Managing Up

When I was a teen or tween, I mentioned to my mom that I never asked her for anything after 9pm or on Fridays. She was tired and would likely say no to giving me a ride, letting me go on a camping trip, whatever it was. My mom still refers to this moment occasionally as a lesson to her in managing up.

You’re probably aware that the impression you make on your boss affects your pay and your performance reviews. You may also have some expectation that they’ll help you improve or grow your career. But when your relationship with your manager feels tense, frustrating, or just flat and awkward, it’s not always obvious what to do. There are many great resources out there on identifying great managers^[1], understanding the your manager’s role^[2], getting the perspective of a manager^[3], or coaching for managers^[4]. I want to talk specifically “managing up”, meaning intentionally navigating the relationships with your reporting chain and anyone else with some authority over you.

It’s a sliding scale

Any relationship takes effort to maintain. When you first start out, that duty will typically mostly fall on your manager. A new grad usually has little experience with anything other than “grading”. Their tasks are well-defined and easily evaluated, and their manager’s job is to set clear expectations and help them ramp up. Over time, you will start to carry more of the responsibility for the relationship as your duties increase in size and ambiguity, your ambitions become more specific, and you potentially report to higher level people whose time is more scarce. Experienced people must show how their work is high quality and high impact, ask deftly for what they need, and identify opportunities and sponsors.

At any stage, having some savvy with your manager will serve you, even if it’s just to make sure they think you’re doing a good job.

Observe

The first step in any new skill to develop curiosity. Managers and senior colleagues are people, and they have individual quirks and values systems. They will not always work the same way or agree with each other.

Values

Think about the people around you. What do they value?

To find out, you can ask them directly. One manager was explicit about being “results driven”, and said that all other skills are useful inasmuch as they further results.

More accurately, you can look at how they tie break difficult decisions. One hard decision is how to spend time. Is their calendar all 1:1s? They might value relationships. Do they make time for article clubs or bringing in external speakers? That points to valuing learning. When the team disagrees, do they go with the decision supported by the majority, the most senior person, or their own technical instinct?

Be aware that stated values and actual values may not be aligned. Once I was told that my projects may not be promotable due to insufficient “technical complexity”, when “managing complexity” was the phrase written into the rubric. This left me nonplussed. What if I chose an elegant solution and reduced complexity, and then my project seemed too simple? To solve this problem, I pointed out that gap to my manager. Second, I really hammered home the technicality of my projects in my self review.

Now that you know, you can figure out how it fits with your values. One of my favorite things to do is figure out how to get a project I think is valuable onto the roadmap by pitching it in terms of something my manager (and usually, the organization at large) considers worthwhile. This can be as simple as rolling refactor costs, which can have nebulous business benefit, into time estimation for a product launch in a very feature-based org.

Last, your values and that of your manager or organization may be completely irreconcilable, at which point it’s time to GTFO.

Fear and aspirations

Sometimes, there is some kind of fear that dwarfs positive values. It’s not a great thing, but it happens. I had a manager who really did not want to be at a loss when asked technical questions by the bigwigs, which resulted in micro-management. In order to keep from getting interrupted, I had to find ways to satisfy that anxiety on my own schedule.

Other times the motives of your manager as an individual will affect things. They might be “resting and vesting” and not be up to fight for you unless you make it very easy for them. Or they might take pride helping you plan and advance your career, in which case take advantage.

Constraints

If you take a human with the same values and hopes and fears and put them into different situations, they will of course act differently. One of the most rewarding questions I ask managers is “what’s on your mind?”. It can explain a lot - they’re pressuring for project completion because the team is new and needs to show progress. There’s an impending reorg in down-low early stages, and that’s why they’re being hand-wavvy about decisions. They spent a lot of time on performance managing a teammate who just exited, and now that it’s resolved, they’ll have more bandwidth.

The question takes the focus off you and your performance, which can be nice, and it gives your manager some space to be heard, which everyone likes. It also has a lovely side effect of helping you figure out if you’d ever want their job and their problems.

As a case study, I specifically relish working on cross-team projects: they’re collaborative and often extremely high impact. The problem is that many organizations put pressure on managers to deliver within their team’s scope and mandate. If part of my work is going to another team, or filling in the cracks of the organization, it will likely be seen as higher cost and lower priority by my direct manager. In order to sell the project, I need to reframe to satisfy my manager’s values and constraints. Alternatively, higher-up managers have a broader view and mandate, and might be able to champion or set direction from above.

Working style

People receive information and requests better in certain modes, or in my mom’s case, certain times of day. I once had a skip level manager who loved charts. Charts are succinct, they’re visual, and this person was busy. If a chart happened to look bad at a glance when the actual content was more subtle, it would randomize the conversation. On the other hand, my direct manager made a small change to turn all of the neutral, grey colored parts of a chart to a light green and it noticeably improved the skip level’s outlook on our work.

People have talents and gaps, too. Some managers will be great at pulling strings, some will be great at laying out the projects to get you to promotion. All of them need feedback and practice to improve. And everyone has emotions, as much as they would like to leave them at home. Having empathy for your manager, without forgetting your own interests, will help you unlock tricky situations.

Align expectations

This is the table stakes of managing up. If you don’t meet expectations, you are likely to be performance managed (not fun), or frustrated at lack of career progression (slightly less but still not fun). First, you need to find out what good work means to your manager. You can ask questions like “what does success look like on this project?”. You can also use tools like a goal setting framework, a career rubric, or a 30-60-90 day plan. This alignent work needs to be redone regularly.

