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Leadership and the permission to fail

20251117 Leadership and the Permission to Fail

November 17, 20254 min read

Key Takeaway: All great stories have permission. Gandalf gave it to Frodo. Morphius gave it to Neo. Fairy Godmother gave it to Cinderella.(Jon Acuff)

Give yourself and your team permission to have controlled failure.

We all as humans fail. In leadership, it’s often a misconception that you or your team should never fail. Are there life and death instances where failure is “not an option”? Yes, but most leaders don’t face that daily.

As a Leader, how you think about failure for both yourself and others is key to ensuring everyone’s growth. Failure is a key component to growth, and it is best in a controlled manner.

If you don’t allow for failure, then it will still exist; you just may not hear about it.

Failure concepts:

  • Failure archetypes by Amy C. Edmondson:

1: Basic Failures (caused by single things like human error) which are not to say they are small failures.

2: Complex Failures (many causes that come together, any factor on its own wouldn’t produce failure, or small deviations from best practice).

3: Intelligent Failures (undesired result as a foray into new territory). It takes place in new territory, with credible opportunity to advance towards your goal, informed by available knowledge, and is no larger than needed to gain the new knowledge.

  • “Fail often to succeed sooner.” David Kelley (Co-Founder IDEO)

  • Allow people the opportunity to take risks. How you react to their failure will influence them taking chances in the future.

My Failure Paradigm

I always ensured my team and I have a NorthStar. That may be the overarching reason we existed (true NorthStar), or just the final goal of a specific project. With that guiding their actions and decisions, I set up some basic rules that mirror driving on the roads (lines and guardrails).

Lines are the simple rules and directions to go towards the NorthStar, but allow for choices (movement between lanes). Guardrails are where you will step in to save them from a catastrophic failure. For example: complete failure of a project with wide implications, something that might get them in trouble, etc. These guardrails help them know where the outer edges are; however, how they moved down the road was up to them as long as they stayed within the guardrails. You are trying to look ahead (like driving) and nudge them if needed away from an accident.

Don’t misunderstand me, at the beginning of any team or your Leadership role it will take time to get this paradigm in place. You should not just turn everyone loose on day one if you haven’t followed the below framework. Just like driving a car, your hand should stay lightly on the wheel, but a little drift from lane to lane is different from needing to take control before hitting oncoming traffic or the guardrails.

Framework Steps

1) Step One: Build Trust

  • Create a safe space. You as the Leader need to ensure the team feels and is supported.

  • You have to build the trust this isn’t just a “Gotcha Game”.

2) Step Two: Failure Paradigm

  • Work with Stakeholders to define acceptable failures, and obtain their acceptance for your plan.

  • Define where you have to ensure there are guardrails vs. just painted lines?

3) Step Three: Communicate with the team

  • Let them know there may be failures, and they will be given opportunities which stretch them to possible failure.

  • Clearly communicate the expected guardrails, expected communication channels, and your support expectations.

4) Step Four: Communicate with Stakeholders

  • Communicate to stakeholders that you have the guardrails for you, someone on your team, or even your entire team to work within.

  • Create expectations on their communication to you if they see a guardrail being approached.

5) Step Five: Keep a light touch on the steering wheel

  • “Watch all things, overlook many things, correct some things.”(David Rice)

  • Ensure small corrections as needed, but do not micromanage.

  • Praise and reward what works.

  • When they present challenges encourage them to bring their preferred solutions.

6) Step Six: Debrief

  • As a team, debrief on what worked and what did not. What can be learned.

  • Ensure you show them that they are not in trouble, but failed in a way to grow.

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LeadershipFailurePermission
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Jeff Hill

I’ve had the privilege of serving and leading in some of the most demanding environments in the world — from hotel management, to the U.S. Secret Service, to Apple’s Global Leadership team. Each step taught me how to bring clarity, purpose, and confidence to leadership, even under pressure. Today, this is my chance to make a difference. Coaching allows me to help leaders avoid burnout, embrace clarity, and lead with confidence.

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