Career guide: How to find a great manager
Best practices from former Slack, Opendoor, Ramp leaders
⭐ This edition is only available to friends of next play, our premium subscription that gets you access to additional content as well as many other perks like: a startup discovery platform, introductions to 100s of potential collaborators, invitations to virtual events, and much more. You can join friends of next play here ($10/month).
Recent friends of next play posts:
The next play career guide is our attempt to find you the best possible answers to your questions. We did that by asking some of the most talented people we know — people like Becky Sosnov, Jeff Morris Jr, Amir Shevat, Sri Batchu, Charley Ma, and 30+ others — for their help in providing thoughtful responses.
Quick disclaimer before diving in: you should read the below as ideas and perhaps some suggestions but NOT prescriptive advice. There’s more than one way to live your life, and so our only advice is that you should think for yourself (if you want 🙂).
“I am trying to figure out who to work for, and I am looking particularly at trying to find a great manager. What should I be looking for? Who is the best manager you have ever worked for? What made them great?”
Most job-seekers are not particularly great at selecting what company to work for. As much as we would like to believe that we are good at underwriting companies (and industries, etc.), it turns out to be a pretty hard job. A job that even venture capitalists strike out at most of the time
A perhaps more likely to succeed approach, in addition to spotting red flags, is to search for a great manager.
You have met many many people in your life. Some you got along really well with. Some…perhaps not so much. You probably have lots of opinions about what makes a person great versus not, and what are the types of people you’d like to work with and learn from.
And so, an approach to choosing where to work - a framework that may really simplify things - is to simply “go for the people.” Go work for and with the people you admire.
If that’s your approach, perhaps the first thing you need to do is define precisely that: “what are the types of people you admire?”
When interviewing leaders, I always look for their willingness to be vulnerable. In my experience, the best managers don't need to be subject matter experts in your field—in fact, I prefer the opposite. A good manager is confident enough to show their flaws, call themselves out, and be open. These are the people you want to build with. It's also a great sign when a leader offers you a chance to speak with their former direct reports without you asking. That says a lot.
The best manager I ever had was a lawyer during my time at DoorDash. Today he serves as Chief Business Officer of the company I was in Communications and, at the time, a team of one while he ran the Legal team. He didn't teach me specifics about my craft. Instead, he taught me how to ask tough questions and go deep. He showed me how to truly check my ego at the door. Most importantly, he recognized my wins and gave me the confidence I needed to build and eventually run my own team.
— Becky Sosnov, Global Head of Comms at Notion
You can also think about the qualities that would make a person effective at their job. Do these people that you may go work with exhibit those qualities?
To find this out, you can simply talk to people who work at the company and also do references with people who have previously worked there and with the people.
Finding a great manager can be challenging, especially since the interview process often doesn’t provide much time to truly get to know them. I recommend aiming to work for someone with a strong track record of staying in their roles long-term. This commitment is essential because you want a manager who will be invested in supporting and advancing your career over time. I once joined a company after being recruited, only to have my manager leave within three months, which ultimately led me to leave as well.
— Jeff Morris Jr., Investor at Chapter One
Also, do not be afraid to run your own references and see how they align with your preferences.
You will learn a lot simply by asking rather straightforward questions.
What is it like to work for this person?
What is the average day like?
What is the average meeting like?
Are they good at their jobs?
What’s the most admirable thing you remember this person doing?
Why do you not work for them anymore?
Etc.
You’ll then take those answers and compare them with your preferences.
Some people want a manager who knows when to give them space to operate.
I had fantastic managers in my career. They recognized that I do not require much guidance, gave me all the resources and support I needed, and challenged me to be a better version of myself. A good manager has very clear communications style, cares a lot about the team, does not shy away from direct and honest conversation. My best manager at Google let me do a project that was outside my job description and helped me scale it to become a global Google Developer Expert Program. Together with my last amazing manager at Amazon I wrote this article about leadership.
— Amir Shevat, investor, formerly Google, Slack, Twitch.
Others see a great manager as someone who really drives the pace and momentum of the team. Sometimes this shows up in the form of “Wow, this person was demanding. But they really did get the most out of our team and help us achieve our goals.”