Replay: The Sales Kickoff is Just the Beginning

Forget the pre-game speech and focus on filling the gaps

Author’s Note: I wrote this article after a sales kickoff planning session with a portfolio company a few years ago. With most SKOs scheduled for Q1, now is the perfect time to do the reflection and planning that every great kickoff is built around. It’s all about deciding where to focus - and creating clarity around what your business needs most. If you’re thinking about how to set your team up for a great 2025, I think you’ll find it helpful.

The Pre-Game Speech

This past weekend, TV cameras caught the Dallas Cowboys’ quarterback, Dak Prescott, giving an impassioned pre-game speech to his teammates. Projected on the Dallas stadium jumbotron for all to see, Dak does everything you’re supposed to do to get people excited. He gathers his fellow players around him. He gets emotive. He addresses people 1:1. He villainizes the opposition and creates a feeling of “us against them.”

Dak’s team responds. A lot of very muscular men in pads, helmets, and and crisp white uniforms all start yelling. I can’t describe exactly how, but the team looks prepared for violence. The Cowboys are pumped.

But then the game starts. And it’s a disaster.

The Cowboys can’t get anything right. Scoring just 7 points in the first 3 quarters, Dallas falls behind early to the 49ers, collecting 14 penalties (an average NFL team is penalized about only 6 times per game) and punctuating an embarrassing loss when Prescott fails to spike the ball in time to stop the clock in the game’s closing seconds. Not exactly the performance Dallas was hoping for.

What is Your Sales Kickoff For?

A big pre-game speech followed by an underwhelming performance. Too many Chief Revenue Officers can relate to this disappointing sequence of events. Too many start their year with a “big bang” sales kickoff — and then act perplexed when the results they hope for don’t pan out. We had a great kickoff. It felt like this year would be different. Why have we hit a wall? Why aren’t we winning?

This epiphany is frustrating to say the least. You sink a lot into your sales kickoff. What’s the ROI on all that time and money? Too often, the answer is “Not much.” So how do you fix it?

Let’s get back to basics for a second: Why have a sales kickoff in the first place? Why are we even doing this? What is this for?

A sales kickoff serves two purposes. First, it resets and refocuses the sales team on what matters most. Second, it creates energy, commitment, and momentum around “what it will take” for the team to succeed. But if that momentum dies out just a few months later, something is missing. Something important.

What’s missing? The answer is often “reinforcement.” Your sales kickoff needs to be part of an intentional plan to change the business for the better. If you’re smart, that broader plan will have three parts to it — a before, during, and after:

1. An honest, data-driven assessment of what’s working and what’s not for your team

2. A focused, simple plan for what needs to change to close your most important gaps — and how you’ll use your kickoff to close them

3. Consistent, shared reinforcement to make the changes stick

Here’s my point. When CROs treat their sales kickoffs as “just an event,” they’re missing something. The best sales kickoffs are more like a crescendo — a focal, moving, carefully-orchestrated experience built within a broader symphony.

Ready to make some music? Here’s where to start.

Begin With a Diagnosis

The number of sales analytics tools and KPIs has exploded in recent years. It’s now possible (with a little setup and cash) to track everything that goes on, minute-by-minute, within your sales team. CRM, call recording, automatic cadencing, granular analytics, pricing calculators… our sales tech stacks get more powerful and more complicated every year. Unfortunately, all this technology doesn’t always create the clarity we hope for. I’m still surprised when I ask CROs to diagnose the #1 problem they’re trying to fix with their sales team. Most don’t have a clear answer.

If you run a sales team, there are really only two questions that matter.*

1. Are we giving ourselves a chance to hit the quarter?

2. Are we setting ourselves up for next quarter (and beyond)?

Question 1 is about managing and converting the deals in your pipeline. It’s about making the most of the precious opportunities to help your customers improve their business. It’s about winning what you can win. Companies with “question 1 problems” get at-bats, but have trouble getting on base. These teams need to work on qualifying, providing value at every stage of the deal, and landing the message about “how we’re different.” You’re getting plenty of nibbles. Now it’s about getting the fish in the boat.

