Building a strong relationship with your boss is one of the most powerful ways to advance your career.

With our expertice in psychology, power dynamics, and office politics, this article provides you with actionable strategies to win over your boss.

Let’s dive in:

1. Flatter your boss the right way

Research shows that ingratiation works.

After all, we all know that everyone enjoys a good compliment.

But some people shy away from compliments in fear of appearing ‘brown-nosing’ or unprofessional.

And they’re not wholly wrong.
Compliments and flattery must be socially calibrated to be effective.

Disempowering flattery

These judge-y compliments is how a superior would speak:

• You’re a great manager
• Good job
• You’re very skilled at X

Good flattery

This is instead how a subordinate pays compliments:

• Thank you for X
• I love this team <— Indirect praises their picks & leadership
• I admire how you…

And a research-backed technique is to turn a compliment into a question to make it seem less obvious and more authentic.
For example, say ‘you’re so good with people, how can I improve my people skills‘.

2. Make him feel in charge

Use what we call here ‘power protection‘ to avoid irking your boss.

Most people know that being aggressive or rude to a boss is an obvious no-no.
But many fail to realize that you can disempower your boss in far subtler ways.

For example:

Boss: Let’s increase outreach volume
You: OK, I agree with that <— It implies your agreement matters, which irks bosses. Agree with your peers, not your superiors

Better:

You: Makes sense, more volume equals more chances, I’ll proceed

2.2. Promote tactfully: don’t overshadow him

Self-promotion is crucial for your career success.

However, self-promotion is an area of conflict of interest because it serves you, but not your boss or team.

Plus, the more successful you are, the more your boss feels threatened and ‘beaten’ by a subordinate.
And he doesn’t want either.

So promote yourself, without overshadowing him:

• Keep your networking hidden
• Frame achievements as team wins
• Credit him for successes

Mostly:

👉🏼 Make him feel you’re a friendly force -and ally- so he welcomes your advancement

Also see:

• Self-promotion techniques at work

10 Techniques for Strategic Self-Promotion At Work

3. Prioritize his tasks

Ie.:

• Answer his emails quickly
• Reply first when he asks on the team chat
• Be the first to finish whatever survey he sends around the team

3.2. Take something off his to-do list 

Former media executive and career coach Fran Hauser says she received her first big promotion because she made things easier for her boss.

Says Fran:

Offering to help is nice, but without volunteering to take on a definite and specific task, it puts the onus on the other person. (…) Instead, make yourself aware of what needs doing and how you can do

In short: observe what your boss needs the most, then offer to help with that.

3.3. Offer him your extra capacity

Ie.:

You: Boss, I finished my previous task. Is there anything I can help you with?

If a colleague tasks you or asks for help, run it by your boss.
Ie.:

You: Chris needs some help, but I wanted to run it past you in case you have other priorities

➕ Bonus: the boss tasks tend to be higher visibility.

4. Grab & create opportunities to get closer

Many do this the wrong way.

And then they get called ‘brown-nosers’ for a reason.

Worse yet, when you force closeness and ‘chumminess’ good bosses are forced to defend their boundaries to maintain a reputation of fair and equitable management.

The solution is to get closer tactfully.
Ie.:

1. Put out hooks for closer vibing
   Ie.:
   • “This weekend I tried X, I really enjoy X…”
   • “I’m planning a new car, how do you like your Mustang…”
2. Go deeper if he reciprocates
3. Stick to non-work topics for as long as the boss allows

🔎 Example:

My boss enjoyed recreational Treasure Hunting.
I’d listen and ask for as long as he enjoyed. It led to a lunch invite, followed by many more. I got another ‘exceeds’ review with him, largely thanks to our relationship.

🔎 🔴 Example of missing a ‘bid for closeness’

We dig deeper with the author’s real-life examples in Power University.

But the concept is this:

If a boss makes a move that allows you to get closer, reciprocating is both an opportunity, and a must.
Failing to do so will break rapport and harm your relationship.

