The 3 Overlooked Obstacles Most Women Find in the Path to Leadership

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We've been knocking on this door called leadership for a long while now. Pundits, researchers, wise men and women, those who've done it and been there have all shared their advice on what can help break that glass ceiling, or whatever else you choose to call it.

Yet, here we are not wanting to be cynical, but still wondering if we need to knock on that door longer, bang on it harder or all together break it down, perhaps. Or build new office buildings and doors of our own with higher ceilings. That's a thought now!

Whatever we do or have done so far, we are still infrequently found in board rooms, executive positions and senior management roles. As per the Workplace Gender Equality Agency (WGEA) in Australia and their latest results from 2017-18 dataset:

Women hold 13.7% of chair positions and 25.8% of directorships, and represent 17.1% of CEOs and 30.5% of key management personnel (WGEA 2019, Data Explorer).

You'd agree that's not nearly enough to say we have equality though we seem to have moved on from worse numbers in the past. Another developed nation we often look to for data on women in leadership is the USA. As per Fortune 500 and Catalyst, roughly 5% women make CEOs of Fortune 500 companies at present. According to Pew Research:

The share of women sitting on the boards of Fortune 500 companies has more than doubled, from 9.6% in 1995 to 22.2% in 2017.

These number while have something for all of us to celebrate and cheer for, make a small % of all CEO, board and executive positions. Yet these women give us hope that they seem to have broken through barriers and got over obstacles that most others are still struggling with. Maybe, a mentor, sponsor or a more gender equal organisational system helped greatly.

How does any of this make sense though? Should we not have been well on our way to equitable leadership roles by now? We apparently have a shocking number of years of waiting ahead of us if things go at this pace. That number ranges from a few decades to nearly 200 years into the future. That would be well past any of our career spans.

Curiously, the solution may not entirely lie in more funds towards Diversity & Inclusion, equitable employee policies, fairer work practices, more informed women's leadership programs or even men championing equality. While more men can certainly bat for gender equity, that alone won't solve our problem either. For that we need to look in places we generally don't.

Because lack of gender equity is a stubborn, multi-layered, cultural and complex issue we must look at it through various lenses.

Most of the time, because it's a monster of a problem, we expend all our energy on the biggest hurdles like, parental leave laws and policies, the persistent gender pay gap, work practices that traditionally favour men, institutionalised recruitment and performance biases and gendered jobs that challenge us to rebuild our education and workforce pipeline.

We are then left with hardly any breath or inclination to tackle the fallouts of long-standing gender biases that have got normalised in our schools, our homes, at our dining tables and therefore, in our organisations. We don't stop to think if what just happened would have happened if it were a man speaking or working instead of the woman in the room.

Here are six hidden and overlooked obstacles that many women reading this, and men who care about seeing more women in leadership, would have experienced and observed.

These rarely get captured in formal documents, like policies or strategy, or even make it to structured training programs. These are just things that happen every day!

#1 Interruptions

According to gender communication expert Deborah Tannen, men speak to determine and achieve power and status. Women talk to determine and achieve connection. Men and women are clearly socialised to communicate differently and these differences crop up at work in ways that aren't complimentary. That's because it's not so much a case of diversity, but that of deep-seated bias in how we view the status of women compared to that of men.

A study from George Washington University found that men interrupted 33 percent more often when they spoke with women than when they spoke with other men.

To try and understand if interruptions between men and women were indeed gendered and "if there was any relationship between gender, status and interrupting, Tonja Jacobi and Dylan Schweers at Northwestern University studied US Supreme Court justices. In this arena, where nine justices must together reach a decision, the ability to dominate the floor can determine the fate of a case", they said. "By documenting court hearings, Jacobi and Schweers found that interrupting was indeed highly gendered, regardless of whether a woman was in a more senior role. Male justices interrupted female justices three times as often as the reverse. Female justices were also interrupted three times more than their male colleagues by male lawyers arguing the cases, despite clear rules against doing so to justices." Interestingly, “Even when women reach such a high pinnacle in their profession, they are interrupted by men, not only their colleagues, but also their explicit subordinates,” says Jacobi. (Source)

Tip: Researchers share that men often don't realise that they interrupt women more than they interrupt their male colleagues. Which is to say, it isn't as calculated as it can seem, but is borne out of gender stereotypes and status differences between men and women through socialisation, often, overriding the roles men and women have at work. Awareness is the key and the person driving this might need to be the leader of the team. When a leader draws attention to behaviours that can help or hinder the team to perform better, people are more willing to listen and learn. It doesn't have to be humourless or deprecating of men, it needs to be a learning exercise and a collaborative conversation that makes it equitable for women to hold the floor and for men to know when to step back and not interrupt them. Also, women need to not fall back and quiet down, instead speak up and stand their ground.