Question 2 is about getting at-bats before you can get on-base. It’s about creating the leads you need to support your future growth. Some VC investors use a metric called the “Lead Velocity Rate” to think about this question. Sounds complicated. It’s not. The lead velocity rate is simply the rate of change — positive or negative — in the number you’re creating every month. That’s it. A positive number means you’re building momentum + creating more leads each month vs. the month before. In other words, you’re getting better at getting in front of prospective customers. You’re setting more meetings. A negative number means your number of leads is going down. A negative number (or a number that jumps inconsistently between negative and positive) means you have a “question 2” problem. Something needs fixing in the lead machine.

When used appropriately, these two questions serve as your “improvement radar.” The best CROs are constantly scanning their sales machine using these two questions and deciding which type of problem — question 1 or question 2 — most needs solving. A good improvement radar is critical. If you misdiagnose, you’ll be treating the wrong illness. The cure you actually need will elude you. That ain’t good.

So — which of these two is your biggest problem? Is it about winning what you can win? Or creating more leads? Do you know? If not, I don’t have to tell you where to start.

Once you decide which question matters more, then it’s time to think about how to use your sales kickoff to fill the gap. Are you giving your reps a tool or skill to help convert deals you’re already in? Or are you helping them with prospecting techniques? Again, I can’t over-emphasize the importance of picking just a single question to focus on. As the saying goes, “the man who chases two rabbits catches neither.” Too many CROs are chasing too many rabbits.

Adopt a “Make it Stick” Mindset

Good sales kickoffs set the tone and create a standard. They help you raise the bar on how your team does its job. The best kickoffs focus on teaching their teams something new — something that’s going to make them better at winning what they can win or just getting in front of customers.

But you have to follow-up. You have to recognize the harm in teaching people something new and then letting that “new thing” slide. Every time you see something that isn’t up to standard and don’t say something, you just set a new standard. The magic isn’t in what you teach — it’s in what you reinforce everyday.

Every sales kickoff needs a plan for “what comes next”: the make-it-stick short list of new things the team is committed to reinforcing. What’s getting in your way as a sales team? What 2–3 behavior changes will help clear those obstacles? What do you want people to do differently? How are you going to remind people to “do this and not that?” Answer those questions in advance of your kickoff and your chances of success go way up.

The best reinforcement plans aren’t just about what you broadcast. They’re also about adopting a new mindset. They’re about getting you and your management team to accept another position beyond their day jobs: That of the Chief Reminding Officer. If you want to learn more about how to become a Chief Reminding Officer and how to make things stick, I’ve done a lot of writing on the topic. But the advice is pretty simple. First, decide what gaps need closing. Then, commit to reinforcing the changes that will help close the gaps. Finally, accept this simple fact: People need reminding. A LOT of reminding.

And all that reminding? That’s your job.

Final Thoughts

Your sales kickoff is your best chance to start the year with a bang. It’s your chance to orient your team to what matters most and to clarify and teach your team “what it will take” to hit your goals. But as I’ve written before, training that isn’t reinforced isn’t training. It’s intellectual tourism.

Now you’ve got a choice. Are you going to teach your team something useful and then make it stick? Or blow two whole days and a bunch of cash on a sales-themed TED talk?

Here’s my advice: Skip the big speech. Or at least acknowledge it’s the least important part of this whole thing. As Dan Coyle wrote in The Culture Code, good leadership is “less about being inspiring and more about being consistent.”

Focus instead on what’s missing: the gap you want to close, the new, reinforce-able behaviors that will get you there, and your plan to follow up to make sure it all actually happens.

And while you’re at it, don’t be afraid to repeat yourself.

All great leaders do.

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* My “two questions” stuff in this article is inspired by Dave Kellogg’s fantastic blog post “The Top Two High-Level Questions About Sales (And Associated Metrics).” My two questions are slightly different than Dave’s. But if you’re going to listen to one of us, I’d listen to him.