A Programmer's Dream

On the Verge of OKRs, and the Work That Almost Was

Posted by Stephen Wrighton on 14 Apr 2025

The end of a role brings with it a certain stillness. You start to see the shape of things more clearly once you’re no longer inside them. What worked. What didn’t. What almost happened.

OKRs fall into that last category.

We were circling them, toward the end. Not formally. Not with fanfare. But with curiosity. The product had matured. The team had grown. And the old rhythms, standups, retros, feature sprints, didnt’ feel like they were enough anymore. We were working hard, but the direction was beginning to blur.

OKRs seemed like a way to sharpen it.

I didn’t get far enough to implement them. I left that team, and whatever happens next will happen elsewhere. But I carry the idea with me, because the thinking it required still feels useful, even now.

What We Needed

Ours was a team that executed well, but not always in concert. Velocity wasn’t the problem. Coordination was. The sort of alignment that doesn’t show up in Jira, but you feel it when priorities drift, or when two teams are solving different problems with the same code.

That’s what drew me to OKRs. They promised focus, but without micromanagement. Clarity, but not at the cost of creativity. A way to move forward together, without needing to overdefine every step.

First Attempts

I kept the early drafts to myself. A scratchpad of sorts. Just to see if the framework fit our context.

One for the dev side:

And one for the business:

I never made them official. But they shifted how I approached planning. They reframed what I asked in one-on-ones. They gave shape to my instincts.

What They Taught Me, Even Unused

OKRs invite the kind of questions that are easy to avoid when you’re busy. What are we really trying to change? What does success look like? Is this sprint pushing us closer to anything that matters?

They also expose misalignment, but in a way that feels constructive. When one lead frames a key result around uptime and another suggests user satisfaction, you’re not in conflict. You’re having the conversation you needed to have anyway.

And even when they stay in draft form, OKRs help you think about outcomes rather than output. They change the orientation of the work, just slightly. But enough to matter.

What Might Have Been Next

Had I stayed, I think we would have piloted OKRs with two teams: development and customer success. Just a few objectives, light process, regular check-ins. Nothing that added friction. Everything designed to foster clarity.

I would be careful not to treat them like tasks. No grading. No bonuses tied to metrics. Just a rhythm to help teams talk about what they were building, and why it mattered.

We weren’t there yet. But we were close.

Now, Looking Ahead

I haven’t found my next role yet. Being in that liminal space between what’s finished and what’s next has a strange kind of quiet to it. But the lessons stay with me. And when I land somewhere new, I know I’ll revisit those early OKR drafts. Not because they were perfect. But because they came from a place of wanting to do the work with more intention.

To build things that don’t just ship, but shift something. For the users. For the team. For the business trying to steer toward clarity in a world that doesn’t always offer it freely.

Tweet me @kidananubix if you like this post.

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