The 6 Steps I Took as a Founder to Conquer My Fear of Leading

A few years back, I was terrified. We had just launched our startup and I found myself at the bank making a pitch for a relatively substantial loan to fuel our company’s growth.

Thankfully, the branch manager was a pretty friendly person. But that didn’t stop the knot in my stomach, the throbbing in my head, and the river of sweat that was rolling down my face and back.

If you know this feeling all too well, you might have a fear of leading. A fear of the high stakes associated with putting it all on the line to make your company a success. The good news is, you are not alone, and there are concrete ways to cope with that fear and become the strong leader you know you can be.

Trust me when I say that lots of people share this problem, and it’s nothing to be ashamed of. I, for example, am normally not prone to fear about these sorts of things. I’m a former military officer and living around the world has helped me embrace new experiences like this.

But that day in the bank was different. What would we do if the bank said no?

One of the key responsibilities of founding CEO leadership is obtaining the right resources that the organization needs to grow. Funding is one of the most important resources. That was at the center of my fear. I hated asking for money from the bank, especially when our company’s value proposition was still a work in progress. For me, it was a combination of the fear of rejection and the fear of not being able to pay back the loan. Does this sound familiar?

If You Have A Fear Of Leading, You Are Not Alone

After interviewing nearly 200 founders during the past two years, I have learned a lot. What’s one of my biggest insights? A significant percentage of us have similar fears as I have described above. And they frequently revolve around leadership.

The truth is, it’s not that founders fear leadership in the abstract sense. It’s that there are usually pieces and parts of being a leader that we often fear at one point in time.

Let’s face it, none of you started your company to become a CEO. You started your company to free yourself from the corporate cube, obtain financial freedom, have an impact, disrupt an industry, and even change the world. But for many founders, the fear of leadership holds us back.

Just ask Ryan. Ryan recently called me in my role as his CEO coach, because he wanted to discuss a possible move into a new office space. He caught my attention when he said, “I think we only need space for 25 team members.” Ryan already had 25 people working at the company and would likely need to hire more. When I asked Ryan if he should consider space for more people, his answer was intriguing.

“I’m not sure I want more than 25 people on the team,” he explained.

“What if your growth and the needs of the marketplace require more than 25?” I asked with a curious tone in my voice.

There was a long awkward silence. I could tell he really didn’t expect me to challenge him on this.

“I’m not sure I can lead a company of more than 25,” he said, with some trepidation. “I’ve never done that before.”

Ryan went on to explain that he wasn’t even sure how to lead a larger number of employees, and was afraid he wouldn’t be successful.

Or take the story of Kristi. Kristi’s startup was growing fast. She was adding team members at a breakneck speed of about 10 per month. She soon realized she needed to hire a VP of Operations and found someone she could trust who had just the right skills for her software as a service (SaaS) company.

Things started to change when Kristi’s new VP of Operations, Jessica, started to handle situations in ways that were not aligned with the culture of appreciation and continuous learning Kristi was attempting to create. Jessica’s vocal tirades admonishing her entire operations team for missed deadlines started having a serious effect on morale.

Kristi was paralyzed. She knew she had to speak to Jessica about this, but she never really had to give feedback to someone who was older, more experienced, and had such a key role to play in her growing company. She couldn’t afford to lose Jessica.

Fear of giving feedback. Fear of giving feedback in an effective way. Fear of losing Jessica. These emotions resulted in so much procrastination that things got worse, fast.

This is normal. It happens to all of us.

We focus time and energy on our goals, but pay little attention to the leadership fears that prevent us from scaling our company.

Can you overcome your fear of leading? Yes! You can.

6 Actions To Overcome Your Fear Of Leading

I have found that there are six actions you can take in order to conquer your fear of leading. Here we go.

Action 1: Answer 4 key questions

Question 1 – What is the source of your fear?

Start by actually defining your fear. Answer this question: Is it a big, multifaceted, or perhaps vague fear that may need to be broken down a bit more, or a specific fear that may be more focused and easier to tackle?

Answering these questions and categorizing your fears like this helps you to understand their size and scope so you can focus a bit more rather than getting stuck on a generic feeling that is harder to process.

Here are some bigger and less defined fears (vague) that many founders have told me. Do any resonate with you?

