12 sales kickoff meeting strategies and best practices for bringing your team together

by Ryan Robinson
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In today’s fast-paced world, the humble sales kickoff meeting might seem like a relic of older, simpler times.

Even if you’ve got exciting product updates to show off, new sales strategies to explain, and techniques to employ, who has the time, not to mention the budget to bring their whole team together for a big event?

Well, we’re here to change your mind about that.

We all know that knowledge is power. And nowhere is that more true than in the sales game. When you’re trying to get your foot in the door with a new prospect or gunning for a quick close, the more you know and can show that you understand your product and how it benefits the customer, the better chance you have.

Sadly, this knowledge doesn’t come easily. And it shows.  

According to Forrester Research, while 88% of key decision makers feel that salespeople can speak knowledgeably about their own products and services, only 24% feel like they understand their business needs.

Even worse, only 15% believe their meetings or calls with salespeople are valuable.  

Today’s buyer expects more. And smart organizations are investing in educating their sales people and providing them with tools, processes, and examples that can help them impress smart buyers.

As acclaimed sales speaker, author and sales kickoff veteran Jill Konrath explained during her interview in this year’s Inside Sales Summit, “The best salespeople are those who’ve done their homework. They’ve invested their time in learning something about me and ask the right questions.”

Want to Watch Jill’s Full Interview? Get Free Lifetime Access to the Inside Sales Summit.

WATCH THE FULL INTERVIEW

Now, before you go off discounting the importance of a sales kickoff meeting, let’s look at all the reasons why you might want to fit one into your calendar.

What is a sales kickoff meeting?

A sales kickoff meeting is an event designed around bringing your entire sales team together, sharing best practices, product updates, new sales strategies, and getting everyone re-invigorated to pound the pavement (or inbox) and bring in new sales.

It’s a huge investment for most sales organizations, not only for travel and production costs, but opportunity costs as well. A full day or two of taking your sales team out of the picture can be a hard sell at any company. But, if done properly, a sales kickoff meeting should send your reps back to the frontlines feeling inspired, confident, valued, and more ready than ever to engage with leads and close sales.

It’s an investment in your future as a company and in your sales team as individual reps. So, to give you an idea of what you should include, here are the 3 key pillars of an effective sales kickoff meeting.

Education

Knowledge is power, remember? To sell effectively, your sales reps need to know your products through and through. They need to be up-to-speed with the latest sales strategies and initiatives, and know what marketing messages are in the pipeline. With the amount of communication that happens in the workplace, it’s easy for sales reps to miss some of this key information, which is why bringing everyone together for a dedicated education session like this is so important.

Engagement

When you’ve got good people on your team, why waste their talents by not letting them share their thoughts, ideas, and best practices? A sales kickoff meeting empowers people who wouldn’t normally have a platform, to talk about their common challenges, frustrations, and solutions. Plus, when reps feel connected to the rest of the team, they’re more likely to be excited about the work they’re doing.

Energy

There’s something more important than money and commission (shocking, I know!) and that’s purpose. Sales kickoff meetings allow you to infuse motivational energy into your team, to connect them to a larger purpose, and let reps feel connected to the work you’re doing on a grand scale. Bring in an electrifying keynote speaker (like Konrath) or organize an awards presentation to keep your sales team pumped for the year ahead.

While these pillars give you a broad view of what you should be including during your event, there are also some best practices we’ve picked up from

The 12 elements of a killer sales kickoff meeting

Depending on the size of your sales team, your sales kickoff meeting could be anything from a handful of people getting together in a conference room or at an offsite retreat for the day, to a multi-day extravaganza bringing in reps from all over the country.

A sales kickoff meeting isn’t just about giving information. It’s a rallying call for your team, preparing them for battle. We look pretty intimidating, right?

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So while the size, format and complexity of your sales kickoff event will vary, here are some best practices you should follow if you want to create an event that doesn’t have your reps nodding off by mid-morning.

Let’s run through everything you should be doing before, during, and after your big sales kickoff meeting.

