Letter to my Future Self (if I become a manager)

Dear future-me,

I hope you’re doing well. Congratulations on the management position that you’ve gotten if you’re reading this. I assume you’ve learned things. I assume that there are challenges you’re facing that I haven’t run into. I don’t have all the answers. There are some things that I hope you keep in mind, though.

Above all, please remember who you are. Remember your values. Remember what makes you who you are. I hope that you maintain your integrity. I hope you avoid letting the voice of your company overshadow your own voice. I hope that you can interact with your employees as a human. That you can be compassionate and honest and understanding. I hope that you remember that being human sometimes means being vulnerable. Sometimes it means being strong enough to hold space for others to be vulnerable. You will make mistakes. Please acknowledge them with grace and take responsibility, then learn from them and move forward. Pointing fingers and shifting blame doesn’t help anyone. Managing with honor, integrity, and pride seems like one of the best ways to attract employees who value those traits in themselves — and right now, I can’t think of much better traits to look for in someone on my team.

Make sure that you’re listening enough. Create space for those you’re leading to talk to you as frequently as you can. When they do, listen. Actively. Respond to them. Use “That’s just the way it is, get used to it” only as a last resort. Or never. Help them discover ways that they can improve things. Perhaps more importantly, listen when they’re not talking. Take the time to notice if there’s not strong communication. Try to figure out why. Is there not time? Is there not trust? Are there not convenient communication channels? Do they not know how? Are they too disengaged to know what to communicate? Or to care? If there’s not active communication, watch. Feel. Pay attention — real attention. The kind that takes energy. The kind that’s hard and scary. The kind that means maybe you’ll find out something you don’t like. And be ready to act on it.

When you do need to talk instead of listening, be careful about what you say. As a leader, your job is to enable others to achieve amazing things. I’m pretty sure that destroying their self esteem isn’t the way to do that. Always, always be respectful. Always do your best to build confidence and improve people’s image of themselves. If my experience is an indication, people tend to live up to expectations. Expecting great things and helping people believe in themselves will help them perform better and will give you a better team. Even if it doesn’t, creating empowered, confident, capable people is the best way I know to make a better world. Please be conscious of whether you’re moving toward that or away from it. In Every. Single. Interaction.

Remain aware of how much power you have. My observation suggests that amount of power is the amount of power the other person chooses to give you, plus or minus the ability to end their employment. I know that’s not how people talk about it. The conversational shortcuts around managers being able to tell people what to do are convenient. Like most shortcuts, there’s value in periodically reminding yourself that they are shortcuts, not reality. I assume you will get to a point where this amount of power always feels like the wrong amount. You’re going to want to have a switch on the wall that you can toggle between “casual conversation with no implication of authority” and “Direct Order Which Will Be Followed”. Neither of those settings exist. At the end of the day, your words will carry more weight than casual conversations would. At the end of the day, you are not the person sitting at a keyboard writing code or showing up to meetings. The final decision about whether to do those things rests with the person doing it. Avoid making them want to prove it.

The best way I’ve found so far to work with the fact that I can’t actually make anyone do anything is to gain people’s respect and trust. To do my best to find out what they want, and make their life a little bit better. If I can provide them with skills they’ve been wanting to develop, they’re a little more likely to want to do things I ask for. If they need calm and quiet to work and I can provide a bubble of that for them amidst the chaos, they’re a little more likely to want to do things I ask for. If I can match them with opportunities they’ve been waiting for, they’re a little more likely to want to do things I ask for. It’s your job to provide value to your employees just as much as it’s their job to provide value to you and the company. Figure out how to do so.

Finally, remember that other people are not you. They want different things. They have different strengths. They have different weaknesses. Don’t assume everyone wants what you do. Be grateful for people who can fill gaps in your skills. Work with diversity, don’t try to make an army of mini-yous.

Thank you for your time. I know that by the time you get there, some of this will probably sound ridiculous. I know that you’ll screw it up sometimes. Remember to forgive yourself, learn, and move on. Remember to let others do the same after their mistakes. I hope that you can also find some encouragement and strength in my naive hopes and belief in humans that comes from not having managed them very much. I hope that when your spirit starts to get crushed by the challenges of management, this can help you believe in the goodness of people. I hope it can give you the strength to manage toward a better world, rather than just trying to get through the day.

Yourself, but earlier

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