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The leaders I work with are smart, experienced, and genuinely committed to their teams. They have good products and real services. So why don’t they all make it?
So many brilliant startups fail. Founders quit, leaders leave.
It’s not because they stopped caring. They’re putting in enormous effort, trying to solve the problem in front of them.
But I’m noticing how often that problem is the wrong one.
I was reminded of this reading a recent LinkedIn post from Mark Manson. He was writing about how health has turned into something we optimize. We track our steps, watch our sleep, count our macros, look for the next breakthrough that might help us live longer and feel better. His point was that a lot of those things matter, but they can pull attention away from something more basic. One of the strongest predictors of how long and how well we live isn’t in a supplement bottle or a fitness tracker. It’s the quality of our relationships.
We focus on what’s easiest to measure rather than what matters most.
The same pattern runs through teams all the time.
Most leaders are trained to look for measurable problems. Revenue, productivity, utilization, turnover, project completion, customer satisfaction. These are real signals and they deserve attention. The trouble is they tell us what’s happening, not why. A drop in engagement scores might not be an engagement problem, it might be a trust problem. A retention issue might be a leadership problem. A productivity dip might have nothing to do with effort and everything to do with people not being clear on what matters most this week.
We gravitate toward the symptom because the symptom is visible. It shows up on a dashboard, lands in a report, gets raised in a review. Once it has a number attached, it feels concrete. We can discuss it, track it, build a plan around it. The cause underneath is much harder to see.
I’ve watched leaders invest in new tools when their people were already drowning in tools. The problem was never technology. Nobody was aligned on what mattered most. I’ve seen leaders worry about attracting talent while avoiding the harder conversation about why their strong performers were leaving. I’ve seen engagement surveys run with real rigor while the same people stayed silent in the meetings that happened every week.
In each case the visible problem got the attention because it could be measured, and the real constraint sat underneath it, producing the same symptoms over and over.
What makes this hard is that working on the symptom feels productive. It gives you something to do. You can launch an initiative, set a metric, assign an owner. It creates a sense of momentum. But momentum and progress aren’t the same thing. You can spend months on a symptom and find that very little has changed. The work wasn’t poor. The diagnosis was.
I worked with a really interesting startup that had everything you’d want on paper. The founders & senior team had the credentials. The product was awesome and after closing a fundraising round, they had real momentum.
And they were stuck.
Not for lack of talent or effort. Every person was working hard. But they were working hard on different things. Ask three people what mattered most that quarter and you’d get three answers. Teams were more worried about looking good than working together.
Leadership kept reaching for measurable fixes. Each one looked reasonable on its own. But none of them touched the actual constraint, which was that the team had never aligned on what they were building toward, and nobody felt safe enough to say the strategy was unclear.
I don’t think this is a fault in any individual leader. It’s how we were trained. Business school rewards analysis because they know organizations reward measurable outcomes. Think about it, many careers get built by spotting a problem, implementing a fix, and showing a result. Those are valuable skills. The risk shows up when we start treating the measurable things as the only things that are real.
Trust is real. Clarity is real. The energy people bring into a room is real. Whether they feel safe enough to disagree, admit a mistake, or tell you the truth is real.
None of it packages neatly onto a slide, but it shapes almost every outcome leaders actually care about. Trust shows up in who stays. Clarity shows up in how well things get done. Safety shows up in whether anyone says the thing that needs saying. A shared sense of purpose shows up in how much people are willing to give. Seeing these things takes observation, curiosity, and a few uncomfortable conversations. It asks leaders to look beneath the numbers instead of stopping at them.
Effort and analysis carry you a long way, not all the way. Some of what separates a team that thrives from one that stalls is timing and circumstance and a fair amount of luck. Part of why we reach so fast for the measurable thing is that fixing it feels like control, and control is reassuring. The parts you can’t engineer are harder. That doesn’t make them any less real.
This isn't only a leadership pattern. I catch myself doing it in my personal life. I'll reorganize my whole calendar when the real problem is I haven't said no to something. The measurable fix is right there, easy to reach for, and reaching for it lets me skip the harder thing underneath.
Here’s something to think about: If trust, clarity, and the sense of safety on your team all doubled tomorrow, what would look different six months from now?
The numbers matter. Keep measuring what you can measure. But the part of leadership that moves things most often starts where the measuring stops.

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