5. Give positive feedback (but pitch it as “honest”)

In the era of Radical Candor management, ‘growth mindset‘ and (naive) self-help gurus, everyone professes an open mind.
But few have it.
And nobody appreciates others for critical feedback, no matter how useful it was.

Principle:

⚖️ Critical feedback helps others grow, but positive feedback helps your career.

How to give critical feedback

Still, critical feedback can be an opportunity to display IQ, social skills, and power awareness.

Here is how to give it:

• Frame the criticism as minor (compared to the positive)
• Frame the criticism as fixable
• Provide suggestions to address it

6. Align with his communication style

To increase rapport and social capital, ignore your preferences, and match your boss’ instead.

Match:

• Direct / indirect speech:
  Ie.: “Please do X” / “Could you please take care of X?”
• Quick / long-winded
• Chit-chat before business talk / straight to business
• Formal / informal
• Rituals of speech 🔜
• Macro / micromanaging
  ➡️ check in often with micromanagers, let them review your work. Be more independent with macro-managers
• In person / electronic

Pay particular attention to the latter as it’s an important sign of extroversion/introversion.

If they avoid in-person communication and you’re trying to talk to them in person, they feel like you’re violating their personal boundaries.

⛏️ Match his leadership style (PU alumni only)

6.2. Match their conversation rituals

Linguistic researcher Deborah Tannen defines conversational rituals as patterns of speech and behavior that work only when both players use them. 

Matching conversation rituals increases rapport, and missing them harms your relationship.

Important conversational rituals include the use of “sorry” and “thank you”.

Imagine this dialogue:

Boss: Thank you for running this by me <— It’s a ritual because the boss doesn’t owe you ‘thanks‘

❌: No worries, cheers / You’re welcome <— Misses the ritual, one-ups the boss

✅ Thank YOU for taking the time to check this with me, boss

The boss had no real reason to say “thank you”. He is expected to keep oversight, so the ‘thank you’ is a ritual, not a real thank you.
The boss is putting himself in the one-down out of kindness, but he expects you to do the same to rebalance power.

When the report does not reply back with ‘thank you’, the report disempowers the boss. Over time, the boss will start resenting this report.

Even worse would be the following:

Boss: Thank you for running this by me
Report: You’re welcome

And the boss will be thinking: “You’re welcome?? For what! Does he think he is the boss now?”

So, what’s a better solution, in this case?
It’s to play the ritual and thank them back. For example:

You: No, thank you for taking the time to check this with me, boss, I appreciate that very much!

6.3. Jump on indirect commands

If your boss is direct and you prefer indirect, you might think he’s an as*hole.

And if he speaks indirectly and you are more direct, you can think he’s a submissive ‘too nice guy’ who doesn’t have what it takes to lead.

However, again, it’s on you to adapt.

And if he’s indirect and you are direct, you can miss the signals.

For example, if a very indirect boss were to say:

Boss: I really have to get this report done, but I don’t have much time <— 📣 🟰 ‘Can you help me do this report’

He is asking you to do it for him.
When you miss the signal, you break rapport -and he will think you’re unhelpful and not so bright-.

Another common indirect request is with questions:

Boss: Do we have a list of invitees? <— 📣🟰 ‘Did you prepare a list, and if not, can you do one?

That is not a real question.
He is asking you whether you’ve done it, or not. And if it’s not done, he’s asking you to do it.
So if you did, you ask him if he’d like to see it. If you didn’t do it, you propose to get that done right away.

7. Turn him into your mentor

On average, the more time you can spend with your boss, the better

As per our article on career strategies, do this:

1. Seek guidance
2. Report progress
3. Grow mentoring from technical realms, to personal development
   • Ask him how to develop traits that you like in him <— 🎓 Shows you want to be like him, flattering him the right way

7.2. Ask what you should improve on

It’s crucial to uncover what your boss likes least about you.
And then work on that with him.

