When projects don’t stack: the fine art of understanding mistakes

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By Mark Di Somma

When things go pear shaped

When a project doesn’t meet expectations, I’m fascinated by what gets asked, who does the asking and what, if anything, emerges as the key learning. My view is that we should treat projects that don’t go to plan not so much as wreckages but rather as breakages: they occur when the picture we have in our minds of what will occur shatters, splits or simply falls a different way than we had led ourselves to expect. That can mean something as elemental as having the wrong picture in the first place – or it can come down to developments that pulled things out of alignment.

Faced with picking up the pieces, here are 22 questions I use to try and get to the truth, and to move on:

1. What exactly went wrong? (What did not happen?)

2. How “wrong” was it – in the sense that how much did it differ from what we had told ourselves would happen?

3. How realistic was our prediction in the first place? (How did we arrive at that prediction?)

4. What did we do right throughout the project?

5. When did the quality change and what was the impact of that?

6. Even though we did things right, what didn’t happen that we expected to happen?

7. What did we base that expectation on? Was that reasonable?

8. Where did the biggest miscalculations occur? What did happen that took us by surprise?

9. Why were we not ready for that?

10. Who was most taken by surprise when things didn’t go to plan – and why?

11. What did we prompt people to do (or not do) that led to that occurring?

12. How did we seek to prompt customers to respond?

13. How quickly did we want them to respond? Why was that timeframe important?

14. If they did respond well and as expected, why did the initiative fail?

15. If they didn’t respond, why didn’t they do what we asked them to do? Because they didn’t want to do it, or because we didn’t provide enough incentive for them to do it quickly enough?

16. Who did we not reach that we should have?

17. Why were they not where we thought they would be? Or did we ignore them?

18. What did that cost us?

19. How did we react when we were taken by surprise?

20. Are we still working under the same miscalculations that saw this project fail?

21. Is everyone truly aware of what part their actions played in the project not hitting its targets? (Has everyone been told the truth about how much of the responsibility lies with them? None, some, a little, more …?)

22. How have we rewarded the people who took part so that they will feel motivated to do their best by the next project?

Photo of “Crazy hills of San Francisco” by Hakan Dahlstrom, sourced from Flickr

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