Leading people is hard sometimes. I want to make everyone happy. I want to be friends with people I work with.
I want to know about their family and friends and what they do when we don’t see each other; then, when they are not performing properly, I can be empathetic and we can have a real, gritty discussion.
But this is not a blog about management, and I don’t think you want to read about how important it is for me to be everyone’s friend.
So instead, I will talk about creating structure.
It’s summer — ripe time for anyone, musician or teacher or startup/small business, to grow their team. Families are on vacation, teachers are on break before the new semester, music festivals have happened.
Our event team started from scratch, when I was bouncing ideas off close friends.
After describing my idea, I say, “Would you be interested in working on this?”
“Definitely,” Benta says.
We look at the calendar, and we count forward four months.
I wanted a flat hierarchy structure in my team. I wanted a constructive environment that was also fun. I wanted to give my teammates autonomy.
The problem was this: with too much freedom, people were overwhelmed and didn’t know what to work on. Nothing got done. Anything outside the scope of everyone else’s responsibilities became my responsibility, and those piled up quickly. I can’t throw a fit because I never told them to do it in the first place. So I tried delegating more.
“Can you contact the warehouse about their rates?” I say. “We can negotiate a bit.”
“Grace,” she says. “I’ve never done this before.”
I pulled in mentors and advisors, which helped, but not much. The root of the problem was that I gave a leadership position to someone who wasn’t ready.
To put that into perspective: Would you marry someone without getting to know them first? Don’t sabotage your team by bringing on people you can’t speak for. That is essentially what I did, and I am trying to fix it as we speak. I wrote bulletpoints for what I wanted each person to achieve.
Your first few members are the most important. The first person you hire will have an exponentially higher impact on your team than the tenth. The first music teacher that a studio hires will shape the studio much more than the tenth. What kind of music do they teach? Are they easygoing or conservatory-style? Because that is what the studio will be known for, moving forward.
Be careful who you hire first.
Think about who you work best with.
In a fast-paced startup environment, you need go-getters. People who come up with great ideas and are not afraid to take risks. (On that note, there is always a fear of hiring that one person who will crumble the entire operation by accident.)
“I don’t think the meeting with the research agency will proceed like you think it will.”
“How should we approach it, then?” I say.
“I don’t know. I think [advisor] will have the best idea.”
The most unpleasant people to work with are not Devil’s Advocates; they are Shut Downers—actively shutting down every idea while not offering anything better. The difference between the two is that the Devil’s Advocate sees both sides and errs to safety while the other is simply terrified of moving forward.
Please do not be this person.
If you want it done best, don’t do it yourself.
If the task is not unique to you, then delegate it. That is the only way you will have room to expand; train someone and give them autonomy.
If they don’t like autonomy, then they’re probably not the best person for the job; you don’t want to hire someone you have to micromanage.
Meet and talk.
Never get upset over email or text; if you can’t bother to express your emotions face-to-face, then the issue is probably not important enough for you to be upset about.
By the time you see the person, you will be able to discuss this in a calm and tasteful manner, unless something has exploded in the meantime.
Break the rules.
One of our team’s unspoken rules is that we ask for help.
The problem is that one of the directors is not ambitious enough for the pace we are moving at, and so she has become the team’s Shut Downer for every bold idea.
“Her negativity is hindering our progress,” I say. “I think she has something against me.”
“I’ll call her,” Benta says.
“Should I call, instead?” I say. I have a sudden realization that it’s my responsibility to manage my team, and that’s my subtle way of expressing it.
See? I’m breaking my own rule about discussing important things in person but there’s a good ending here, I promise.
I call the team director and ask how she is feeling. She has been fighting every opportunity I’ve given her so now I am trying to do damage control for giving her a strong leadership position.
“What can I do to help?” I say. “Do you need more mentors? Resources? A bigger team?”
We chat long past midnight where I tell her to dream big and tough it out and metaphorically pat her on the back.
A few days later, we are looking at tasks on our project management board.
“Can you see what the bank account is about and compile xyz?” I say.
“Consider it done,” she says.
That is a small move forward, and it might not even be a move forward because that is a menial task, not a leadership one.
My challenge is pushing the team to dream big. Because when all the weight of the world is crushing you and you have friends and family and taxes to do, what is going to keep you going the extra mile at midnight? My mother has long ago acknowledged that I am a bit crazy but I’m not sure when she will accept it.
My challenge is following through, because I am still looking for the right time to let go.
My challenge is spreading positivity when the team is dragging their feet. That’s what the best leaders I’ve seen, do.
We can all be leaders in different areas of life.
We get tired, I know, and that’s okay. You are amazing. I’ve been feeling tired more often these days.
But be ambitious. Be mindful about execution.
Above all, be passionate, because you can’t follow through on your dreams without it.