The Dark Arts of Managing Up
Among the many dark arts of the workplace, none is more mysterious, maddening, and occasionally soul-crushing than managing up.
Some days, I felt like a Machiavellian mastermind, deftly navigating my boss’s priorities, quirks, and shifting moods. Other days, I’d come home thinking:
“Ohhhhh fuck… the boss hates me.”
It’s not just that every boss is different (duh). It’s that every boss has a different idea of who they are, a self-image full of tacit, unspoken assumptions about how they work and how the world works.
How does your boss make decisions?
To manage up effectively, we can’t stop at understanding why our boss made a particular decision, it’s important to understand the how.
Do they lean on the strength of an argument’s logic or do they demand hard data?
Do they seek out external opinions and benchmarks or prefer the perspective of other Staff?
Or… do they just want to hear their own ideas echoed back to them?
Often times, these questions go unasked and most certainly unanswered. I firmly believe the more we can turn the implicit to explicit, the better. So in every training, I survey all of the participants and their bosses.
Both reports and managers needed to force rank 1-5 how the boss made decisions, with “5” meaning it’s the most important input into their decision-making.
Here’s the data from 70+ respondents, across 20+ countries and all levels of seniority:
Mimicking Logic Data External Opinions Internal Opinions Report 2.48 3.43 3.11 2.84 3.14 Manager 1.78 4.00 3.44 2.59 3.19
The gap that matters
Sure, there are a few differences here. But one jumps out:
Reports think mimicking the boss’ own opinions is pretty important. The boss thinks its far less important. The difference can basically be explained by the role of logic. The boss thinks logic plays a far more decisive role in their decision making than the report.
So… do bosses just want to hear themselves?
Kinda. But not because they’re vain, or dumb. Because they’re human.
Derek Thompson’s TED Talk on how to sell anything reintroduces a concept from Raymond Loewy, the most influential industrial designer of the 20th century: MAYA — Most Advanced Yet Acceptable.
Loewy put it like this:
The consumer is influenced in his choice of styling by two opposing factors: attraction to the new and resistance to the unfamiliar. When resistance reaches a “shock zone,” the design has reached its MAYA stage: Most Advanced Yet Acceptable.
Humans crave the balance between the new and the familiar. Bosses are no exception.
Most Advanced — Yet Acceptable
(Most) bosses don’t want their opinions simply mirrored back to them. They want to be pushed. They want the Most Advanced version of your idea or project.
But because they’re human, they need it framed in Yet Acceptable terms. That means using references, language, and mental models that sit inside their comfort zone.
Want to find your boss’s MAYA zone?
Pay attention to:
The books they read
The podcasts they subscribe to
The leaders and companies they admire
That’s your map. It shows you where “acceptable” lives and how far you can stretch toward “advanced” without tipping them into the shock zone.
The takeaway
Managing up isn’t about flattery. It’s about design.
Find the sweet spot between pushing your boss forward and keeping them anchored in the familiar and you’ll master one of the most powerful workplace dark arts.
