21 Conflicts of Interest (Your Boss Doesn’t Want You to Know)

symbol of work conflict of interest with tug of war

Political awareness, as much as any good social and life strategy, starts with a good understanding of the conflicts of interest.

This is true across all socialization.
Understanding conflicts of interest is a foundational aspect of learning advanced social skills, power dynamics, as well as the scope and opportunities for collaboration (or for manipulation).

conflict of interest represented with business people tug of war

And the same concept applies to the workplace as well.
Once you know how and where the interests diverge, you will better understand the political chessboard -and you will be better placed to play that game-.
On average, the areas of diverging interest are also the areas where you must be most careful, as you can expect more manipulations and lies.

As a rule of thumb, there is more potential for conflict of interest at work than in most any other social exchange (including sexual ones).
See this great post from John when he realized this much.

This is why, albeit most of this website’s strategies are geared towards increasing the scope of cooperation and realizing win-win, keep in mind that at work, on average, you must be more guarded, and dial-up your Machiavellianism.

Which is not to say that you should become an asshole, quite the opposite.
And this is also not to say, of course, that there cannot be win-win.
All our basic principles apply.
Seeking win-win, using cooperative frames, aligning interests, assessing others when they have more power… These are all sensible strategies no matter where you’re at.

But, at work, you must be slightly more towards your cynical side, less vulnerable than you usually are, and more generally guarded as to your real thoughts and feelings.

Now, let’s review the conflicts of interest:

Boss VS Employees

This is between you and your boss.

1. You want to work for yourself, your boss wants you to work for the team

The better the team performs, the better it looks on your boss.


  1. The better the team performs, the more you’ll struggle to stand out
  2. The more you do “for the team”, the less you can do for yourself

Solution: Listen to “team you”

Leadership comes at a cost.
But those costs are smallest at work, while the rewards are the biggest.

And while you’re revving up for leading, don’t forget that alongside the “team” there is “team you”, and both of them need your attention.

2. You want to move up, your boss wants to keep you in the team

The general rule:

The better you are at your job, the more your boss wants to keep you within the team.

If you move up, you won’t be helping your boss anymore.
So if he lets you go, or he helps you advance, it’s because he’s a good boss.
Some are -and many more simply don’t have a choice-.

But keep it in mind.
Some unscrupulous bosses might work behind your back to thwart your advancement opportunities.

3. You want to take credit, your boss wants to take it for himself -or the team-

You want people to know about your good work because:

  1. It increases your status
  2. Puts you in the fast promotion track

And of course, because it makes you feel good as well, which is equally important -and fair to demand-.

But your boss does not want you to take credit for your work.
The ideal team for your boss is a team of faceless and anonymous individuals whose good work all fall under his name.

And the opposite is true when the team makes some major mistakes: then he wants to be able to point finger at someone and assign the blame.

Solution: Intelligent self-promotion

This is where self-promotion must meet good political strategies.
Also read here:

4. You want to keep your best customers close and for yourself, your boss wants impersonal relationships, or contacts shared with the team

Valuable contacts, be customers or powerful people, are power.

You want to keep them to yourself only, because that gives you leverage. And if one day you leave the company, you might be able to bring them with you.

Your boss instead wants you to share all your contacts with the team, so that they become more of “teams’ customers” instead of your personal friends.
That increases his personal power as well as the team’s resilience, but it decreases your leverage.

Example: Law firm doesn’t want lawyers to answer “thank you” emails

Bel shares that in his former law firm lawyers were discouraged from answering “thank you” emails from customers.

On the surface, that doesn’t make any sense. Who would want such a rule, and why?
Well, now you can guess why.
Because the partners didn’t want the firm’s customers to grow too close to their employees -it’s a risk if that employee then decides to work with the customer outside the firm, or that he might leave one day and take “his” customers with him-.

Owners VS Employees

Rich owner meme
You want a raise? Sure, talk to HR here behind me

“Owners” refers to anyone with a sizable stake in the company -and its revenues-.

It can be the founders, the shareholders, or the upper management with stock options.

