Failing Forward

There's power in granting our people the freedom to make mistakes

If you asked 100 people to describe the conditions needed to be satisfied with their job, at least 90 would inject the word FREEDOM.  In fact, most of us would say that when our jobs lack freedom they become suffocating and lifeless.

Yet, if pressed for a definition of freedom we’d likely struggle to offer a crisp one. Defining its elements would be even more difficult.  To a leader committed to offering freedom to the people they lead, this makes the task of granting it elusive.

If you know me, it’s no mystery I’m a fan of Dr. Tim Kimmel.  Tim, an expert on marriage and parenting, has studied this in great detail and pinpointed 4 Freedoms the human heart desires.

Today I want to touch on one such freedom…the freedom to make mistakes.

Broadly speaking, I mean mistakes in the context of the workplace to include lapses in judgment, blunders, errors and omissions, forgetfulness, shortsightedness, and outright failure.  So just about everything that could go wrong.

To be sure, this is not a treatise on the need for process, planning, cost benefit analysis, checks-and-balances, cross-functional postmortems, or the like.  Although all of those things are advisable.

Instead, I’m approaching this from a purely relational aspect.  After all, our employees desperately want to succeed.  They want to achieve WINS with their leader.  And when mistakes are made, vital relationships are either strained or strengthened.  Granting the freedom to make mistakes lets others know our relationship isn’t contingent upon their performance.

Before I mention specific things we can do as leaders to convey this message, I want to highlight that mistakes are an inherent part of work…much like in sports.

  • Basketball: John Stockton, the NBA’s all-time assist leader (15,806), also committed 4,244 turnovers.
  • Tennis: Andy Roddick, 3rd on the all-time ace list (9,068), also faulted on his first serve 35% of the time and had 1,581 double faults.
  • Baseball: Reggie Jackson, #14 on the list for career home runs (563) is also the all-time leader in strikeouts by a batter (2,597).

In basketball, if a player misses 40% of their shots…they’re amongst the shooting elite.  In baseball, if a batter gets a hit 1 out of every 3 at bats, they’re likely in the Hall of Fame.  So if mistakes are such an accepted part of sports, why would we expect the workplace to be any different?

Terry Kearney, my high school basketball coach, always said, “Never put your head down.” Much like basketball, Terry’s advice applies to life and business.  Both move so fast that when you make mistakes, putting your head down causes you to miss opportunities to make plays.  Case in point: John Stockton who committed 4,244 turnovers, interestingly racked up 3,265 steals.

If you’re sold on the idea that mistakes are acceptable the question becomes, “How do we create a culture where people know mistakes are tolerated?”

Here are five tips for balancing the realities of mistakes with our desire to value relationships.

Watch the Non-Verbals

When your people screw up, they become keenly attentive to your response.  And your physical reaction speaks volumes.  Be self-aware of sighs, eye-rolls, looks of disgust, and your overall countenance.  Think back to when you were a kid and broke something of value.  Your parents’ immediate reaction set the tone for how things would go…and it’s no different with your employees.

Acknowledge the Obvious

When people make mistakes, they harbor fear that can inhibit performance if left unaddressed.  It’s not uncommon for people making mistakes to question their job security.  Wondering where they stand with you, leaves them walking on eggshells.  To not acknowledge the impact of mistakes (financial or otherwise), would be disingenuous. Rather, you should address the impact head on.  The important distinction, is to separate the cost of the mistake from the value of them as a person.

Offer honest feedback

There are times when mistakes are simply that…mistakes. Other times they’re indicators of deeper performance issues. As a leader, you’re obligated to candidly and honorably discuss these things with your people.  Mistakes are golden opportunities for development.  You must decide if you are a Coach or Critic…and choose the former over the latter.

Allow the consequences

Granting the freedom to make mistakes doesn’t mean withholding consequences. In fact, allowing consequences is one of the most gracious things we can do for our people. Withholding them lacks wisdom as it deprives our people the opportunity for growth.  At the same time consequences shouldn’t permanently damage your relationship.

Make investments

When people make mistakes, they often assume they’ll be written-off.  Doubling down on your investments in your people when they expect you to write them off is deeply encouraging.  It gives them hope.


Mistakes will happen.  Responding in a way that addresses the mistake yet values the relationship…is powerful.  What this will say to your people is, “It’s OK to make mistakes.  They don’t mean I’m a failure and it isn’t the end of our relationship.”

If we want the teams we lead to do big things…we sometimes have to swing for the fence.  But as Reggie Jackson demonstrated, that might mean we’re going to strike out.  Maybe a lot.  But if our people play it safe and never swing for the fence…they’ll never hit it out of the park.

As a believer, my ability to do this is anchored in my understanding of how God does it with me.  If God assigned a value to me based on my performance, based on how well I deliver for Him… I’d fail. Miserably!  God would write me off. But He doesn’t.  Ultimately, allowing mistakes is about treating others the way God treats us.  He lets us make mistakes…and we should let others do the same with us.  That’s the very essence of grace.

Question: I’d love to start a conversation about how a leader handled a mistake with you in the way I’m suggesting. What was the impact on your relationship…and your career? You can leave a comment by clicking here.

Please note: I reserve the right to delete comments that are offensive or off-topic.

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