How Reasonable Decisions Create Dysfunction
I’ve lost count of how many times I’ve heard that leadership doesn’t understand product management.
They don’t empower teams. They don’t create the right conditions. They say they want outcomes but keep asking for roadmaps, delivery dates, and commitments.
I’ve said it myself. Many times.
We’ve been having this conversation for years. We’ve read the books, implemented the frameworks, trained teams, and hired experienced product leaders. So why do we keep ending up in the same place?
Maybe we haven’t explained it well enough. Maybe the people making the decisions aren’t listening. Or maybe understanding product management isn’t really the problem.
One thing I’ve noticed over the years is how clearly people can describe what everyone else needs to do differently.
Executives want teams to take more ownership. Teams want the authority to make decisions. Business leaders want technology to move faster. Product and technology teams want priorities that don’t change every week.
And from where each of them sits, their concerns often make perfect sense.
The trouble is, they’re all looking at different parts of the same problem.
Consider a business leader with a major customer at risk of leaving. They ask the product team to prioritize something that might save the account. It’s a reasonable request.
A few weeks later, another executive needs something delivered to meet a regulatory deadline. That matters too.
Then sales needs a commitment to close a significant deal.
Each request makes sense. And each gets added to the team’s priorities without anything else coming off the list.
A few months later, leadership is frustrated that the team keeps missing deadlines. The team is frustrated that priorities never stop changing.
Nobody necessarily made a bad decision. But together, they’ve created a situation where the team can’t possibly deliver on everyone’s expectations.
I find these situations fascinating because there’s rarely a single moment where someone decides to create a dysfunctional organization.
It’s usually a series of reasonable decisions, made by people responding to the pressures and expectations around them.
And over time, those decisions become the way things work.
Often, the behaviors contributing to these problems are the same ones that have helped us succeed.
We ask product managers to challenge assumptions, but they’ve spent years being rewarded for delivering what stakeholders ask for.
We ask teams to experiment, but still expect them to deliver everything they committed to at the beginning of the year.
We ask leaders to empower teams, but they’ve built successful careers by making decisions, managing risk, and being accountable for results.
It’s easy to talk about empowerment, accountability, trust, or psychological safety. The real test is what happens when someone challenges a decision you’ve already made, recommends stopping an initiative you’ve championed, or makes a decision you disagree with.
And people pay attention to what happens next.
You can tell people it’s safe to question decisions and challenge assumptions, but if nothing ever changes as a result, eventually they’ll stop bothering.
Trust me.
We spend a lot of time talking about the conditions organizations need to create for people to work differently.
But those conditions aren’t created in isolation. They’re shaped by the decisions we make, the behaviors we reward, and the ways we respond to one another.
Before asking why people won’t change, we might want to examine what we’ve taught them about how to succeed.
Sound familiar? What’s worked for you? Join the conversation on Substack.
This article was originally published on The Roadmap to Nowhere, our Substack.