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Leadership Confidence Comes From Doing the Work

Writer: Karen Gregory
Karen Gregory
Sep 13
5 min read
Karen Gregory's book Let's Talk Leadership  sharing how leadership confidence grows through experience.

When I first became a manager, I was confident I could do the job. I was even confident I could lead. What I didn't understand yet was that believing I could be a leader and actually feeling confident while doing the work of leadership were two very different things.


When I was assigned to my branch at the bank, I was sent in on my own to introduce myself to my new team. The branch wasn't close to the rest of the management team, so there wasn't anyone walking through the door beside me. I had prepared for the position and felt ready to take on the responsibility, but there's a difference between preparing to lead and suddenly realizing that you're the person everyone is looking to as the leader. From the moment I walked through that door, it was time to put what I knew into practice.


Within my first week or two, I had to conduct my first disciplinary conversation. I was nervous before the conversation. I wish I could tell you that once I started talking, all that nervousness disappeared and confidence took over. It didn't. I stayed nervous. But I knew what I needed to say, I understood the policy and the issue we needed to address, and I delivered the message in an empathetic way. The employee understood where the expectation hadn't been met, and we got through the conversation. When it was over, I remember thinking, Okay, I can do this.


Leadership Confidence Doesn't Require Feeling Ready


That first conversation didn't magically make me confident. The next time I had to have a difficult conversation, I still had nerves. But I had something I hadn't had the first time: experience.


That's an important distinction because leadership confidence isn't something that suddenly appears after one successful experience. It builds incrementally. Each time I had a conversation with an employee, colleague, or supervisor, I gained a little more experience to draw from the next time. Sometimes I was delivering good news. Sometimes I had to address a problem. Sometimes I was listening, explaining a decision, answering a question, or working through a disagreement. Every one of those interactions helped me become a little more comfortable doing the work of leadership.


We sometimes assume confidence should come first. We think we'll have the difficult conversation when we feel more comfortable having it, speak up when we're more certain of ourselves, or step into something unfamiliar once we feel ready. My experience has taught me that the order is often reversed. Sometimes confidence is the result, not the requirement.


Leadership Confidence Builds One Conversation at a Time


One of the things I stress when teaching leaders about difficult conversations is that they have to actually have them. We can teach a process. We can talk through what to say. We can practice. All of those things help, but eventually the leader has to sit across from another person and have the conversation.


Then they need to have more conversations.


This is also why I believe so strongly in leaders building relationships with their people before something goes wrong. Talk to your employees when there isn't a performance problem. Ask questions. Listen. Give feedback. Recognize good work. Explain decisions. Have regular one-on-one conversations. Those everyday interactions don't just strengthen the relationship with the employee. They give the leader practice communicating, listening, responding, and becoming comfortable having meaningful conversations. The conversations that feel ordinary today are helping prepare you for the conversation that won't feel ordinary tomorrow.


The first time I stood in front of a class to teach, I experienced another version of that same Okay, I can do this moment. I didn't suddenly become a completely confident instructor after one class. Confidence came through standing in front of another class, and then another. Experience gave me something that preparation alone couldn't give me.


Prepare for the Conversation, Then Have It


None of this means you should walk into an important leadership conversation unprepared and hope confidence carries you through. Confidence isn't a substitute for preparation, and preparation isn't a substitute for experience. You need both.


If there's a difficult conversation you need to have, do your homework first. Understand why the conversation needs to happen. Know the facts surrounding the situation. Identify the expectation that wasn't met, what should have happened instead, and why it matters. If you're uncomfortable with what you need to say, practice the conversation with another leader before you have it. Then have the conversation.


That's the part you can't practice your way around. At some point, you have to sit down with the person and do it. And afterward, you'll have one more experience to draw from the next time.


If there's a conversation you've been avoiding, our free Communication Clarity Worksheet can help you organize your thoughts and prepare what you need to communicate. Use the worksheet. Practice if you need to. Take a deep breath if that's what it takes. But then have the conversation.


Leadership Confidence Keeps Growing With You


You might think that after years of teaching leadership, facilitating conversations, standing in front of classes, and helping other leaders develop, I would be finished encountering things that make me wonder whether I can really do them. I'm not. The challenge just looks different now.


Recently, that challenge was writing a book. I had never written a leadership book before. I had years of experiences, stories, lessons, and things I wanted to share with new leaders, but having something to say and knowing you can turn it into a finished book are two very different things. Once again, I found myself doing something I wasn't completely confident I could do. So I started writing.


One chapter became another chapter. I kept working, rewriting, questioning, and moving forward. Eventually, all of those chapters became Let's Talk Leadership: Practical Mentorship for Leading People Well. The finished book isn't proof that I was confident enough to write one. It's proof that I was willing to begin before I was confident.


Today, I'm excited to share that Let's Talk Leadership is officially available. I wrote it for newer leaders who may be experiencing some of the same uncertainty I felt when I first walked into that bank branch, but it isn't only for leaders who are just beginning. It's also for experienced leaders who want to refresh the fundamentals, revisit practices that may have gotten lost in the demands of everyday leadership, or simply feel like they've plateaued and are ready to grow again. It's practical mentorship built from the lessons I've learned about the everyday work of leading people—building relationships, communicating, holding people accountable, making difficult decisions, developing employees, and continuing to grow yourself along the way.


And maybe that's one of the things I understand about confidence today that I couldn't have understood when I first became a manager. Leadership development doesn't eventually take you to a place where you'll never feel uncertain again. Instead, it gives you experience to draw from when the next unfamiliar challenge comes along. Whether you're stepping into leadership for the first time or you've been leading for years, there will always be opportunities that ask you to stretch beyond what already feels comfortable.


So think about something in your leadership that you've been avoiding because you don't feel confident enough to do it. Maybe it is a difficult conversation. Maybe you need to speak up, change an approach that is no longer working, take on a new responsibility, or try something you've never done before. Prepare for the things you can prepare for. Ask for help or practice when you need it. Then take the next step.


You don't have to wait until you feel completely confident to move forward. Confidence is built through experience, and experience only comes when we're willing to do the work. Sometimes you have to lead so that confidence has a chance to grow.



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