Managing Your Boss For Ruthless Career Advancement

how to manage your boss

Managing your boss means establishing the type of great work relationship with your boss that helps you advance your career.

Any effective “boss managing” strategy must take into account the realities of human psychology, including its more selfish and darker sides, as well as the office politics.

This post will show you how to manage your boss to maximize your career progression -this is the “political” way of managing your boss-.

employee gives a gift to his boss

#1. Be realistic: most bosses are average

The first principle.

Most problems with bosses stem from unrealistic expectations and from black and white thinking.

And this is an even bigger problem for highly driven individuals.
Highly-drive individuals work on themselves tirelessly, they place high demands on themselves… And they expect the same high standard from the people around. But if you don’t cut people some slack, you become unable to accept average.
When that happens, you are the problem, not others. You -or “we”- are the “weird” ones, not others. I know this is an issue for me, for example, which I also carried over in my intimate relationships sometimes.

But simple math says that most people are not striving to be the best persons they can be. 
Your boss also has his strengths though, and his positive sides. And he’s likely to be an OK person. It’s up to you, not to him, not to let his weaknesses overshadow his positives.

As a general rule, the more you like your boss, the better your relationship will be. And that is something you can control.

1.2. Accept he might not take an immediate shine to you

And since you’re there, accept that your boss might not like you, or he might not stand behind your every idea.

Expect divergences of opinions instead, bonuses that are smaller than you wanted, and expect to have days that you will rather not have him around at all.

If you don’t get along “naturally”, that’s when it comes down to your people skills and self-control.

Remember: being able to get along with people you don’t necessarily love is a sign of emotional maturity.
Immature people think in black and white: either great or asshole, best friend, or enemy.
Mature people instead accept shades of grey, and find a way to make it work even with people whom they don’t exactly revere.

#2. Accept that your boss has authority over you

Some people struggle to accept the power their boss has over them.

This is especially an issue for smart and driven men, and for people who are high in power -again, those are most likely to be reading here-.

And it’s also an issue for visionaries and passionate people. 
They cannot stand that someone could not see how genius their idea is, and implement it right away.

And who knows, maybe many of their ideas are genius.
But remember, Steve Jobs said: real artists ship. And to ship, you need political savvy and a positive relationship with your boss.
There is no glory in being the genius who gets shown the door because he was too rebellious.

If you can’t stand being in a hierarchy, and that someone can have power over you, I sympathize.
Take it as a challenge for you to learn how to operate and thrive in an environment that you dislike, while you find long-term solutions.

Ultimately though, dealing constructively with the constraints in one’s life is also part of developing emotional maturity. Living in a complex society also means that no matter who you are, sometimes someone will have some sort of authority over you. And you must make the most with those situations, as well.

#3. Flatter your boss the right way

Almost everyone enjoys receiving a compliment.

And still, some people feel that it’s not OK to compliment their managers because:

  1. Compliments should only go from top-down
  2. Bosses see through the game

They are not wrong: compliments from the bottom up can seem condescending -see “soft power“- and too open flattery can make you look like a brown noser.

And yet, the generalization of “not complimenting bosses” is dangerously wrong.
As Robert Greene brilliantly notes in “The Laws of Human Nature“, leaders can secretly grow resentful.
They take the credit for the team, and that’s what everyone focuses on. But bosses also shoulder much of the responsibility for the team, and most reports easily forget that.
When they get no appreciation whatsoever, bosses feel like their reports are being ungrateful.

Robert Greene, in his usual Machiavellian ways, suggests to compliment bosses on what they are insecure about, or using different words to express their own opinions. 
I agree with both techniques. When you hear your boss telling you “exactly!”, you know you are doing it right.

Bad way of complimenting your boss

Anything that your boss’ boss might say to him is a bad idea.

Topics such as leadership, leadership style, personal performance, team performance, and the likes are off-limits.
Those are compliments that people his paygrade would say, and when it comes from you, it feels like you are trying to position yourself above him. 
It’s jarring, and only socially unaware people do it.

Here is how that would turn out in real life:

Report: You’re doing a great job as a manager. The team is very cohesive and the guys love you


Boss: Hmmm thank you (but thinks: who the hell is this little cunt to assess my work as a manager)

Do that a few times, and you can rest assured your boss will prefer you out of the team instead of inside of it.