Before your sales kickoff meeting

1. Clearly define what a successful sales kickoff looks like and work that into a theme

There’s a risk in running a sales kickoff meeting way beyond just the cost in time and resources.

If you don’t do a good-enough job of giving your team a reason to be at the event, this unique opportunity you have to motivate and inspire can fall flat. So, before you start planning sessions, booking keynote speakers, or finding a venue, ask yourself “What would a successful sales kickoff meeting look like?”

What do you want people to be thinking while they’re there? Is this an emotional, education, or rationally led event? How will you measure success after the fact? Are there milestones ahead that you’re directly trying to affect through your sales kickoff?

Generally, there are 4 reasons you want to bring your team together, and which you can create a theme for the event around:  

  1. Celebration: The “we killed it!” event. This is where you want to make sure your team feels recognized and appreciated for all the work they put in. Your events, team exercises, and speakers should all be about entertainment and keeping people excited. The outcome of a meeting like this is enthusiasm that will carry through the rest of the year. For themes, think things like “Beat (competitor name)”, “Portraits of Success”, or “Leading the Pack”.
  2. Motivation: The “things are changing” event. This sales kickoff meeting is all about challenging and inspiring your workforce. Look for personal hero speakers who can drive home the motivational message and set up events and sessions that are individual and personal to get reps to dive deeper into what moves them. Some themes could be “Better. Stronger. Faster.” or “We Own This”.
  3. Provocation: The “we need to think differently” event. Are there changes ahead in the market or at the company? Are you going to change the way you sell or bring in new sales tactics? Are there internal side projects that are taking off and need a fresh sales strategy? Bring in industry speakers who can shed some light on the situation with data and create events around team assignments and exercises so your reps get used to coming up with creative solutions to new problems. Try themes like “Breaking Barriers”, “In It to Win It” or “Purpose and Passion”.
  4. Information: The “here’s what’s actually going on” event. At this kind of sales kickoff meeting you’re either dispensing information or “resolving the unknown”, such as dispensing rumors that have been floating around. The theme is all about transparency, so bring in key people from within the company to announce and share what’s new and going on. You could set a theme such as “Creating Customer Connections”, “Sharing Solutions”, or “Champions by Design”.  

Decide what’s most important to your company right now and build your event and theme off that base. If you’re looking to motivate, then create a theme around success and how that looks. Bring in some heavy hitter reps to run through big sales. Tying it all together like this lets reps know what’s going to happen so they can align their expectations.  

2. Use technology to let your reps guide what the Kickoff will look like

While you’re thinking of the theme and what success will look like, you can also be polling your team to know what they feel is most important to their own success.

People are more invested in what they’re learning when they’ve had a hand in shaping it (it’s called the Ikea effect), so ask reps what they’d like to see. Involve them in pre-planning by asking them what’s most valuable to their career and growth. What frustrations are common? Where are people seeing room for improvement or issues that should be addressed?

To get this information, start sending out surveys or polls a few months out from your event. From these, you can start to identify common knowledge gaps and then dig deeper into exactly what people want to learn.

The sales kickoff meeting is a unique opportunity to hear from your whole team and to let people feel that they’re heard.

3. Align your meeting content with your company goals

This sound like an obvious step, but it’s one that is too easily skipped if you get too invested in a theme early on. For your sales team to do their job, their actions need to be aligned with company goals. Your sales kickoff meeting is a unique opportunity to communicate those goals or higher level strategies that might not be trickling down for leadership.  

“People need purpose (other than just commission),” says Joe Wilburn, Director of Sales for Brooks Group. “Lay out the strategy and exactly how each player will be expected to contribute so your salespeople can clearly see where the company is going and their role within it.”

This kind of open and transparent discussion around company strategy and goals helps your team see the bigger picture and can be a powerful motivator. Use this opportunity to weave your company narrative into the story your kickoff is telling.

