Dear Marie,

I’ve been in tech for over five years now, but I’ve never really had a traditional manager relationship in my roles. Recently, I’ve been dealing with a not great manager relationship that’s made me question a lot. On days I have 1:1s I’m filled with anxiety and stress, and I think it is time for me to go.

I’m curious, what kinds of questions would you ask a potential manager to see if a new role on their team is a good fit?

Sincerely,
Struggling

Dear Struggling,

I’m so sorry to hear that your current work situation with your manager is so stressful. It sounds like you’re making an excellent call to get out now.💖

Before you talk to hiring managers about specific roles and the kinds of teams they lead, have a clear picture in your head of what you want. To judge if a role is a good fit, you have to know the shape and boundaries of the space you’re willing to offer them and what you want in return.

You might already have a clear vision of the kind of work you’d like to do and the team and manager dynamics that you’re looking for. But if not, here are some questions to get you started:

• What’s important to you in your next role? In your long-term career?

  Do you have a specific goal you’re trying to reach within the next year, or five years? Do you have a dream job that you’re working your way towards? Are there any skills or experiences you’d like to develop?

  Or maybe you don’t have a specific goal in mind. Maybe you’re looking for a place where you can do good work for 40 hours a week and then go home and live your life. Maybe you just want a good job.

  At a high level, what do you want your next step to look like?

• What are your dealbreakers? What are the nice-to-haves?

  Get specific about what really matters to you in a role, a team, and a company. What are the things that matter a lot versus the ones that you can budge a bit on?

  Here are a few examples:

  • 📟 A light oncall rotation, or none at all
  • 📆 Flexible schedule for childcare, eldercare, or self-care
  • 🌴 Really good PTO and vacation benefits
  • 🦷 Amazing health/dental/vision insurance and 401k matching
  • 🖥 Ability to work remotely
  • 🛫 A lot of travel
  • 🏡 Absolutely no travel
  • 🚎 Short commute
  • 🧩 Challenging technical problems
  • 🤝 Support from team to do open-source and community work
  • ✨ Building a new app with no legacy code to support
  • 📚 Working with a specific framework or language
  • 💖 Diverse team, where you aren’t the only person who looks like you
  • 😍 A mission and product you are passionate about

• What kind of team would you like to join?

  Do you like small, scrappy teams where everyone is working on the same project? Do you like big teams where each person has a very distinct specialty and area of focus?

  Are you looking to be surrounded by senior engineers who you can learn from? Are you stepping into more of a senior role yourself, and looking for folks you can mentor?

  Is it important to you to work cross-functionally? Do you want to join a team that has a dedicated designer and PM, or do you want to be able to wear your own design/PM hat?

  Do you have a preference about teams that are all based in a single or a few physical locations? Do you prefer remote, distributed teams?

• What management style works best for you?

  What’s worse—being given too much direction or not enough? Do you enjoy being given a high-level task and then left to your own devices? Would you prefer having a more hands-on mentor, who will listen to your current approach and point you in the right direction?

  You said that you’ve “never really had a traditional manager relationship” so you may not have a clear vision of your favorite management style. But you can also think about what has worked and what hasn’t so far in your career!

  What does your current manager do that makes you feel stressed out and anxious? Think back to when you first joined this team. Were there any warning signs early on that seem obvious in retrospect? Are there questions you could have asked at that point that would have made you reconsider joining?

  Some of the best questions when looking for a new role come from hard-won experience and the spirit of “I’m never doing that again, and I know what to look for this time.”

Once you have a clear vision of the kind of work, team, and manager you’re looking for, you can approach talking to managers from a mentality of “this is what I’m looking for—is that something you can offer me?”

You might already have some questions to ask about the specific situation based on what you’re looking for. For example, something I asked a lot in my last job search was:

I’m looking for a team where I can learn from senior engineers, with a focus on front-end development. But it’s also important to me to be able to mentor other engineers, and to learn in a collaborative environment. Is that something I could find in your team?

There are also some good general baseline questions I like to ask managers to get a sense of what their team is doing, where they are going, and an inkling of who they are as a manager. Here are a few questions to get you started and inspire you:

• What’s your vision for this team? Where would you like to see it grow?

  Does this manager have a bigger picture idea of what this team should be doing? Is the goal just “work through the backlog”? Can they articulate a vision for how the team is uniquely positioned to contribute to the company? Do they have a future of the product in mind?

  I consider this especially important at a larger company, where managers may have to actively advocate for funding.

• What are the big projects your team is working on right now? What’s next?

  Knowing what the team is currently focused on can give you some insight into what work is prioritized, and the kinds of things you’d actually be doing when you join.

  Pay attention to how this answer might differ from the ideal vision for the team. Does the manager address that, if there is a difference?

• If you could change anything in this team/company, what would it be?

  This is a great way to hear about some of the downsides of a situation—and get a sense for the tact and discretion of the manager. If they begin ranting in detail about a person or department or specific decision, that’s a warning sign.

  You want a manager who is honest and can talk about what’s not working or what could be improved, without disclosing the sensitive information they’re privy to. Especially if that information is about you.

• What is your job as a manager of this team? How do you know when you’re successful?

  There are a few different approaches to management¹. I don’t necessarily think there is one Definitely Right™ answer, but there are some that are Definitely Wrong™.

  For example, if a manager judges their success by “everyone on my team likes me,” that’s a sign they probably won’t deliver valuable constructive feedback or have hard conversations—which is their job. Or if they are entirely focused on “this team is successful if I ship this product,” they may not actually delegate to their reports or look for ways to develop their team’s experience, preferring to just jump in and do it themselves.

• How many people have joined or left your team within the last year?

  Is this team growing rapidly? Are they able to keep up with the changes and onboard everyone individually or will you be expected to hit the ground running?

  Is there a pattern of people leaving shortly after joining? If so, can they give a convincing explanation as to why?

If you have specific concerns or questions about the team, ask! This is especially true if you are looking at teams within your current company, as you likely have unique insight into challenges or opportunities they’re facing.

And if possible, do try to chat with a member of the actual team to get a different perspective. If you know them personally, you can also get good backchannel information about what their manager is like and what day to day work on the team entails.

Trust yourself and your judgment. Even if you haven’t had a lot of experience with “traditional” managers, you know what you like and what makes you feel bad.

Pay attention to the little clues and feelings you have whenever you talk with a manager. If you feel a bit off, don’t immediately dismiss it as nerves. Investigate that sense and see if it leads you to a concern or question.

You deserve to be in a work situation that does not fill you with a sense of dread and anxiety. I hope that you can treat yourself gently during this time. If it’s possible for your interactions with your current manager to improve, I wish that for you. And if it’s not, I wish you a speedy search process.

I am sending you so much encouragement, and hopes for a manager that sees your potential and actively partners with you to help you achieve it, and a team where you can thrive. 💖

Warmly,
Marie

Written by Marie Chatfield Rivas, an amateur aspiring advice columnist, certified Emoji Enthusiast™, and purveyor of fine tweets.