Sales Success Is a Bracket, Not a Bet

By: Lief Larson

Over the past week, my NCAA March Madness bracket has ranked as high as 7th place in the nation — out of millions of entries. And I’m still holding strong (as of March 26th ranked 222).

Before you chalk that up to luck or a one-off fluke, let me stop you there: I’ve been filling out brackets for years. Each March, I’ve taken mental notes, adjusted my approach, tested new theories, and reflected on what worked — and what didn’t.

This year that all came together. And it made me realize something:

Sales works the exact same way.

If you're approaching sales like a bet, throwing a pitch, crossing your fingers, and hoping it lands, you’re playing the wrong game. Sales success is more like filling out a March Madness bracket: it’s strategic, iterative, full of risk-versus-reward calculations, and impossible to get perfect. But when you take the long view and learn year over year, you dramatically improve your odds of winning big.

Here are the five biggest sales lessons I’ve learned... not from a sales conference, but from March Madness.

1. The Power of Iteration

In my early bracket years, I overvalued top seeds, fell for hype stories, and underestimated underdogs. Sound familiar?

It’s the same with sales: your first deal, your first script, your first follow-up cadence — none of it will be perfect. But if you treat each experience like data, you build a better strategy every time. Great salespeople aren’t born brilliant; they just never stop refining.  Why?  Because they have DRIVE!

2. Strategic Risk-Taking Wins

No one ever ranked in the top 10 nationally by picking all favorites. You’ve got to choose a few bold upsets — but you better pick the right ones.

Sales is the same. Safe plays (like leaning on warm leads or legacy customers) will keep you in the game, but real growth comes from bold moves: entering a new vertical, testing a radical offer, or chasing that long-shot enterprise deal. The trick? Be smart about where you take those risks.

3. Use Data — But Don’t Drown in It

Yes, I check KenPom. I read team matchups. But I also trust my gut.

Sales leaders love data dashboards. But too much data can lead to analysis paralysis. Your CRM might say one thing, but your intuition about a prospect, based on body language, tone, or nuance, might say another. The magic happens when data informs your decisions but doesn’t override your human instincts.

4. Confidence Builds Momentum

When your bracket starts off strong, everything feels easier. You trust your instincts more, second-guess less, and ride the wave.

Sales is no different. Early-quarter wins breed confidence, and confidence breeds performance. It’s a psychological edge. That’s why your sales motion should front-load achievable wins: focus your best reps on early closable deals and let that success echo through the rest of the quarter.

5. Prepare for Chaos — and Stay in the Game

This year’s bracket? It’s been chaos. Upsets everywhere. Big programs falling early. You can’t plan for every curveball.

In sales, your biggest client might go dark. A competitor might drop prices out of nowhere. The decision-maker might quit the day before you close. These things will happen. But if you’ve done the work — if your strategy is sound — you can pivot and recover.

Great salespeople don’t crumble in chaos. They adapt.  Why?  Because they have DRIVE!

Final Buzzer: Sales Is a Season, Not a Shot

Just like in the tournament, you’re not going to win every sales deal. Some will get away. Some will blindside you. But the people who rise to the top year after year? They’re the ones who treat every quarter like a bracket — full of choices, learnings, and opportunities to play smarter next time.

So here’s my question for you:
 What did you learn from your last “bracket”? And what will you do differently in the next round?

Because in both sales and March Madness, the difference between average and elite is rarely a single move — it’s dozens of small decisions, made better each year.