Symbolic image for fear of failure. Shows two narrow boards stretching high above a city. Viewpoint is from person balanced on those boards, looking down at their shoes, standing on the boards, with the cityscape far below.

Fear of Failure and How to Lead Your Team Past It

Dave Labowitz Leadership

Symbolic image for fear of failure. Shows two narrow boards stretching high above a city. Viewpoint is from person balanced on those boards, looking down at their shoes, standing on the boards, with the cityscape far below.

Most leaders crave a team dedicated to excelling in their roles and who have the grit to push through fear of failure when it holds them back. Most team members dream of a boss who is excited to support them by making it safe to take risks and who has the experience to help them grow. In many cases, though, leaders and team members fail to connect in a way that addresses how much fear of failure hold them back.

This article will show how your team member’s fears are actually an opportunity to help them to shine in their roles,  achieve significant personal growth, and create an elevated level of trust in your professional relationship.

How does fear impact your career?

There is no doubt that fear will hold you back in every area of your life if you fail to conquer it. In fact, you’ve probably had to conquer some sort of fear every time you’ve triumphed in life. Think about the fear you felt getting behind the wheel of a car to drive for the first time. If you hadn’t conquered your fear, what would your life be like? Fortunately, in that case, you were able to see that the reward of pushing through the fear was worth it (freedom to go where and when you want), and the pain of failing to push through the fear was not (trying to date with just a bus pass). In all likelihood, you had a parent, older sibling, or friend to push you forward, help give you confidence, and ultimately coach you through conquering your fear. But what about fear in the workplace? How much is fear holding you or your team back? And what are you doing about it?

Fear of failure in the workplace can sneak up

Fear can sneak up on you at work. Think about the projects you have on your plate. Is there a project you’ve been putting off, thinking in the back of your mind, “I just don’t like this task?” If you ask yourself honestly, there’s probably some aspect of fear in your reasoning. Maybe you’ve been putting off calling an upset client. You know your company let them down in some way and they’re going to give it to you both barrels. It’s going to be unpleasant. But what makes it unpleasant? Odds are it’s because of fear. Maybe you fear the confrontation. Maybe you fear how it will feel to be told you let someone down and know they are right. In all likelihood, the issue goes deeper and you fear to judge yourself as a failure. Ultimately, it’s the fear that causes you to put off calling the client. The best thing to do, in order to move forward, is to identify you have fear, figure out why, and then push through it.

This type of fear-based procrastination is going on at varying levels in every member of your team. Why? Because they’re human. And at work, the incentives for pushing through fear on any given project are only abstractly related to the project (they’ll get their paycheck anyway), so it’s easy to fall into a pattern of avoiding the stuff they’re afraid of, or at least, putting it off.

Fear is a signpost pointing at success

The good news is, if you can identify the things your team fear, they are flashing neon signs pointing at ways they can improve as professionals and people. If fears are holding them back, causing them to avoid or put off parts of their job, then conquering these fears will lead immediately to greater success in their role, not to mention a substantial boost in confidence and self-esteem. If you want real growth in your team, this is a way to access it!

How to use fear of failure as a leadership tool

You obviously aren’t inside your team’s heads so you don’t know which fears are holding them back. You’ll have to ask them. Getting an honest answer to this question will require some trust, so the stronger the relationship you have with your team the better this will work. Try asking them these questions: “Think about the tasks and responsibilities in your role you have fear around. Which fear is holding you back the most? What are you afraid of happening? If you could conquer that fear, how would it help you excel in your role?” Listen deeply, and feel free to ask probing questions to help your team member drill down to their most profound truth. The better they understand the root of the fear, the better you’ll be able to help them beat it.

Coach your team through fear

Once you’re clear on what your team member’s fear is, and how it holds them back in their job, work together to build a project which allows them to work through the fear and achieve the previously unachievable accomplishment. In order for them to commit, it’s imperative you are able and willing to offer them enough support they can feel safe during the undertaking. Think through what this will take and make sure you can offer it. Do you need to talk to them more often? Or be reachable immediately after they take on their challenge? Do you need to be present? Or listen in? Do you need to reassure them that it’s ok if they fail, and there is a path forward if things don’t work out the first time? Do you have the technical skills to answer any questions that come up? Or do you need to secure additional resources for them? Be extra sensitive to their needs even if it feels like you’re doing more than normal, or even more than feels right. You’re asking them to stretch and grow, so in this case,  be prepared to put in the extra time and effort to support them.

Once you have it sorted, ask them for buy-in, “If I am willing to support you through this project and make it safe for you, are you willing to take on and conquer this challenge?” Once you’ve each made your commitments to each other you’re on your way. It is mandatory, mandatory, mandatory, that you, as the leader, live to your commitments and support them however necessary. This type of project forces your team into a vulnerable place and gives you an opportunity to build substantial trust. On the flip side, you can irrevocably damage trust if you encourage them to go out on a limb and then let them down. Take the opportunity to be there for them! Remember they may not succeed on their first try. Be prepared for that. Pick them up, dust them off, give them helpful feedback, and support them in trying again. With your help, they’ll get there.

Celebrate and repeat

At the end of your process, your team member will have worked through their fear and hit a business target they were previously unable to hit. Celebrate this, as it’s a big win. Not only did you both get the desired business result, your team member will have learned how to conquer a fear and built a new and productive skill. Their confidence will be higher. It’s entirely possible their self-esteem will be higher. They will know it’s ok to trust you, and that you want to help them grow and succeed. You get to feel good about changing their lives for the better. You’ll also have laid the tracks for future growth.

Repeat this exercise regularly, but not necessarily frequently. If you’re drilling down into fears deeply enough, there will be some challenging projects, not just for your team members who are going through it, but in terms of your time commitment. Afterward, it’s best to give your team member a break from the emotional intensity of a project that forces them entirely out of their comfort zone and enables you to get back on a normal schedule cadence. If possible, consider giving them some similar projects soon after in order to hone their new skill into a competence and prevent the fear from regaining control.

Bonus round

If you really want to take this exercise up a level, put on your vulnerability hat, find a fear that’s holding you back, pick a project, commit to it, and share it with your team. Let them know that you’ll be facing a challenge alongside them and that you’ll keep them abreast of your progress. Not only will this serve to further enhance your relationship with your team, it’s great for you. Why leave all the outstanding personal growth opportunities to your team!

If this approach to leading your team past their fear of failure resonates with you, please share to help spread the word! Thank you!!

FREE DOWNLOAD: The Culture Statements Compendium
Mission and Vision Statements are only half the picture! If you want a truly intentional culture, you'll need Core Values and Operating Principles, as well. This document, complete with instructions, examples, and even a questionnaire for your team, will show you how to make your culture actionable rather than abstract.