Good way of complimenting your boss

Compliments that work great are what he has done for the team or for you.
As a rule of thumb, “thank you compliments” are safe. “Well done compliments” are risky.

For example:

You: I love this team so much right now, we have such a great atmosphere, you really picked some great people, boss

That’s a compliment delivered as a team member, to the team captain. Plus, it highlights that you love it there and, indirectly, it frames you as an integral part of that team.

Here is another example:

You: I just checked the last quarter’s financials of SpinWeb: it’s the biggest customer we have so far. Thank you for getting this one for us, boss

#4. Promote tactfully: don’t overshadow him

Self-promotion is crucial for your career success.

However, there is an inherent conflict of interest between you and your boss when it comes to self-promotion: you want to look good for yourself, while your boss wants the team to look good, which reflects well on him.

And the conflict of interests doesn’t end there:

  • Lion VS cub conflict: A guy who self-promotes assertively comes across as confident, but that translates to “cocky” for male bosses who want to be the only roosters in the team
  • Teacher VS learner conflict: if you’re doing the same job, the boss will resent if you’re getting better than him
  • Master VS subordinate conflict: if you get really good, the boss will fear you’ll take his place (this is the “never outshine the master” of “The 48 Laws of Power“)

Does this all mean you should not self-promote, just so that you can save your boss’ face?
No, unless he’s a rising star going straight to the top, you don’t want to stay stuck out of fear of making waves. 

What to do then?
Well, the trick is to promote tactfully.
For example:

  • Tout your achievements, but frame them as “wins for the team”: people will get the message you’re good, but you come across as more of a team player
  • Tout your achievements, but frame it as “team efforts”: this indirectly sends some love back to “his team”, so you don’t look like you want to hog the spotlight
  • Tout your achievements, but also credit your boss: pass some credit to your boss saying he mentored you, explained how to do it, or gave you the opportunity

Self-promoting by sharing credit is not something you do for the boss only, but it’s part of a good strategy of self-promotion.
Also see:

10 Techniques for Strategic Self-Promotion At Work

#5. Prioritize his tasks

So simple, yet so effective.

Prioritize his tasks in your to-do list, but also:

  • Answer his emails quickly
  • Reply first when he poses a question on the team chat
  • Raise your hand first after he’s done a presentation
  • Sit front line and applaud when he gives a presentation
  • Be the first to finish whatever survey he sends around the team
businessman running

Move slow to project power. But act quickly for your boss to get real power

The Machiavellian approach is that if you can save 10h of work to your colleague or 1h of work to your boss with the same amount of effort, you help your boss. 
And if your colleague is in direct competition with you, you shouldn’t probably help him anyway.

5.2. Take something off his to-do list 

Former media executive and career mentor Fran Hauser says she received her first big promotion because she took care of making things easier for her boss.

Hauser proposed her boss to take meetings with smaller outside vendors to free his time and worked extra to deliver consolidated financial reports that also saved his time.
Rather than offering generic help, it’s best to approach him with a specific offer.

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. (…) figuring out how you can help her is just one more thing she has to do. 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.

5.3. Create unexpected value

Career strategist Dan Rust says that a great way to become your boss’ darling is to find ways to deliver unexpected value on top of your usual tasks.

For example, if your boss mentions how useful it would be to get more customers’ feedback, start recording it and present it to him.

#6. Never complain about your boss

Some complaints will eventually reach your boss.

And, most of all, it will influence your own behavior in unconscious, negative ways. Avoid making your boss the villain in your mind first and foremost.

Do not partake in any group that spends time talking crap about your boss. Those people usually don’t go anywhere.

#7. Match his emotional distance

It’s OK for a boss to make the first step towards getting personally closer.

But it’s more dangerous if it’s the report to make that first step.
Many bosses don’t like it when employees get too chummy because it decreases their authority.
And it’s never good when a boss has to step in to enforce his boundaries of authority.

Be friendly and warm, but not as you’d be with a colleague -no jokes about him being gay, and no talk about women-. Show that you respect his authority position.
If it’s your boss who wants to get closer, then great. Take advantage of it. But don’t start it yourself.

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

man telling his boss all is great

Everyone professes an open mind.
But few have it.

And in the era of Radical Candor management, everyone will profess a willingness to get real feedback.
But few really appreciate the tough love of real feedback.

