On mid-career and managers

When I first started to get into my “mid-career” phase, I felt like I was going through a string of bad luck with managers. Part of this was true — due to several reorgs and other company-level things that were outside of my control, I did end up changing managers far more often than would have been ideal. But the sheer number of managers I had didn’t explain some of the other frustrations I kept feeling.

There’s a saying, “If you run into an asshole in the morning, you ran into an asshole. If you run into assholes all day, you’re the asshole.” I’m not calling any of my managers assholes — far from it! My thought process was actually that somehow I was the problem. Maybe I was so burnt out that I was accidentally being horrible to everyone around me. Maybe I had unrealistic expectations of my managers — but after years of experience, it felt like I was getting better at setting expectations, not worse.

Eventually I figured out that while I was the common factor, it wasn’t that I was doing anything wrong, it’s just that what I needed from a manager had changed over the course of my career so far. As you enter mid-career, you will likely also find that your managerial relationships end up changing, both in terms of what you can expect from those relationships and in terms of what you end up needing from them.

Earlier in my career, I was looking for a fair amount of career guidance from my managers. As a junior engineer, most of my career focus was figuring out “how do I become a senior engineer?” and I looked to my managers to help me do things like identify gaps in my knowledge that I couldn’t see, tell me what I should focus on in order to level up, and provide hands-on guidance when I got stuck. This would often take the form of both career direction (“I’d like to see you work on your leadership skills; let’s try to identify some small areas you could start taking more of a lead in”) and technical direction (“You should look into X tool for this; Gaining more expertise with system Y would help you here”).

Once I got to a certain point, that type of direction became less helpful. This isn’t to say that I know everything. But by now I’ve gotten a lot better at figuring out for myself what I need to learn and how to learn it. I’ve got nearly 15 years of practice learning on the job—- in my earlier work environments, I often had no choice but to figure everything out myself since I didn’t have access to things like conferences or training budgets. I’m pretty good at identifying what I need to work on, and I know how I learn best, so having a manager tell me “You should take this specific type of training class in language X” is not helpful to me anymore, whereas something like “the top priorities for the team this quarter are Y and Z; I think X would be a good scope of project for you to lead to help us meet our goals around Z” is. As you get more senior, you’ll likely find that what you want from your manager is more big-picture guidance and less day-to-day advice.

Another big way in which managerial relationships can change is in relative skill and experience levels. As a more junior engineer, odds are good that your manager has more experience than you, both in terms of the specific tech skills you need and in terms of overall career/industry experience. The longer you’ve been working (at least if you tend to work in startups or other companies that skew younger), the less likely this is to be the case, and the more often you’ll find yourself reporting to someone with less industry experience than you.

This isn’t to say that you won’t get any benefit from reporting to a less-experienced manager, but it does change what that relationship will look like. You’ll probably need to do more managing up, and to be very clear with your manager about what you do and don’t need from them. If you need guidance for things like how to expand the scope of your work beyond your direct team or how to align your individual goals with team and organizational priorities, and especially if your direct manager hasn’t managed someone at your level before, you will probably need to start building what Lara Hogan calls a Manager Voltron - a group of different people who can each help support you in different areas.

So what might you need from your manager (or Manager Voltron) as a mid-career engineer?

Identification of priorities: At both an organizational level and at the team level, a manager should be able to help figure out what are the most important things to be working on.
Support in coordinating larger efforts with upper management: If you’re working on things like cross-team projects, organization-wide process changes, or efforts like fixing technical debt that might be a harder “sell”, your manager should be able to help you facilitate those efforts with your skip-level/director/other relevant stakeholders in management.
Finding opportunities: If there are specific types of work you’d like to do, a good manager can work with you to find ways to try and make that happen — and if they can’t, they should let you know directly and help you find someone else who can.
Feedback and career progression: - Whether you need a champion to help take you through a complicated promotion process or honest and thoughtful feedback on the work you’ve been doing, a manager should do as much as possible to support your continued career growth.
Facilitating technical guidance: The more senior you get, the less likely that your manager will be providing direct technical expertise (as opposed to being a sounding board), so they should give you space when you need it, and if they can, help you to connect with people in your organization or industry who can provide additional guidance.
Help figuring out what you need from a manager: In an ideal world, as you enter your mid-career you will have an experienced manager who can talk with you about how your managerial relationships and needs are evolving and guide you through this process — it’s not always easy to figure out on your own!

Once you’ve figured out the various things you might need from a manager/Voltron at your current point in your career, you’ll need to figure out how to best communicate this. Especially if your manager is junior to you, being able to clearly identify and communicate what you’re looking for can help that relationship for both of you. This might mean having a conversation where you say something like, “I’d like to look for opportunities to lead a larger, cross-functional project. I thought that X and Y could be good candidates, based on our team priority A this quarter. Would you be able to help facilitate some conversations with the managers of those teams and see what might work out for us?”

This might also mean figuring out how to communicate what you don’t want or need — “I’ve noticed that you have been giving me technical advice on how to do X. That’s an area I already have a lot of experience in — is there something in particular you think I should be doing differently? If not, I think I’ve got a handle on the technical details for now, but please let me know if the priorities on this change.” This can be a tricky area to navigate. People want to feel like they are being helpful, so telling someone that you don’t need a particular sort of help from them should be done with care. A manager could end up feeling insecure or worried that they aren’t needed (especially if they’re more junior and still figuring out all the different types of work that people management entails) which is why it can be beneficial to talk about what kind of support you do want from them in the same conversation.

Because what you need will change over time, it makes more and more sense to start building a broad support network even if you do have a great manager right now. Learning how to figure out and communicate what you need is a skill that will serve you well throughout your career. Finding a range of people who can give you guidance and feedback will help you get a clearer picture of where you’re at, and can help manage undeserved bias. Having a solid group of peers you trust to give you honest and useful feedback might be able to deal with a couple negative outliers in a promotion process, or at the very least can be a useful barometer for you to understand where you are and where you need to improve.

One final thing to note is that you might run into situations where you can’t get what you need from your manager. Determining and communicating what you need can be a big help — people can’t support you if they don’t know what kinds of support you need — but that won’t necessarily be enough. If you’re trying to do the type of work that has impacts throughout the company, you will need a certain level of organizational support for that, and even if your manager wants you to succeed, they might have people above them who haven’t bought in to your work yet. Even if you have a manager who means well and is trying to help, they can run into limits of what they can do in practice. I don’t have any magical answers for “how to single-handedly fix an entire organizational structure” but I can say that these things do happen, it’s not necessarily your (or your manager’s) fault, but not all situations are fixable. If you feel like you’ve been having the same challenges and same conversations for 6+ months and haven’t made any meaningful progress, it might be time to consider moving on to something new.

Managerial relationships start to look different when you’re in your mid-career — this isn’t anyone’s fault and doesn’t mean you’re doing something wrong. Once you’ve figured out what you want to work on next in your career, you can start to look at what support you need to get there. You can talk to your manager about what types of support would be more or less helpful to you at this point, and should start looking to build up a network of other managers and peers in your organization who can give you support, guidance, and feedback as well.