The Work Beneath the Work
clarity before change
For the past few months, I’ve been writing about signals. About drift. About the ways organizations teach their teams what really matters.
If you’ve been reading for a while, you know the patterns I’ve described. A release slips, then another. A quality initiative launches with enthusiasm, and then fades. A new process appears that makes sense on its own, but it makes things feel more cloudy than clear.
No one is incompetent. In fact, most of the people involved are thoughtful and trying hard. That’s what makes it frustrating. Everyone’s making reasonable decisions. They’re just making them inside a system that is reinforcing something unintended.
Over time, reinforcement like that becomes culture. And culture is stubborn.
What I’ve Seen
I’ve watched this play out across decades and companies. Microsoft. Unity. NBCUniversal. Different organizations, different scales, same underlying dynamic.
When performance drifts, leaders act responsibly. They add oversight. They add checkpoints. They add new language to clarify expectations. It feels like progress.
Sometimes it is. More often, the deeper incentives and motivations remain unchanged.
What I’ve come to believe is that most engineering problems that look like execution problems are actually system problems (and yes, often those system problems are driven by people problems). Structure. Incentives. Feedback loops. The signals that tell people what will be rewarded and what will be ignored.
The Questions I’m Hearing Now
Lately, a lot of my conversations have the same flavor.
People don’t ask questions like, “How do we move faster?” anymore.
They’re asking, “Why are we working so hard and not getting the results we want?”, or “Why do the same things keep happening under different names?”
Those are different questions. They require slower thinking and more examination.
And they’ve pushed me toward something practical.
Why Now
About ten months ago, I stepped away from my last full-time role.
That was intentional. After decades inside large organizations, I wanted to give my brain a vacation, and hike the Pacific Crest Trail. When I got back, I wanted space and time to thin. To write, And to think some more. I took a lot of time to reflect on what I had seen repeated across teams and companies over my career.
I did a lot of thinking on trail. As I thought about work and what I do best inside organizations, something became clear.
The part of the work I miss most isn’t status meetings or planning cycles. I miss being in the room when a leader says, “Something isn’t making sense,” and we slow down long enough to understand why.
I miss the conversations where I can look at patterns and help teams find the real problems.
The writing here has helped me articulate some of these ideas. But the ideas aren’t meant to live only on a page. They’re meant to be tested against real constraints, real teams, real decisions.
That’s why now feels right.
A Natural Extension
Over the past few months, I’ve decided to lean into working directly with leaders who are wrestling with questions like these.
I’m not launching a program or a course catalog, or turning this newsletter into an acquisition funnel. I’m creating space for focused work around the issues I’ve been writing about all along.
In practice, that work tends to show up in three ways.
Sometimes it’s one-on-one leadership coaching. Helping a Director, VP or CTO think through tradeoffs under pressure and make decisions they can stand behind.
Sometimes it’s stepping back and examining the system itself. Where does authority actually sit? What gets measured versus what gets rewarded? Where is friction structural rather than personal?
And sometimes it’s working specifically on quality, not as an inspection step at the end, but as something that emerges from how the organization is designed.
Most engagements start the same way: with a conversation. We can look at where delivery friction, quality drift, or decision fatigue is showing up and ask a simple question.
What is the system reinforcing?
Sometimes that conversation clarifies the path forward. Sometimes it leads to deeper work. Either way, the goal is always clarity before change.
If This Feels Familiar
If you’re leading an engineering organization and you recognize yourself in this, it might be worth talking. Or, if you think I could help a leader in your organization, feel free to send them a link to this post.
You can read more about how I’m thinking about this work at angryweasel.com.
Or you can just reply to this email or leave a comment on substack. I read every response.
I’ll keep writing about systems, signals, and drift - and hiking. That part isn’t changing.
This is just an extension of the ideas.