Remember: highly critical feedback positions you as a non-friend and a potential enemy.

Here is the rule of thumb: bosses might learn the most from critical feedback, but they prefer promoting the sycophants who support them.
I’m not happy to say that, and I’m happy that there are exceptions. But, on average, that’s how it goes.

Treat your boss’ requests for negative feedback like you treat the interview question of “what’s your biggest weakness”. Pick a good trait, and frame it as a negative.

#9. Align with his communication style

Remember the importance of studying people?

At work, it will be most useful with your boss.
Learning people’s communication styles will serve to align yourself to your boss, and since people like people who are like them, your boss will also like you more.

NLP practitioners focus on communication styles such as kinesthetic (“it feels like… “), visual (“I can see why..”) or auditory (“I hear you.. “).
I’m not against it, but I recommend you prioritize more obvious -and more important- factors such as:

  • Direct / indirect
  • Quick / long winded
  • Chit chat before business talk / straight to business talk
  • Formal / informal
  • Rituals of speech (next paragraph)
  • In person / electronic

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

People who avoid in-person communication feel like you are violating them if you keep seeking in-person interactions.
And people who prefer talking in person will feel like you are shifty if you write instead of talking.

So put aside your preferences and power-align instead.
Once you will be the one in power, then you will then demand that others adapt to you.

10.2. Match their conversation rituals 

Linguistic research Deborah Tannen presented her research in her seminal book “Talking From 9 to 5“.

Conversational rituals are patterns of speech and behavior that work only when both players use them. 

When one party uses conversational rituals and the other doesn’t, communication is less effective and, most importantly, it damages rapport.

Some of the most relevant conversational rituals, especially from a power dynamics perspective, include the use of “sorry” and “thank you”.

Imagine this dialogue:

Boss: thank you for running this by me <— this is the ritual


Report: no worries, cheers <— misses the ritual

The boss is expected to keep oversight, so the “thank you” there is a ritual, not a real thank you.
The boss had no real reason to say “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”, it makes the boss the one down. Over time, the boss is likely to 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:

Boss: thank you for running this by me


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


Boss: Thank you for saying that, it’s my job and I am happy when I can help

Now the boss will be thinking “this guy gets it”.

10.3. Jump on indirect commands (& avoid taking offense on direct ones)

As we saw in “how to look confident at work“, some bosses prefer direct commands, while some others prefer going indirect.

If your boss is direct and you prefer indirect, that might rub you the wrong way and you might think he’s an ass. You need to reset that.
You need to realize it’s a question of culture, personality, and preferences. You can’t judge a person’s moral code based on whether he prefers direct or indirect talk.

On the other hand, if he speaks indirectly and you are more direct, you can think he’s a submissive cuck who doesn’t have what it takes to lead. Same as before, though, you need to change your perceptions.
If he’s indirect and you are direct, you can also miss the signals that he wants you to act.

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

He is asking you to do it for him.
If you don’t get it right away, he might have to ask you again, this time more directly. But you will be forcing him to act out of character, he will feel you two don’t get along, and that you’re not very bright.

Another common way of issuing indirect requests is this:

Boss: Do we have a list of invitees?

The boss is not asking your opinion on whether we have it or not.
He is asking you to either send him, or to prepare one if you don’t have it.

#10. Remove awkwardness, establish friendly relationship

Sometimes, there can be some awkwardness between boss and employee.

The problem with that is that bosses tend to promote those they feel good with, not those they feel awkward with.

So you have to take it upon yourself to normalize that relationship.

You do it by first by getting over the fact that he’s your boss (entry N.1).
Then, by eliminating any personal reserve you might have. And third, by seeing him as a person.
Then you can find an opportunity for some humor, building on his jokes, or commenting on something he likes.
Best of all, go to lunch together sometimes.

#11. Turn him into your mentor

boss talking to employee

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

Those who elect their bosses as their teachers win major brownie points.

Better yet, turn your boss into a mentor.
Mentors often put their mentees on the fast track. That’s all you need to know, right?

Here are the steps:

  1. Start asking questions on how you can accomplish something at work
  2. Go back with the results and say his advice helped you (this is the “work-level mentor”)
  3. Branch out to what really matters: advice on people, and work situations (this is the career mentor)
  4. Try discussing politics, competitors, and job opportunities. If he bites, you effectively turned him into a sponsor.

