You are a freshly minted manager. You come full of rage and frustration at the poor management you’ve endured and witnessed in tech, and you are god damn determined not to repeat all of those mistakes.

You are tired of reporting to a manager who isn’t transparent with you, who hoards critical information and isn’t forthcoming about changes that impact you. You are tired of not being listened to or treated like a cog, so you swear to really listen and take your reports seriously.

You have seen sooooo many managers who failed to develop their people or sponsor them for growth opportunities, who blamed their team and hung them out to dry instead of having their back behind closed doors. Managers who didn’t seem to care about you as people, or who never made it feel safe to say, “I need a mental health day”. Managers who dangled the promise of a promotion, but even though you are doing the work, the recognition never comes.

Fuck that shit. You aren’t going to do ANY of it.

And … you don’t! 🎉

🌸🍃 You make time in your 1x1s to ask about their personal lives and hobbies — you are careful not to pry or be intrusive, just showing that you care. You urge them to take vacation, often. You remind them, firmly, not to be a hero. You model the behavior of taking mental health days to show that not only is it safe, but managers need them too.

🌸🍃 You ask them about their career goals and aspirations. You make it your personal mission to get them promoted, so you frequently check in with them to make sure they’re on the right path. You keep an eye out for things they do that are above and beyond, and for strengths that make them special. They always know you are on their side.

🌸🍃 If you hear about a clash or a conflict between them and another team member, you quickly jump in to figure out what’s going on and make sure it gets resolved, with each person feeling heard before the conflict has time to marinate or fester.

🌸🍃 When reviews comes around, you write warm, passionate essays for each of your direct reports, listing all the things they have done and all the ways they have grown. You go in to manager calibrations fully prepped to advocate for each of your people to get the promotions and rewards they so richly deserve.

🌸🍃 If someone on your team ends up needing more help, whether that’s keeping them productive and on track or helping with prioritization or conflicts… whatever it is, you are there to help turn the situation around. This person was struggling under their old manager, maybe even close to being let go, but under your care they are thriving.

🌸🍃 Nobody ever leaves your team. This is a point of quiet pride for you. People want to transfer to your team, but never from. There may have been a couple close calls, but you are always able to save the day by talking it out with the person and figuring out what they need in order to stay.

🌸🍃 You take pride in your transparency and the democratized ethos of your team, where you collectively determine your priorities and no one feels pressured into doing something they don’t want to do.

Bottom line: you are a GREAT manager.

Right???

After all, your team ranks sky high on every company survey on employee happiness, manager trust, and autonomy and sense of purpose. Your team fucking LOVES YOU. You’re pretty sure they would follow you to your next job, if you left. So maybe you ARE the world’s greatest manager.

Or maybe…you are heavily optimizing for one aspect of the management role, the part where you interface with your direct reports as an ally and coach. You might even be optimizing to the extent that you are neglecting or outright harming other aspects of the job.

Rookie Mistake #1: Only Managing Down

But management means coaching and supporting the people on your team, right? What else is there?

Well.. a lot, actually. Like, the business needs to succeed, for starters. ☺️ And there are a bunch of other relationships that matter besides your own direct reports. A good, strong manager needs to care about:

• Goals and planning. Managers are generally responsible for crafting a team roadmap out of the impossible mess of company strategy requirements, requests from other teams, product roadmap commitments, and KTLO (keep the lights on) work. Some companies also use OKRs.
• Right-sizing workloads. There is always at least 10x as much work to be done as cycles to do work, which means estimating how much your team can deliver, planning that work, and dealing with the inevitable surprises that come up during execution. How do you balance urgency vs importance? It is YOUR job to make sure your team isn’t overcommitted.
• Stakeholder management. Does your team have a reputation for delivering quality work when they say they will, more or less on schedule? Are you a good neighbor to other teams, or do they feel like anything they ask for goes into a black hole? This is largely determined by you.
• Managing up. Your manager relies on you to provide enough visibility into your team that they can (at minimum) make good decisions where your team is involved, and help head off any problems or conflicts before they escalate.
• Managing up (another sort) is the relationships you build and impressions you leave with your skip-level and other adjacent leaders. You are your team’s representative and ambassador. Leaders form a view of the org based on scraps of data. For the sake of your team: give good scraps.
• Managing out horizontally. Building great relationships and a web of mutual support with your peers. Sharing context with each other. Managers are like the nervous system, carrying signal from point to point.
• Contributing to the organization your team sits in, and its standards, policies, and structural integrity. This is the one most likely to suffer if a manager is laser focused on their own team. This means things like…applying the job ladder fairly and consistently, without playing favorites. Engaging in a dialogue with the ladder rather than bending the rules or making an exception.

As a manager, you have been granted certain formal powers by the org, to be used for the benefit of the org. This means you have a responsibility to care for the organization, and your team within that context.

You shouldn’t be advocating for the benefit of your team members, you have a greater responsibility to the rules and categories of the system, which you collectively maintain and agree upon. The system can’t survive if every manager is gaming the rules on behalf of their team. The system only works if every manager is playing fair.

