How to Plan an Awesome Annual Kick-Off Meeting

It’s getting to be that time of year again. You know, the one where sales and sales enablement leaders—who strategically use resources to improve a team’s productivity and increase revenue—are planning annual kick-off meetings. And it’s no small task. In addition to the logistics of selecting a destination, blocking rooms and finding meeting space, there’s always an unspoken pressure to top last year. How can we make it bigger and better? Which guest speakers will truly inspire? What awards will be valuable to our top performers?

We get it. We’ve actually attended many of these ourselves. Overall, it seems that trying to understand the customers’ perspective is the best place to start. Here are four customer-centric ideas to make this year’s kick-off the best one yet.

1. Rethink Mainstreams and Extremes

At a kick-off meeting, time is reserved to review which products and services can increase revenue, and thereby solidify partnerships with top accounts. Sure this is important work, but it can quickly become insular—me, me, we. So how can you reframe? Reconsider your strategic accounts in terms of extremes and mainstreams. Your mainstream customers could be larger accounts with larger purchases. But you should also consider including some of your extreme customers: Which customers are doing the most interesting things with your products and services? Invite them to join in a customer panel to discuss strategic accounts.

2. Let Top Performers Shine

Sales people work hard—and your best sales people can become easily isolated in the field. For many reasons, it’s crucial to recognize your top performers in front of their peers. One way is to invite the customers of your top performers to speak about them. You could also give them an award, a way to publicly thank and instill them as role models for the rest of the team.

3. Problem-Solve with Solved Problems

Clients often voice a desire to inspire. Customers want to work with motivated sales professionals who can help them think “outside the box.” This is where analogs come in. To come up with a great analog, reflect on a specific issue your business is trying to overcome. Then, consider completely different contexts where people have cracked that same problem.

Here’s an example:

One team we worked with didn’t think it connected enough with its customers. The team felt too much behind the scenes, which resulted in a loss of motivation. Being in New Orleans, the team meeting was brought to one of Emeril Lagasse’s famous restaurants. Much like the team, the chefs and sous chefs were working behind the scenes, yet their work is what customers ultimately enjoyed.

4. Skill-building

Our final tip relates to building the skill set of your sales force. Sales people are always looking for ways to hone their skills. Given our theme of customer-centricity, we’ll share a favorite exercise of ours.

We like to send sales people where they feel most comfortable—out in the field! Research retail centers in the location of your kick-off. When looking for these stores, try to locate pairs of low- and high-end centers within a common vertical. For instance, a Chevy and a Tesla dealership would offer this balance for cars. The objective is to take notes on which strategies both increase and decrease customer engagement. We guarantee that teams will come back inspired by the amazing (and awful) things they experienced. Additionally, fresh insights will benefit their own customer relationships.

We encourage you to shake up your next kick-off and try these ideas to keep your customers right where they belong—at the center of everything.

Ashley Welch and Justin Jones co-founded Somersault Innovation, a design-thinking consulting firm that provides a unique approach to sales development. They are the authors of Naked Sales: How Design Thinking Reveals Customer Motives and Drives Revenue. For more information, please visit