I don't think we have five years before agentic coding becomes the mainstream context in which professional software development happens. I think we're talking about two or three. Possibly less.
If that sounds alarmist, I'd ask you to consider how it would have sounded in 1983 to tell a mainframe developer they had about eight years before their core expertise became a niche. Or in 1994 to tell a desktop developer they had about four years. Both of those statements would have seemed extreme at the time. Both were accurate.
When leaders ask teams to "go faster," they're usually not asking for better outcomes. They're asking for more output. More stories delivered. More code shipped. More visible progress.
Implicit in that ask is a pretty big assumption: that we already know exactly what needs to be built, that the plan is correct, and that execution is the only thing standing between us and success.
So "go faster" becomes shorthand for "execute the plan harder."
That's where things start to go wrong.
The problem with "fail fast" is that it too often becomes "move fast." Failure is hidden or spun as success, speed is rewarded, and the learning part gets lost entirely. At its worst, "fail fast" is an excuse to rush into the next thing without pausing to understand what just happened.
What I want to promote instead is Observe Often. The shift in language is intentional—when we say “observe,” we bring focus back to what matters: seeing, measuring, and learning from what we do. And “often” reinforces frequency over haste. It’s not about reckless speed; it’s about small, deliberate moves and frequent feedback loops.
When I say I’m joining Test Double as their new VP of Delivery, I’m not just making a career move—I’m making an alignment move. This is a company that already values the things I value. They’ve built a strong culture, a strong team, and a strong set of practices. I’m not joining to overhaul anything. I’m joining to help make something great even better.
Today, I’m excited to announce the beta launch of Collaboration Contracts, a lightweight app designed to help teams—especially distributed ones—quickly define and manage their roles in decisions. Whether you're using it to bring clarity to one-off decisions or baking it into how your team operates every day, the app is built to support alignment, accountability, and smoother collaboration.
Stewards focus on creating value. When the market shifts, they figure out how to keep contributing. They are perpetually employable. Strip miners focus on extracting value. When the market tightens, the seam runs out and the extraction ends. They are no longer employable. And, frankly, should have never been.
In the past few years, we at OnBelay have had the honor of working with companies who are looking to improve their engineering culture.
One key tool we use today is the Experiment Canvas. My partner, Diane Zajac, and I co-developed the canvas. It is based heavily on our experience with A3s. It is still a work in progress, but I want to share with you where we are to date. Please feel free to use it and give us feedback.
Dinner together as a family was a key part of how we raised our children and how we kept our family so tightly knit for years. No matter what you had to accomplish in a given day, you did your damnedest not to miss dinner. I often left the office, came home to share a meal, and headed back into the office.
There were no boundaries at the dinner table. There didn't need to be. We talked about everything.
A hat tip to Tyler Jennings for the title of this post. He and I were in a meeting some time ago, along with a lot of other interesting people from Groupon Engineering. We were sharing our thoughts on team leadership and the role of managers. There was talk about how decisions need to be made close to the work and how managers need to not just seek advice, but actually provide others the opportunity to make decisions.
I was recently contacted by a colleague looking for a bit of advice.
C: "We are thinking about merging two teams together and we're not sure how to message the change."
D: "What do you think will be your biggest challenges?"
C: "Well, for one, we're not sure how the funnel flow team will respond to being folded into the purchase page team."
Some time in mid-January, I was thinking about various organizational patterns and how companies run. I was thinking, in particular, about the idea of a "leadership team". I tweeted that leadership teams may be an indication of dysfunction.
I got a few different responses, all of which amounted to "please say more about this."
I think I saw Daniel Pink's TED Talk on "The Puzzle of Motivation" for the first time in 2011. I'd been reading some about leadership, management, and organizational psychology up to that point, but Pink's talk and his distillation of these complex concepts into a simple framework (Autonomy, Connection, and Excellence) inspired me to read more on the topics. Over the course of the next couple of years, I consumed a decent amount of material. You can view my Goodreads account to see what books I was reading. Unfortunately, there is no easy way to share all of the scientific articles and other sources I also consumed.
It is not only the things we reward that shape culture, but the things we allow. Perhaps the easiest way to shape a culture is to do nothing at all.
When a rockstar employee yells at, denigrates, or refuses to help teammates and you let it slide because the rockstar is valuable, you are shaping a culture. When a teammate tells a racist or sexist joke and you say nothing because nobody present is a member of the target group, you are shaping a culture. When an executive abuses power, when a coworker engages in gossip, when a team cuts corners to make deadlines and you decide it isn't your problem, you are shaping a culture.
We have an application internal to Groupon called the "Love Monster". It was written, in large part by Devin Breen. There are other contributors, but Devin is the one that made it happen. He didn't do it because it was on a roadmap or because it's part of our quarterly objectives. He did it because he and others wanted something like this to exist. So he willed it into existence.
In 5 Tips for Building Trust | Globoforce Blog, Darcy Jacobsen suggests the following steps for building trust within your organization:
I've worked for essentially two types of companies - those that have clearly defined job ladders and those that don't.
A clearly defined job ladder provides people a clear picture of what they need to accomplish and what skills they need to display in order to move into a new role. A clearly defined job ladder provides a baseline for performance appraisals. Everyone in the organization knows what is expected of people in each role. Are you displaying these attributes with a level of proficiency requisite for the role, or are you not? Job ladders make the expectations of progress and the opportunity for advancement clear and consistent.