#2 The 'assertiveness' double bind

While I suggest in my last piece of advice above that women stand their ground, we know through experience that women are liked less than men when they display behaviours we correlate with assertiveness or decisiveness. Many women worry, often not without reason, that if they ask for that pay rise or voice an unpopular idea in a meeting, they will be met with an underwhelming sense of welcome. For the same behaviours men are likely considered decisive and strong, women are seen as bossy and difficult. The hard part is, even when no one is saying as much, women assume that they must be disliked for being assertive and must pay the 'likability' penalty or choose to quiet down to balance out the imagined backlash. I've had women say this to me in mentoring conversations and that they decided not to take the lead even when invited, just in case there was a backlash later.

Women are not penalised for competence when they speak up, as much as they are for likability. Which means, while they may be considered competent, they might still not be hired or promoted as much if they are labelled 'aggressive' or 'dominating' in their performance reviews - a significant dataset in promotions. Those who are both likeable and competent probably have a higher chance of being promoted or selected. So, women are not only liked less, but also stand to lose out to men on promotions and projects when equally qualified or more competent for the job.

There does seem to be a double standard we apply to being assertive based on gender. An article in the Harvard Business Review, which looked at 200 performance reviews within one company, "revealed bias in this type of feedback. The results tallied the number of references to being “too aggressive” in the reviews and, not surprisingly, 76% of the instances were attributed to women, while only 24% of men were identified as having such a communication style."

Tip: Even if we took gender out of the equation, employees in general find their managers wanting in how they review their performance or provide development feedback. While we have a persistent issue with giving gendered feedback, we also have an overall issue of skills needed to provide useful and fair performance feedback. So, it's a bit much to expect managers to know how to tackle their own bias and navigate performance conversations based on good judgement or past experience alone. We need to actively hold managers to account for their development, provide them opportunities to learn and create inclusive team cultures where bias can be dealt with as a team goal, not a person specific fault to be righted. Managerial development programs provide performance review learning, but often ignore talking about gender bias as a key obstacle in the path to fair performance feedback. It's still considered a sticky topic, especially, when you are talking to a roomful of male managers! It's up to the leader and HR to collaborate and bring this learning out as a cultural priority.

Something I recognise many informed women do is to stay communal in how they make a request (as opposed to being outright assertive), but stand tall and decisive in their posture, tone and volume of voice. Think of Amy Cuddy and her power poses! Which is to say, we have a tricky balance to strike between adhering to masculine leadership traits through showing dominance in our body language, but conveying alignment with our feminine stereotypes through our content in order to avoid the 'likability' penalty. There is research to suggest this works for many women, and I can vouch for it myself. But I love what a noted researcher in this field, Larissa Tiedens says in response to these strategies, "At some point in their careers, women leaders will need to make explicit (rather than implicit) demands of others, and requiring that women express dominance only in specific, relatively narrow ways is not a path to gender equity.”

#3 What leadership means

What we understand of good or effective leadership and what we know of masculine stereotypes are uncomfortably similar. Think of words like assertive, decisive, ambitious, analytical and confident. In essence, our stereotypes of good leadership overlap with that of masculine stereotypes. Which means, feminine stereotypes such as warm, nurturing, empathetic and cooperative don't make the cut and can be seen as signs of poor or weak leadership. Given decisiveness is a prized leadership sign and men are rewarded for being decisive and women are not, we end up with many more men being selected or tapped for leadership duties than women. After all, why would you willingly choose someone who showcases behaviours and skills we don't associate with good, strong leadership? Here's another proof that leadership is associated with maleness. Men who don't choose or lack traditional masculine traits of dominance, assertiveness and competitiveness are also often seen as poor leadership material. Much like women, these men pay a price for valuing what we think of as feminine strengths. We are fairly consistent in our biases to the point that we can find data and reason to back our judgements such as, there just aren't enough women in the pipeline or women don't choose these roles. Often, overlooking the underlying reasons for long-standing and accepted bias being at the heart of why women aren't in the pipeline or even part of educational courses that would lead to more women in those disciplines.

Tip: Leadership training and performance management tools and traditions in most organisations needs a significant overhaul and scrutiny to ask if they are indeed propagating gender stereotypes while also not addressing gender bias in leadership, which is a double whammy. I have been part of both being trained on noted leadership programs and accredited on world class leadership content. None to my memory ever spoke at length about how leadership affected men and women differently at work or was appraised differently based on gender. While the programs spoke of being empathetic as a leader, few asked if everyone in the room thought of empathy as a skill they were comfortable with or even considered important. The next best solution has been to gather women in a room and share with them how they can break through some of their own hesitations and lack of practice with leadership, and step up to challenging roles. While a lot of this content is useful as women haven't historically had as many leadership opportunities compared to men in organisations, this conversation is incomplete without also speaking to men. Many of these women leadership aspirants have a male manager who stays disconnected from the gender equity narrative. To complete the picture, we must include managers and their part in providing women a more level playing field.