4. Be deliberate (and careful) with how you set your agenda

A full sales kickoff agenda does not mean an agenda full of just “stuff”. It means an agenda full of content that’s related and relevant to your overarching theme. While the majority of your sessions might be speakers, make sure to break up your agenda with break-out groups, team exercises (both team building and teamwork), as well as smaller sessions or just time to mingle.

“We have a lot of execs who want to talk about their area,” explains David Freeman, VP Corporate Sales at Nutanix who hosts sales kickoff meetings for a team of hundreds of reps.

“We have to limit the airtime for people who just want to get up there. We have to focus on what the participants need. We may give them another opportunity to address the team, but we’re not giving people airtime just because they ask for it.”

Another suggestion from Freeman is to skip product updates or releases unless they’re relevant to the theme and motivation behind the meeting. If it’s just a one-way session or information packet, there are better ways and mediums to communicate that information.

5. Get salespeople excited with some ‘pre-roll’ content

Set expectations of the employees coming to the event. You need to be prepared to give outside speakers the theme and goals of the event and get them connected. Interview the speakers who are presenting and a few people who are attending ahead of time, and create a short video teaser to release and get your team pumped up.

“Just like a comedian has a warm-up act, so too should you be in order for your sales pros to be excited and prepared when they arrive,” says Art Sobczak, author of Smart Calling.

To set expectations for your team before the event, send out prep work designed around your theme or get keynote speakers to put together videos or webinars beforehand. To get people even more excited, you could even tease that you’ll be announcing a new compensation package based around your event’s theme for Q1 of the year.

During the sales kickoff meeting

6. Create an atmosphere of healthy competition

Sales is all about competition, and bringing a bit of that healthy competition into your sales kickoff meeting is a great way to not only get your team fired up, but keep them engaged and entertained throughout the event.

The point here is to create a fun environment, so think of creative activities that can both engage with the material being presented and feel like a game. Some ideas could be:

  • Gamified leaderboards based on daily quizzes
  • Pitch competitions throughout the event with the finals on the last night
  • Awards ceremonies for top reps

7. Provide time for interaction and unexpected conversations

The best ideas can come from the most unexpected places. So, while it can be tempting to jam pack your event with keynote speakers, breakout sessions, and team-building exercises, leaving some intentional space for mingling is equally as important.

If you’re a bigger company or distributed team, think about how few opportunities you have to bring all your reps together. While modern technology has made remote working easier than ever, few things really inspire us like meeting face to face.

And because everyone at your event shares a common interest, you can’t imagine where the conversations might go. Those drinks at the bar one night could turn into a new sales process, or that conversation over coffee could get your reps thinking about a new way to reach out to prospects. Collaboration is the key to coming up with creative solutions, so give room for those unexpected conversations to happen.

8. Bring out your big hitters to share relevant success stories

Recent research found that only 21% of executives felt sales reps had relevant examples or case studies they could share with them. That’s pretty bad. The problem often isn’t with having the examples, however, but with sales reps knowing them and being able to use them during their process.

As part of your sales kickoff meeting, bring out some of your most successful reps to talk through successful sales or use cases. It’s a unique opportunity to circulate this kind of knowledge, plus it lets your heavy hitters know that you appreciate the work they do. To make this even more effective, get someone to turn these stories into case studies you can share internally or externally so the information doesn’t get forgotten after the event.

9. Change things up with a number of different sessions

Just like you need to be deliberate in how you plan your agenda, during the event you’ll want to be deliberate about not keeping things too similar that people get bored.

So, while this is a ‘sales’ kickoff meeting, don’t just limit it to sales. Bring in people from other departments to share their ideas and inspire, such as marketing, product teams, and customers as well as founders and CEOs.

10. Make your customers part of your sales kickoff meeting

Who knows more about your customers than your customers themselves? It can be incredibly enlightening to get your reps in a room with current clients in a no-pressure situation. As part of your event, book sessions where you can get current customers to talk about their pain points and give honest feedback about what was good and bad about your sales process.

