Student Question
Hello Master, I work in a technical role. I have no issues on the technical or business side. My question is: how do I practice upward management? When communicating with superiors, how can I achieve my goals while also maintaining some measure of balance with them?
Master Chi’s Response
Let me cover three main points.
First: Understand the Rules Before You Play — and Understand Others Before You Help Yourself
Every organization, large or small, has its own unwritten rules. The relationship between superiors and subordinates tends to be subtle and complex. The norm is that distance creates appreciation. The harder you chase something, the more it slips away.
Some people actively court their boss’s favor and still end up sidelined. Others seem indifferent, yet get singled out as top talent. Some spend all their energy networking and building relationships, yet remain invisible to leadership. Others barely cross paths with their boss and are somehow never out of that person’s thoughts.
Second: Build Leverage and Set the Stage
When offering suggestions to a superior, a subordinate must first understand their intent and grasp the unwritten rules. From there, work with the current — riding the wind is far more effective than fighting the tide.
Do the groundwork beneath the surface. If what you’re about to present isn’t ready, it’s better to hold back. Make sure your foundational data is solid — especially the surrounding context — before moving forward. At the same time, state your own position openly.
When presenting leadership with a suggestion, always frame it as a choice — let them make the judgment call. Have a clear stance, but don’t be one-sided. You need to articulate the benefits and explain how to mitigate the downsides.
Put yourself in their position — specifically, look at the problem from your superior’s vantage point, in service of their objectives and circumstances. Find the point where your interests converge: one key opens one lock.
Factor in the time dimension. When discussing the past with a superior, do summaries that align with how they see things. When discussing the future and broader trends, leave room for flexibility. Being too attached to a superior’s vision makes you look like you lack independent judgment — and frankly, most leaders are rarely right about everything. Very few can truly balance management and operational expertise simultaneously.
In short: you need to understand your industry’s trends and know how to communicate with nuance and clarity, in a way that actually lands. Neither can be neglected. And through it all, keep your own internal compass. Don’t get so deep in the game that you lose yourself in it. Stay clear-headed; know when to bend and when to hold firm.
Third: Contradiction Is the Norm — Accept It, and Bridge People with Work
When working across levels of an organization, differing views are completely normal. Most of the time, when our suggestions aren’t approved, it’s because we haven’t figured out what leadership actually wants. The other scenario is this: within a system, if you can’t access what someone truly wants at their core — you can’t win their support, and no one else can help you either.
So in the everyday work environment — and you mentioned your technical and business skills are solid — you’ll inevitably need to address the next frontier: interpersonal competence. This is a linear stage of professional growth; there’s no skipping it. That said, some people are naturally wired for the relational side of things — they have an innate fluency with people. But my overall read is this: moving from people-skills to technical mastery is relatively manageable. The reverse — a technical person learning to develop relational intelligence — tends to be a much harder transition.
Regardless, bridging people and work is the prerequisite for advancing further in your career. Only when you’ve unified the two can you truly return to your authentic self, find ease in your own skin, discover your real value — and move through professional life with genuine freedom.