Sometimes non-owners also act like owners.
These are “company’s loyal squires”, but you might offensively refer to them as “kapos”.

They serve the company’s interests, sometimes flatly against their colleagues, without even having much stake in that company.

Sometimes they are in HR, and they feel they need to defend the company’s interest against all the other employees.
But sometimes they are low-level employees who are happy to play the guardian role for a pittance more than the bare minimum.

Don’t you dare being one of them :).
And let’s keep on learning:

1. You want to put yourself first, owners want you to put the company first

Owners try hard to instill a mindset of “we’re a family”.

The more they can convince employees they are all a family, the more the employees will work hard for the company, without caring what they will get back.

That’s why much of corporate slogans and values are about “teamwork”, “team first”, “we” or, at the extremes, “family”.

Businesses and CEOs love to talk about their organizations as families.
CEOs autobiographies gush over their love for the people and employees. And they sob and weep at the heartbreak of having to fire their own family members when hardships strike.

I have seen a similar theme across business titans biographies such as Howard Schultz (Starbucks), Phil Knight (Nike), Sam Walton (Walmart), as well as CEOs and VCs (Ben Horowitz).

And then, guess what?
They fire people anyway. Multiple times if needed.

Ultimately, the only entity to gain when employees think of their workplace as a family is the business itself -and the owner-.

2. You want to be compensated with real cash, owners want to pay you with “motivation”

This is where corporate manipulation kicks in.

And this is how you get slogans like:

  1. We’re changing the world
  2. We add value to our customers
  3. We care about… (whatever)

This goes back to intrinsic and extrinsic motivation (Vallerand, 1997. Or see Pink 2009, for a more general public approach).

In short: the more the owners can reward employees with ideals and emotional rewards (extrinsic motivation), the more output they can get out of those employees while also paying them less monetary rewards (intrinsic motivation).

Solution: Money Talks, You Listen

Money talks straight, owners manipulate. Listen to money.

The Power Moves

Lemme preface this actually:

There is nothing wrong with extrinsic motivation, ideals, and values.
Actually, they are a great thing, and they provide real mental -and even physical- benefits.
But also: don’t lose track of the hard-cash transaction.
Enjoy the values, ideals, lofty goals and all the extrinsic motivation you can get. But make sure you also get your full financial compensation for the value you bring to the table.

3. You want to pursue alliances with colleagues, but the company prefers to deal with you as an individual

meme for conflict of interest between boss and employees
Divide and conquer disguised as teamwork

Why do owners hate unions?

Because alliances make you stronger, and can enable you to increase your leverage and negotiation power vis-a-vis with the company.

Owners don’t like internal cliques, personal alliances, or organized groups of workers.
Not only owners dislike them because they empower you, but alliances also channel your allegiance away from the company and towards your friends. The company doesn’t like that.

You can see this same conflict of interest repeated at national and government levels, as well.
The government frowns upon -or outright bans- any congregation that might potentially pose a threat to the government itself -or to its ability to collect taxes-.

4. You care about doing well personally, the company wants you to care about the company doing well

There is some overlap here.

If the company does well, its workers are more likely to do well.

But the overlap is not nearly as strong as the company would want you to believe.

Yes, it’s true that a “rising tide” lifts all boats, but as political strategist Brendan Reid correctly points out (Reid, 2014), it’s also true that you don’t really advance much when everyone else is advancing.
You advance comparatively, not absolutely.

And it’s often during crises and restructuring that opportunities for rapid advancement arise -at least for those who know how to take advantage of the turmoil-.

5. You want to increase your skills, your company wants you “just good enough” to do your job

Personal value is a two-edged sword for owners:

On one hand, a skilled and driven workforce is a boon.

But on the other hand, the more you improve, the more you will want to move up the corporate ladder, ask for more money or, potentially, move to another firm.

Skills empower both you and the company.
But while you are always empowered with more knowledge and skills, the company does not always and equally gain n all circumstances.

The company does want some of its employees to move upward, but not everyone.
And it certainly doesn’t want too many people striving for more, and asking for more.

