10 Team Leadership Lessons I Learned the Hard Way

I wasn’t a leader of any sort of team when I was growing up. I never captained sports teams at school, I was never a prefect in High School, I didn’t even find a way to lead the band I was in even though that band only had three members. To be fair, drummers seldom lead bands to good effect, but the point is that I was mainly a follower of other leaders. Until, as a pastor, I got given a staff team to lead. I had studied some leadership principles and read some leadership books, but nothing really prepped me to lead other people so closely in pursuit of a mission. I had lots of critique that was readily available for other leaders, but not much experience or expertise on how to do it well myself. What follows then are ten principles of team leadership that I have learned over the last decade, and as the title suggests, these were learned through the hard lessons of disappointing people and then just trying again. In other words, I failed in these areas, and so learned more through failure than through success, which is how a lot of learning seems to happen. I hope they are helpful.

1 – Conflict Delayed is Conflict Doubled

I don’t like conflict, but I have learned that it only gets worse when you know that it needs to happen and you delay it happening. We expect time passing to diminish the conflict, but it usually doubles it. It has also been my experience that the actual engagement is seldom as bad in person as you fear it will be, and so I try to handle all of these scenarios in person. People will say stuff and posture in a way online or on text or via email that very few will do face to face. People are more nuanced, more conflicted, more doubtful, more gentle, more human in person. Don’t delay, go have the chat.

2 – Clear and Constant Communication Builds Trust

People need constant input and communication. The difficulty is that as a leader, you have been living with and thinking through things organizational issues, plans and visions and so you expect people to buy into them after you have spoken to them once about it, when you may have been thinking through these things for months. The old communication adage: “Tell them what you are going to tell them, tell them, then tell them what you told them” is true and probably isn’t even enough. Communicate clearly and repeatedly, and know that leaders create lag and so it will take a while for things that are intuitive to you to sink in for others. In the absence of clear communication, your teams will create their own narratives of what is actually going on, and once those exist they are almost impossible to eradicate. Shape the narrative, invite people in, tell people more than you think you need to tell them. The clearest communicator gets the most loyal team.

3 – Decision Fatigue is a Real Thing With Real Consequences

It turns out that calling the shots is kind of exhausting, and so leaders can hamstring teams when they experience decision fatigue and still have people waiting on them for decisions that would free them up to move forward. There are a few ways around this. First, delegate as many decisions as you can away from you. You may get this wrong and need to take some back, but give people enough rope so that you aren’t making every call. Second, give and get clear deadlines on decision, and give yourself enough runway before the deadline. High pressured decisions that you have to make on the spot can be the straw that breaks your back. Third, put dedicated space in your schedule for thinking. We live in a very stimulated age, and so time with devices away and interruptions unlikely allow the time to think through some of the appropriate input needed to make sound decisions.

4 – Leadership is Lonely, So You Shouldn’t Do it Alone

It is a lonely journey, and that is the reason you need other leaders around you making sure you don’t get isolated. Find some peers who understand the pressure you are under and journey with them. Better yet, bring some leaders to the table with you and let them share the burden. I have found that the dynamic changes with people when you let them feel the weight of leadership. Some thrive, some flounder, but all have a better understanding. Don’t lead alone.

5 – Not Everyone is Gonna Like You, But You Should Still Be Likable

Leading as a people pleaser is going to exhaust you. I said when I first stepped into leadership that if people didn’t like me it was fine and that they could leave. Then some didn’t like me and did leave, and it sucked massively and seriously smashed my confidence. It is true though that some people just won’t appreciate your decisions and won’t like your style of leadership. Don’t be a jerk, and still be likable, but don’t lay down the work in order to try to persuade people to like you.

6 – Sometimes People Just Need to be Heard

I am primarily a preacher and so my tendency is to think that the best way to change people and the best way to fix brokenness is to speak to it, to shape it through my words. What I discovered in team leadership is that some people just need to be heard, and need to feel heard. This was difficult for me because it meant listening to some things that I thought were irrational or unreasonable, but in the process of hearing them two things happened…I became more empathetic towards the struggle of the person, and the person felt heard and so became less irrational and unreasonable. Listening is a currency of sort and very few people are rich in that currency. In a world where we are all distracted an attuned ear is a loving act that yields lots of fruit. Hear from your team.

7 – They Might Be Struggling to Understand You, Because You Haven’t Tried to Understand Them

I lead in a way that I would like to be led, but not everyone wants to be led that way. I like a big picture vision and then to be left to go pursue it without interference, but that is terrible for some people who need structure, guidance and clear expectations at different points in the process. That sounds like hell to me, but that helps others thrive and that is kind of the point. Take the time to understand your team and what makes them tick and you will get much more out of them. Some need lots of affirmation, some not. Some like pressure, some like space. Figure it out. Also know that you will have varying levels of capacity and capability on your team and you shouldn’t expect everyone to carry the same load or to run at the same pace. Keep everyone accountable to their expectations and monitor that regularly with accountability but don’t drive everyone with a single set of expectations. It won’t work.

8 – Have Fun AND Get it Done

Your people will catch productivity and positivity from you. Try to be a good mood architect and good example of hard work. We tend towards one of those things but a good team leader can and does do both. If it is always just about productivity, then the place will feel heartless and hopeless. If it is all about goofing around then people will feel rudderless. They will be looking to their team lead as the one who sets the pace of productivity but who also sets the culture of hopefulness and fun.

9 – Anyone Can Create Workers, but Real Leaders Create Other Leaders

The real success of your leadership will truly only be known when you are gone. Having recently transitioned away from a team and to a new one, I know that the work that I did while on that team is now only evidenced in the leaders I left behind. Don’t be threatened by other leaders in your space, be excited. Give them space, develop them heartily, and let them lead. This won’t make you look like less of a leader, it will actually show your true leadership capacity. It is easy to get people to implement vision that only you can see. It is harder by far to release leaders to start to pursue vision that you cannot yet see. But why would you want to pursue something so small that only you can see it?

10 – Embrace the Kingdom Principle of Leadership

Jesus taught about leadership greatness in Matthew 20. The mom of James and John was hoping that her boys would get some much needed leadership recognition. Jesus said:

“You know that the rulers of the Gentiles lord it over them, and their great ones exercise authority over them. It shall not be so among you. But whoever would be great among you must be your servant,and whoever would be first among you must be your slave, even as the Son of Man came not to be served but to serve, and to give his life as a ransom for many.” – Matthew 20:25-28 (ESV)

In secular society, great leadership will get you more removed from your team. In the Kingdom it will press you deeper in. In the world it will get you tons of recognition, in the Kingdom it should get you lots of anonymous serving. In the world it will mean gaining the good life, in the Kingdom it will require giving your life away, again and again.

There are many things I have learned, but haven’t crystalized yet in my mind. What a privilege it is to lead a team of image bearers with so much potential. My prayer is that I steward that responsibility well, and that I teach others that I lead how they can do that too.

Press on.

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