As a line manager, the work you do interfacing with your team will likely be 50-75% of your time and energy … and impact. But this ratio changes as you go up the org chart. As a VP? Maybe 10-20% of your energy and time can go to your direct reports.

The higher up the ladder you go, the less important your bedside manner becomes and the more important your strategic direction becomes. You are first and foremost responsible for the company’s success, not for your reports’ feelings and career development.

Rookie mistake #2: Helicopter management

If rookie manager mistake number one is thinking that management consists of coaching and interfacing with your team, mistake number two is closely related. Mistake number two is … overmanaging the team, coddling people, and basically never allowing anyone to fail. I think of it as “helicopter managing”.

Helicopter management consists of overly identifying with your team and their needs and wants, instead of taking a step back and considering them in the full context of the organization, or letting them take risks and stand on their own two feet. You’re their manager, not their babysitter.

I have a personal story to illustrate this.

Once upon a time, many years ago, I had a team member who was energetic, highly talented, and a little high strung. I ended up spending a lot of time managing their relationships with other team members, keeping them on track with their projects, and helping them manage their emotional state in general. They nearly left in a dudgeon one time, and I think most managers would have let them go, but I saved the day and they stayed. I was actually really proud of the fact that I had retained them and kept them high-functioning for years. If you asked me, I would have shelved this under my successes, maybe even “proudest manager moments”.

Years later, though, I look back on this situation through very different eyes. Yes, I retained them at the company / on the team, with decent relationships, and they did a lot of good work! But should I have?

At what cost?

Most weeks, I probably spent 50-75% of my total emotional bandwidth on this one person’s needs. For years. Is this the best thing I could have done for the company with all that time and energy? Probably not!

Was this the best thing I could have done for them? I don’t even think it was that either! All that my coddling ultimately did was teach them the wrong lessons, and prevent them from learning the right ones. It delayed those lessons by a few years, and made learning them all the more painful when they finally came.

There are no clear bright lines here. But it’s worth checking in with yourself from time to time, and asking hard questions.

• You spent all that time coaching and doing a diving save to retain that person …. but should you have? Is this really the best place for them to be at this point in their career?
• Or let’s say you managed to turn around someone’s performance from failing to succeeding. Great!! But are you confident they are set up to excel, or are they always going to be hovering on the lower bound of acceptable performance? Are you going to be having this same discussion again next quarter?
• Consider all that time you spent intimately entwined with every detail of every technical project your entire team was working on, reading every PR and design doc. Should you have? Or did you unintentionally deprive them of some agency, while cheating yourself out of time you should have spent becoming a better leader, strengthening your org, or understanding next year’s challenges?
• Are you giving people only positive feedback? This is a common rookie manager mistake, and it often comes from a place of kindness, or overcompensating for overly negative environments. But you are not only cheating your people of opportunities for growth, you are teaching them that growth is something to be feared and avoided.
• Or are you cheerleading people so intensely that they come away with a lopsided view of how valuable or advanced their skills are? Are you promoting fast and loose, so they grow to equate promotions with career development? Have you been spoon feeding them growth, or are they developing autonomy over time?

This can be especially unfortunate at higher levels, where autonomy is part of the definition of being a senior+ engineer. You might be stifling them and not allowing them to exercise that agency, or even develop that skill. For senior contributors, autonomy is what they bring. You gotta let them do it.

This shit is challenging. There are no simple answers. The “right” answer is often only obvious in retrospect, months or years later. Everyone needs help sometime, some of us more than others, and that’s okay.

But is it sustainable? What price will you pay?

What I do know is that if you haul someone over the finish line, that is not a success. If you’re going to be having the same hard conversations with them again in one month, three months, six months…that is not success. If they are going to have a rough landing the next time they change teams, that is not success, nor is it in their best interest. And if your team is overly dependent on you, you aren’t actually doing your job.

And honestly? People really WANT to be challenged. They crave it! Or at least the people you want to work with do.

Rookie Mistake #3: Your view of the system is incomplete

I’m only going to touch on this one very briefly; it’s long and complicated, and probably deserves a post of its own.

Systems thinking is a core skill for both managers and engineers. It’s not a skill we are born with; it takes a lot of practice and failure to develop good instincts for debugging complex systems. As an engineering manager, you may have spent 10+ years writing software and learning how computers work, but you have hardly begun to understand how business and organizational systems work.

This explains a lot when it comes to the empathy gap between engineers and management, I believe. 🙃

We spend a lot of time talking about empathy these days — empathy between teams, people, neurotypes; holding space for the fact that nobody is always at their best, etc. Yet engineers can still be incredibly dismissive and judgey towards management actions and organizational decisions.

We see a decision that doesn’t make sense to us, or that we wouldn’t have made, and we write it off as being selfish, uninformed, incompetent, stupid, money-grubbing, bureaucratic, untrustworthy, craven, selling out. Or — maybe worst of all — we shrug and say something cynical about how this kind of thing always happens in business. Or they’re out to get us, or they never listen to us, or it shows how much they don’t give a shit about us..

