You're not just a manager, you're also a boss

Many engineering organizations are ignorant (often willfully) of power dynamics and how they affect management.

I am the Senior Director of Engineering at Wistia, a medium-sized tech company providing a video marketing SaaS product. I am a career coach, facilitator, rubber duck, mentor, mediator, and often a friend to the folks who report to me. I’m also their boss. This is a position in which I hold power over others. In this article, I want to talk about what that means, and why it is important.

This is an odd time to be writing about power, with an armed insurrection fomented by a sitting president having just violated the U.S. Capitol. It’s also exactly the right time to be writing about power, because it is in part the failure to pay attention to the fact of power and how it works that has led us to this terrifying juncture.

It is in the nature of power to become invisible to those who wield it, and for the acquisition of it to become a goal unto itself. The only way to prevent this is to be constantly vigilant.

As software engineers, as managers, and as tech workers in an industry that (it has become obvious) is powerful enough to topple governments, we hold many kinds of power and privilege.

The coup attempt has been an extraordinary abuse of power at multiple levels and by multiple people. The power we hold as managers is, to be sure, not the same as the power we hold (or lack) as citizens, parents, humans. But all power is dangerous, and all power leads to abuse unless it is under constant scrutiny – not only by others, but by those who hold it.

‘Isn’t that a bit dramatic?’ you may ask. Maybe so, but the fundamentals of power within systems are the same whatever the system is, whether it be an entire government or a single scrum team.

Hah, with that introduction, let me take us back down from world-shattering events to the daily business of tech capitalism.

What does it mean to be a boss?

So, you just took on management responsibilities. Or maybe you’ve been managing for a while, but you haven’t stopped to think (or been asked to think) about power dynamics. This is common for engineering leaders. Tech, after all, is the world of, ‘We have a very flat organization’, and ‘Management is just a different role’. But no organization is completely flat and no manager is not also a boss. You may think of yourself mostly as a coach, or mostly as someone who unblocks others, or mostly as a tech lead who does a little management on the side. You may not think of yourself as a boss. You may not want to be a boss. But you are a boss. And you need to understand what that means and make peace with it, because if you don’t, at best you will be a less effective manager, and at worst you could end up abusing your power (possibly without ever even noticing that you are doing so!).

What does it mean to be a boss? It means you have some measure of direct power over the working conditions, career growth, and livelihood of everyone reporting to you (and all the folks in your reporting structure). You can promote people, you can give them raises, you can provide them with a safe, inclusive workplace, and you can offer them juicy opportunities. You can also fire them, dismiss their needs, stifle their career growth, or contribute directly or indirectly to an unsafe workplace by violating their personal boundaries or allowing others to do so. You can deploy your power responsibly, or you can pretend it isn’t there and end up using it in hurtful or irresponsible ways.

Acknowledge your power

The first step in managing your power responsibly is to acknowledge it and make it visible – both to yourself, and, importantly, to the folks you manage – and to do so repeatedly. Something that is visible can be discussed.

The most important implication of acknowledging that you hold power over those you manage is the recognition that they behave differently toward you because of it. People don’t tell managers things they’ll say to peers, especially things that might be interpreted as critical of the manager. They will hesitate to tell you when you’ve violated their boundaries, when they’re struggling or unhappy, when they’re having difficulties with other people, or experiencing harassment, exclusion, or discrimination. As a manager, you may even be excluded from social events that you used to take part in. That can hurt, and you need to accept it.

Commit to continuous reflection on how you are using power

One of the best ways you can learn to wield your own power wisely is to surround yourself with a diverse group of people: peers, friends, colleagues, coaches, therapists, employees, and family – and to earnestly and regularly seek their counsel on the question of your own behavior. And, on your own, you should continue to study and learn and consider power dynamics in the world. You should think about when and where in your life you hold authority, and when and where you do not. This is how you think explicitly about power.

Of course, there are many things people will tell you are crucial to succeeding as an engineering manager: scoping big projects, managing risk, hiring, 1:1s, giving and receiving feedback, organizing and reorganizing your teams and processes, offering a clear vision, and helping folks navigate their careers. But a slowness or failure to master those aspects of engineering management will not determine whether someone leaves your employ with a scar that they may carry with them to every future role. To reckon with your own power, however insignificant it may seem to you within the scope of your business or the world, is to accept that you may cause harm to others with it. You may cause harm whether or not you mean to. Ultimately, that is the reason why you should think so carefully about power, so as to know that when you cause harm (as you might, for example, if you need to fire someone), you are doing it as carefully and empathetically as you can.

Once, I went with some director-level peers to dinner with a new Executive Vice President for our division. The wine flowed freely. He told us about how he used to make limoncello in big batches in his big backyard in his big house. Then he asked each of us at the table if we were married, and if so, how long we had been married for, and if they were for each of us our first marriages. He congratulated each of us on how long we had been married. This was uncomfortable enough, but in addition, while I tried to decline additional pours of the wine (I was trying to cut back on drinking at the time), he urged me again and again to accept them. He was goading and making fun of me for declining. The man was two levels above me in the organization. I barely knew him. To this day the thought of limoncello turns my stomach.