12.2. Remove behavioral stumbling blocks to mentorship

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

Why so?

Well, first of all, if there is anything your boss truly dislikes about you, he will not help you.

And second, if you don’t address it with him, his negative neuro-associations will always frame your behavior negatively.

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

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

But if you tell your boss you’re committed to working on your issues, things change. Now it’s not anymore an exception to the rule, but it’s you changing for the positive.
And if you change thanks to his feedback, he’s investing in you, and becomes part of your change. Your win, becomes their win.

PRO Tip: Show you want to be like them
Mentors will never say it, but most of them will like you the most if you seek to become just like them.
To show you strive to be more like him, you can ask things like “you look always so calm and in control. I’d love to be the same. How do you do that”.
If you see him smile, you know that your indirect compliment has hit the mark.

#12. Offer him your extra capacity

It’s nice to help a colleague when you got the chance.
And sometimes, you should.

But this is an article on how to leverage your boss relationship to advance your career.
And from a political point of view it’s best to offer your extra capacity to your boss.

If a colleague asked you for help, you can say yes, but run it by your boss first. 
For example:

You: I’m planning to help Chris on the McKenzie brief, but I wanted to run it past you first in case you have other priorities or need a little extra help.

If you finish a task or project ahead of time and now are free, say something like this:

You: Boss, I just wanted to let you know that I finished the project ahead of schedule, so I have some extra capacity. Do you know of anyone who could use my help?

This is a double whammy: he gets to know you are done early, that you want to help, and that you respect him so much to ask him first.
Now he will put you either on his priority, or company’s priority, thus further increasing your visibility.

#13. Protect yourself from jealous colleagues

As you develop a stronger relationship with your boss, your colleagues might get jealous.

How do you handle that?

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-.

Most of all, make sure that you never brag about your special relationship with your boss, and never make it seem like you two are in cahoots.
That’s the best way to ruin that relationship. Do the opposite instead, hide and deny.
If someone says you’re close to the boss, play it down.
Say: 

You: I don’t know, but I like him. I’m learning a lot from him, I’m glad he’s our boss. 

And then, move out of the topic:

You: The whole team is great. I’m happy to be here. 

That way, you take the high road and slightly shame them for implying you’re “close to the boss”. No, you’re just a friendly guy learning as much as he can.

#14. Adapt Your Strategy to His Power

Finally, you need to assess your boss’s strategy against his power.

How powerful is he in the organization?
And what’s his career trajectory (ascending, stationary, or descending?).

  • If he’s powerful and going up, you can gain in becoming his right-hand man, or mentee
  • If he’s not moving, develop a good relationship but don’t tie yourself to him.
  • If he’s losing power and possibly on the way out, keep it professional but don’t get too close

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

#15. Go past him: smooth talk, resolute overtake

This is something that superstars and very ambitious people need to plan for.

If you want to grow quickly and your boss doesn’t help, then your boss might be a potential roadblock.

This is why it’s all the more important that you frame your relationship as collaborative, that you show that you are a friendly force and, possibly, even that you are an ally.
The last thing you want is to develop a confrontational relationship with your boss.

Most of all, you want to avoid a confrontation while he still has power over you.
If you are delivering great work and networking with the higher-ups, you are already overtaking your boss.
But before you are fully released from his formal authority, it’s still important that you keep “sterilizing” your wins as not to make him feel threatened.
Say publicly that he’s N.1, that you’re learning from him, that you owe to him. And make big shows of deference in your 1:1s.

I like this example from racer Marc Marquez:

law of power number 1 example

Talk him up with words, overtake him with deeds

Marquez was destroying his official team captain. But he kept pretending his teammate was N.1.
Then, once he bagged that title, he was free to drop the game.

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.

SUMMARY

In the ideal workplace, “managing your boss” means developing a relationship that prioritizes work and efficiency.
Then, you will get promoted as a consequence of your great work.

That’s the ideal workplace that people write books about. 
But the ideal workplaces barely exist.

Maybe one day you’ll build your business as an ideal workplace, as the boss, or as the founder. 
I hope so.
But before getting there, you must learn the realpolitik first.
This post showed you how to manage your manager to make him love you -and promote you-.


This is an excerpt from Power University, workplace module.

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