The truth is, all companies need someone doing some monkey jobs. And someone has to keep doing those monkey jobs, for peanuts salaries.

So, for a good chunk of employees, the company prefers them to just stay put where they are.

Solution: Take all training and growth opportunities you can get

You can only gain from personal growth.
Take all training and stretch assignments you can.

This is exactly where working in a company is good from a Machiavellian point of view: you can fuck up, and not be on the hook as if you were working on your own.

There are plenty of people who escape responsibilities and seek the easy way out.
Just make sure it’s not you who remains stuck in the monkey business.

6. You want to cover your ass, the company wants you to trust them

The company wants you to trust them.

First because when you feel like you can trust your employer you perform better, second because you don’t waste time in “cover my ass activities” and, third…

Because when worst comes to worst, if you did not cover your ass, you have no leverage whatsoever and you’re screwed.

Some companies will also try to break or bend the law when they smell that an employee can be pushed around, so be particularly careful.

But even if you’re not the guy to be pushed around, you won’t go far unless you can state your case with evidence.

Solution: Collect Evidence

Machiavellian power move:

Leave no traces of bad conduct, no matter how minor, while you start recording all infractions from your employer.

You don’t need to use those records.
And you might not even want to use it.
As a matter of fact, I recommend you always go for win-win relationships, even with your employer.

But simply knowing that you have the power to win a lawsuit immensely increases your power and leverage.
And it’s just good insurance policy.

7. You Want to Keep Your Best Strategies Private, The Owner Wants You to Share Them -Better Yet, Codify Them-

The principle is simple:

Knowledge that you only have, empowers you. Knowledge that is shared within the company, empowers the company.

Hence, you want to keep your best trade secrets to yourself, while company owners want you to share the information.

As a matter of fact, the company owners want to have that knowledge codified in simple format so that even a monkey could do what you’re doing. So that they can hire monkeys and pay monkey salaries

BTW: monkey is terribly offensive, but that’s exactly how a founder I spoke to addressed his people in operations-.

See this example from “The Wolf of Wall Street:

Owner: So, what do you say?

Everyone: (reads from a script like a bunch of sheep)

That’s the dream of every owner: everyone is the same, and everyone is easy to replace.

Solution: Machiavellian Hoarding of Wisdom

Now you want to be strategic here.

Emptying your knowledge can and making your results replicable without first ensuring you get your fair share is too risky and should be avoided in most cases.

But not sharing anything will make you come across as a poor team player (and you lose an opportunity to showcase yourself).
Remember that it doesn’t matter who you are and what you know, it’s what others see.

The Machiavellian approach is to share information and knowledge that sounds helpful and deep, but that truly adds little value.

Another good technique to add value is to make sure that you will get something back before you provide that value.
If you can systematize your knowledge in a way that everyone gains, go for it, it’s a great opportunity. But first make sure you negotiate your fair compensation for it.

Old-Guard VS New Generation

representation of Conflict of interest between new generation and old genereation

1. You want respect & personal power, they want you to be an obedient grunt

Culture has changed -luckily-.

Back in the days, the expectation was for lower-level employees to be at the beck and call of senior folks.

But the senior guys did go through that mild hazing culture.
And so today the senior guys want to have the same hazing rights over the new guys joining in.

They are also secretly resentful if you get to experience too much of an easy life and, of course, they don’t want to give up their “right” bossing you around.

That’s how you get all-too-common tropes:

  • The new generation is soft
  • They are entitled without giving anything (sometimes true, but not as much as some people like to parrot)
  • They don’t appreciate the value of hard work

Most of the times, these are indirect cries for appreciation.
They all actually say “look at how hard I worked, how ethically I’ve played the game, and appreciate me for it”.
So throw them a bone, make them feel good, then frame yourself as a hard worker who “wants to be like them”, and you’ll be good to go.

2. The Slower They Climbed, The Slower They Want YOU to Climb

As a rule of thumb:

The slower they moved upward, the slower they want YOU to move upward.

Anything less will make them feel bad about themselves.

