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The People Who Challenge You Can Make You a Better Leader

Writer: Ian Gregory
Ian Gregory
3 days ago
4 min read
Leader and employee discussing different approaches to work as part of ongoing leadership development.

When we struggle with an employee, our natural tendency is to focus on what that person needs to change. Why won’t they listen? Why can’t they follow the process? Why do they insist on doing things their own way? I’ve asked those questions more than a few times during my leadership career. What took me longer to learn was that sometimes the person who needs to change isn’t only the employee.


Earlier in my career, I thought passion would take me a long way as a leader. If I believed strongly in where we needed to go and what we needed to accomplish, I thought that would be enough to get people moving in the same direction. Over time, I learned that the trick isn’t getting people to do something because I want them to do it. Leadership is getting people to want to accomplish it themselves.


Some of the people who taught me that lesson were also some of the people who frustrated me the most. They challenged how I thought leadership was supposed to work. Looking back, I’m grateful for that. If everyone I led had responded exactly the way I expected, I might have spent a long time believing my way of leading worked for everyone.


Leadership Development Sometimes Starts With Frustration


I once had an employee I thought was lazy. He could be difficult to motivate, and he wanted to do things his way. I wanted him to do things my way. We were both stubborn, and that made for an interesting combination.


For a long time, I focused too much on how he was getting from the beginning of a task to the end. If he wasn’t following the path I would have taken, I saw a problem. Eventually, I had to ask myself whether his way was actually wrong or whether it simply wasn’t my way.

That distinction changed how I led him.


If the work was completed correctly, the quality met our standards, and it was finished within the required timeframe, I had to consider why I cared so much about the exact route he took to get there. I began to realize I was placing too much importance on the journey and not enough on the end result.


I didn’t need to lower the standard. I needed to loosen my grip on how he reached it.

That was a significant leadership development lesson for me because it required me to change something about myself. I had to learn to trust others like I trusted myself.


Leadership Development Requires Us to Adapt


If you are going to lead people well, eventually you have to accept that people are different. They don’t think exactly like you. They aren’t motivated by exactly the same things. They won’t approach every problem the way you would, and they may see possibilities you don't.

I had to learn that adapting my leadership to the individual wasn’t compromising. There is a big difference between compromising your standards and being willing to compromise on your preferred method.


Quality can be non-negotiable. Safety can be non-negotiable. Deadlines, customer expectations, ethical standards, and the desired result may all be non-negotiable. But once those expectations are understood, there are times when a leader needs to give people room to figure out how they can successfully get there.


That doesn't mean disappearing and hoping for the best. The conversations beforehand matter. Set the standards. Establish the goal. Make sure you both understand what a successful result looks like. Then follow up. Measure what is working and what isn't. If something isn't working, talk about it and make adjustments. The leader remains involved, but the employee has room to think, make decisions, and take ownership.


High Standards Don't Require Everyone to Do It Your Way


One of the hardest things for me to accept was that I didn't have the perfect way of doing things. Neither did the employee I was struggling with. But together, we could often find the best way. That required me to separate my preferences from the things that truly mattered.


I think that's a worthwhile exercise for any leader who finds themselves repeatedly frustrated because an employee won't do something the way they've been told. Before assuming the employee is the problem, ask yourself what you are actually holding firm on. Is it a standard that truly matters? Or is it the way you would do it?


If the employee isn't meeting the agreed-upon standard, address it. Leadership doesn't mean looking the other way when expectations aren't being met. But if the quality is right, the timeframe is right, and the result is right, it may be worth asking why the method matters so much to you. Sometimes we discover that we're not protecting a standard at all. We're protecting our own preference. That can be an uncomfortable realization, but leadership development isn't always comfortable.


Let Difficult People Develop Your Leadership


I wish I could tell you that every leadership lesson I've learned came easily. It didn't. Some of them came because I had people who frustrated me enough that I had to stop, think, try something different, and eventually recognize that my leadership approach needed to grow.

That's one of the reasons I believe leadership development doesn't have a finish line. You can have years of experience and still encounter someone who challenges the way you've always done things. The question is whether you see that person only as a problem to solve or whether you're willing to consider what the experience might teach you.


The next time you're frustrated with someone you're leading, take a moment before focusing entirely on what that person needs to change. Ask yourself a second question: What might this situation be asking me to change?


Hold onto your standards. Be clear about the result. Then be willing to trust people enough to let them find some of their own way there. Some of the people who challenge you the most may turn out to be the people who help you become a better leader.


Leadership development often happens through experience—especially the experiences that challenge how we think. In The Sweet Spot, Ian shares more of the experiences and lessons that shaped his perspective on work, leadership, purpose, and finding fulfillment along the way.


Want to better understand how different people communicate and approach their work? Explore our Communication Styles microlearning workbook in the LIA Leadership Library.



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