Being interrupted, the likability penalty and our popular notions of effective leadership can often stand as silent and hidden obstacles in the path of women aspiring to rise in their careers. Without calling out factors such as these that are deeply embedded in social constructs and organisational cultures, all the money in the world might not help. We need brave leadership, especially from men, and those few women at the top, to bring these obstacles to our attention if we are to see equitable leadership within our lifetimes.

3 Ways Men Can Become Compelling Allies to Gender Diversity Efforts

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Men are powerful allies to Gender Diversity and equality goals. That is, when they choose to be or when the organisation has well laid out strategies to involve them.

That's one reason I keep writing about how men can help gender equality goals.

Men helping to improve the poor representation of women and minorities in leadership roles makes organisational and financial sense as proven by many research studies.

Your contribution can make a significant difference to the careers of women and minorities around you. That in itself can be a very satisfying outcome. Moreover, your involvement with gender diversity can help enhance your leadership influence. It firmly establishes you not only as a successful leader, but as someone who cares about fairness and equality, and actively works to strengthen the organisation's future. 

Needless to say, it is in men and women's professional interest to be Inclusive Leaders and promote diversity at all levels of leadership.

It's not a question of if we need to work together to progress socially and economically, it's about how quickly can we create that reality for all of us. Everyone wins when we progress together instead of at the expense of one of us.

Yet, the well established benefits of having more women to balance out the men in leadership positions stands in stark contrast to the data for 2017 across the largest corporations globally.

The latest finding of the Chief Executive Women (CEW) ASX 200 Senior Executive Census 2017confirms that men still hold the majority (79%) of roles in ASX 200 executive leadership. This is important to think about because it means Australia has just 11 female CEOs on the ASX 200 or 5.2% of women CEOs. More startlingly, 41 of the nation's largest companies don't even have a woman on their executive leadership. Which means, we won't have more women CEOs anytime soon.

Female CEOs in the Fortune 500 aren’t quite the norm yet either, but they have been making strides. As of 2017, there are 32 female CEOs on the list, meaning that 6.4% of the U.S.’s biggest companies (by revenue) are run by women. This small number is the highest proportion of female CEOs in the 63-year history of the Fortune 500.

Has there been a dearth of gender diversity programs and strategies over the last three decades, one might ask?

Not really. Literally billions of dollars have been invested in these efforts. Among many complex reasons for why a lot of them leave us wanting, a crucial reason for their failure is perhaps, not involving men who continue to be decision makers.

A Gender Diversity initiative that does not consider the crucial ingredient of men as advocates and allies is likely to fail and not have long-term positive shifts.

Here's a shout out to men who might want to contribute to seeing their wives, sisters, daughters and female co-workers have a fair go at work, but don't know how they can make a difference.

#1 Seek out sponsoring opportunities

Men might need to go out of their way to find opportunities for women and minority leaders. This is because women and minorities are pushed so far behind that it's time to bend over backwards to try and level the playing field for them. Sponsorship is a great way to push a deserving leader's career ahead. This does not have to arise out of formal organisational programs. “Often times organisations haven’t factored men into the equation upfront,” says Eleanor Haller-Jorden, General Manager, Catalyst Europe. Who can you see around you that you know has the potential, but lacks the advocacy they need? As a leader you have all the freedom to say I'll sponsor a leader who I know most likely won't have a fair go at a senior leadership position.

#2 Role model flexibility at work

Men are really far behind in helping organisations become more flexible. Most of the responsibility and career backlash of flexibility falls upon women and minorities. Men are also fathers, husbands and sons. They have equal responsibility in being a crucial part of their households. Yet, women bear the brunt of most such responsibilities and the consequences this has for their leadership careers. While there are deep-seated reasons for this imbalance, we have to begin somewhere. As a senior male leader, how about setting an example of working flexibly, so everyone around you feels the permission to do the same. Unless more men leaders step away from their daily grind to do school runs or relieve their partner of a few responsibilities, so she can get ahead in her career, flexibility will stay a women's or people with disabilities issue.

#3 Support women in their absence

Behind closed doors, it's fairly easy and common to dismiss what women and minorities can accomplish and the opportunities they deserve. Sadly, the people being spoken about are generally not present in the room, so that they can be represented fairly or speak for themselves. As an advocate for gender diversity, make a point to speak out and communicate with your peers (most of whom are likely men) on how these assumptions might be just that. A leader who keeps their integrity and the organisation's best interests at heart often stands out. Let's not underestimate your own leadership influence when you speak up and advocate for what might help the organisation perform better and keep up with its rapidly diversifying customer base. These might not just be words that sound right, doing the right thing is a proven strategy to have a long and influential career while helping gender diversity goals.

Hope this helps us think of how men can contribute and be active participants in gender diversity goals, instead of being passive by-standers, who don't know what their place is in our quest for diverse leadership.

Your thoughts? Do you have comments and observations that might help this conversation? Would love to hear back.

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I am am Inclusive Leadership speaker, writer and facilitator. Check out for how I can help your organisation build Inclusive Leaders.