The Art of Impressing the Boss: Less Flattery, More Strategy

Communication with decision-makers can be a true art form. On the one hand, you want to impress them, but on the other, you don’t want to come across as someone who would bring them an extra-foamy coffee just to get noticed. The goal is to be professional, useful, and strategically smart—without resorting to meaningless flattery.

Here’s how:

Preparation is half the battle (and it prevents awkward moments)

If you’re going to talk to someone who holds the reins, the last thing you want is to be caught unprepared. That would be like going to a job interview and answering the question, "Why do you want to work here?" with, "Uh… well… the pay is good?"

Research the person and their priorities – What keeps them up at night? What’s important to them right now?

Prepare clear arguments – If you’re proposing something, have numbers, examples, and potential obstacles ready.

Anticipate questions – If you know what they might ask, you’re less likely to be left speechless.

Be concise – They didn’t come for a lecture.

Be brief—they didn’t come for a TED Talk

Decision-makers often have schedules as packed as an inbox after vacation. There’s no time for epic monologues.

Bad approach: "Well, I was thinking, you know, and I believe we could maybe, but of course, if you think differently… well, maybe it’s a good idea after all…"

Better approach: "This solves problem X, reduces costs by Y%, and can be implemented in Z days. What do you think?"

Quick, clear, and to the point.

Position yourself as a partner, not a fan

Your role isn’t to nod along to everything they say, but to be a useful conversation partner. Think like an ally, not a subordinate.

Smart questions instead of empty approval:

Speak the language of value (tell them what they want to hear)

You know that moment when you’re trying to convince someone of something, and they just say, "Okay, but what’s in it for me?" Well, decision-makers are often wired exactly like that.

So, talk to them about:

Cost savings

Increased efficiency

Improved company reputation

Time savings

If your proposal can help in any of these areas, you’ve got their attention.

Confidence is key—but don’t force your ideas

Imagine you’re at a family dinner, and your grandma serves her famous soup. You take a spoonful and realize it’s got double the salt—but you know that telling her directly might get you written out of the will.

"Grandma, this soup is practically seawater!" → Not great.

"Grandma, I think you experimented with the flavours! Maybe next time we could try a little less salt?" → Much better.

The same goes for the business world. If you see that a decision-maker idea isn’t the best, don’t say it bluntly—be tactful:

"Interesting approach! How do you think this might impact X?"

"Maybe there’s a way we could improve this further?"

This way, you express your opinion without stepping on anyone’s ego—which is crucial if you want to be seen as a smart conversation partner, not a problematic critic.

Nurture the relationship—don’t be the person who only shows up when they need something

If every time they see you, they expect you to ask for something, you’ll become as annoying as spam emails. Occasionally send them something useful—an article, an interesting insight, or a piece of data they might find interesting. This builds a relationship without making you seem like someone who’s always asking for favours.

Be useful, not annoying

You don’t need to shower anyone with compliments to be taken seriously.

It’s enough to:

Come prepared

Speak clearly and concretely

Ask good questions

Show understanding of their perspective

Build a long-term relationship

This way, you’ll stand out as someone who has something to say—without handing out fake compliments or running around fetching coffee.