Forgiveness and Leadership

By Drew Dudley

Updated Over a Week Ago

Minute Read

I’m almost 36 years old, and I’ve been to the funerals of 15 of my friends. I’ve been to only six weddings.

I’ve learned a lot from the people I’ve lost.

When I was 19 years old, my parents let me host the last-day-of-school party (the one that’s been recreated in countless high school comedies) at our place on the lake.

I remember leaning against the cottage, snapping a photo of two of my friends as they snuggled watching the sunset, and lamenting out loud how I didn’t have someone special in my life.

My friend Scott, one of those musicians/athletes with the perfect left-brain/right-brain balance, sat quietly next to me for a moment before saying, “Drew, for a guy who has a lot going for him, you spend a lot of time talking about the things that you don’t have.”

The Person You Are

Too young to recognize the value of a friend who tells you what you need to hear instead of what you want to hear, I shot back:

“You just think I have a lot going for me!  You don’t know what it’s like to have all this pressure! To have everyone telling you how much they expect you to accomplish in your life!  You don’t know what it’s like to try to live up to what everyone wants!”

Scott looked at me for what seemed like an awfully long time.  Finally, he said quietly,

“Drew, you don’t give your friends enough credit.  We don’t care about you because of the guy that you might become one day.  We care about you because of the person you are now.  You should try doing the same thing.”

A few weeks later, Scott was rear-ended while driving our friend Tim to work.  Both of them were killed instantly.

Leaders of the Future

Profoundly Valuable Lessons

When I got a job at my university bar, a young man by the name of Jason Abraham worked with me on Tuesday nights. He was tremendously well-liked on campus, and I asked him once why so many people seemed to be drawn to him.

With a laugh, he told me, “I just try to avoid doing things that might cause me to have to say ‘I’m sorry.  I’ve found the best way to do that is simple: every time you talk about someone, act as if they’re standing directly behind you.  Your life gets exponentially better.”


In late February of 2000, Jason was diagnosed with stomach cancer and was gone less than a month later, a few days short of his 24th birthday.

Never diminish the person you are in the name of what you hope to become. Speak of people in such a way that you’ll never be ashamed to know that someone has heard.

These are two profoundly valuable lessons I learned from friends who never got to become the people they were supposed to be.  The thirteen others that were taken too soon left me with equally important insights that shape me to this day.

I share their wisdom wherever I can, especially to remind young people to avoid a mistake that I made: assuming that their value to the world can only be delivered “one day” instead of today.

No Universal Measuring Unit for Pain

Recently, after a presentation where I shared some of these stories, a young woman approached me.

“Drew, I just wanted to tell you how much I enjoyed your presentation,” she said.  “And to let you know that I feel terrible for all of the pain you’ve gone through in your life.”

We began chatting for a few minutes, and she started to share some of her own powerful stories.  She was an international student studying in British Columbia, but before she had come to Canada, the war in her home country had forced her family into a refugee camp, where she lost both her parents and her grandparents to illness.

Stunned, I asked her, “How can you say you feel terrible for the pain I’ve had in my life when yours so obviously dwarfs mine?”

“Well,” she said, “I’ve discovered that there is no universal measuring unit for pain.  The Hurt just hurts.  So why bother comparing it?”

“The more important lesson I’ve learned about pain,” she continued, “is that only hurt people hurt others.  So if I want to be the type of person who does not hurt others, I have to let go of the things that have hurt me.  I have to heal.”

Only Hurt People Hurt Others

On the plane home, as I thought about that conversation, I realized the profound implications of accepting that fundamental truth: leaders must heal in order to lead.  We have to let go of the things that have hurt us to ensure that they don’t rise up and cause pain to someone else.  I realized that meant that leaders have to forgive.

Forgiveness can be tremendously difficult. The reason that we allow so many conflicts to go unresolved is that we want to win.  We feel as if someone has wronged us in some way, and though the continuing conflict sucks value from our lives, we’re not willing to finally put it to rest or forgive until someone acknowledges that we were right.  That we rightly “won.”

The most inspiring leaders I know aren’t interested in winning—they’re interested in succeeding.  I think it’s crucial to remember that sometimes success is not possible if we insist on winning.

There is no weakness in forgiveness. In fact, I think that leadership often begins only where forgiveness begins.

Healing Leadership

Having lost so many people in ways that I could not control, I now tell anyone who will listen that if you can save a relationship, business or personal, simply by saying “I’m sorry” or hearing “I’m sorry” (and the latter is often harder than the former), do it.  The fact is that most people reading have someone who is no longer in their life which they wish still was. Often, the only reason they’re not still in your life is that you haven’t been able to say “I’m sorry” or hear “I’m sorry.”

And guess what? That’s making you a less effective leader.  I’m not saying it’s making you an ineffective leader – but it is making you less than what you could be.


The difficulty for me? I’m not good at forgiveness.  As I sat on that plane flying home, realizing that I could never be the leader I wanted to be without letting go of some of the things that have hurt me, I was rocked by the fact that I simply couldn’t do it.  There were certain people I wasn’t yet ready to forgive, certain feelings I couldn’t yet let go of, even though I knew I had to.  That remains true to this day.

