Painful Generosity (Or…How to Not Be a Greedy Leader)

Great leaders cannot be greedy.

Greedy Leaders

Giving is the most impactful and the most rewarding when it is most difficult.
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Notice that I did not write “good leaders cannot be greedy,” or that “leaders who happen to be at the helm of a great organization cannot be greedy.” Great leaders cannot, by definition, be greedy. That’s one reason why I’ve never been a great leader.

When I first became a leader at the ripe old age of 26, I had never known business success. I had never had a great mentor in the business world either. All I knew about business was that the purpose was to make money…at all costs. I was a greedy leader. The only thing that mattered was the bottom line. I wanted it all, the money, the fame, the awards, the Swiss bank accounts, but I did not care at all about what anyone else got from working for me.

Success was for me. Not for anyone working for me. I felt that way for years until I learned that my own greed was holding me back. I learned about the concept of painful generosity.

It had always been easy for me to give when things were going well.

Tell five team members they are doing a great job? Sure, I’ve got some time right now.

Write a check to a ministry? Sure, we had a great month. I’ve got plenty of extra money.

Write Christmas cards to ten clients? No problem. My meeting cancelled and I can hammer those out right now.

When giving was easy, I did it well. Whether it was my time, my money, or myself, I gave freely when there was no pain.

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However, I’ve found that giving is the most impactful and the most rewarding when it is most difficult. (Click to Tweet)

When your business had its worst month, everyone knows it. That is the time to take the team out to lunch.

When you’ve only got five minutes today, but you scribble out a meaningful thank you or congratulations card to a team member, they notice it.

Or when you’re like the widow in the 30’s (as in AD 30-ish) who put two small coins into the synagogue treasury when that was all she had and cause  the angels of heaven and Jesus in human form rejoiced on earth. That is when rewards flow and our hearts are full.

Leaders must let go of all greed. Leaders must surrender their right to their time and recognize their team’s needs first. Leaders must give when it hurts and if they feel no pain, give until they do.

If you are quiet and reserved, learn to be outgoing in your praise. If you are short on time, find someone to mentor. Write thank you notes until your hand cramps and your pen runs dry. Then write one more (you can get a new pen). And on a personal level, find a worthwhile charity and write the largest check you have ever written.

Leadership is hard. It is sometimes painful. So is generosity. They go hand in hand.

Be a generous leader. Give until it hurts.

Question: What is the best example of a non-greedy leader you have seen? You can leave a comment by clicking here.


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  • People who can put aside their own stuff and nurture others? I’d have to say that the best examples I can think of aren’t business leaders.

    They’re moms.

    • Well said Bret.

      Just like my wife who gave up a career and lifestyle to raise our daughter. Every day she sacrifices adult communication, financially, and emotionally to do what is best for our daughter, who is reaping the rewards.

      All moms, stay-at-home or otherwise, pretty much rock.

  • So LOVE this post. Generosity is not if it doesn’t hurt. If you give from what you have left over, you’re no better than anyone else. THANKS for this great reminder.

    • If you give from what you have left over, you’re no better than anyone else.”

      That is powerful! Wow.

  • wow – powerful stuff. Really makes me stop and think – not sure any of the leaders I’ve had fit this bill. And I’m not sure I would fit in that category. Need to really work on that. Great post!

    • Glad I made you think Carol. As I wrote it myself, I was like “oh man I failed here, here, here, and here…today” haha

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  • Ouch! It hurts to know that I haven’t done that. Just like Carol, “powerful stuff”. Very motivation to push a little hard so I can give even more.

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