Three Simple Hacks to Manage your Manager

In one of my startup jobs, I worked with a colleague who had suddenly gained one of the founders’ strong trust and support. The two of them would be seen huddled over, talking animatedly in the hallway. In a small startup, people notice this sort of thing. Over gossipy after-work beers, people would roll their eyes when his name came up and complain about the quality of ideas being allowed as a result of this sudden closeness. Why, I wondered out loud, couldn’t the co-founder see what we saw?

An Engineer friend, a few beers deep, spat out the answer — “He’s really good at upward management”. For years after that, I associated upward management with sucking up, politicking and bad ideas.

I was wrong to think this. Dead wrong.

Upward management — defined here as understanding how to successfully interact with and communicate with your own manager can propel teams and companies forward. It can also propel your own career forward without engaging in the dark arts of flattery or manipulation.

Here are three things you can do right away that will help you, your manager and your team.

1/ Curate, Synthesize and Structure: Managers believe they are pressed for time. But their scarcest resources, in fact, are actually attention and energy. At any point in time, there are more initiatives underway than any manager can give productive attention to. There are more people-related problems occurring in parallel than most managers can engage with in depth. Of course, this is increasingly true as managers expand the breadth of their scope. As an example, the organization I lead at Square spans 12+ products and nearly 700 people. My manager, the Head of Square, spans twice as many products and several times more people. Unsurprisingly, I am generally aware of everything that will occur in the year — goals, strategic plans, progress metrics, key blockers, even monthly or quarterly progress in every product — but the areas where I can or should engage more deeply are far more limited. For my manager, yet more so.

It follows logically that the key to a manager’s effectiveness, then, is to pick areas that will get attention and energy extremely well. While there are a variety of ways to do that, a key tool in a manager’s toolbox is the recurring 1:1 with their own direct reports.

This is where upward management makes a key difference, by helping to direct your manager’s attention and energy to the most productive places. The first step to doing so is to take curation seriously. Many 1:1s are structured as a combination of scattershot updates, venting about intractable issues and anything else that simply happens to be top of mind. What is far more helpful, instead, is to step back and think like an old-school print newspaper editor publishing to a busy consumer with finite attention and with finite space. What is worthy of the manager’s attention right now? What can wait? What can be safely ignored altogether even if it feels salient in the moment? What sort of update or FYI would plant a seed for a future conversation? This type of curation should result in topics that can actually direct your manager’s attention and make them more effective at their job while also helping you along the way. As a concrete example, my 1:1s with my manager are 30 minutes every 2–3 weeks. During those weeks, I will collect topics when they occur to me over weeks of working with my teams. Before we meet, I will filter and prioritize them to ensure that we focus on topics that we should cover instead of the many, many more that we could cover.

In addition to curation, it’s critical to synthesize and structure well. In a complex, fast-moving environment, any topic you pick will have richness and depth that would take hours to truly unpack. But who has the time? Once again, thinking like an old-school print reporter helps — what are three bullet points that can convey most of what is needed to help your manager engage with you in the moment? What is the order in which information should be presented to bring them along? What are 1–2 key questions tied to this topic that you need your manager’s input on? In my experience, most people think minimally or not at all about synthesis and structure, resulting in worse conversations and lowered effectiveness for their own manager. To build upon my own, prior example — even though my 1:1s are only 30 minutes long, I may have spent well over 90 minutes writing out my own bullet point notes to get the most out of the time.

2/ Problems over Solutions: Have you heard the advice around not bringing your manager problems unless you also have solutions? As with all powerful-sounding plausible ideas, it has spread far enough to lose nuance and become dumb.

There’s a (likely apocryphal) quote attributed to Einstein — “If I were given one hour to save the planet, I would spend 59 minutes defining the problem and one minute resolving it.” Even if Einstein never actually said this, we can apply it to upward management.

Bringing your manager high-quality, well-defined problems is actually far more important than bringing them lovely but ultimately irrelevant updates about all the things you’ve already solved or easily can yourself. Tricky, knotty problems can create the space for your manager to be a sounding board. Since most managers talk to all their direct reports, hearing about similar problems from different people can elevate its importance and direct the manager’s attention to it. Finally, good problems can also serve as the terrain upon which your manager can apply their experience, their pattern-matching capabilities and their emotional distance from the problem to help yield possible solutions.

As you curate, synthesize and structure — be sure to bring well-defined problems. The net result will be more effectiveness for your manager and yourself.

The nuance here is the obvious one — the list of problems has to be filtered and curated just like everything else. Use your manager’s help to find the water line on the types of problems that should be in-scope for discussion. The answer varies by seniority, scope and the manager’s own idiosyncrasies.

3/ Build a Bridge: A constant challenge for any manager is to reach their entire organization when providing direction or feedback. As expected, the challenge simply magnifies with the size of their organization? Got a team of 5? This is a highly solvable challenge — simply talk to everyone in detail, confirm expectations were understood, monitor on a recurring cadence. That’s about it. But what if your organization is 25? You can still talk to everyone in detail but have to leave the detailed expectation-setting and follow-through to your managers. What about 700 or even a few thousand? Not only can you not talk 1:1 with everyone, you can’t even guarantee that 100% of the humans will read an email or slack from you.

Good upward management helps by building a bridge between your manager and your team. This is especially true if you yourself are a manager but also helpful even if you serve as an IC. How can you re-contextualize anything you got from your manager into a way that would translate best with your direct reports or your peers? How can you collect and synthesize feedback on behalf of your team for your manager when an initiative that your manager wants done isn’t going well? How can you use your direct access to the manager to create more nuance with peers and directs in cases where the manager is doing something immediately unpopular but ultimately correct?

Upward management done badly features carrying water blindly for your manager — the classically cringeworthy “we need to do this because the boss said so”. It also features unfiltered information pass-through, by sharing everything you learned from your manager with no regard for nuance. Finally, it features hoarding information that you learned from your manager purely out of paternalism or, worse, petty power tripping.

But a bridge? A good bridge is a source of leverage and effectiveness for your manager. Instead of having to rely on top-down prescription by fiat, your manager will know that you will help achieve their goals the right way — with the right context, the right level of nuance for different audiences, the right follow-through — and the right feedback back to the manager based upon progress and problems.

While each manager is different in their own way, rooted in their own human quirks and idiosyncrasies just like anyone else — these broad themes around curation, synthesis, good problem statements and bridge-building should apply somewhat universally. Beyond this, choose your own adventure. The most important thing, as always, is to just keep working at the never-ending task of getting better at managing yourself, your team and your manager.

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PS: If you liked this essay, check out my newest essay on the Overton Window.