The Businesswoman Guide to Win in Male Organizations

picture of a businesswoman with skyscrapers background

Men and women approach business very differently.

As it’s to be expected, after all.
Men and women are biologically different, are brought up differently, and move within different cultural expectations.

Whether culture, nature, or nurture matters the most is a hotly debated topic. Luckily, we can skip the discussion and focuses on practical solutions.

And for our practical purposes, we can recognize two different approaches to business for men and women.
One is not superior to the other, of course.
However, different situations tend to favor and reward either the male style or the female style.

Historically, workplaces have been environments that functioned with the male style.
There are exceptions, of course. But in most cases, if women want to make it to the top of their organizations, they need to learn the men’s way of doing things.

This table summarizes the two different approaches:

comparative table of female and male approaches to business

Bookmark it here at high-resolution.

Note that I didn’t say that women have to adapt to the male style.
A woman can:

  • Find a way to be successful in her own feminine way
  • Find more feminine-oriented cultures
  • Say “screw business success”
  • Build her own business

But if she wants to make it within male-dominated organizations, she must learn to work the male way. And, in any case, she can only gain by understanding how men differ.

The Higher You Go, The More The Male Style Wins

Women are well represented in the workforce and in managerial positions.
But are still struggling to make it into executive and board positions, and this is why:

In Junion Positions the Feminine Style Works Great
Women can enjoy great success early on by being nice and submissive.
They focus on being pleasant, doing great work, and they do well.

In Middle Management the Feminine Style Works Great
Women still enjoy good success with the feminine style in management positions.
Low and mid-management levels are seen as nurturing and collaborative: taking care of the team members, and keeping the team cohesive and harmonious.

At Exec Level the Feminine Style Struggles
Things change when you get into executive positions.
To make it into executive positions you must be -and be seen- seen as hard-driving, ambitious, strong and, in some organizations, ruthless. That’s the male style.

On average, to make it to the top you need to learn to play the men’s game.

Why the “Go-Getter” Male Style Goes to The Top

driven businesswoman

Some women are natural go-getters. Others need to develop those skills

Bradberry surveyed 500.000 employees, managers, execs, and CEOs (1.000 CEOs, to be precise).
Bradberry found out that EQ (emotional quotient) increases with titles up until middle management.
Then it starts steeply declining with executives, and it reaches the bottom with CEOs.

Why do CEOs score the lowest in emotional intelligence?

Is it because companies promote lower EQ folks, or the tasks linked to their position lowers their EQ?
Even Bradberry, who is a big proponent of Emotional Intelligence (EI), acknowledges that it’s a bit of both -hence, he’s also saying, being low in EI helps you get promoted-.

There are two more factors at play, though.
One is that people in power do not need to be empathic towards the ones below them.
Says Goleman describing the “politics of empathy”:

Those with little power are expected to sense the feelings of those with power, while those in power feel less obligation to be sensitive in return.

And second, and most important, it’s not that CEOs are (necessarily) emotionally stupid. They just have different priorities.
CEOs are more concerned with power, winning, and getting things done than with what help you score high in emotional intelligence -things such as understanding what others feel, protecting people’s egos, nurturing relationships, and “getting along”-.

And if you want to make it to the top of most organizations, it helps to know the game that those execs and CEOs are playing.
Even if you want to transcend those rules once you’re at the top, you still need to learn them.

This post (and Power University) is about learning those rules.

The More Autocratic the Leader, The More Extreme the Male Style

As a general rule:

The more autocratic the CEO, the more the male style permeates the organization. And the more the male style is necessary to climb hierarchies.

You can see it with Donald Trump.
People who are successful around him are sworn allies to the man, not the organization. They respect the hierarchy and honor the boss (notice how meek vice president Mike Pence is around Trump).

And when the boss is not around, they all have an aggressive, “results-no-matter what” attitude.

See here an example with Mike Pompeo, one of Trump’s favorite and most successful allies:

Mike Pompeo: Our adversaries should know this (..) this organization will be more vicious, more aggressive, more inclined to take risks (…)

Pompeo’s way is the extremization (caricature?) of the male style. It’s all about aggression, domination, risk-taking… And enemies that need to be conquered.
In that Trump-environment, a more pro-social and kinder female-style would be seen as weak and ineffective, and it would never reach the top.

The 3 Traits to Master The Male Style

In the table above there are many entries, and I recommend you read it all.
The main ones you need to care of, are:

#1. Competitiveness: Be More Competitive Than the Average Woman

Going up the corporate ladder, in good part, is a matter of competition.
To do well in business means getting good at competing.

Men are more competitive and more comfortable with competition, and that gives them an advantage both at work, and in power dynamics in general.
Says Deborah Tannen:

If one person is trying to keep everyone equal and working hard to save face for the other, while another person is trying to maintain the one-up position, the person seeking the one-up position is very likely to get it, and to succeed in assigning the one-down position to the person who has not been expending effort to stay out of it.

