5 Fears of Mid-Level Leaders — Fear of Failure

Dec 6, 2023. By Lori Brewer Collins

DC from Lincoln to Washington by Jake Brewer

“Please don’t tell anybody, but I’m scared. My organization has invested $100M in this new initiative, and the outcome will brand my career. If it succeeds, I’ll be a hero. But if it fails, people will look at me as the person who squandered all the work hours, all the equipment, and all the resources this initiative has consumed. There’s a chance I’ll lose my job over this. Then who will want to hire me?”

What if I fail?

Leaders confronting this fear are high-potential individuals who are receiving lots of leadership development opportunities. They’ve been identified for grooming, with the possibility of executive-level leadership—maybe even C-suite roles—sometime in the future.

This fear emerges when these “hi-pos” feel they have been given a make-or-break situation. The organization has heavily invested in them and now it is calling in its chips. It is time for the high-potential leader to execute a significant part of the business strategy.

People in these situations feel the excitement of leading a new undertaking, but they also know they’re on the edge of a cliff. They must be both strategic and tactical. And they must up-level their thinking and their ability to work with others.

Their new role may or may not have existed before; therefore, it may or may not have clear lines of authority and decision rights. They may or may not have a roadmap for how they should operate. The work they are being asked to do will likely involve creating something—a new team, a new initiative, a new market—rather than just improving an existing area of the organization. Or the executive committee may be looking to them to complete a strategic endeavor that underpins an acquisition or an organizational restructuring. Whatever the work is, the situation will be dynamic, with many moving parts; even if they put together a perfect plan, there will still be many contingencies.

What’s at Risk?

Make-or-break situations are scary. Both you and the organization face risk. For you as an individual, it is your reputation that is at risk. For your organization, it can be share price, reputation in the marketplace, or even the future of the company.

Failure is always hard. You do a lot to avoid it. You lose sleep wondering who will want to hire you? Who will want to work with you? What will happen to your reputation? What will happen to your relationships, both inside and outside the company? And what about the allies and partners that will feel let down?

Key Issues & Challenges

  • Walking into unknown terrain
  • Working across the matrix with global and virtual teams
  • Coping with expectations and demands
  • Creating new structures and systems
  • Holding it all together.

Antidotes to the Fear of Failure

1. Develop greater agility.

Agility is akin to exquisite radar. It requires the ability to see around corners, to anticipate the future. It’s the wisdom to know how to lead others into and through unknown terrain, all the while keeping them present to a vision of where the company is going.

Agility carries over into the team you’ll assemble to drive this new initiative. There are many levers to pull here: from identifying the right talent for each job to using your positional power and personal savvy to convince people to leave their “comfortable” role and join you in this bold new venture.

2. Admit to mistakes you make—and learn from them.

Even the best of leaders will make mistakes along the way. I’ve met many HR people who say they’d never hire anyone who hasn’t had at least one major blow to their career, whether it was from the individual’s choice or because of other circumstances. What they want is evidence of resilience. The truth is that not everyone is wired to lead in all situations.

You may want to talk about your mistakes with a trusted colleague, your partner, or a close friend. Be completely honest with yourself. Transparently share the circumstances and how you chose to respond. Discuss what you learned—and what you would do differently next time. Reflect on how you are a better leader because of that experience.

Photo Credit: DC from Lincoln to Washington by Jake Brewer

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