3. You Want More Flexibility, They Want You to Sweat Blood and Tears

I remember years ago, when I was “SHINE talent graduate”.

We were presenting new ideas to the board comprised of all the most powerful heads of our IT center.

My idea was to change the policies around home office. “We should remove the 2 days cap a week, and scrap the need for the manager’s prior approval”, I opined.
That way, I argued, we could attract and keep more talent.
And if people abused the system, great! Such an easier way to find out who the bad apples are, and who we need to let go.
I had data in hand: the new generations considered flexibility as important as salary.

The answer from the board?
A big laugh.

“These new guys want to come to work and chill with a beer”, said the biggest boss.
And all the other senior yes-men jumped on the chance.

Of course: they did NOT have flexibility during their career.
So they resented people who could now enjoy or, sacrilege, demand it!

It was my mistake, of course.
The mistake was in the framing of the request.
I should have framed it as a win for the company instead of “making new recruits happy”.
And I should have paid homage to hard work and the importance of face-to-face interaction as well, a wink to the “real” way of doing business, the way they did it (plus: it’s true that face-to-face trumps online).
Machiavellian twist: I could have joined them in laughing “at the new grads”.
“But if these simps want to stay home with their moms, let’s give it to them, and we’ll even save money in office space” (see what a Machiavellian power move? You power-align with them, pretending to laugh at the people who instead you’re going to help. That’s Machiavellianism for win-win).

Individuals VS Team

And here we come.

Those whom the company frames as your closest brothers in arms, your colleagues in the trenches… Are also your biggest competitors.

meme of teamwork conflicts

That picture says a lot about the conflicts of interest at work.
Especially, about the inherent conflicts between “teamwork” and the obviously limited opportunities for career advancement.

1. You want to be promoted, and all your colleagues want to be promoted

This is at the heart of the individual/team conflict of interest.

Most people prefer to move up the corporate ladder rather than staying put. But there are only a finite number of spots.
And that’s how your beloved colleagues turn into your number one competitors at work.

2. You gain a comparative advantage by keeping the best information, while your colleagues want to learn as much as possible from you

The better you get at your job, and the more knowledgeable and skilled you become, the more you become a valuable resource for the team.

Theoretically, you could teach a lot to the team, and help them reach your level.
But then, what happens?
If they all reach your level, your comparative advantage for promotions diminishes. And if everyone is asking to receive your salary, there is less money to go around for your next salary increase.

So while those rabid dogs want to suck you dry of all you know and who you know, and what you know… You actually prefer to keep it all for yourself.

Also read this post for more information on sharing knowledge:

3. You want to shine for yourself, the team wants you to share credit

There are two levels of conflict of interests when it comes to team work and promotion:

  1. You want to take as much credit for yourself as possible, the team wants the credit to be shared
  2. You want to make great work, the team prefers you to do average work

The more you shine, the more you make the team look bad by comparison.

Solution: The Competition Switch Mindset

Separate human kindness from business competition.
Internalize within you that friendly and friends go together with competition at work.
Outside of work, an increase in warmth and friendliness means a decrease in competition. But not at work.

Also, if your friends are lower-level performers, be friendly and warm enough so they don’t turn into enemies or frenemies (remember the general rule that enemies disempower).
But make your warmth descend from a position of superiority, as if you were already their leader.

4. You want to be close to your boss, the team prefers you to stay away from him


There is an inverse proportion between how close you are to your boss, and the likelihood that your colleagues will have to shine and be promoted.

You do want to be close to your boss, but sterilize your closeness with being warm and friendly to everyone in the team, so it doesn’t seem like you’re a brown-noser.

5. Men want to keep power, women want to upset the system

This one deserves its own post.

It intersects with general intersexual dynamics, as well as with manipulation.
Women overblow the “patriarchy” -which is not completely made up-, while men tend to play it down -including male academics who study this stuff and who should know better and be more honest-.

Also see:

And more befitting to the workplace:

Execs VS Stakeholders

This conflict of interest might be one of the best arguments against unfettered capitalism.