If their expectations seem unfeasible to you, it’s an opportunity to get extra support to bridge the gap, or else present an alternative that is tailored to satisfy their values/constraints/fears/working style etc. You will also need to show evidence that their current expectations are not feasible. If there’s an untenably bad mismatch between your expectations and theirs, it may be time to move on.

Showcase what’s hard about your work

An incident occurred about 2 years into my career:

A project was harder than I thought it would be. I holed myself and hid my struggle, demotivated, but not sure who or how to ask for help. I worked on the wrong things, went about it inefficiently, and I made little progress. Eventually, team leadership noticed, and I had some of the hardest conversations of my career to date.

I wasn’t fundamentally incompetent, but I was doing something unfamiliar and I wasn’t surfacing my challenges or getting the support I needed. Senior team members sometimes identify a potential project and assign it to someone new without thinking too hard. The new person assumes it’s worthwhile, assumes it should be easy, and then runs into a bunch of unexpected complexity. Or, they lack context to gut check the purpose of the project and waste time. If they stay silent, no one can course correct.

Even as a tenured team member, you can encounter many sneaky sources of difficulty: technical debt, organizational impediments, unreliable dependencies. If you explain the novelty of the problem and showcase your solution, people will ooh and aah, the organization will learn, and you’ll get credit. Sometimes they’ll find ways to pitch in and make your life easier. If you give into imposter syndrome and hide the difficulty, everyone loses.

As for how: performance reviews, standups, and one-on-ones are obvious ways to celebrate your challenges. Also, lightning talks and write-ups - things that take an hour or less to prepare (you don’t want to take away too much time from doing the work). Asking questions in public channels. Elevator chats. Twitter.

Nominate yourself for opportunity

This has been said a million times before, but it took me a while to absorb: if you don’t ask for things, no one knows that you want them.

It’s vulnerable and uncomfortable, but it works. I had a manager who tended to shrug off things I asked for when I first brought them up, and then come back a couple of weeks later with progress made. This happened when I gave evidence I was underpaid (lol), but also when I wanted to work on higher impact projects with more stakeholders. Among peers, I’ve vaguely mentioned career goals and then been forwarded related opportunities. Hardest of all, you have to raise your hand: propose that project, submit abstracts to that conference, apply to that job, set up a meeting with that new co-worker. You are a business of one, and no one else cares more than you about your success.

Seek psychological safety

There has been a bunch of jazzy headlines^[5] recently about creating psychological safety (the belief you won’t be punished when you make a mistake) on teams. It also applies to relationships. Your manager will always be balancing multiple interests besides your own, but feeling like you can show that you’re struggling or bring up conflict will make every other part of this post easier.

Psychological safety takes time. Ideally managers go about fostering trust proactively, but you will probably encounter less-than-stellar managers in your career, so the ball is also in your court. The ways in which I’ve sought out trust vary by what I’ve observed about my managee, and takes iteration.

Making their jobs easier helps. Create visibility into your work, deliver on what you promise, present solutions alongside problems. Managers are in a tough spot, since they are accountable for the team’s work but often don’t have bandwidth or skills to directly push it along. Maybe to start, you need to over-communicate and write down everything you do. As you get traction on trust, you can move towards lighter weight mechanisms for syncing their expectations and your work. Going forward I want to make a point of running my priorities past my manager each week.

Giving feedback helps. Start small and use COIN^[6] or other feedback best practices. If you acknowledge your manager’s strengths, and if they can be imperfect in front of you, they are more likely to reciprocate.

Being a full(ish) human around them helps. Talking about bands with one (relatively reserved) manager meant filling awkwardly quiet time during one-on-ones, and afterwards I noticed they brightened up when they saw me in the hall. “How was your weekend” chit-chat can be painful, but open ended question allow people to share at their comfort level and set them at ease.

And finally, literally seeking out individuals who you trust helps. If every interaction with your manager feels like fighting a dragon, it may be time to switch teams or jobs. If you work really well with someone, it’s reasonable to prioritize staying with or following them. It can be stultifying and cliquey to always operate in a bubble of the same comfortable people, but if someone sees your value and creates opportunity for you to grow, it’s a boon.

On sponsorship

When your boss trusts you, they can be your sponsor. A sponsor is someone who does some of this managing up for you. They talk up your accomplishments. They nominate you for opportunity.

A lot has been said about finding mentorship, and I’d argue it’s more clear-cut. A mentor is someone you can learn from, and companies and organizations set up mentorship programs as a part of learning development. All it takes to be mentored is to find someone whose skills and perspective your admire and ask them to chat. All it takes to be a mentor is to give someone your time and answer questions.

A sponsor is taking a chance on you. If they throw your name in for a project, and it goes poorly, they can lose clout. Therefore, a sponsor has to see your value. It helps to find people who see something of themselves in you. Glibly and problematically this could be demographic similarity, better it’s someone whose career experiences are mirror yours, best is someone who aligns on values or viewpoints.

I’ve noticed that people in roles who do not have representation in the higher level of management tend to flounder. It’s harder to show value as the first SRE in an org with no executive understanding of the purpose of reliability. It’s harder to get promoted when the managers who hold the keys have not tried doing your work and get why it’s hard (see above for some ways to combat this).

So how do you find one? All of the above. Notice the values and working style of those who might be able to push your career along. Show what is hard about your work. Communicate what opportunities you want. Foster trust through both vulnerability and excellence. And when you find someone, cherish it and prove them right.

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Editing help from Chen Lin and Trucy Phan