Will Your 2027 Sales Kickoff Equip People for the Conversations Ahead?

I’m not an astronaut, a mountain climber, or an ultra-marathon runner.

Neither are most of your sales professionals.

Over decades of attending annual sales kickoffs, I’ve listened to remarkable people describe extraordinary accomplishments. I was often impressed that our company could attract them. I enjoyed their stories. Sometimes I left personally challenged to be more disciplined, more courageous, or more persistent.

But I also remember wondering how to connect their experience with the customer conversations waiting for me—and the quota I needed to achieve in Q1.

“Go big.” “Don’t give up.” “Reach for the stars.”

I appreciated the encouragement. I was already motivated to succeed.

What I needed was help figuring out how.

What happens after the applause?

If you’re planning a sales kickoff for early 2027, you’re making decisions about what deserves your team’s attention.

Your executives have a vision to communicate. Sales leaders have objectives to establish. Product and marketing teams have priorities to explain. There are achievements to recognize and regional plans to discuss.

Those things belong at a kickoff.

But consider the experience from the salesperson’s seat. By the end of the meeting, they may know much more about what the company expects them to accomplish.

Will they be better equipped to accomplish it?

Picture that person’s first customer meeting after the event. The customer understands the presentation but sees no reason to change. A demonstration answers every technical question while missing the business concern beneath them. An enthusiastic executive sponsor struggles to explain the value to colleagues who weren’t in the room.

What from your kickoff will help your salesperson in those moments?

A remarkable story still needs a bridge

An extraordinary personal achievement can carry meaning far beyond the circumstances in which it happened. A speaker doesn’t need a sales background to offer something valuable to a sales audience.

But the connection deserves examination.

Before choosing a speaker, I would ask:

What will our people recognize from their own work—and what could they approach differently because of this session?

A standing ovation tells you something about the experience in the room. It doesn’t yet tell you what will happen when someone returns to a difficult account.

Ask a prospective speaker how they will discover what your team is facing. Ask how their ideas apply when a customer is interested but hesitant, when a competitor has an established relationship, or when the greatest obstacle is simply staying with the familiar.

Listen for whether they become curious about your people before explaining their presentation.

That conversation may tell you more than the highlight reel.

The gap may not be motivation

For most of my 45-year corporate career, I carried a quota and worked with clients, prospects, and business partners. During my years as IBM’s Chief Storyteller, I had opportunities to explore, test, and refine different approaches to those conversations.

One lesson kept returning: people can understand an idea clearly without believing it enough to act.

When that happens, our instinct is often to explain more. Add another feature. Offer another slide. Repeat the benefits with greater enthusiasm.

Sometimes more information helps. Sometimes we haven’t yet discovered what the customer needs to believe—or what experience makes that belief difficult.

A correct answer can still miss the reason someone asked the question.

Helping salespeople notice that difference gives them something they can use. They can become more curious about the customer’s situation, connect a possibility to something that matters, offer evidence that addresses a real concern, and leave room for the customer to express the meaning in their own words.

That is the work I explore in The Journey of Belief.

Give them something they can carry into Q1 and 2027

As you build your kickoff agenda, leave room for inspiration. Then look closely at the conversations your people will need to have after the event.

Where do those conversations stall? What do customers understand but hesitate to trust? What assumptions might your team need to question?

Let those answers help you choose the speaker.

My hope for a sales kickoff is that someone leaves with a particular customer in mind and thinks, “I have a different question to ask when we meet again.”

That could be the beginning of a more useful conversation.

If that is the kind of experience you want for your 2027 kickoff, I’d welcome a conversation about your audience.

Explore my speaking themes and download the speaking package.

Bring the challenge your team is facing. That’s where we should begin.