Top Three Things I Would Do Differently as a Leader

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.

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.

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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 in 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.

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

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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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  • Great post, Matt. I love the transparency here. When so many people are shouting, “Go faster!” or “Give me a leadership role now!” it’s refreshing to hear someone say slow down.

    Leadership is difficult. We’ll never be perfectly prepared for leadership and will alwas have to learn from mistakes on a daily basis, but one thing is for sure: those mistakes hurt more than ourselves. Putting the people you lead ahead of yourself is key, even if that means someone else should lead them.

    When I first applied to work at the Lampo Group, they tried to put me in a leadership role. Thankfully, through their interview process, it became clear or wasn’t a fit. I needed to grow. A year later, after soaking in that culture of leadership, they moved me to a new leadership position. I’m so thankful for that year to learn and make mistakes without those mistakes hurting others.

    • Dude. As usual, they showed awesome leadership at Lampo by not putting you in leadership.

      This is an incredible quote: “Putting the people you lead ahead of yourself is key, even if that means someone else should lead them.”

      Totally tweetable :)

      Thanks for sharing Luke!

  • I stayed out of town on 9/11 to run a sales call. I would have went home to comfort my wife.

  • What a great post!! I can very well relate. I was offered a leadership role when I was 28 and pretty much the same story. I wasn’t a “punk with no prior leadership experience and no training at all”, but I did have little experience and little training. I crashed and burned. It was BAD! I was definitely not the right choice for the job, so much so that I only lasted 6 months in it. First and last time that’s ever happened to me.

    I think ego gets in the way and you think you’re a hot shot because they’re asking you to do it. However… I can say I’ve been through it and help others not make the same mistake.

    • LOL at ‘I wasn’t a “punk with no prior leadership experience and no training at all”‘

      The good thing is that you learned from it. Your leader set you up for failure. Of course, you had the option to turn it down but very few people do that and a good leader knows better. That is why I like the comment from @lukestokes:disqus so much. Both he and his leaders knew the timing wasn’t right.

      Now you are ready though!

  • Oh man, I wish I could go back. I would have found a mentor. Actually I’m still looking for one.

    • Me too Jim. I am close thankfully but still not fully there on that search.

    • I’m right there with you Jim. I’m searching now as well. It’s tough, isn’t it?

      • As we say in Boston – Wicked Hard.

  • There’s so much I could have learned about leadership. I started in a leadership role at 16. I became a Crew Trainer at Hardees. Six months later I became a Shift Leader (supervisor). By 18, I was an Assistant Manager. By 19, they would have made me a General Manager if I didn’t go off to Bible College.

    I didn’t really know what leadership was. I knew how to work hard and get the job done. I could to administrative stuff. I could schedule and organize things. Delegation – had no clue.

    • Wow Joshua. At least you got some on the job training :)

      It has been said so many times by others but one of the biggest mistakes owners/leaders make is making the best/smartest/longest serving person in a job the leader.

      Just because you are the best fry cook, does not mean you have the skills to lead twenty fry cooks.

  • Dude, #1 is spot on! Why do we always have to be on some stupid fast track before we’re ready? I tell people now, that their first 10 years shouldn’t be about $ or position… It should be about becoming.

    Matt, tell Doc to fire up the Flux-Capacitor! That is a tempting thought isn’t it? I’ll pass on the do-over, though. We have done exactly as we were supposed to do to be who we are supposed to be right now. The toughest part of that is regret and forgiving oneself. Regret is destructive. Sure, we would all like to go back (me, more so for other people that I didn’t serve well than myself) but we wouldn’t have Earned our lessons. Still, I would have been Me Now sooner if I had just become Me Now sooner.

    • Nice Jeremy.

      Unfortunately we had the same philosophy as so many companies: Well, you are the first hire and now we hired two more, so you should probably be promoted to manager. Dumb.

  • The thing I would do differently that I still struggle with today is that I would not try to do so much myself. I am not a good delegator, and many times feel (wrongly) that it’s quicker and easier to do it myself, when I need to be training and trusting other team members instead. Not only does that lead to me being overwhelmed, but I am not empowering my team. thanks for the great post.

  • I would be more intentional in finding a mentor.

  • I wouldve stopped trying to teach people things I didn’t learn myself. You read something out of a book and you want to share it with people. I did that. The problem was I didnt learn what I was trying to teach. But that’s just me 😉

  • Chance Smith

    I know that when I hire my next leader I will guide them into a leader first. The role does come with mistakes and experience, but I think a lot of mine could have been avoided too.

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