Far be it to me to excuse corporate venality, or to try and blow smoke up your ass about your leaders’ motives. But in many, many of these situations, this actually represents a failure of systems thinking when it comes to imagining the complex business, corporate, and people systems your leaders are operating in.

When you find yourself thinking things like:

• “Why am I hearing this feedback so late, in such a roundabout way? Why didn’t they just come to me right away and tell me directly, and I could have fixed it so much sooner!”
• “Why would they hire someone external to fill that role, instead of promoting the person who has been doing the work just fine in the meantime? Typical exec move; they never see the potential in the people they have, they always want to get someone who has already done the job before.”
• “Why is our roadmap changing yet again? Why is this getting dropped in our lap? Our director doesn’t seem to know anything about building good software.”
• “Why didn’t I get invited to that meeting, when it was about MY budget and MY workload? You can’t even get a seat at the table around here unless you have a director title or report to the CEO.”
• “Why is that person being given ANOTHER chance? If they weren’t a straight white guy, they would have been fired a year ago.”

… or anything else that boils down to “other managers are stupid, hypocritical, or bad at their jobs”, stop yourself, and first try to understand “under what circumstances might their action be a reasonable one, or even the right one?”

Approaching people systems problems with curiosity, empathy, and the full awareness that you may never know the entire story (and there may be good reasons for this!) will make you a better coworker and a much more effective leader.

And if you are working as a manager at a company where you have enough evidence to prove that you cannot, should not take such a generous view of your peers, then maybe don’t. Like, if you have a professional responsibility to represent an organization you can not ethically represent… I would suggest not doing that. ¯\_(ツ)_/¯ If you can.

Your View of Your Manager Is Incomplete

One of the most challenging things to deal with, in my (limited) experience as an exec, is when you have a manager who is well-liked by their team but fundamentally ineffective in the role, so you have to replace them. Then you are left with a team left feeling bereft and confused, and you can’t just give them a list of all the ways their manager was actually dropping the ball and not doing their job well, because people deserve some privacy and dignity. You pretty much just have to suck it up, and hope that you have enough trust banked for them not to quit.

It’s entirely possible for a manager to be beloved by their entire team, while having a corrosive effect on the system around them. Sometimes it’s their very willingness to bend the system for their people’s benefit that generates that loyalty.

An unwary manager may create a sort of island within the company, where the team does not feel part of — may even feel separate from, superior to, or suspicious of — the broader org or the company. Team members may feel like “this is the only team I would ever want to belong to at this company”, or “my manager is great, they protect us from all the big company bullshit”, or “it’s us against the world”, or “nobody understands us, except our manager”. These are seductive dynamics to slip into because tribalism is so powerful. The more apart you feel from the company, the more tightly you may bond with each other.

I’m not judging you. I was that manager at Parse, to some extent, after the Facebook acquisition. I did not give a shit about the org, I only cared about my team. So…I get it. I still wouldn’t want me as a manager in my org.

What would you do?

Put yourself in your senior leadership’s shoes. What would YOU do if you had to choose between a good, reliable manager who gets the job done for the org and isn’t particularly beloved by their reports (she’s not awful, the team thinks she’s “fine”), vs a manager who is beloved by their reports and cares about their career growth deeply, but is weak at everything else? What will manager #2 cost the rest of the org, and who will bear those costs?

Don’t make your leadership make that choice. Be a manager who is good to your team, and good to the organization too.

Honestly, it is healthy for a manager to not identify too closely with their team. You should stand with them, but a step or two apart. After all, your job is to be pushing or pulling them in a direction, not just standing still and … marinating.

If you identify with them too closely, it can get very hard to tell your reports hard things. You may empathize with them so much that you put their feelings above the need to get shit done. You can be friends with your team, just like parents can be friends with their children, but the friendship doesn’t come first. Your formal role comes first.

On being a new manager who cares a lot

There’s something really beautiful about the energy and dedication that brand new managers bring to the role. Some of the most spectacular results I’ve ever seen for individual team members have come from teams with first time managers, who are determined and idealistic and pouring their whole heart and soul into the people reporting to them. They haven’t yet learned to pace themselves or to be more well-rounded with their time and energy, and sometimes a person can soak up that attention and turn a failing situation around into a thriving one.

I would never tell a manager that they should care less. Caring for people is the beating heart of this job. It doesn’t matter how efficient and effective you are at delivering feedback, managing people out, and planning roadmaps if you don’t truly give a shit about the people you serve. Even as you rise in the ranks and people-interfacing becomes a smaller % of what makes you good at your job, caring is still absolutely essential.

So I hope the message of this post doesn’t come across as “you think you’re a good manager, but here’s why you actually suck”. ☺️ You got into this role because you cared, and this is valuable. Never lose touch with it.

The message is simply that it took me years and years to learn that there is more to being a great manager than caring about my team. I hope you can learn it faster than I did.