What's Keeping You From Being Data-Driven?
The emotional obstacle on the road to data-driven leadership
I'm spending a lot of time on chapter one of the next edition of The Sales Metrics Playbook. A lot more time than when I first published it a few years back.
This first chapter is where I talk about our philosophy around reporting. It's where I lay out why this stuff matters to us as investors, and why this is the playbook (along with our hiring handbook) we use most consistently across our portfolio.
Why am I spending so much time here? Well, before we share our template-by-template approach, I think it's important we frame up the problem. The fact is, most companies (and their people) struggle to become more data-driven. And I want to make sure we unpack why that is. Not only taking inventory of the operational reasons that becoming data-driven is hard, but the emotional ones, too.
See, I think becoming a data-driven leader is also about becoming a more honest leader. And honesty is a scary thing. It's a vulnerable thing. When you share data honestly and openly, you're exposing yourself: to questions, criticism, and scrutiny.
Most people shy away from that kind of exposure when they decide how to share their numbers. They don't outright lie with their data, but too many out there treat it like a defense attorney treats evidence: It's only there to get them out of a jam.
This isn't done out of dishonesty. It's done out of fear. Fear of what the numbers might say about them. Fear of looking exposed in front of the board. Fear of admitting that, despite all their dashboards and reports, they're not entirely sure what they need to do next.
So what do they do? They cherry-pick the flattering stats. They share high-level numbers without context or introspection. They try and guess what their investors want to see instead of using data as a tool to understand the problem. They focus on looking in control instead of being in control.
And look, on some level, I get it. Sharing the raw, unedited data that shows exactly how you're doing (especially in scorekeeping-obsessed disciplines like sales or marketing) feels like you're giving up control.
Because the data doesn't care about your narrative. It doesn't care that you were off your game, that you were distracted helping to lead some other big initiative, that you were short-staffed, or that the leads were soft or your demos were weak or your sales team’s value prop isn’t quite there yet. It simply shows what you accomplished, and what you didn't. That level of transparency can feel exposing. Like you’re pulling the covers off the parts of your business (and the parts of yourself) that you'd rather not look at. The parts that you'd rather show anyone else. The parts that you'd rather not confront until you're good and ready.
The result? You pull back from transparency. You don’t share the whole story. And sure, that keeps you safe, I guess. At least for a while.
But what does that actually get you? Conversations that weave in and out of the numbers without landing on the actual truth. Debates around the definitions of metrics instead of discussions about what's really driving the results. And opportunities for real improvement missed because no one is willing to stare at the uncomfortable numbers and ask:
"Why is that happening? And what are we going to do about it?"
But here's the paradox: The discomfort you feel in that moment? That's also your opportunity.
The best leaders don't hide from their data, and they don't shy away from that discomfort. They use that feeling as their signal that it's time to get curious.
When they see conversion rates dropping or pipeline velocity slowing or a dent in sales team performance, they don't rationalize it away or blame it on macro trends. They double-click. They go looking for the controllable factor causing the weakness, and they get introspective about whether their heroic individual efforts are masking systemic problems. They use the data to find the places where their star sales rep is carrying a broken process, where their MQL counts are just high-volume noise, and where their last-minute saves are covering up what they should have fixed two quarters ago.
Basically, they use their data to get uncomfortable, then curious, then better, faster.
In the next edition of the Sales Metrics Playbook, I’m not just going to give you a bunch of reporting spreadsheets. (Hell, you can have most of our templates right now. They're right there on our website.)
I'm going to show you how to build a reporting rhythm that brings you closer to the truth of what's actually happening - and gives you the confidence to talk about your problems and progress in a more open, honest, transparent way. In a way that helps you learn, act, improve, and win.
Because becoming a data-driven leader isn't about being a math genius. It’s not about being cold, mechanical, or robotic. And it's not about turning over the unavoidably-instinctual parts of running a business to a spreadsheet or an AI agent.
It's about being honest enough to see and talk about what's really going on.
And brave enough to do something about it.
If you’d like a copy of the next edition of the Sales Metrics Playbook when it comes out later this month, you can sign up at this link (and grab the last edition of the playbook and our reporting templates while you're at it).
And if you’d like to read more of my stuff on what it takes to become a data-driven leader, this is the best place for that.