Over the years, I’ve seen many engineering and adjacent teams recoil at the notion of making estimates. The thinking usually goes something like this:

  1. Estimation is one more task. I don’t want for those.
  2. You’re asking me to predict the future. That’s silly.
  3. What’s more, you’re just going to hold me to whatever I say.
  4. Therefore, I’m going to heavily pad my estimates. And now, you’re not even getting accurate estimates, making this an even more pointless exercise. See? This is silly.

Just about all of these thoughts (and the behaviors that follow) are symptomatic of one fundamental truth: trust in the estimation process needs to flow both ways, and it’s currently not.

Let’s flip the script. How often do you hear these conversations happen?

  1. I realize that we’re adding a bit of overhead to our process. The idea is that with better capacity planning, we can better set priorities and proceed at a reasonable pace, without burning out over it.
  2. No one can predict everything. But with practice, we can make better predictions over time.
  3. When we make a commitment as a team, we’re accountable as a team. It’s not great if we miss, sure, but it’s not the end of the world, either. We’ll talk about how to improve, dust ourselves off, and move on.

Comparatively, probably not often enough.

Teams that don’t feel safe aren’t equipped to provide good estimates, because the process is being framed as adversarial rather than collaborative. Good estimates can only come from teams that have fully bought into the process. And that buy-in just isn’t going to happen without knowing that those estimates won’t be weaponized against them.