Break Your Own Rules, Part 5: Play to Win

Thinking Patterns that Hold Women Leaders Back (and How to Replace Them)

By Jill Flynn and Kathryn Heath, Ph.D.

As women, we face many challenges throughout our careers. We can’t fix all of them but there are many we can. In this six-part series, we examine the Old Rules, or limiting beliefs and assumptions, that prevent many women leaders from achieving the level of success they’re destined to reach. We then outline the New Rules, alternative thinking patterns, and behaviors to adopt instead.

Check out all six parts of this series:

Break Your Own Rules, Part 1: Take Center Stage

Break Your Own Rules, Part 2: Proceed Until Apprehended

Break Your Own Rules, Part 3: Project Personal Power

Break Your Own Rules, Part 4: Be Politically Savvy

Break Your Own Rules, Part 6: It’s Both-And

Out with the old, in with the new

Change is uncomfortable; there’s no doubt about it. But what’s even more uncomfortable is allowing limiting beliefs to block your path to power and the career of your dreams.

We focus on limiting beliefs and thought patterns because the thinking that motivates behavior is the fuel that sustains the behavior. We must address the underlying assumptions and stories we tell ourselves to overcome them.

And while there are many conditions that are important to advancement, some are within your control, and some are not. This article series and the book on which it’s based, Break Your Own Rules, focuses on the areas you can change and control. But know that there is no magic bullet for this work. Changing old thought patterns requires time and effort, but the outcome could be life changing.

The Old Rule: Work Harder

Judy was a very focused and disciplined person. She loved her job.

Yes, she consciously broke many of her own rules in order to prepare herself for a bigger role. And yes, she succeeded in getting on the short list for a promotion to the senior ranks.

However, when the big boss called Judy to offer her a promotion, he didn’t offer her the job she had in mind and offered her something totally different.

Her world was rocked by his phone call. She stuttered and stammered and began to tell him why she was not prepared for the job he had in mind.

Luckily, she caught herself after a minute or so and asked if she could call him back. She talked to a few people (including her coach), who helped her realize that (1) the job the big boss was offering was better than the one she had in mind initially, and (2) she had the skills to do most parts of the new job and the capacity to learn the parts that were new to her.

Suffice it to say, this turn of events would present a major dilemma for most of us. What Judy said she struggled with most in this situation were the risky unknowns. To succeed, she would need to put herself way out there—manage more people, reach higher revenue goals, and increase sales targets.

She believed she needed to know how to do 100% of the job she was being offered and wasn’t certain she was comfortable enough with the risk to make this new situation work.

Judy is not alone. It’s normal to feel ambivalent amid major change. Change is risky and takes us out of our element, but these days it’s everywhere in business. Success, then, for both women and men, requires a fairly high degree of comfort with change and risk. So how do women leaders fare in regard to mastering this capability? The signals are mixed.

There is clearly a stereotype, one that may have some wind left in its sails, which says that women, in general, are not natural risk takers in most cultures and societies.

Much of the academic and clinical research on the topic is very focused and refers to specific types of behaviors that are unrelated to business. It indicates a higher rate of risk acceptance among men in such activities as driving over the speed limit or gambling, for example, as opposed to taking risks for high-potential career opportunities.

In contrast, a recent study in Psychology of Women Quarterly reported no evidence for overall gender differences in initial risk-taking in the workplace. Even more interestingly, the study did find a difference between women and men in the consequences of risk-taking

The men evaluated in the study reported more positive consequences of risk-taking, even when the risks taken were more normative for women. Conversely, women experience less rewarding consequences of taking risks, thereby leading them to potentially avoid risk-taking more than men.

“Workplace gender equality initiatives should therefore tackle any inequities of consequences rather than encouraging women leaders to ‘lean in’ and take more risks, according to the study. The question as to whether women in particular are truly risk avoiders may be too close and nuanced to call, but the reality is that there is the perception of a gender divide. And perception matters.

