Executive Mindset: Advice for Women Leaders to Navigate the Glass Ceiling

Discussions of the “glass ceiling,” an invisible barrier to the progression of women (and other underrepresented leaders) from management to the executive ranks, has traditionally focused on discriminatory dynamics. But there’s more to the glass ceiling than discrimination. Executives who make it to the top learn to build an effective executive mindset, demonstrating proficiency in working ON the business in addition to IN the business, and project an authentic executive presence. 

The modern glass ceiling is largely a function of unconscious bias

Most executives today think of themselves as tolerant, open and accepting of people who look different than they do and come from diverse backgrounds. They often have a desire to see more diversity in their leadership ranks. And yet, that diversity at the top doesn’t happen often enough. Despite comprising less than 50% of the population, men still hold two to four times the number of senior management positions compared to women, and far more than black professionals of any gender. Despite their stated intentions, it is clear that unconscious bias is at play. This is easiest to parse out when candidates are rejected for the only reason that “they’re not a good cultural fit.” And so, the glass ceiling remains strong.

However, there are many executive groups that do operate in a more diverse and open group dynamic, and yet those who have not made it into the executive ranks yet still feel the solid bump into an invisible barrier that looks and acts like a glass ceiling. What’s happening there?

The modern glass ceiling is about more than discrimination

In my work with female leaders, and working on executive teams myself, I have come to understand that the glass ceiling is more complex than the relatively “straightforward” effects of unconscious bias. Many promising women in leadership I work with have strong senior executive champions and sponsors (some of whom hire me to help these leaders.)

These strong sponsors are critical to any leader’s ascension into the executive suite, but even they cannot help some people get past this other dimension to the glass ceiling. Why? Because receiving an invitation to the executive ranks, and succeeding there, is a rare thing and requires more than smarts and even superior performance. The fact is that there just aren’t that many slots at the top. It is by nature a highly competitive path and what distinguishes someone ready for the executive suite goes beyond proficiency and excellence.

What distinguishes someone as ready for the executive suite goes beyond proficiency and excellence. Via @DanaTheus <==Click to tweet  

To invite a high-performing leader up to the top, current executives have to believe the aspiring executive can operate effectively IN the business as well as ON the business, which is what the top leaders must do. Executives who make it past this invisible barrier must prove they can:

• produce business-critical results in their areas of expertise (these are table stakes to join the game)
• strategize business dynamics across disciplines while also contributing directly by managing their own discipline
• have excellent judgement in others they entrust to carry out day-to-day business critical functions, and the ability to coach those leaders effectively
• inspire confidence in employees and investors alike, especially during challenging times

…among other things. 

To understand why these additional levels of performance and talent are so critical, it’s important to know that the top level executive team is more than the sum of its parts. Running a business is its own challenge, apart from marketing, operations, product development or any other individual business discipline. By the nature of their jobs, typically the CEO, CFO and COO are the ones who see the business more holistically than other senior leaders.  But as CXOs have begun filling out the C-Suite in recent decades, it provides the opportunity for people with specialties in other disciplines to contribute to the synergies of the business at the most strategic level. Candidates for these top slots can be excellent at their own disciplines, and still fail to inspire confidence that they can see and lead the business effectively from this strategic and holistic point of view. 

What they lack is what I call an executive mindset, and the skill at knowing when and how to use it.

Executive mindset: flying from the weeds into the treetops across disciplines

Broadly speaking, an executive mindset is a strategic perspective that inherently includes a systemic understanding of:

• The organization’s business model and profitability dynamic
• an understanding of the broader/global market context and trends
• the operational drivers and dependencies within the business
• the needs and desires of all key stakeholders. 

This is a “treetops” view of the business and its environment that is impossible to gain if a leader, no matter how capable, has never had accountability outside their core discipline. 