These are vague fears that are not yet focused. Our goal is to refine them and get more specific so we can more easily overcome them. It’s OK if these are some of your fears and you are unable to further refine them at this stage. It’s a starting point to ask yourself which element of this bigger and more vague fear is really driving your feelings. Take the time to think about a few situations where that fear was aroused and see if you can pinpoint a more specific source of that larger fear category.

If you are able to quickly identify a more specific fear, great! The key is to zero in as much as possible on the one that provokes the most fear in your heart and is blocking continued growth.

Here are some “specific” fears that many founders have told me. Do any resonate with you?

Question 2 – What’s the impact?

As founders, we are constantly testing and probing the marketplace to understand the impact of our product or service and the timeframe it takes to obtain new customers.

The same thoughts can be applied to our fear of leadership. Ask yourself this question: What’s the impact and timeframe of my fear? Will the source of my fear have a short-term, low impact, or a bigger and more long-term impact?

You may want to look at it this way:

Consider classifying yours fears from one through four. For example, my fear of asking for money would have a big impact on our business at that time, because the money was needed to buy marketing services that were vital to our success. The consequence of not buying these marketing services would have immediate consequences, because we would have missed some opportunities that were time-sensitive. Therefore, I would classify this as a 1.

Classifying a fear as 1 means I need to spend time tackling the fear now. If I had labeled this fear a 4, then I might not need to spend the time confronting my fear right away. I might ignore a fear labeled 2 until it was relevant, and I might wait on a fear that was labeled a 3 until the consequences were more timely.

Question 3 – Is it out of my control?

There are so many things that lie outside of our control. Ask yourself this question: Is there an action I can take to get over my fear? Or is it really outside of my control right now?

For example, I really could not control the requirements the banks created for the loan approval. However, I could have walked next door to the bakery and indulged in an apple danish (yum) in order to give my mind a break from my fear of asking for money. Since they were closed, I went to my car and meditated for a few minutes. I recognized what I could not influence in the situation, and took an action that helped me overcome my fear.

Question 4 – Is this a performance issue, related to a lack of knowledge or personal motivation?

Is this fear related to a performance issue? That’s the next question you can ask yourself. If that seems like a possible source of your leadership fear, then questions similar to David Whetten and Kim Cameron’s performance management questions can help you dig deeper into this.

Performance issues can stem from either a lack of knowledge or a lack of personal motivation.

So, first, you might ask yourself if this is an “ability” issue. This just means you may not currently have the knowledge or skills, and this lack of ability is causing some level of stress or fear. If this is you, you may consider asking yourself these three questions:

For example, a founder recent told me that he dreaded working on financial projections. He realized it was because he was never really trained on how to do this and it caused significant fear because his investors expected a level of excellence for which he was not trained.

The second performance question to ask yourself relates to your own personal motivations. Are you really motivated to to do the thing you fear? If not, these three questions might help you to zero in on the angle of motivation that may be linked to your fear:

For example, maybe your board chair has been cryptically leaving hints that she is discontented with your company’s performance, even though you have been meeting all goals. This dents your motivation, creates a low level fear around confronting her about the issue, and begins to impact your leadership performance.

Action 2: Write it down

Write down the answers to these four questions I just discussed. This will help you manage your fears by making them become more tangible and less ambiguous. I prefer to use a Moleskine journal for this. I use one that is designed to work with my Evernote subscription, because it’s easy to capture it digitally.

Another way to accomplish this step is to draw a picture of your general or specific leadership fear. If you tremble at the idea of having a team meeting to give your perspective on the direction of your company, then draw a picture of what that looks like. Get it out of your head and onto some paper.

For example, here’s what I drew when I was doodling about my fear of asking for money from the bank.

Action 3: Share your work


Share your answers with a group of peers or at least a trusted confidante, preferably a fellow founder.

I facilitate a group of founders each Tuesday where we tackle leadership issues and fears. Each person reports receiving a great deal of value in simply sharing their fears and apprehensions with fellow founders. The act of sharing Actions 1 and 2 helps us to further clarify and manage our fears even more.

There are many places you can find a group of trusted, peer founders to share your work. Your local chamber of commerce often sponsors groups like this. There are curated groups like Foundr Club and Trail Team 10 that you can join. And, of course, you can tap into the graduates of the startup accelerator or incubator in your city and create your own group.

