you stop working. One of the big advantages of inbound sales is that it keeps generating leads even if you stop doing it. But as soon as you stop doing outbound, it stops generating new business.

Pros Of Outbound Sales

Now let's look at the flipside of the coin.

It Works


Yes, it's 2014. Yes, 'the buying cycle has changed', we're living in unprecedented times with social networks having changed the game of sales. But the fundamentals of salesmanship that worked in 1914 are still working now, and will still work 2114. Outbound sales brings home the bacon.

Predictable & Scalable


Once you have developed a sales process, you have a predictable, scalable growth mechanism for your business. Hire a new sales rep? You know how the actions you take now will affect your revenues three, six, nine months from now. Ask any business owner - that kind of simple formulaic predictability is a beautiful thing.

Power To Choose Your Customers


Outbound empowers you to pick your customers. Outbound is hunting - you pick a target and go for it. Inbound is fishing - you hang a fishing rod in the water and hope that a fish will bite, but your control over what kind of fish will bite is miniscule.

You Determine The Timing & Medium

Outbound sales gives you control to determine when you want to interact with prospects. This is the flipside of the "interruption" coin - rather than having to wait prospects to reach you through inbound requests when they are ready, you reach out to them when you are ready.

You also determine the medium of your interaction - be it an email, a phone call, meeting them at industry events or even knocking on their doors.

Immediate Results

Outbound sales can generate new business quickly, whereas inbound takes a long time to build up. If you want fast growth now, outbound is your friend.

Targeted Reach

If you're selling to professionals, outbound allows for much more targeted lead generation. This kind of laser focus allows you to execute with a higher level of precision and accuracy, and thus be much more effective. Want to reach the VP of marketing Citigroup? Good luck trying to get his attention with inbound tactics. 

Higher Level Of Engagement


The most impactful and influential sales outreach possible is a human one-on-one interaction. It allows you to truly engage with the buyer. Everything else pales in comparison when it comes to the impact you can have on an individual buyer.

Is Outbound Right For You?

It really depends on what the focus of your business is now, how fast you want to grow and what kind of business you want to run.

Your Strenghts

Whether or not you've got what I call the "hustle DNA" and are a natural born sales person - you should be doing some outbound sales, just for the lessons it'll teach you. But don't try to force yourself and break your back over making outbound successful if you have other means for growth.

Your Market

Are there other companies doing outbound successfully? If yes, how are they doing it? Study their outbound sales process and learn from the market.

Your Results

old cash register

Ultimately base your decision on the results you get. Outbound is probably the least trendy, hip, cool, awesome, amazing thing a startup can do to grow the business. But you're not in business to get admiration from your peers and the press, it's not a popularity contest.

Business is about the bottom line. The only thing that matters is: does outbound sales make your business more successful or not?

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