That man abused his power over me and I suffer for it still.

This is an article about how not to do such things. It may be of little interest to those who need it most. The man who made limoncello certainly wouldn’t have wanted to read this. He understood quite well how power worked already, and that is why he was so dangerously effective at abusing it. (I cannot help but think, again, of the parallels to the calamitous political situation of January 6, 2021.)

Say, then, that you have not yet held quite so much power yet in your life. Perhaps, you haven’t yet considered its implications. It may seem a long way from making a hiring decision to publicly tormenting an underling over their personal choices to leading a coup, but it is not. No one has perhaps yet suggested that you should consider its implications, so I will. This article is intended for you to begin to see for yourself how you hold your power (however limited and small in scope it feels to you now), how you wield it, and to begin to put into practice the habits that will help you manage that power with care.

Be polite

Never be so polite / You forget your power / Never wield such power / You forget to be polite – Taylor Swift, ‘Margorie’, Evermore, 2020.

I once worked for a different man who sent the most inscrutable emails at the weirdest times. Those of us who received them referred to them as his haikus, and would share them with one another in an attempt to decipher their meaning. They were short, abrupt, partial thoughts –  full of misspellings and no punctuation. But because they were from him and because of when they were sent, they always felt important and urgent. Receiving important and urgent yet indecipherable emails felt terrible to me, and I thought he was incredibly disrespectful to us, his employees, for sending them. I also didn’t understand why he sent them.

As my own responsibilities have grown, however, I find it’s easy to slip into this kind of communication. I remember something I wanted to say that doesn’t even need an immediate response but I don’t want to lose it.  I’m in the middle of cooking dinner or helping a kid with something, and it’s not important to me to look professional anymore because I don’t need to, so I don’t bother with full sentences or correcting my typos. I just dash something off and hit send.

This behavior, which now feels natural and ok to me (well, obviously they know I’m busy, they will get the gist, they will know I don’t mean now), is essentially the same behavior I resented from a manager in my past. It’s easy to tell myself I’m different. But I’m probably not. Those emails and Slack messages likely come off the same way to folks I manage as they did to me. Did any of us ever tell that manager we resented those emails? Of course not! Can I expect folks I manage to do so? Nope. Giving critical feedback at all is challenging, and giving upward critical feedback is almost impossible – even for folks who are good at giving feedback. It’s on me to notice the ways I’m not being careful or respectful toward my employees, and it’s on me to do something about it – for example, by at least scheduling emails I send so they arrive during business hours.

This may seem to be minor. But most people who end up abusing their power don’t do so deliberately, they do so because as they gained power they paid less and less attention to it, so that they came to expect that whatever they did was magically ok with others. (Check out John Mulaney’s bit on working with Mick Jagger for the endgame here.)

Remember that you take up more space

As you gain power, you take up more space in a room. People listen to you more, take what you say more seriously, hear it more frequently as a demand whether or not it is. You will need to be clear about whether you are floating an idea, making a suggestion, asking a question, or issuing an order. Be especially clear about that with folks who are much more junior than you. If you have a director title and you idly ask a question of a junior engineer who isn’t even in your reporting structure, there’s still a strong chance they’ll think they need to drop everything to find the answer. Don’t pretend you are only making a suggestion when you are, in fact, issuing an order. Of course, as managers, we feel we shouldn’t be issuing orders (due to the command and control model we understand to be ineffective and outdated in a modern product org), but sometimes we will have to. Just as sometimes we may need to give difficult feedback or fire someone who isn’t working out. Issue few orders, but do not pretend you are making a suggestion when in fact you are issuing an order. Be as direct and transparent as you can. ‘I understand you would like to do x, but I need you to do y now. Let’s figure out how you can do it.’

Remember that as your career grows and you gain more responsibility, the circle of people who will be affected by your power also grows. When you are a new tech lead with a small engineering team, ICs in other departments may not feel the impact of your power. As a director or VP, many more folks across your organization will experience the power imbalance and it will impact all your relationships with people in your org. If you have any kind of public-facing role, give talks frequently, or have a strong network of powerful people, then your power will be felt even by people who are not in your organization. Be sure to reassess regularly where the boundaries of your power are as you grow in your career and act accordingly.

Watch your boundaries, and check in frequently with people about theirs (don’t dump down, check in obsessively)

We often become friends with people we manage, or start out as friends/peers and then become their managers. This is normal. And there’s also value in being able to be authentic about our own difficulties and where we are struggling at work and in life. For example, because I, as a leader, speak openly about my bipolar disorder, and when I’m struggling with it or with something else in my life, folks I manage feel freer to bring their whole selves to work. They can talk about and seek help from those they work with to alleviate the challenges they are experiencing. So, there’s a benefit for me to be open. But, the people who report to me are not my therapist, and they are not the right people for me to process my own emotions (about work, about life, in general) with. It’s not their job to make me feel better. One thing I do is make sure folks know that even when I am disclosing to them that I’m having a difficult moment, they don’t need to worry about me or take care of me. Brené Brown’s book Dare to Lead covers in detail how to be authentic with your team while maintaining appropriate boundaries with them. I am not perfect at this, but I keep it in mind.