And it becomes especially salient during times of financial crises -especially in the banking sector-.
Then, when the ship risks going down, you’ll see all the captains trying to ransack the ship, and leaving everyone else to hold the bag.

1. Executives want short-term profit, even if it might create problems in the future

Some classes of powerful people have an interest for short-term profits, even if that means creating far bigger problems down the road.

Politicians sometimes belong to this category.
Borrowing today, for example, helps politicians keep power, maybe even (indirectly) taking some of that money, while pushing the problem of repaying that money to the future generations (de Mesquita, 2003).

Sometimes the cycle of “gain, let someone else pay for it” is even shorter, with simply the new class of elected politicians having to deal with the mess.

You realize you are in such a short-term profiteering environment when the bosses are pressuring people to say and do what’s expedient instead of what’s true and, in the most blatant of cases, to forego obvious standards of morals.

When that is the case, from a purely Machiavellian perspective, it’s best for you to work to help the bosses line up their pockets and interests, and that will help you make a great career.
Then you can move somewhere else before that ship will start sinking (bad management doesn’t make for great companies).

Note of caution:
As Bel correctly noted, you must be very careful here. Because many (psychopathic) bosses try to push their employees to do illegal acts and then blackmail them and hold their careers on the line. 
Or use them as scapegoats.

See an example here from the documentary “Capitalism”:

William Black: People who will give you the wrong answer, but the answer you want are invaluable and they often get promoted precisely because they are willing to say and do absurd things.

There is also a different approach possible though:

Dare to be black sheep

Once you’re pressured by those in power, there are strong incentives of both self-interest and self-preservation to act unethically (and screw the invisible majority).

Still, know that there is a different road.
And it’s potentially even more powerful (albeit riskier).

William Black himself from the video above does pretty well for himself.
Di Pietro, the man who fought the Italian corruption system and gave birth to the huge movement called “Clean Hands” also did great as a lone fighter (and he got my first vote as soon as I could vote).

Being the lone fighter is riskier, and can either get you kicked out very quickly, or it can make you the leader of a new movement. Doing so requires lots of interpersonal skills and power awareness, though.
And if you go that way, make sure the law on your side, and that you operate within the law. Otherwise, it’s too easy for those in power to dispatch you.

2. Execs and owners want to privatize the gains, and collectivize the losses

Similar to the above, and the two often overlap.

The further away and the more powerless the stakeholders are, the more the few in power want to enrich themselves whilst pushing the costs to the many.

This issue is huge in politics, since politicians have access to tax money and the power of the taxpayers once parted with their money is severely limited.

Owners and shareholders often have similar incentives to cut down the costs and let the have-nots to pay the price.
The costs aren’t always a direct cost on people. Sometimes it’s indirect, paid with common goods pollution, contamination, or depletion.
That’s even easier for shareholders to pull off, since people are even more unwilling to rebel for what they don’t feel it’s even theirs.

There can be power, and even some potential personal benefits in making yourself the “leader of the forgotten good cause”. But only if you do it outside of the corporation or political party.
Doing it from within, especially if you do it too loudly, is political suicide.

You Can Still Work Through Conflicts of Interests

Reader beware here:

being aware of conflicts of interest does not necessarily mean that you must withdraw from the exchange, or refuse to give the other party what it wants.

Conflicts of interest do not preclude indeed that there can be a win-win, mutually beneficial relationship.
There are conflicts of interest everywhere after all. Even among mothers and children (Buss, 1988).
Yes, mothers do care about their children, and few would argue with that notion.


Awareness of conflicts of interest forms the basis of political intelligence.

Now you are aware of the major conflicts of interest at work.

This post was high in cynicism, and it’s your task to make sure you don’t become too cynical.

Remember that the general rules still apply: staying out of the exchange, no matter how flawed it might be, is usually far more costly than partaking to the exchange.

And whenever you can, seek win-win and collaboration -especially with other high-value players-.

And now that you are better aware of the workplace conflicts of interest, you are also far more empowered to base your win-win on real-world power dynamics, rather than on naive ignorance.

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