Why so?

Because people mentor people they like.
If there is anything your boss dislikes about you, he will not help you.

And second, if you don’t address it with him, he will filter whatever you do or say with a negative bias.

Says Goldsmith in his popular “What Got You Here Won’t Get You There“:

We view people consistently with our existing stereotypes.
If I think you’re an arrogant jerk, I filter everything through that perception. If you do something wonderful, I will this it’s the exception. Within that framework it’s almost impossible for us to be perceived as improving, no matter how hard we try.

Asking him what you should improve on allows you to get to the root causes of personality mismatches.

Address that -🐍 or simply act to his liking- and you remove major stumbling blocks to mentorship.

8. Protect yourself from jealous colleagues

Your colleagues may get jealous of your great relationship with the boss.

How do you handle that?

First off, never brag about your close relationship.
Play it down instead.

Here’s how:

• Be warm with all <— Prevents accusations of boss brown-nosing
• Frame it like ‘just another good relationship you have’
• Say good things about your boss <— Sub-communicates your special relationship as genuine
  • Say you admire him <— Frames attackers as jealous and cynical

The trick is to be friendly and gregarious with your colleagues as well.
That way, it never seems like you’re particularly “working” your boss. It seems like you’re just a friendly guy who’s just a little bit more attentive towards his boss-.

9. Understand, act, & strategize on “loyalty tests”

Every boss prefers loyal subordinates.

But to some autocratic bosses, loyalty is a requirement, and they will test for it.

Types of Tests

There is a multitude of tests, including:

• Carrying his luggage 🟰 Subordination test
• Assembling furniture 🟰 ‘Go outside the job description’ test
• Firing or reprimanding on his behalf 🟰 Enforcer test
• Taking the blame for him 🟰 Put your reputation on the line test
• Staying weekends and evenings 🟰 Sacrifice your personal life test

A career coach shared this test:

Boss: What kind of American car will you buy? <— He covertly requested to buy American

⚠️ Risks of loyalty

Tests imprison you to their agenda

You never pass a test and be done for good.

Each passed test sets new expectations.

On the plus side, successful loyalty-demanding bosses can take you far, fast.

However, it’s a risky strategy that requires subordination.
Loyalty-demanding bosses want obedient squires, not empowered men.

That ends badly when you reject total obedience and subordination to the boss’ interests.

Cohen made a great career as Trump’s legal pitbull. But he was discarded when he tired of total subordination

💡 Solution

To maintain power, independence, and honor, we suggest a different approach that we share in our flagship program.

10. Adapt your strategy to his power

Let’s be honest:

You want a good relationship because it helps you advance.

However, not all bosses can help your relationship.
So you must assess the workplace power structure to assess how helpful your boss really is.

Then, adapt your strategy:

• Powerful and upward trajectory: prioritize your relationship, become his right-hand man, or mentee
• Stationary: develop a good relationship but don’t tie yourself to him.
• Downward trajectory: keep it professional but keep a healthy distance

You must never tie your fortunes to falling stars, no matter how cool they are and how well you get along.
Also see:

• Common political mistakes

Bonus: Go past him. Smooth talk, resolute overtake

If you want to advance fast and your boss doesn’t help, he’s a roadblock.

The key is to move past him without turning him into an enemy.

Here’s how:

• Make him feel like the boss
  • Call him boss
  • Offer help
• Be warm to sub-communicate you’re no threat
• Admit some vulnerability
• Fully outshine him only when he has no power over you

🔎 Example: paying homage while overtaking

Motorbike racer Marc Marquez Marquez was beating his official team captain in his rookie year.

But he kept pretending his teammate was N.1.

Then, once he bagged that title, he was free to drop the game.

Talk him up with words, overtake him with deeds

Remember: until your boss has official authority over you, you’re not out of the tunnel, yet. 
Once your overtake is complete, then you can stop the game. But not before.

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This is an excerpt from Power University, workplace module