Aside from that, even the boldest among us can benefit from learning how to build smart risk assessment into our portfolio of career skills and promote what risks we have taken.

Before we suggest how to have a healthy and productive relationship with risk, let’s first review some of the patterns of operating that we consider Old Rule thinking. These types of mindsets hold women leaders back.

I like my comfortable role

A little comfort is a good thing. Comfortable routines make us feel safe and allow us to relax. But being too comfortable in a job is not necessarily productive. It signals that the challenge is gone, and with it, the opportunity to thrive and grow. It may seem that you’re stuck.

Why is it that we allow ourselves to stay stuck in a job that’s going nowhere, even after we’ve hit a wall in terms of challenge and upward mobility? Here are a few reasons:

Staying put feels emotionally safe. Perhaps we’re succeeding—even coasting along—in a current role. Going after something new is risky. It puts the delicate balance of our current life in jeopardy. After all, what if we can’t handle all the demands of the new job? Where would that leave us?
Fear of failure. Our status in the community, as well as the identity we’ve built for ourselves, depends on maintaining steady career success. If we try something new and fail, we’ve set ourselves back in a number of ways. But a comfortable job may not be as “safe” as it seems. If you’re not feeling challenged, chances are you’re not really firing on all cylinders. And when you’re not on your toes, there are things that will eventually sneak up on you, such as industry changes and organizational realignments.
Staying put until the job is complete. We think we need to have all projects tied up neatly before we can move on. We say things like “It will hurt my group” or “I have not finished yet.” The reality is that there is never a “good” time to leave, yet moving on might be what’s right for your career.

I don’t like sales

Not all of us are natural-born rainmakers. Closing deals and bringing in new business require not only contacts but—perhaps more important—confidence. We’ve found that the art of the deal is something that many very smart women feel uncomfortable cultivating. It’s beyond their comfort zone, so it feels risky.

This is an important point because without the ability to sell—yourself, your ideas, your company—it’s almost impossible to rise high in the ranks of most organizations.

Whether you’re comfortable or not, sales is a skill worth developing. We’ve seen many women back away from jobs that entail persuasion and deal making because they have a negative perception about sales or perhaps about their own skills related to selling.

But sales, after all, is the lifeblood of most companies. In most cases it’s where the growth comes from. You can bet your bonus that the senior management team knows who the rainmakers are in your organization—and they are not just in the sales and marketing department.

From our experience, we’ve seen consistently that women leaders who make it to the top have had sales experience and were good at it. Product developers sell their ideas to secure funding. Managers persuade their teams to achieve company objectives. CEOs bring shareholders on board to support their initiatives. We all need to be good at selling products and ideas.

If a woman perceives sales to be outside her comfort zone, we always beg to differ. How do we know? We’ve seen some of the best salespeople in action… and they are women. What’s more, they are women using the skills that come easily to them. After all, selling is about having conversations, attracting interest, using one’s passion, gaining trust, and forging relationships. We’re great at this!

I shrink to fit

In the 2010 big-screen adaptation of Clare Boothe Luces’ play The Women, the character played by Annette Bening, a high-level female executive, says that women “shrink to fit.” This line captured our imagination because it illustrates one of our pet peeves: women are playing it safe by staying neatly within the lines—in other words, feeling obligated to meet the expectations that other people, or perhaps society, set for us. Here are three of the ways we’ve seen women fall into this trap:

Exhibiting “only” behavior. Many times, we are the only woman in the room and it’s intimidating. We’ve observed what we call “only behavior.” You are glad to be there; you are unsure about the rules, norms, and unwritten code of behavior, so you are quiet and do not ask questions or make comments. It’s smart to get your sea legs before you put any major proposals forward, but don’t completely refrain from participating in the conversation or generating ideas simply because you are the only woman there.
Staying in traditionally female roles. Inside big corporations, women are overrepresented in human resources, corporate communications, marketing, and other support roles. In fact, each of us has spent time in these fine functional areas during our careers. However, they are not areas that CEOs come from. P&L jobs gain you more stripes and badges than support-function jobs and they have more status.
Doing volunteer work at work. This was introduced in a previous post from this series, but we’ll mention it again here because it’s a variation on the playing it safe theme. For some reason, the office extras—recruiting, staff development, and organizing charitable giving—always seem to fall to women. Some of you may feel that you can’t push back and say, “No way” but we respectfully disagree. These are legitimate tasks, yes, but they do not showcase your leadership abilities. It’s far riskier to accept these assignments than it is to turn them down. Say yes too often and you’ll be typecast. As one male leader once told us, “Women can get oversubscribed here.”

I let others take the lead

Another way to play it safe is by stepping aside and allowing other people to call the shots or make the tough calls.

It may seem safer to let someone at a higher pay grade take the biggest risks, but often it is the big picture decisions that offer the best opportunity to establish your credibility as a leader. But taking the lead is easier said than done and some of us fail to step up due to a lack of confidence—it takes nerves of steel to take responsibility in a high-stakes situation.

Studies show that self-confidence is critical to advancing in a leadership role. However, there are often nuances related to how women appear self-confident in the workplace. According to a study published in Human Resource Management, self-confidence is directly correlated to exerting influence in the organization. The study states, “Through self-confidence appearance, job performance directly enabled men to exert influence in their organization. In contrast, high-performing women gained influence only when their self-confidence appearance was coupled with prosocial orientation.” In other words, women had to also show an intent to benefit others in order to be perceived as self-confident (see above regarding volunteering at work). We can only hope that, as more women demonstrate courageous leadership and take bold actions to advance their own interests, this trend will diminish.

I might fail

We recently worked with a new group of high-talent women. When we asked them what their career goals were, most said, “I am not sure.” We were shocked by their lack of clarity. They had no clear line of sight on their next job. Given that Catalyst Research indicates that women are as ambitious as men, we wonder if women are just afraid to say so.

Perhaps this is due to fear a failure, or perhaps, as Pat Heim says in her books and speeches, it is a preference women have for flat organizations. Heim Argues that women are more at home within horizontal power structures. We eschew hierarchy and, therefore, do not step out from the group to boldly brandish our ambition. Group acceptance trumps revealing our aspirations.

Given the scarcity of women and top spots on the org chart, it’s no wonder women prefer flat organizations. Nevertheless, the reality is that success in business still requires women to set themselves apart in top leadership roles. That requires ambition.

The New Rule: Play to Win

Success requires bold moves and ambition, but also necessitates tradeoffs. Let’s look at some of the new rules that are associated with the Play to Win mindset.

It is a game

In our coaching, we’ve found that women think promotions are based on merit. Kathryn was once surprised when a male colleague said to her, “It is a game. You will go crazy if you do not realize that. It is rough and tumble… so get in or get out.”

Truth be told, it is more fun when you realize this. It is a mindset that women need. Know the end game. Know what winning is. Is it important to have a high score, as in bowling, or a low score, as in golf? Get a clear picture of how to succeed at the game.

Reinvent yourself

Staying put in a job that’s lost all appeal and isn’t leading you to better things is riskier than taking a chance on change. The longer you stay put, the more difficult it can be to summon the courage and vision required to tackle what’s next. Here’s what we remind our clients to consider:

