Estimations are a Two-way Street

Mistaking estimations for project planning causes unnecessary stress and friction.

Knowledge you need to estimate is acquired mid-way through the project.

That puts you in a tough spot at the beginning of the project.

What is the root cause?

Without enough context, engineer teams may come to the assumption that the business owners have no prior estimations going in.

This is usually false.

💰 Anyone asking for an estimate starts from a base assumption of “I think it should be this much, how much is it from you?” or “I think it should be this much. I cannot spend more time/money on it.”

Emotional Baggage

Without proper nurture, these negotiations can erupt into “Oh no, that’s too much!”.

I have observed and shadowed meetings where engineers cringed and withdrew physically, thinking they are being reprimanded for giving an estimate when in reality it is the business owner’s original assumption conflicting with the given estimate.

It remains a business problem to be solved, nothing more. But if the emotional link is established to a developer, it can lead to non-cooperation and shifting towards blame very early on in the project.

Planning vs. Estimating

Processes are tricky. Without clear nuanced language, it is easy to misconstrue an estimate for a valid, accurate component on a roadmap or project plan where it immediately ends up being used as a commitment of delivery.

To navigate this well, always ask questions of “How will this estimate be used?”, “Who needs it?”, “What decision will be made with it?”. Get a clear picture. A project plan is not estimation. It’s part of the project and someone is likely paying setup or discovery fees.

A practical approach

Tech leads and engineers, here’s 5 tips to align your roadmap better:

• Give several options, e.g. you can have X in a week, Y in a month

• Your business partner also has an opinion on how much it “should” be - align with that first

• Estimates are always correct estimates, but are not “facts” about the future

• When in doubt, set several, shorter deadlines to get bad news sooner

• Ask questions that expose more constraints. More constraints, easier re-planning.

Timing

The best estimates emerge during daily and weekly re-planning.

Focus on giving pre-work estimates quickly.

Most of your knowledge will emerge on the first half of the project.

The important bits only after launching.

And remember: separate out estimates from a commitment to a project plan. Project plans need care and detail. Estimates are about alignment.

Thank you!

This was our first daily post of Crafting Tech Teams. My name is Denis and I welcome you to a wonderful journey together!