What three things would you do differently as a leader? That was the question posed to me from a good friend of mine. Three years into our business, we had more than fifty team members and were on pace to have more than $18 million in revenue in year four. It was a wild ride but I left knowing that I had made numerous costly mistakes.

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So when he asked me this question, I had no shortage of things I would have done differently. The hard part was narrowing it down to three.

Within seconds, though, the answers became clear…and surprising to me. They had nothing to do with strategy or specific moments in time. Nothing to do with bad hires or bad financial moves. Nothing at all to do with marketing or our IT infrastructure. Those were easily identifiable areas where we made mistakes and that had tangible monetary losses attached to them.

My three things all go back to the very beginning. As a future leader of the company, I would have done these three things differently.

1. I would not have become a leader when I did.

How is that for a leadership decision?

We went from just three of us (two partners and me) to four other people. Real people with real problems, real needs, and in need of real leadership. And I was the one expected to lead them. Ha!

I was not prepared for leadership. If I could go back in time, I would have demanded that I not be put in a leadership role then. If that meant we didn’t hire anyone for a while, so be it. If it meant that the owners had to step in and work part-time from our office, so be it.

Don’t get me wrong, I am not suggesting that I would have stayed out of leadership forever, but when I was a 26-year old punk with no prior leadership experience and no training at all, I was clearly the wrong choice.

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2. I would have asked for a lot of training and passed it on.

If I could go back in time, I would have made sure that all of us leaders would have gotten more training. I would have become a dedicated student of leadership long before I ever became a leader. Instead of struggling to keep up and always working from behind due to the mistakes I had made, I would have made sure I was fully prepared to be a great leader.

Then, and only then, would I be in a position to lead effectively and pass it on. I would have made sure we developed leaders around us as well.

3. I would have made sure my personal life was in order.

When I assumed a leadership role for the first time, I was a wreck personally and it handicapped my leadership abilities.

My anger problems did not magically disappear when I walked through the office doors each day. My rageful acts nearly destroyed our company early on and nothing short of the hand of God held us together in the first year. If I could go back in time, I would have focused on getting the help I needed then, long before I assumed such a high pressure role. The lesson I learned here is that I should never have waited until my rage had shown up five times or even one time in the office. I should have addressed before it showed up.

When I finished telling him these three things, I explained how these three changes would have impacted everything that happened in our company. We would have spent less time dealing with complaints about me and more time working on the business. We would have developed a culture of leadership and created a much better work environment.

What would the results of those differences have been? Who knows? But I have to think it would have helped the business.

The great thing about this is that I will never make those same three mistakes again and hopefully neither will you.

If you could go back in time, what are the things you would do differently as a leader (at work, at home, or anywhere)?

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10 thoughts on “3 Things I Would do Differently as a Leader – #1 Might Surprise You

  1. Let's Grow Leaders says:

    Oh great. I’m getting ready to go on stage and now all I can think of is that Cher song… thanks, Matt 😉 I love your disclosure and authenticity in this post. Every time I move on to a new gig I take time to write down my key learnings from the last assignments. It’s such an important exercise… and I share it with my team.

    Here’s my latest reflection … perhaps it can save someone some time 😉


    1. Matt McWilliams says:

      I can’t stand the song, but it seems I get it stuck in my head at least once a month myself. Today will be that day in July I guess 🙂

      #4 and #9 are powerful on your list. I learned them WAY too late and spend more time than I should have to making up for them.

  2. Steve Daniel says:

    I think my main regret is starting my first company out of desperation. I was just trying to survive financially and the company I chose to work for did not make that possible. I loved the company, so I made up the difference by creating my own company. I think instead I would have taken one of the other opportunities offered to me by another company, and have a secured paycheck instead of scraping through on a full time and part time job long before I was ready to actually lead. Don’t get me wrong, I learned a lot, but it cost a lot more than I could really afford. Thankfully my employees were my brother and best friend. Forgiveness from them was easy, thank goodness that it the only ones I had hired. Since then, I have quit chasing paychecks and started chasing my calling and that is what has made the difference in my life.

    1. Matt McWilliams says:

      “I have quit chasing paychecks and started chasing my calling and that is what has made the difference in my life.”

      That is the key that, sadly, only a small percentage of people get. Glad for you Steve that you did.

  3. Tim Gradoville says:


    I enjoyed reading your post, especially because you discuss your weaknesses and what you’ve learned from them which is rare in this day of “put your best face forward online”. One thing I do want point out is sometimes we are thrown into situations like the one you mentioned in this post to prepare us for what’s in store down the road. God allows us to go through some challenging, difficult, and sometimes painful times in our lives for what can be several things. One is to get our attention and other times it’s to mold and shape us for something bigger in the future. Ask yourself: would you be the leader you are today if you didn’t go through those early struggles as a leader after being put in the position a bit earlier than you wanted? I know it wasn’t ideal for the company early on and took some financial hits because of it, but may have been a valuable learning experience for all parties involved. Great post and this will help people in leadership positions and those thinking about leadership positions to learn from from your experiences!

    1. Matt McWilliams says:

      Good points Tim. I’d like to think that I am better for my errors, but at the same time I was playing with people’s livelihoods so even if I am a little better, I’m not sure it was worth it (for them) 🙂

      I don’t think we can ever better truly ready to lead 20 people when we’ve never led a soul. Sometimes we screw up. If I had to add a #4, it would be that I would have admitted to my team that I wasn’t fully prepared and asked for more forgiveness.

  4. Zechariah Newman says:

    Great post Matt. I did alot of damage early on in leadership. Everything negative that someone did was disrespect in my eyes and I would get angry quick. It is funny that the less I care about if someone respects me the more respect I get from those I lead. Servant leadership does not come easy or natural but it is worth it:)

  5. Joseph Lalonde says:

    I would have begun preparing for leadership sooner.

  6. Joshua Rivers says:

    My first leadership role was as a shift leader at Hardee’s when I turned 17. A year later, I became Assistant Manager. I acted more like a glorified team member than a leader. I didn’t have a grasp of delegation. I knew I could do the tasks quicker and better than the others…so I did. I eventually learned how to delegate, but I had trained my team that I was “supposed” to do it. That would be one thing I would change.

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