Have a plan. One reason women stay put in a dead-end career is that they haven’t outlined a long-term plan for themselves. It’s easy to lose sight of your personal goals if you’ve never identified what they are and committed them to paper. When you create that plan, be specific and descriptive, and revisit or update the plan often.
Get a posse. In addition to a plan, reinvention requires an army of supporters. Having friends, connections, and sponsors throughout your industry—and beyond it—makes getting unstuck much easier. These people are not only your lifeline but also your eyes and ears out in the wider world of work. When you are ready to make a move, you’ll be glad you cultivated support.
Get past the impasse. According to Timothy Butler, reaching a dead end personally or professionally can be stressful and painful—but it is a necessary step to clearing the impasse and arriving at a new and better place. “When we have run aground, we sometimes fail to realize that this is a necessary crisis, without which we cannot grow, change and—eventually—live more fully in a larger world,” Butler explains in his book Getting Unstuck. These crises are almost always good things because they are wake up calls. Louise, a woman Jill coached, once said, “If my career hadn’t stalled, I wouldn’t have taken the time to figure out what makes me happy and what I really want to do!”
Make a major change. Although you’ll want to be able to leverage your hard-earned experience and competencies, as well as your network, don’t be afraid to make a radical change if that’s what’s required to achieve your personal and professional goals. After all, our objectives sometimes change mid-career. Perhaps an entrepreneurial endeavor is more appealing than a corporate job and better suits your needs. Both of us left jobs in corporate America and started our own business. It has been exciting to learn new skills—skills we hardly knew we had.
Consider perception. Helen Mets-Morris, vice president and general manager of Avery Dennison, told us what she learned about personal power and perception: “Very recently my feedback from my boss was ‘Helen, often a person’s first impression of you is that you are young, attractive, and nice… But it takes them a couple of interactions to realize that you’re also very smart.’ That really had an impact on me. [Since then] I’ve worked on being far more intentional about my impact. Going into a meeting, I am aware of my agenda, what the challenge in the meeting will be, and I’m deliberate about how I want to be perceived.”

Leave your trapeze

There comes a time for each of us when playing it safe just won’t get the job done. Maybe you’re competing for the job of your dreams. Perhaps you have a new product idea that’s so bold and audacious the possibilities are keeping you awake at night. It could be that you are simply frustrated by the status quo and are finally ready to make a radical change. Regardless of the specific reason for change, now is the time to let go of your fear and take a leap into the great unknown. If you aren’t a natural risk taker or don’t like putting yourself out there, here is our advice to help you leave your trapeze:

Get a new mantra. You need to prepare your mind and get your competitive juices flowing. One great way to do that is by giving yourself a pep talk. In fact, we even suggest that you have a personal mantra or affirmation (for example, This is my time or This promotion is mine). This phrase—to be remembered and repeated—will help you envision achieving your goal.
Have a vision. Before you take a major risk and go after something big, it’s important to formulate a clear vision of what success looks like. Close your eyes and imagine being successful with the risk you are taking. If you are successful, what will people be saying? What will be happening?
Just do it. Try not to overthink things. Sometimes it’s best to simply step up and take a swing. Have that vision in your mind. Think about your mantra. And take that leap.

Be a risk taker

Becoming comfortable with risk and change is one thing, actually leading the change is quite another. Still, if you are frustrated with the inefficiencies you see all around you, why not take the initiative and improve the situation? It’s a great way to establish yourself as a leader and a problem solver.

In an interview, Helen Mets-Morris of Avery Dennison told us her perspective on risk:

“The farther you go up the career ladder, the bigger the decisions are that you have to make—so the risks and opportunities become bigger as well. I’ll always have somebody on my right-hand side checking through the data, but for me what’s important is relying on my intuition. That is an element where females have an advantage—our internal intuition.”

Be a rainmaker

Women who can sell are powerful. There’s no two ways about it. As we mentioned earlier in the chapter, rainmakers get promoted. Why? Because they bring in business! And you don’t need to be on the sales team to be a rainmaker.

If you are managing client relationships, closing deals of any sort, or even managing a team of customer-facing contributors—you can use your skills to become visible by bringing revenue and customers into the organization.

In our experience, we’ve found that a few simple rules of thumb can help you bring in new business for your organization.

First, selling is about cultivating relationships. As in negotiation, it is important that both sides perceive the transaction as being transparent and fair.

Second, the more that you can demonstrate genuine passion, the more you’ll be able to gain the trust of clients and customers. Selling is about trust and authenticity. Women are outstanding at this!