I’ve shared this idea in a number of places and have often been told that this is a common problem: forgiveness isn’t something we can always just “do.”  Recognizing its importance is one thing, but acting to make it a reality is another.

The fact is, this article isn’t intended to tell you that you need to let go of everything that’s ever hurt you and everyone who has ever wronged you right this moment.  However, we need to recognize just how profoundly important it is and to try to do it as soon as possible.

How important it is to ask ourselves each day, “Am I ready to forgive?  Am I ready to make myself and my life better?”

Questions Are Powerful

The answer may not be yes today. It may not be yes tomorrow. It may not be yes for a long, long time.

I am convinced that recognizing the importance of the question is a crucial step in leadership.  I believe that the answer to a question asked every day will come faster than to a question asked every week, month, or year.

Questions are powerful in leadership.  Oftentimes, they don’t bring us answers, and they remind us of the importance of seeking them.

How Has Forgiveness Helped Your Leadership Skills?

If you have ideas you feel like sharing that might be helpful to readers, share them in the comments section below. Thanks!

Would you like to contribute a post?

Drew Dudley
Drew Dudley
Drew is the Founder and Chief Catalyst of Nuance Leadership, Inc., and the former Coordinator of one of Canada’s largest leadership development programs at the University of Toronto.
  • Ramdeo Choudhary says:

    Forgiveness is a virtue which has to be cultivated through practice under scriptural guidance. It is not for week, strength is needed to exercise this virtue. Strength of mind has to be subdued under Strength of heart and it’s wisdom. Consciousness levels have to be transcended by meditation practice to tap into the vast treasures of Heart.

  • Bill Matthies says:

    “I’ve learned a lot from the people I’ve lost.”

    Yes you have Drew and because you have you haven’t really lost them.

  • Sonya DeBurr says:

    Thought provoking…

    I agree that you must be able to let go in order to move forward.

    I believe that when you implement the lessons learned from people who have left us, you honor them by allow them to continue to live through you. This is particularly true when the lesson is one that is a significant challenge for you.

    I feel that leadership is the ability to genuinely learn the hard lessons, be brave enough to be vulnerable, guide others through example and offer others the freedom to take the lead.

    I heard somewhere, “You’re not leading if no one is following, you’re just taking a walk.” You have to learn and grow in order to teach, coach then cheer.

    Great piece Drew … thank you for sharing.

  • Nick Wright says:

    Hi Drew and thanks for sharing these reflections. I like your comments about the relationship between leadership, healing and forgiveness. Very moving and real. With best wishes. Nick

  • You ask powerful questions, Drew. It seems to me that the essence of your questions around leadership come back to “Who are you BEING as a leader?”, rather than “What are you DOING as a leader?”

    You draw a powerful link between healing, forgiveness and leadership. What’s less explicit in your post is the importance of self-forgiveness…. because usually where we struggle to forgive others is a kernel of something within ourselves that we have not yet forgiven.

    Thanks for your words, your thoughts and your leadership – I look forward to reading more.

  • Rose Green says:

    Really powerful and challenging article.

  • Cardrienne says:

    Hello Drew, Thank you for your transparency. This is an amazing article. Forgiveness is a process. However, it serves to enhance one’s credibility as a mentor, coach and leader. a I look forward to reading future articles.

  • Mark Foss says:

    Your observations about how we view ourselves today and how we talk about others are spot on. I like your observations about forgiveness.

    I also struggle with forgiveness for some very old wounds. I would like to add to your comments the idea that forgiveness for serious repeated or deep offenses is an on-going work. It isn’t a one-time choice. It is a path to be walked. It isn’t a single event – a conversion. It is a continuous choosing to release that person from my personal judgement and to treat them better than I was treated. Essentially, the practice of forgiving lances the infected wound and continually drains its poison.

    Thanks for your article. It spoke deeply to my heart.

  • David McCuistion says:

    Drew: Thank you for the enlightenment in the is article.

    Greenleaf talked about healing in his Servant Leadership writings. I found a comment in the article most telling:

    “The more important lesson I’ve learned about pain,” she continued, “is that only hurt people hurt others. So if I want to be the type of person who does not hurt others, I have to let go of the things that have hurt me. I have to heal.”

    Leadership that is focused on others can result in a healing also. In “Leading With Soul”, Boleman and Deal talk about the healing that comes from leading with soul.

    I think you have experienced this by the writing above. Keep the Quest Alive.

  • Michele Leamon says:

    Hi Drew. I heard of you from the Langer family. Erin is my daughter in law.
    i just read your article and am truly inspired. I have a family situation that is currently causing much pain and hurt for me and my siblings. I am a forgiving person and you are right on the mark. I am having trouble forgiving someone in my family. I know i will forgive that person, but I also know my pain will continue until I do. And as you said, sometimes forgiveness takes longer than other times.
    Thank you…

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