Try, Try Again: Failure and Organizational Culture

By: Eric Menzer

I’m not a big fan of business clichés but there is a line I like – it goes to the question of what makes an expert. The answer?  “Someone who has made all of the available mistakes in a given field.”

Failure is a challenging thing to think about. Certainly, there are lots of catchy slogans in business that would make you think failure is a good thing. Culturally, failure seems to have become more acceptable, or even something to be celebrated. How often do we read about an Internet entrepreneur who failed at her first three ventures before hitting it big? Or a baseball player who spent 14 years in the minors before making his big-league debut (as did former Revolution player Scott Rice this year). In fact, baseball is often referred to as a “game of failure,” where the very best players fail at the plate more often than not.

Heck, even my mom used to say, “if at first you don’t succeed, try, try again.”

But it can’t be that simple. After all, if we all just went around failing all the time, that wouldn’t work out very well, either.

On the other hand, while “failure is not an option” is a slogan you hear a lot, we all know that that is just cheerleading, because failure is ever-present in our lives, our organizations, and our businesses. Furthermore, just repeating “failure is not an option” to your employees or co-workers is asking for trouble, because it will make people either incredibly cautious or turn them into good cheaters and liars as they try to cover up inevitable failure.

So the obvious question is where does failure fit in for you personally, and for your organization and employees?

Let’s start with the second part – how do I and how should we think about failure as managers – how does failure fit in our organizational culture? One thing I’m pretty clear on is that we shouldn’t discourage it, because that will drive creativity and experimentation out of our organizations, and as suggested above, intolerance of failure will just lead to cover-ups. The balance is in the context and the frequency of the failure – is it a result of laziness or does it happen repeatedly?

I am fond of saying to my employees that the mistake I really care about is the same one you make a second time. I hope this is making a point – on the one hand, letting them know that the first mistake, particularly if borne from experimentation, is OK – not literally, of course – but figuratively. On the other hand, letting them know that at some point, execution and performance really do matter.

Another thing I’m clear on: I will never let myself get pinned down to a precise “this is when you are allowed to fail,” because there is no answer to that question. In my view, the key is creating an environment where people figure this out for themselves.

A key for us as mangers is not assuming people automatically “learn from their mistakes” – often I find I have to talk people through what they learned. It is a critical part of my job as a leader to make sure that not only did they learn a lesson, but that they learned the right lessons. Particularly with young employees, I often need to help them work their way “upstream” – to find the real source of the failure.

Here’s another way to look at it – this was given to me by the leader of a nonprofit here in York. He said to me, “If you focus on the wrong failure, you’re probably focused on the wrong successes.”

This puts the onus for using failure as a management tool back on the leader – which in reality is where it belongs. It reminds us not to worry about the petty mistakes – those need to be driven out, but we need to understand what the REAL failure is in any situation – things like the failure to plan or anticipate – the failure to leave enough leeway in a situation to accommodate disruption.

In my company, we talk all the time about not setting yourself up for failure by requiring perfection in a situation to achieve a successful outcome. A plan that has to have everything go right to achieve the desired result is not, in fact, an adequate plan.

Being able to analyze your own failure is really critical to your career and life success. I don’t have a magic formula for doing that, but I will observe that if I look at my biggest mistakes they were things I did not do, typically situations involving problems I didn’t confront early or forcefully enough.

Personally, I know that the lessons I learned the best were the ones that hurt the most.

Remember - really great leaders aren’t without faults or weaknesses – they just figured them out early and are particularly good at compensating for them – not covering them up – just devising systems or approaches to address them – typically after trying all the other alternatives!

If at first you don’t succeed, try, try again. Maybe Mom was right.


Eric Menzer became President of the York Revolution in 2010. He also manages the Codo Development Group, a real estate development limited partnership working in downtown York. Eric is active in community affairs and civic leadership. He chairs the boards of the York County Convention and Visitor’s Bureau and Community First Fund, and serves on the boards of Downtown Inc, Better York, the Strand Capitol Performing Arts Center and the Crispus Attucks Association.

Eric was previously the Senior Vice President of Wagman Construction in York. Prior to that, he served for eight years as the Director of Economic Development for the City of York, and previously as the Executive Director of the York County Transportation Authority.

He is a mentor for Leadership York's Mentorship York program, and recently moderated a panel discussion for Leadership York's Lunch ON Board program.