Coaching Advice:

  1. Embrace competition: To go up, you need to compete more -as simple as that-
  2. Reframe competition as good for all: Reframe competition. It’s not mean, it’s how the best idea or the best candidate comes out on top, and that’s good for everyone (minus the one who lost)
  3. Reframe ambition: Hegelsen says that women are wary of ambition because they accept someone else’s negative definition. Change the definition of ambition. For example: ambition is the desire to maximize your talents in the service of work you find worthwhile and rewarding
  4. Acknowledge that you can be friendly and competitive: competition doesn’t mean you’re enemies. You can compete fairly, while being respectful of others

#1.2. Learn to Settle Disputes Through Competition

Psychologists Kilmann and Thomas developed the managerial grid model, listing the following behaviors to settle disagreements:

  • Accommodation (giving in)
  • Avoidance (“let’s pretend there is no issue”. It can lead to resentment and passive aggression)
  • Compromise (negotiating the different interest, we both gain a bit and lose a bit)
  • Collaboration (we seek a way that will lead to win-win)
  • Competition (I seek my way, you seek yours. One will win, and one will lose)

While women ten do to avoid competition, competition is exactly how conflicts are resolved in many boardrooms (and in some cultures).

For more information, self-assessment, and tips on how to compete, read here:

#2. Power Dynamics: Learn to Respect -and Be Respected- In Hierarchies

Men move in a world of top-down hierarchies, while women are more accustomed to flat hierarchies.

This is not to say there are no alpha females and no female hierarchies at all, but they are less pronounced, and follow different rules.
This is what you need to know about male hierarchies:

  1. Male bosses expect you to honor the hierarchy: act like he is a boss to be respected and listened to, and he will like you more than if you pretended you two are “just two human beings”
  2. Male bosses expect loyalty to honor the hierarchy: in male hierarchies great team players show loyalty to the man above and to the team. Not showing loyalty will put you at a political disadvantage. And be wary of loyalty tests
  3. Male colleagues will try to one-up you: men seek a hierarchy also among peers, so they might try to one-up you. Banter and teasing are also part of the one-upmanship games. Try to respond in kind
  4. Men seek and respect hierarchy status symbols: bigger office, bigger salary, (bigger) expense budget, (bigger) company car. When women give them up, they give up power and male respect.

Many of the above rules may seem petty to some women. In many ways, they are. But if you flout them, you are likely going to pay the political price.

Also read:

Feminine AND Powerful: 9 Tips For Women Bosses

Common mistakes to avoid:

  • Ask “why” and expect the boss to explain the tasks
  • Tell the boss why you think he is wrong
  • In interviews, telling male interviewers what work you do and what you don’t want to do
  • Try to change the boss’ mind publicly (persuading someone is a sign of soft power, the boss will not like it)
  • Doing voluntary work outside the team without his approval (including charity work)

#3. Goal-Orientation: Develop “Bottom-Line Mindset”

Men revere winners.

So they tend to be goal-oriented, thinking about the fastest and most effective way of reaching the goal.
Only after they found the quickest way, men consider the rules and constraints.

Women tend to be more process-oriented, valuing fulfillment and harmony as important parts of that process.
To men, that can look like women don’t want to win badly enough.

At work, a bottom-line first mindset is most likely to carry you to the top.
It’s not that corporations are evil per se, but the interests are simply aligned that way. People who are financially invested in the business want to see their money grow.

A bottom-line first mindset is the mindset that Wall-Street, investors, and owners love. It means they can entrust you with their money.

Common mistakes to avoid:

  • Perfectionism: perfectionism tends to focus on the process instead of getting it done
  • Over-worrying: worriors are seen as weak in the “winning-first mindset”
  • Lack of prioritization: men tend to focus on one thing at a time. They will think you’re scatterbrained if you do too many things at once
  • Hiding your drive: if you hide your ambitions you will come across as uncompetitive, and “not exec material”

Coaching Advice:

  • Present your idea in terms of bottom-line impact: since men value bottom-line thinking, frame your opinion in a way that saves money or makes money.
  • Make yourself less available: studies show that women are far more available than men. Being too available communicates you’re not giving enough priority to your bottom lines

3.2. Develop “Bottom Line Talking”

Deborah Tannen talks about “rapport talk”, that women engage in, and “report talk”, that men prefer.

Women talking to other women often like to start with a backstory, like how they came up with the idea. And that can be OK… As long as you quickly tie it to the main point.
Too long a preamble, and men lose patience fast, especially at the executive level where time is money.

