Letting people fail

If you’re anywhere near the startup ecosystem, you’ll consistently hear the mantra of “fail fast.” 

Personally, I’d rather focus on the outcome, which is / should be about learning fast. But failure does teach us…and if we’re paying attention it gives us information that we can take further than the specific moment or situation. 

What gets less attention is the importance of letting other people fail, and that’s a shame because it’s a critical skill that isn’t well understood or talked about enough. 

Mentoring / advising, for example, has a lot of moments like these. Good mentors understand that you can’t control a situation, nor can you save someone from themselves. 

It’s useful to break that moment down, because where people need to fail and learn from that failure can be subtle. 

As a mentor it often looks something like this for me: 

  • Big problem or set of complexities, entrepreneur recognizes they exist and tells me about them
  • I clarify what’s happening to make sure I understand, then try to help them frame their own understanding
  • Here’s the important moment: Entrepreneur looks at me and says or implies outright “this sucks / I don’t know what to do / this is really hard and/or complex”
  • Even if you’re a good mentor (friend, boss, etc) it can be easy to skip right to “ok here’s how you fix it” or “why don’t you try X.” 
  • In reality, what needs to happen in that moment is that the entrepreneur (friend, family member, employee) has to recognize the structure around the problem they’re having, and you can’t make them do that. 

This can happen in a personal or professional context. The key is to understand that there is a choice involved.

If you are the person working through the problem or set of complexities, sometimes it means realizing you are in a bad piece of structure that you need to get out of. Sometimes it means recognizing that you’ve created some or a lot of that structure. Often it is both. 

If you are the person helping or advising, this process can be uncomfortable. The person may ask you directly to do something that you don’t feel will help them. Or you may care about the person and their growth, and want to make sure they don’t experience hardship or pain. 

Here are a few questions that help me avoid skipping steps, and prompt the entrepreneur to do their own work. 

  • “That sounds intense — how would you like to structure our time so I can be of help?” *suggests that they should ask for / define what help they need
  • “How are you thinking about approaching the problem?”
  • “What do you think needs to happen for you to work on it?”
  • “Is there a general beginning / middle / end that you see for solving this?”
  • “What information do you think you need to solve this problem and/or where do you go to get that?”

I’m speaking mostly here about entrepreneurship, but you can apply this approach to most situations, including co-workers, family, friends, significant other, etc. 

Letting someone fail can be one of the most graceful and compassionate things you do, and if you’ve created a supportive work environment, friendship, relationship, etc. they’ll learn fast and be on their way to greater things.