It’s common to hear conventional advice to “confront your fears.” But leadership fears can be a bit more challenging. Sharing your answers from the questions above with those who have similar leadership responsibilities is a subtle, yet effective way of confrontation through accountability.

Action 4: Focus on small, achievable wins

What really gets us going are small wins. Authors Teresa Amabile and Steven Kramer knows this all too well. In their book, The Progress Principle: Using Small Wins to Ignite Joy, Engagement, and Creativity at Work, they detail the psychological triggers that propel us to tackle things like fear and increased creativity. In an Harvard Business Review article they state, “The power of progress is fundamental to human nature.”

You can use the “progress principle” to your advantage as a young founder and conquer the fear of leadership. Just focus on one small win.

For example, if you have a fear of speaking to your team in a group format, start small. Prepare your thoughts in advance and record a video. But, here’s the catch. Watch the video with your team. This exercise will help approximate the feeling of fear, but reduce it a bit because you can join the group as an observer of the video. And, you can also ask for their feedback.

This small win may help boost your confidence. As your confidence grows, you’ll find yourself working on additional leadership small wins and climbing the four stages of learning:

This process, although not linear, helps you enter the “confidence/competence loop.” As you get better and gain competence as a leader, your confidence will likely grow with each skill you develop and each stage of learning you attain. This often creates momentum and helps to shrink your fears.

Action 5: Conduct an ‘after-action review’


Founders have way too much going on 24/7. So your small leadership win may not have a chance to take root and reduce your fears if you don’t get a chance to walk through your feelings and sort through what you learned.

A friend of mine likes to say that “life is a debriefable event.” It’s so true. After conquering a leadership fear, share the experience with your group or a trusted fellow founder. We learn by integrating new thoughts and experiences into established ones.

I recently spoke with a founder, Mike, who not only overcame a serious and life-threatening illness, but then used that experience to overcome his fear of approaching a top investment firm, by getting an appointment with its founding partner. When I asked him to debrief the experience with me, he said, “Wow, I never really thought about how these two experiences have helped me teach my team to fearlessly grow our startup and tackle new challenges.”

It wasn’t until he had a chance to talk about it that it became more real and more tangible. He simply had an opportunity to think about how he would employ these new insights again and more consistently.

Reviewing your actions and their impact helps you dissolve your leadership fears.

Action 6: Reward yourself

The final key action is to reward yourself for overcoming a leadership fear you are beginning to conquer.

Let’s say one of your top leadership fears is speaking with your lead investor, Sam. Every time you call him, you break out in a cold sweat and lose your ability to speak intelligently. He is demanding, sarcastic, and always asks about your numbers. And he just left a voicemail for you to call him.

But you were smart. You got in touch with your feelings and identified this as a specific fear. You recognized the relevance and impact of not calling him back. As you think more about it, you realize that you can manage your feelings and influence how the call transpires. The thought occurs to you that you just haven’t had enough experience dealing with him.

You journaled about these feelings enough to have a conversation with your friend, Ned, who runs a startup in Sydney. Ned suggests that you role play with him in order to practice how you might speak with Sam. Ned says you did a decent job handling the role play exercise. You both consider this a small win.

The call with Sam goes better than you expected. Ned calls to ask how it went and you review what happened and what you learned. The additional feedback from Ned raises your confidence and you feel better prepared for the next call with Sam.

Now take a friend out to your favorite sushi bar and celebrate your slaying of this leadership dragon. The good feelings that will follow will create an imprint on your mind and encourage you to tackle this fear with greater competence the next time around.

Putting it All Together

Fear can be a temporary state if you are intentional about putting these six actions into practice.

Remember Ryan? He started putting these steps into action and soon realized that his general fear of growing his company beyond 25 employees was more of a training issue that he could overcome. After sharing his thoughts, journaling, and breaking down his fear into smaller, specific elements, Ryan started the process of overcoming his fear of leading more than 25 employees.

In fact, he specifically said he now sees his fear of leading over 25 employees as arbitrary, and is working on a growth strategy without this fear limiting his or his company’s potential. He took a trip with his family to celebrate his new-found confidence.

You can do this too.

Start now.

Share with us one of your leadership fears in the comments below, and I’ll do my best to share some additional actionable advice.

You’ve got this!