Bad estimates are a missed opportunity 😱

Happy Friday!

My beekeeping season has ended prematurely. I could write a lot about that story, but it'll have to wait. The bottom line is that this year I moved my hives to a new location, and that new environment brought some new challenges I wasn't expecting, and my hives all died this past month. If you aren't a beekeeper, you probably won't be able to guess what it was, and if you are and would like to guess, let me know.

Here's the lesson, though: What worked in one environment won't necessarily work in another.

Moving on.

I have a confession. I have never really minded estimation. To me, it was an imperfect way to answer an important question, and I'm alright with taking imperfect steps forward. Even as an engineer, estimation was a chore but hardly the most objectionable one.

I get the deep frustration that engineers up through leadership feel. Estimation feels like punishment. The act of it is painful, and the reward is usually punishment for poor estimates.

But I think a missed opportunity is hiding in there.

The overwhelming mode folks operate in is avoiding problems and issues. In estimation, this leads to padding estimates, hedging on deadlines, and other tactics to avoid the problem of being late. It also creates pressure to "estimate better" with no real guidance on how to do it.

This belief that we have to avoid problems is the key thing that needs to change. When you operate this way, problems that actually exist are buried under the veneer of problem-free work. We can acknowledge issues, but always in a positive light to make them seem minor.

Don't believe me? When was the last time anyone in your company was honest about what your estimates actually said about when something will get done?

I say stop the theater and just faithfully represent the data. Tell your boss the 6-month project is estimated to take 3 years. This is the opportunity.

You see, when we avoid, bury, and downplay problems, we also can't take advantage of the success. We've written a story where so little goes wrong you can't prove you did a good job because nothing tested you. No challenges to overcome, so the reality of what it took stays invisible.

You can't prove you can handle tough challenges if you never let people know they exist!

Estimation is a missed opportunity. Own the estimates, be honest about them, and solve the problem. It lets you show everyone what you're made of instead of hiding it. If the work is the same, wouldn't you like to be seen as the one who overcame the challenges that came with too much scope, tight deadlines, and demanding stakeholders? Why are you hiding this?

One more thing for your consideration. As normalized as it is, we all know when folks are bullshitting. Everyone knows when they hear those things, they can't really trust what they hear and that there is a whole different story underneath. Know what happens when you stop the theater? Relief and trust. Peers will relax as they can just listen for a change without the extra effort of figuring out what the truth is. Trust builds because their lie detector stops going off and they know they'll get a straight answer out of you.

Being honest with upsetting news builds respect and trust while also giving you the opportunity to show what you're made of when you solve these thorny problems. Don't waste it.

So, here's my question: How did this land with you? Do you see an opportunity to show what you're capable of by creating a little more transparency? Reply back and let me know.

Sincerely,

Ryan

PS: I want to hear about how Code Reviews are changing for you! I personally think they should be eliminated. Email me or schedule a call. I want to know what you're experiencing.