Things often don’t go as expected, whether it’s a new business venture, major initiative, partnership, team, or new hire.

Yes, there are things you “should have” seen before, and external conditions that can influence results.

But hindsight is always 20/20, and the environment is never perfect.

It’s easy to assume you made a wrong choice and it’s possible to make a better choice next time.

Maybe that’s true. But it’s also too simple.

It puts you in a place of thinking you’ll do better without being specific about *how* you will do better.

It puts you in a position of judging the total acceptability of something based on that thing’s overall characteristics – not how the particular thing manifested in that specific environment.

It can also lead you to avoid similar situations or people altogether – which limits your options and the range of experiences that can create success.

Instead of focusing on where the experience, effort, or other person went wrong, try looking at where you can adjust your approach going forward to get a better result.


  • What tools, resources, information, perspective, or access did I have that I could have shared with others to help increase shared understanding or autonomy?  
  • Where did I not take the time to develop and articulate my expectations, but rather waited and hoped they could figure it out with hints that it wasn’t on track?
  • What assumptions did I make about prior knowledge, attributes, characteristics, skills, experience, ways of working, ways of thinking, or capabilities that I didn’t fully define, test, or vet?
  • Where did I wait to speak up when I noticed things weren’t going as expected?
  • Where did I assume things would work themselves out, without me taking ownership of my own role and responsibilities?
  • Where did I not ask for help or guidance in areas where I had a somewhat limited understanding of the situation, or was too close to the situation?
  • What did I pretend not to see?

Many of us avoid these questions because it is hard to sit with the idea that we may have made a mistake. It can bring up feelings of inadequacy or fears about how it will go next time.

It is easier to push that aside and insist we can spot a good choice, that we must have missed something about the opportunity or the person, or that it’s different this time…. without really looking at how the approach has changed.

The questions above can help answer the ultimate question: How does this change my approach to thinking, planning, decision making, communicating, expectation setting, onboarding, hiring, or launching going forward?

If you can specifically point to where and how the approach has changed, you’ll absorb a wider range of lessons from the situation.

Your capability to make wise decisions the first time will grow. You’ll have more confidence in doing the next thing. And you’ll be more likely to get the results you want.

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