Getting Estimation Wrong Will Hurt! Here’s How to get it Right(er)

Hi there,When I ask people to estimate a simple task on my training course, I get a huge range of answers. Some people think laying a concrete slab will take 2 hours, others think it will take 50. Who is right?

The answer is (of course!) it depends!

Without a good understanding of the task itself, the capabilities of the team, the constraints of the organisation and the tools that are available, either person could be right (and in fact, they are both wrong).

When we spend 10 seconds “estimating” a task without discussion we get it wrong. That hurts, because all the planning in the world can't help if the estimate is wildly off.

When we spend 3 minutes discussing the task with the actual team who will be doing the work, we are much more likely to uncover the assumptions, risks and constraints that are making our estimates bad and destroying our credibility.

Planning Poker can turn estimation from a one-person guess into a structured team conversation.

Here’s how it works:

1. Each person privately chooses a card from the Planning Poker deck — 0, ½, 1, 2, 3, 5, 8, 13, 20, 50, or 100. (The bigger the number, the more uncertainty it reflects).

   
   

2. Everyone reveals their card at the same time — no anchoring, no “senior voice first”.

   
   

3. The team talks about why the estimates differ.

   
   

That third step is the crucial one.The differences in the numbers reveal problems that might otherwise stay hidden:

• A hidden dependency on another team or supplier

• An approval step nobody remembered

• A technical limitation only one engineer knew about

• A risk that was sitting quietly on someone’s mind

  
  
  
  

With that information on the table, the team can now make a new estimate — one based on real, combined experience rather than optimism.

And because the whole team helped create it, they’re far more likely to believe it and achieve it.

Planning Poker is one of the quickest, simplest, highest-impact changes you can make.

And the beauty of it is how small a change it is. Five minutes, a deck of cards, and a short conversation can save you from setting the expectations of your client or stakeholder incorrectly and paying a heavy price later.

You can watch a short video of me explaining it here:

👉Watch the Video here

Here’s to low-stress success,

James

(P.S. You can also use a tool like https://planningpokeronline.com/ if you are virtual or ping me on LinkedIn if you’d like to get some sets of my cards for your team)