What I Learned from My Top Ten Leadership Mistakes

by Andy Wood on March 21, 2012

in Enlarging Your Capacity, Five LV Laws, Leadership, Life Currency, LV Alter-egos, LV Cycle, Pleasers, Principle of Legacy

There’s a well-known philosophy in some leadership circles that leaders never admit their mistakes.  This being an election year, you can expect to see that in full force.

The problem with that philosophy is that being in a position of leadership – formally or informally – puts you out in front of people where they can see your mistakes loud ’n’ clear.  So when you pretend you don’t have any, you look worse than proud.  You look rather stupid.

The biggest issue with mistakes in leadership is not whether you make them, but whether you repeat them.  Show me a politician, a corporate executive, a pastor, or any other form of “leader” who dodges the issue of failures, I’ll show you a leader destined to repeat the same mistakes.

On the other hand, if it’s true that being a leader means being “first learner,” then one of the best places to start is with your own lessons learned the hard way.  Here are 10 lessons I learned by getting it wrong before I ever got it right:

1.  Never separate yourself from your people at a time of crisis.

I did this twice.  The first time a bus filled with teenagers and sponsors broke down and I, driving a truck, was not available to help solve the problem because I took a different route to the destination.  The second time I walked off a job site I was supposed to be managing without calling for help – that one got me fired. People turn to leaders when bad things happen.  If you’re not available, they won’t be turning to you very long.

2.  People will forgive you for a lot – but they won’t forgive you for not understanding them.

I once brought in a guy to lead a retreat.  I thought he was awesome.  Funny, sharp, talented.  My people hated him.  Never connected at all with him.  Some of the toughest words I ever heard:  “If you don’t know your people any better than that, you may need to resign.”  Ouch.  Fortunately, I got ahead of that situation and lived to see another day.  But I learned my lesson (I hope).

3.  Nurse your wounds if you need to, but not too long.

Leaders are human and bleed when they’re cut just like anybody else.  And while people appreciate your honesty and vulnerability, at some point they expect you to “get over it” and move (lead them) forward.  One of my greatest places of ministry success almost became a bust because I nearly languished too long.

4.  Don’t jump too soon.

You’ll probably ignore this, but I’ll say it anyway.  Every “great opportunity” is not a “God opportunity.”  And just because it’s a little bigger, pays a little more money, or offers a little more authority doesn’t mean it’s from God.  If your work remains unfinished, consider sticking it out.  Never believe the lie that this will be your last opportunity for anything.  Opportunities are cheap.  Fulfilling potential and executing on the current opportunity is priceless.

5.  Nobody ever solved a conflict by trying to avoid criticism.

You can certainly avoid conflict situations.  But the minute you start leading humans, you start inviting conflict and criticism.  And if your only approach to dealing with it is to try to please everybody, the only thing that goes away is your influence.  Don’t invite conflict just for the sake of keeping things interesting.  But if you know it’s there, move toward it, not away from it.

6.  An isolated leader has a fool for a counselor.

The Bible makes it clear that isolation is for idiots. It is quite possible to live a very public life, yet remain complete isolated in the deepest parts of your life.  I know – I lived it and it nearly destroyed me.  In the Roman Catholic system, even the Pope has a confessor.  Every leader needs to have at least one, if not four or five, people in his life who ask the tough questions and question the tough answers.  My leadership has always been stronger when I had that, and caved in when I didn’t.

7.  Deal thoroughly and quickly with personal discouragement.

I have written on this before. Discouragement is spiritual cancer.  It spreads from one part of your life to another.  It will also spread from one part of your organization to another.  You may not think that your financial discouragement or your assistant’s marriage problems have anything to do with the performance of your organization, but they do.  And if you don’t take the time to aggressively deal with it (translation:  encourage), then like holes in a boat hull, it will eventually sink your leadership.

8.  One of your most important tasks is developing other leaders.

True leaders beget other leaders.  When you fail to do this (and I have), the leadership ends with you.  Think about it:  It took Jesus a matter of minutes to heal the sick or cast out demons.  It took him three and a half years to train 12 men to carry out His plan for the church.  Which do you think was more important to Him?  Leadership development is slow, demanding, and non-glamorous.  If you don’t have a plan for developing new leadership, then your influence ends with you.

9.  Nobody is going to ask you if you’re getting enough rest and renewal – it’s up to you.

Any worthwhile leadership endeavor will always take all you can give and more.  And pretty soon, unless you have a personal rest and renewal plan, you will be running on fumes – spiritually, emotionally, and physically.  That’s why the Bible spends so much space dealing with various forms of Sabbaths… and why you need to take them seriously.  That’s especially true if you’re engaged in a job or leadership task that you absolutely love.

10.  People will disappoint you and betray your trust – love them and trust them anyway.

I’m not sure I’ve learned this out of failure, but I certainly have out of experience.  The call to leadership is an invitation to pain and betrayal, power struggles and disappointments.  What?  You thought leadership was going to be easy because you’re, well, you?  OK.  Call me and let’s talk when you’ve stepped on a leadership land mine.  But let me urge you in the meantime – don’t take the betrayals and disappointments to heart. If you can lead difficult people without becoming bitter, if you can develop a thick hide but keep a soft heart, then you can lead for the long haul.  Otherwise, you’ll end up on the leadership trash heap because you took your anger out on somebody who didn’t deserve it – and you never trusted anybody to actually follow your influence.


I’m sure there are more – those are just the first that come to mind.  How about you?  What leadership lessons have you learned the hard way?  Feel free to comment below.

One thing I can attest to:  Leadership failures don’t have to be the end of the story for you.  There are lessons to be learned and more opportunities to follow.  All it takes is someone willing to admit, “I blew it.”

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