Coaching practices for How to Improve Estimation

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Does this sound like the set of challenges you might be facing?

• My guesses never seem to get any better because I make them, find out the real answer, and then just move on
• I’m late on something, I shrug, update the calendar, and immediately forget I ever thought it’d take half as long
• I build my estimate from my own optimistic story first and only glance at how long these things usually take at the very end as a sanity check
• Every time I plan something I walk through the steps in my head and it feels totally doable in the time I’ve got
• I tend to blurt out one confident-sounding number and act like it’s solid, when honestly I have no business being that sure

Practices that may help

1. Track your estimates and calibrate
   Compare your Fermi estimates to actual figures when you can, and use the gap to improve future estimates.
   Fermi Estimation
2. Log actual vs. estimated time for every task
   Build a personal database of your own estimation errors so you can calibrate future predictions.
   The Planning Fallacy — Why Your Estimates Are Always Wrong
3. Anchor on the base rate before adding inside-view details
   Start your forecast from the class median, then adjust — do not start from your narrative and adjust to the base rate.
   Reference Class Forecasting
4. The Planning Fallacy — Why Your Estimates Are Always Wrong
   The planning fallacy is the well-replicated tendency to underestimate completion times even when you know your past projects ran late. The fix is not to "try harder" — it is to switch from imagining the ideal future scenario to consulting your own base-rate history and similar projects.
5. Reference class forecasting
   Before estimating, look up how long similar past projects actually took — not how they felt.
   The Planning Fallacy — Why Your Estimates Are Always Wrong
6. Estimate in ranges, not point estimates
   Instead of "my estimate is 500," say "I think it is between 200 and 2000."
   Fermi Estimation
7. Sanity-check against known extremes
   Test your estimate against the clearly too-high and too-low bounds to calibrate your range.
   Fermi Estimation
8. Decompose tasks and sum the pieces
   Estimate each sub-task independently, then add them up — the sum is closer to truth than a top-down estimate.
   The Planning Fallacy — Why Your Estimates Are Always Wrong
9. Check units and scales for consistency
   Catch order-of-magnitude errors by ensuring your units are consistent across the estimate.
   Fermi Estimation
10. Practice confidence interval estimation
    Estimate ranges for factual quantities and check how often the true value falls within your range.
    Calibration Training

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