This explains why executive development mentoring programs, both formal and informal, seek to put rising leaders into broadening assignments, running operations outside their specific areas of expertise. It’s also why effective executives typically have career-defining accomplishments in more than one discipline. For example, a senior sales executive likely to make it through the glass ceiling to Chief Revenue Officer (CRO) may have negotiated key business partnerships and launched successful product campaigns in addition to blowing out their regional quota year after year. And a Chief Technology Officer (CTO) on her way to CEO may have led a major operations refit or merger integration.

How do they do it? 

While each person who makes it to the top has a unique story, one skill consistently appears in their narrative. Top line executives master the ability to operate in the treetops. Looking at the big picture, motivated past obstacles by the vision, undeterred by bushwhacking details; successful executives master the ability to sidestep overwhelm, ferret out key priorities and dip from the treetops to the weeds with a deft skill. Successful executives also gain the ability to determine when a weeds-level intervention is truly warranted on a situationally appropriate basis. 

All the ‘executive presence’ in the world won’t help someone succeed as an executive who hasn’t mastered the ability to get out of the weeds. Via @DanaTheus <==Click to tweet  

Thus, to excel in higher levels of leadership, and to gain credibility with the executives already operating there, high potential leaders must develop the ability to get “out of the weeds” and operate “in the treetops” with this higher level perspective. They must think, act and speak at this level with confidence and a clear eye on which details matter to the big picture and why.

This isn’t a skill most people have the chance to learn until they reach mid-career positions. Early career professionals inherently focus on developing skills, experiences and accomplishments within their specific field, for example, sales, engineering or finance. Having achieved a certain level of mastery in one or more of these disciplines, they have developed competence managing and leading “in the weeds,” which is good because down in the details of the business (e.g., customer transactions, testing code and financial audits) the devil truly does lurk. However, being effective ferreting out devilish details does not give a person the perspective, exposure and opportunity to see what happens in the weeds in its larger context.  A treetops view, puts the weeds (and their details) into perspective.

The glass ceiling is more than a function of discrimination, which it most certainly is. Via @DanaTheus <==Click to tweet  

This can be especially challenging because getting into the treetops isn’t always a skill encouraged early in one’s career, so it’s easy to run into the “what got me here won’t get me there” challenge mid-career when most leaders start to target the top.

Challenges for Women in Adopting an Executive Mindset

Do women struggle more to think in strategic, tree-tops-level, ways? No and yes. No, in the sense that once they understand the importance of thinking this way, those who do belong in the executive suite quickly learn to fly up and down the tree trunk as necessary. 

And, yes. In my experience more women than men struggle to get their minds around this concept of tree-top level thinking and leading. They don’t struggle because they can’t do it but because they’ve had so few mentors in their life giving them positive reinforcement for being in the treetops. 

Here’s what I’d like these women, and their mentors to understand. A professional woman who’s made it to the point in her career where she’s being considered for an executive position has gotten there in large part because she’s mastered the details. She’s worked harder and smarter than many of her colleagues (women and men), she’s cleaned up after other people’s messes and she’s made managing the details a big part of her comfort zone. To go to the treetops, where over-focusing on the details isn’t possible or helpful, often makes these women feel vulnerable and uncertain how to succeed. 

Without a strong mentor or coach helping her see that the tree-tops aren’t an alternative to the weedy details, but a new skill set to explore in her stretch zone, many women find it more comfortable to stay in the weeds. They bake their weeds-level proficiency into their personal brand identity. When they deliver awesome results this way and believe they should receive an invitation to the top but feel the bump of the glass instead, they believe they’re being discriminated against. 

And maybe they are. 

Men are far more likely to receive informal mentoring — and role modeling — that show them the value of tree-tops level thinking. Men are far more likely to feel comfortable letting other people clean up the messy details. And men who want women to join them in the treetops are far more likely to tell women what they shouldn’t do (e.g., “get out of the weeds!”) than what they should do (e.g., “come check out these super cool treetops and learn to fly!”)

There is no simple answer to these dilemmas. But I encourage women seeking executive appointments, and the mentors who want to help them get there, to focus on helping them develop their executive mindset. Help them get comfortable living and leading in the treetops and see what happens. 

Photo by Ono Kosuki from Pexels