In my last post, I touched on the importance of knowing when it’s time to move on from an environment that isn’t working. At the same time, difficult situations can teach you things that are hard to learn any other way. Some of the best leadership lessons I’ve learned have come from working for poor leaders.

I’ve had bosses who were judgmental and bosses who provided almost no direction at all. Each experience taught me something about the kind of leader I wanted to become.

Here are a few of the lessons I’ve carried with me.

1. It’s All About Me

I once knew a Chief Development Officer who had about 500 donors in his portfolio.

That sounds impressive until you realize he only had the bandwidth to manage about 75 of them well. He hoarded donors, particularly the top donors, because having a large portfolio made him feel important. His bragging created jealousy and friction among those working under him. Eventually, it contributed to significant staff turnover.

His approach to leadership reflected the same attitude. When employees had one-on-one meetings with him, he required them to be escorted into his office. He wouldn’t enter a staff meeting until everyone was already seated. At the time, I remember thinking his actions made him seem selfish and insecure. That “honor the king” attitude feels demeaning as an employee trying to do their best. It may elevate the leader in his own mind, but it does nothing for the organization.

Beyond that, his portfolio was essentially wasted. He had contact with hundreds of donors, but he certainly couldn’t steward those relationships effectively. The potential for generosity was enormous. Production, however, was less than average as one person clung to far more than he could reasonably manage.

Pride gets in the way of good leadership. When leaders value status over mission, they begin making decisions based on what makes them look important rather than what helps the organization succeed.

My dad used to tell me that 98% of people go to bed at night starving for recognition. I’ve thought about that a lot over the years. I never saw that development officer encourage anyone. That experience shaped my own thinking about leadership. I want to be an encourager and a supporter.

Most of the successful people I’ve worked with have been genuinely good people. They understand that their success doesn’t require everybody around them to be smaller. They recognize others’ contributions, share credit, and help the people around them succeed.

A rising tide lifts all boats.

If I have 500 donors in my portfolio but only have the time to develop 75 relationships well, I’m not accomplishing anything by keeping the other 425 names to myself. The organization would be better served by sharing those relationships with people who have the time and ability to cultivate them, even if that means I wouldn’t get the credit.

Leadership should make the whole organization stronger.

Leadership should make the whole organization stronger.

2. You Can’t Lead If You’re Still Following

When I was completing my dissertation, I learned that the most successful organizations had two things in common: a systemic approach and high accountability.

On the flip side, many organizations experiencing mediocre results were blinded by short-term thinking.

That taught me something important about leadership. You cannot lead effectively if you are constantly reacting to whatever happens to be in front of you. If you enter the office each morning and start to make a plan for what you want to accomplish that day, you’re already behind. You can’t lead if you’re still following.

The best organizations start planning for the next year in November. They determine what their touches with each donor will look like, when those touches should happen, and what type of visit is appropriate. Once the plan is in place, the work becomes execution.

That was especially clear to me in my first fundraising position. My supervisor gave me little direction or accountability. I was essentially handed a group of donors and told to go get them.

If I hadn’t been driven, the results would have been extremely poor. Instead, I set for myself daily, weekly, monthly, and annual goals. I learned that what you measure improves, but measuring something that hasn’t been planned doesn’t accomplish much.

Plan. Measure. Evaluate.

That rhythm informs how I lead today. When I give someone an assignment, I set clear due-by dates and expectations. Then I let them do their job.

Good leaders don’t think for those they supervise. More often than not, the person closest to the situation has a better understanding of what will actually work. My job is to establish objectives. If I have a strategy in mind, I want their input. That is our job together. Strategies have to be realistic. If they are developed in a vacuum, they probably won’t be.

You can’t hold somebody accountable for an expectation you never established.

There is a balance between providing no direction and micromanaging every detail. Long-term thinking helps you find it. Direction with delegation allows people to use their own judgment while still understanding where they are going.

When expectations are clear, you can evaluate whether the work is getting done and, if it isn’t, determine why. Without a plan, accountability becomes much harder. You can’t hold somebody accountable for an expectation you never established.

3. Accountability Should Educate, Not Punish

The best boss I ever had was highly skilled in pointing out your successes. People loved working for that man. He still held people accountable, but it was never primarily punitive.

What went wrong? How can we remedy the situation? How can we avoid this mistake going forward?

He wasn’t looking for wrong-doing. He was looking for ways to help people be better.

I had another boss who was judgmental and critical, and I watched people become afraid to do anything because they were afraid of what would happen if they made a mistake. When people are afraid of making mistakes, they stop taking initiative. Eventually, they stop bringing you problems, too.

The biggest lesson I learned from judgmental leaders was that I didn’t want to be like them.

When I’m gone, I want people to say, “He was the best boss I ever had.” That’s a big motivator for me.

As Michael Scott from The Office said, “Would I rather be feared or loved? Easy. Both. I want people to be afraid of how much they love me.”

Michael’s heart was usually in the right place. He was certainly an encourager. His problem was that he sometimes confused encouragement with avoiding hard conversations, and good leadership requires both.

People need to know when they are doing something well, and they need to know when something needs to change. The goal of accountability should be improvement, not humiliation.

When people know that mistakes will become opportunities to learn, they are more willing to take responsibility, tell the truth, and try again. That’s how failure turns into progress.

Be a Leader in Any Position

If I found myself working under poor leadership like I did early in my career, I would handle it differently today.

When I was younger, I was afraid. I went along with things because I felt insecure. Now that I’m older and grumpier, I would sit down with leadership. I would tell them what I was seeing, explain how it was affecting my work, and give them an opportunity to respond. Then, I would give them some time and see whether anything changed. If it didn’t, I would leave.

I’ve learned that I can’t change what I don’t know. As someone who now sits on the other side of the desk, I want to have the opportunity to improve. You have to give people a chance to change.

Leadership isn’t limited to those with “chief” or “director” in their title. You can be a leader from any position in an organization. You can encourage the person beside you and tell the truth when it would be easier to stay quiet. You can make the people around you better.

And if you find yourself struggling to find your footing in a position of leadership, remember that you’re not as important as you think. Worry less about yourself and more about others. That shift is humbling, but it’s freeing.

We’re in a relationship business, and that applies to those we work with just as much as it does to our donors. Kindness is one of the greatest keys to success. Doing unto others as you’d have them do unto you makes practical business sense. And it doesn’t hurt that it makes people feel good, too.

People work harder for leaders who recognize them. And when you help other people succeed, you usually find that you succeed right along with them.

People work harder for leaders who recognize them. And when you help other people succeed, you usually find that you succeed right along with them.

©2026, Eddie Thompson, Ed.D., FCEP
Founder and CEO, Thompson & Associates

“If we merely aim for the industry standard, then our goal is mediocrity. Emulating the average nonprofit, we are destined to live with all the problems the average nonprofit faces. So, we suggest you aim to be exceptional in your approach to fund development.”