Highs & Lows of Leading a Team

“I have up and down weeks. This week, I feel like I’m doing pretty shitty.”

I recently had a 1-1 call with another lead from Automattic. We routinely pair up with other leads for several weeks at a time to learn and share with one another. In this particular call, we were talking about the emotional rollercoaster of leading a team.

One week, you’re crushing it. Goals are moving in the right direction, and everyone on your team is rockin’ and rollin’.

A few short days, hours, or even minutes later? You’re failing miserably, and the sky is falling.

I often oscillate somewhere between feeling like I’m crushing life and feeling completely incompetent.

A graph depicting the highs and lows of leadership

The highs and lows of leadership depicted in graphical form!

Here are three secrets:

It’s normal. It’s not just you. It’s not just me. Every single person I’ve talked to has felt this way in some capacity.

It (generally) makes you a better leader. If you felt like you were crushing life 100% of the time, you would feel less of a drive to improve, to push the status quo, to make stuff happen.

It’s not as bad (or good) as you think. You’re probably your hardest critic. When you’re in a slump, recognize that it’s probably not as bad as you think. When you’re on top of the world, there’s probably more you could do. Reality is likely somewhere closer to the middle.

When I’m at either extreme, I have several different ways to pull myself back to the middle.

First, I would encourage anyone to find a buddy to chat with on a regular basis. Pick someone that has an intimate understanding of your work. Setup a 30 minute chat on a weekly or biweekly basis and just talk. Vent, celebrate, cheers, pat each other on the back, cry, commiserate—whatever the situation calls for.

On to the specific situations.

When you feel completely incompetent, try this:

First, take a deep breath and realize it’s (probably) not that bad. Then, it’s time to claw yourself out of this whole.

Celebrate something that went really well this week. Maybe it’s a conversation you had. Maybe one of your team members is crushing life. Write it down. Give yourself a pat on the back. The sky isn’t falling. Bonus points, set a reminder to do this every week!

Figure out what got you into this mess. Maybe your lead isn’t providing the guidance or leadership you need (That’s your fault, not theirs). Maybe you failed to prepare for project ahead of time. Whatever it is, make a list of everything that feels overwhelming. Make a plan for dealing with each item on the list.

Make a list and get back to basics. What are the fundamental 2-3 things you need to do to get back on track? Sure, leading a team is difficult, but there are a handful of action items that will get you moving in the right direction. Have 1-1’s with every team member. End every 1-1 asking what you can do for them. Find out some way to reinforce the goal. When you feel lost, get back to the basics.

When you feel like you’re crushing life, try this:

First, take a second to celebrate. Things are apparently going well! Then, realize it’s time to get back to work.

These are more questions than actions. The truth is I’m not sure what you should do. Here are three questions to ask centered around people, gratitude, and the future.

Are any of your team members bored? Bored people quit. Even if the team is firing on all cylinders, some teammates might feel overlooked, overwhelmed, or under-challenged. You should be asking this question on a regular basis, but it’s always good to circle back if you’re thinking, “Well, my job here is done. Nothing else to work on. Might as well kick back with a beer.”

When was the last time you said thank you? If you feel like you’re crushing life, it’s probably because your team is actually crushing life. Gratitude is a renewable resource. It never hurts to say thank you and point out the awesome work they’re doing.

What’s the next thing on the horizon? To prevent yourself from feeling completely incompetent next week, what can you get ahead of this week? What’s the next challenge your team will face?

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