I like this example from Margin Call:

When the junior employee starts sharing his background story, the CEO immediately tells him to cut to the chase. But notice that it’s different when the background story relates -and leads- to the main issue

Advice for Career Success

Most career strategies apply to both men and women. But there are several significant peculiarities women should be aware of:

#1. Find a Mentor

Having a mentor is helpful to anyone, but it’s especially important for women in business organizations.

The authors of “Breaking the Glass Ceiling” found in their survey that only 38 percent of successful men had mentors, but all of the women executives had mentors.
Pat Heim believes that’s because women need to re-learn the rules of the game, and a mentor helps them navigate that new world.

Should you get a male or female mentor?
The short story: ideally, you will have both a male and a female mentor.
Research shows that female mentors help get more promotions, but male mentors help women earn significantly more.

#2. Approach Relationships Issues With Work-Talk

Women are comfortable talking about relationships and feelings.
Men are not.

You make men uncomfortable talking about your relationship, even if you mean “work relationships”.
So if you need to talk about interpersonal issues approach it by saying “how to work better together”.

2.2. Watch Out for The “Factual Power Moves”

Some men might try to avoid a needed relationship talk by sidetracking you.

We will see more examples in the relationship module, but for work, imagine that your colleague has taken your idea to the boss and got all the credit.
Now you confront him:

You: Matt, when I tell you my ideas and you take them to our boss pretending they’re yours, I feel I can’t trust you. There’s a big problem with us working together
Matt: Well, your idea wasn’t that good. I can think of lots of better ways to streamline the process

The attack is the sidetrack.
If you start defending your idea, you fall for the bait.
Instead, you must maintain your frame and take it back to the relationship issue (in this case, trust):

You: Matt, the issue is not who has the best idea. The issue is trust. And when you behave like that, I don’t feel I can trust you

At this point, in the most extreme cases, men can use the “emotional power move”, which goes a bit like this:

Matt: Oh, you women are all alike. So emotional about everything. Let’s just keep this professional

Again, he is trying to sidetrack the conversation to avoid fessing up to his wrongdoing. You want to keep insisting on the real issue.

#3. Act Swiftly On Catty Female Subordinates

woman boss

Pulling ranks on insubordinate employees after they refuse to change their ways is the only way to maintain your authority

When a woman is promoted to a managerial position, other women can grow resentful.

Don’t take it personally, often it’s a knee-jerk reaction to their own female bias.
To a woman, a woman becoming a boss is a betrayal of the female unwritten rules (flat organization and “power dead-even”).
Read more in this forum entry.

To handle it, I recommend this approach:

  1. Get personal: go to lunch, get to know her, use indirect ways of commanding (“female style” solution)
  2. Coach her on how business works: explain that business is a hierarchical organization and you had to learn yourself. Now, you’re happy to share with her (coach solution)
  3. Tell her you’re the boss and she must execute: if the two above fail, try the top-down approach. This is likely to make her even more resentful though, so be prepared (autocratic solution)
  4. Fire her: a toxic employee is undermining you and your team. If she can’t work well, it’s your duty to let toxic employees go

#4. More Bullet-Advice

And here are more female-specific advice in shorter format:

  • Avoid volunteering for non-business critical tasks
    have you ever seen a man collecting money for Christmas gifts, or sending around birthday cards to sign? Me neither.
  •  Develop relationships that increase your power: women are uncomfortable building alliances that further their goals. But alliances are a critical path to power and success
  • Don’t talk behind men’s back: women are used to talk about their friends with other friends, but to men that’s a personal betrayal. Avoid talking about a man’s way of working to other women
  • Dare to lead: women often feel uncomfortable taking leadership positions. Especially if there are men around. But if you have to make it in a male world, you might have to push yourself to get in the lead
  •  Take criticism in strides: women more than men tend to take feedback and criticism personally. Never show that criticism is getting to you because men consider that an emotional weakness (develop an antifragile ego and growth mindset
  • Use your budget: Loils Frankl says that women tend to be conscientious about their company’s money. That’s great, as long as you aren’t inconveniencing yourself to save a few bucks
  • Beware of father figures: if you tend to behave unnaturally childish or “girly” around men with authority, beware you’re not seeing him as a father figure
  • Avoid over-apologizing: some women have a tendency to over-apologize. Apologizing profusely for inconsequential slips shows insecurity
  • Avoid playing the gender card: unless you can prove anything, you will get little support
  •  Don’t waste too much time on early ideas: Fran Hauser says that men knock on their bosses’ door to share a business idea. Women instead prepare presentations before they even get simple feedback. Before you invest much time, mention that idea in a casual conversation first.
  • Network with both men and women: women tend to cluster with other women, but that’s a mistake. In organizations where most top executives are men, it’s men who have the most important information

And if you’re feeling like crying?
Read this forum entry on how to handle tears.


This is a preview from Power University, the workplace module, where you can find more real-life examples and practical advice.

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