Do-overs are fine

As Thomas Edison famously said, “I have not failed. I’ve just found 10,000 ways that won’t work.”

The case we’ve been making throughout this post is that it’s far riskier to hold back than it is to put yourself out there and play to win. Of course, the reason many of us hold back is that we’re afraid of what failure will bring. It’s embarrassing, disappointing, and costly.

But there’s more than one way to snatch a slice of victory from defeat. A great method for changing your perspective on failure is to think like an entrepreneur.

Because most startups sink, most serious entrepreneurs fail multiple times before they succeed. Every failure—if handled appropriately—is viewed as another step closer to success. In fact, venture capitalists rarely hire A CEO who hasn’t crashed and burned at least once. A taste of failure is considered valuable experience.

But the important part of failure is the ability to learn from your mistakes and to pick yourself up to start again. In many cases, do-overs are fine because past experience makes you smarter.

Start Playing to Win

Success is about taking calculated risks. Some organizations have a much higher tolerance for risk taking than others do. And like organizations, some of us are born rainmakers in the purest sense, whereas others persuade and manage change by deftly cultivating close relationships.

Regardless, it’s important to know where you are on the scale and be ready to move closer to the risk-taking side when a great idea or opportunity presents itself. We are not suggesting that you should act ruthlessly… just go for the win!

In part six of this series, we’ll look at Rule #6: It’s Both-And. In this article, we’ll examine a notion that has crept into dozens of our coaching files over the years: having it all. It’s a notion that leaves many women feeling disappointed and frustrated. We’ll discuss how black-and-white thinking does not lead to career success or personal satisfaction and is just one example of the type of extreme thinking that pushes us off the path to success—and we’ll discuss the New Rules to help you get back on track.

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An Important Note: Employers Must Break Rules Too

While the focus of this series is on the limiting beliefs and thought patterns women must address in their own career journeys, it cannot be overstated that the bulk of responsibility for change falls on the organizations that employ them. For every Old Rule a woman can change for herself, there are dozens of Old Rules that organizations must change. From outdated policies and work/life imbalance to inherent bias and lack of development opportunities for women, there are many ways employers can—and must—break their own rules.

For a more in-depth analysis of these Old Rules and our recommended New Rules to replace them with, check out our book Break Your Own Rules: How to Change the Patterns of Thinking That Block Women’s Paths to Power.

About Jill Flynn

Jill Flynn is Managing Director in the Leadership Acceleration practice at Bravanti. She is a co-author of Break Your Own Rules, How to Change the Patterns of Thinking that Block Women’s Paths to Power and The Influence Effect: A New Path to Power for Women Leaders. Jill is a founding partner of Flynn Heath Leadership, which was acquired by Bravanti in 2020. She specializes in partnering with corporate clients to design and implement tailored strategies that result in higher retention and promotion rates for their women leaders. Read more >

About Kathryn Heath

Kathryn Heath, Ph.D., is a managing director of the Leadership Acceleration practice at Bravanti. She was a founding partner of Flynn Heath Leadership, which was acquired by Bravanti in 2020, and co-author of Break Your Own Rules, How to Change the Patterns of Thinking that Block Women’s Paths to Power and The Influence Effect: A New Path to Power for Women Leaders. Kathryn serves as a coach, a researcher, and a developer of leadership programs. One of the hallmarks of Kathryn’s work is addressing organizations’ speciﬁc business targets through customized programs that move leaders forward faster. Read more >

About Bravanti’s Leadership Acceleration Solutions

Bravanti’s Leadership Acceleration practice offers customized skill development sessions combined with individual coaching, cohort support, and targeted feedback, equipping your leaders with the necessary skills to realize their potential. Our programs include customized approaches for women leaders, underrepresented groups, and high potentials. For more information on our Leadership Acceleration services, contact Brenda Wensil, Managing Director & Practice Leader, Leadership Acceleration, at bwensil@bravanti.com.