Of course, there are multiple other boundaries that we need to be cognizant of as managers. I give a lot of casual compliments to people of all genders: about shoes, makeup, quarantine beards, cufflinks, etc. I call people of all genders ‘dear’ a lot. I also know that some people in some circumstances might feel icky about any of these things while others simply won’t. When I slip up and am not sure how something I just said landed, I ask, ‘I’m sorry, please tell me if that did not feel ok to you.’ I ask this a lot about very minor boundaries because then people get the message that I care and if I inadvertently violate them they can tell me so. This isn’t a perfect system. But I have found that if people get the message that you care about how you make them feel then when you make them feel bad they are more likely (not guaranteed, but more likely) to tell you so. People want to give you grace for screwing up. If you constantly show that you care whether or not you hurt people, if you show up for them, and if you ask, they will tell you when you have screwed up, you can apologize for it, and you can recover. But if you don’t leave that space for them, you can’t.

Learn to listen to what people aren’t telling you

I was once in a conversation with a direct report who was feeling frustrated with the pace of hiring in their area of engineering. They felt safe enough with me as a manager to pretty freely express the frustration, which was great. But what they didn’t say was that if I couldn’t resolve the issue soon, they’d probably end up leaving the company. Even when you have a good relationship with your manager, that’s a very awkward conversation to have, and it risks coming across as a threat. Threatening or appearing to threaten departure often leads to being shown the door immediately, and their trust in my good faith could not overcome the baggage they came to me with from previous managers. I thanked them for sharing their frustrations and asked if I read correctly that they’d likely start looking elsewhere soon if there wasn’t a change. Yes, they said, this was true, but they hadn’t wanted to threaten. I reassured them that I didn’t read it as a threat – that it was, on the contrary, useful information. Yes, I might not have been able to provide what they needed, and then we would have had to have a conversation about how they could peacefully leave in favor of an employer who could. Being able to plan for such orderly departures is beneficial for everyone involved. But it can only happen if you assume that folks are not disclosing everything to you no matter how friendly you are.

Other things people might not disclose: difficult personal circumstances such as mental illness or other invisible disabilities, harassment they’ve experienced, interpersonal challenges. People fear retaliation, stigma, career stagnation, and job loss. However friendly a boss you are, these are existential threats. You have power over them, and the less power someone holds in society, the more they will have experienced other folks abusing their power. Some baggage is so big it can’t ever be dropped completely. The best you can do is to enthusiastically welcome whatever information you can get (even when you do not feel the least enthusiastic about it), make educated guesses about when you are missing information (something not making sense?), and ask directly while acknowledging why it might be difficult to talk about. When someone with less power is speaking to someone with more power, they speak differently. They use what’s called mitigated speech. Learn to listen for mitigated speech and ask about it. Listen not just for what’s not said, but for what is said quietly, surrounded by caveats or apologies, or as a question. Follow up.

Actively manage the emotional burden that comes with power

If you don’t mind being irresponsible with your power, it’s not much of an emotional burden to carry. If you do want to hold your power responsibly, then you need to accept that it will be emotionally difficult. Employees trust you with their careers, their feelings, their promotions, and their raises. It’s a big responsibility. There will be times in your management career where you will need to deliver painful feedback, coach someone into a different role or even a different employer, or outright fire someone. If you are taking your responsibilities seriously, none of these things will feel good to you. They may feel terrible. I feel like vomiting every time I go into a 1:1 where I need to deliver difficult feedback, and even when it goes well I come out of it emotionally exhausted. I have learned to leave buffer time before and afterward to allow myself to recover. I have learned that if I need to tell someone I don’t have a place for them anymore, then I will have to give myself the rest of the day off to recover from the pain of doing so. I don’t mean to imply that it is more difficult to be the manager delivering this news than the person receiving it, but I do mean to say that if you don’t feel pretty bad after doing these things, you likely aren’t taking your responsibility as a boss seriously enough. What you say and do has a direct and potentially life-altering impact on the people reporting to you. If that responsibility starts feeling easy to bear, you should start asking yourself why.

Conclusion

John Dingle, who served in the US Congress for decades, wrote an op-ed before he died. In it, he wrote, ‘In democratic government, elected officials do not have power. They hold power — in trust for the people who elected them. If they misuse or abuse that public trust, it is quite properly revoked (the quicker the better).’ As managers of at-will employees in a job market with more open roles than engineers to fill them, we too hold power only so long as our employees consent to it. This is a real responsibility – to the people, to the business, and to our industry.

I hope this article has begun to illuminate some of the ways in which you can think critically about power in the workplace, and about your power as a boss. Being careful with power is difficult but important. Ask, reflect, admit mistakes, apologize when necessary. Be polite, kind, honest, and direct. If this sounds like it’s a lot of work, that’s because it is. If it is not work that brings you satisfaction, the best advice I can give is to step away from it. There are many ways to contribute that do not require such careful shepherding of your power as a boss and do not carry with them the potential to cause so much damage to others. Good luck!