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During our last Close.io retreat, we video conferenced in one of our customers to talk through what they get out of our sales CRM, the most compelling value propositions that motivated them to purchase, and how the product  experience has been since getting onboarded. 

“Conduct at least 5 win and 5 loss interviews,” suggest consultant Joshua Meeks. “During the interviews ask the customer about the process they went through to come to their decision. Why did they choose to do nothing, go with the competition or select us? What was their opinion of us? It is important to ensure the content covered and the skills developed are in sync with buyer needs.”

After the sales kickoff meeting

11. Reinforce the concepts you’re teaching

You’re putting in a lot of time, effort, and resources to create an inspiring event. But unfortunately, research has shown that more than 80% of the information reps take in during a sales kickoff meeting will be forgotten within weeks, if not days.

This has nothing to do with your sales kickoff meeting, it’s simply human nature. So, instead, you need to find ways to continually reinforce the concepts you’re teaching.

One idea is to start meetings or conference calls with your team with a recent story that illustrates the theme of your kickoff. For example, if your theme was around provocation, talk about a recent example where a new strategy outlined during the kickoff worked out. Just a small reminder like that is enough to bring that information top of mind again.

You can also create awards or incentives for people to continue engaging with the materials from your event. One great method is to have your reps actively teach each others, the lessons they learned at the kickoff event. Multiple studies have shown how when we have to teach someone what we’ve learned, we hold onto that information longer. If you had smaller sessions that not everyone could attend, have people that did teach the material later and reward your employees for it.  

12. Collect and act on feedback from the event

If you’ve run your event right, there should be a lot of feedback and ideas to go through afterwards. You don’t want these to go to waste, so make sure you find ways to capture feedback through surveys or polls and then put processes in place to execute ideas that are worth it.

Like I’ve said throughout this whole piece, the sales kickoff meeting is a unique opportunity to bring your team together, and by acting on the feedback you get, you’ll be keeping your team inspired and motivated to keep hustling. 

Plus, as an added bonus, you can also take the lessons your team learned at the kickoff event and use them to fuel your brand's content marketing strategy by working closer with marketing around the new strategies, tactics, and goals moving forward—thus filling your pipeline with higher quality leads. 

The case for running a virtual sales kickoff meeting

Now, at this point you’re either amped up to start planning your next sales kickoff meeting, or you’re sitting there saying some form of “sounds good, but there’s no way this fits into our budget.” Which is fair. A sales kickoff meeting is a big opportunity, but it’s also a big investment.

And you need to be sure you’re going to get what you need out of it before investing.

One option that might work for you if you’re on the fence is to put on a virtual sales kickoff. What this means is creating an event that’s done online, accessible by all your team, and saved for watching later.

Yet while the cost savings could be huge, there are some downsides to taking your sales kickoff online.  

Benefits:

  • Lower costs from not bringing out your entire sales team to an in-person events
  • Presentations and talks are recorded and can be accessed later
  • Ability to engage more with reps during the event through polls and surveys
  • Content can be added to throughout the year giving more weight to the theme

Downsides:

  • No opportunity for chance encounters
  • Less engagement with speakers due to not being in person
  • Harder to get excited and rally around a virtual event
  • Less buy-in on theme as reps don’t have as much of a reason to be excited

In the end, it’s up to you and what works for the size of your company and your budget. For distributed teams, doing meetings like this online might be the norm, whereas if your company culture is much more personal, it could be a bit of a departure.

Final thoughts on sales kickoff meetings

Your sales kickoff meeting, whether virtual or in-person, is an opportunity to reunite your team, build camaraderie and educate them on the tools and processes they need to compete in today’s cutthroat environment.

It’s a unique opportunity and one that you shouldn’t overlook simply because you think you don’t have the time or the resources. Great companies invest in their team as much as in their tools and a sales kickoff is a great way to show your reps you’ve got their backs.

Want more insights to help plan your sales kickoff meeting? Watch Jill Konrath’s full interview in the Inside Sales Summit and grab all of her key tips & advice.

WATCH THE FULL INTERVIEW

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