Hooray! You Screwed Up

For most anal-retentive business founders and CEOs it’s not easy to step back from your natural habit of having a hand in everything. You built your organization by sweating every detail and now it feels unnatural to somehow now start ignoring those details. The truth is once you leave those details to other people, you face yet another challenge, because those people are guaranteed to make a lot of mistakes.

But learning how to let go, how to empower your people to screw up, to make mistakes, is just the prescription required for you to grow your organization. I’ve often discussed this issue with founders of growing and successful companies. My advice is always: “In order to scale your company, you are going to need to hire people who are going to do things in ways you’ll not agree and some things are going to get f**ked up.”

At the risk of sounding paternalistic, the process of building a team is not that different from raising a healthy, self-sufficient child. It’s not possible to be there with them constantly to ensure that they do the right thing all the time. You need to trust that with the right guidance they won’t get themselves in too much trouble. And when they do get in trouble, when they fall and skin their knees, it’s your role to help without being judgmental. You want them to learn from their mistakes and the resulting painful consequences.

When you do that and trust people to do their jobs, inevitably some of them will breach your trust. Even if you are certain you’ve clearly stated your expectations and are satisfied your staff is fully trained, on some days they will let you down. When they do consider it a learning experience. But rather than be passive about it, take action.

Take a tip from the US Air Force, where teams routinely assess what they can learn from the outcomes of their most recent mission. After each mission they hold a timely, objective, no-judgment appraisal of what happened, where performance could have been better, and then collaborate on an action plan to address the areas requiring improvement. The Air Force culture is built on the assumption that the surest way to compound an error is to ignore the opportunity to learn from it. And screw ups when you are flying a jet at more than 500 miles per hour likely have worse consequences than anything one of your well meaning employees can conger up in your organization.

There are organizations I’ve worked with where the founder used to make mistakes a cause for celebration. He would announce mistakes that his direct reports had made in a company-wide meeting that functioned a lot like after-action reviews. They were intended to identify how and why the underlying decision went wrong, in order to give meaning to the resulting failure. The founder usually made certain to compliment the effort that led to the error—making it clear that trying new things in the face of risk was vital to the company’s growth.

Promoting a culture that encourages risk taking, questioning the status quo, and even challenging the company founder is the best prescription for healthy growth. You want to embrace the kind of employees who have enough guts to call your baby ugly if that’s how they see it. Exhibiting the confidence to bring others into your organization that might just disagree with you is a critical ingredient of scaling.

There are many strong-willed founders who can’t tolerate this kind of environment, much to their detriment. Too many founders with early success develop a belief system that they know better than anyone, that they are always right—right enough to stop soul searching or listening to others. Founders of this kind often protect their fragile egos by hiring friends and family members who don’t dare question the boss, because they know their main function is to exercise loyalty, not competence. Then, when a mistake happens, the founder can’t possibly hold an open and honest review of the problem because it might expose the ineffectiveness of his loyal inner circle. The overall effect—one that smells a lot like hubris—can sow the seeds of doubt and dysfunction throughout the organization, and inevitably lead to the organization’s downfall.

For founders who want to tip the odds in favor of growth, you’ll have to give up to grow up. Hire great people who have their own ideas. Give them clear direction, training, encouragement and the space to screw up. Help them understand how those screw ups can be remedied. And empower them to tell you what they think – especially if they differ from your ideas. They may scape their knees at first, but you’ll soon find them propelling your organization to new and higher heights.

This guest post is courtesy of Les Trachtman. He is currently the CEO of The Trachtman Group – focused on helping companies grow and scale, as well as managing director (and majority investor) of Purview, an early stage company focused on disrupting the medical imaging business. For the past two decades, Trachtman has lectured at numerous universities across the country including the Harvard Business School, the MIT Sloan School of Business, the University of Southern California, Rensselaer Polytechnic Institute, Kent State University, University of Maryland Smith School of Business, Union College, and Quinnipiac University School of Business. Trachtman has published articles in the Harvard Business Review and Quinnipiac University Business. A portion of his career is chronicled in the Harvard Business School case study; Les is More Times Four, which educates entrepreneurs at leading business schools. Learn more about Les Trachtman at Founder Transitions, and connect with him on FacebookTwitter, and LinkedIn. Don’t F**k It Up is available on Amazon and wherever books are sold.


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