Why you might need to become more ‘difficult’ if you want to progress your career

‘Be that difficult voice in the room, the one asking “why?” or “why not?”, and “what’s stopping us?”.’

This was the rallying cry of a speaker at the 2023 everywoman in Tech Forum. It was a powerful call to action and a point that resonated with many of the everywomanNetwork members present. For the senior leader making this statement, the act of constructively agitating was not only useful, but essential—both for career progress and for the growth and evolution of business itself.

In a fast-changing modern business world, companies are more in need of fresh thinking and different perspectives than ever before; people who challenge possibilities and current realities are critical to their success. In this environment, an ability to be bold and unafraid to question things leads to intentional, impactful momentum to turn that consciousness into action.

In practice, that means leaders (and leaders-in-the-making at every career stage) must ask the tricky questions, call for clarity, debate accepted wisdom, and generally be as awkward in the situation as they need to be to catalyse change. The sticking point for many women, as research suggests, is that this space for asking the tricky questions can in itself be tricky—containing the kinds of disagreements and conflict that women often lean away from. So how can we become that difficult voice in the room in a way that doesn’t feel too uncomfortable?

Are you rocking the boat a bit too gently?

Gender stereotypes dictate that men are the aggressors, the change-makers, and the disruptors of the status quo, while women lean towards the role of empath and peacemaker. Many exceptions aside, we see countless examples of this played out across history and even in today’s work, where female politicians or business leaders, for example, are labelled ‘aggressive’ or ‘difficult’ while their male counterparts demonstrating the same behaviours are simply seen as ‘doing their job’.

With such a loaded history surrounding ‘difficult women’ and the continued pressure of implicit societal gender norms, it’s unsurprising that many women may find it challenging to challenge. Even if you are engaged in debate or are happy (or at least willing) to speak up, perhaps you’re still holding back from truly pushing boundaries.

‘When I’m in team meetings, I often find that while I’m contributing and discussing things, I’m pulling my punches a bit so as to not create tension in the room,’ notes senior retail manager, Maya. ‘I might ask questions, but they’re usually to clarify—not to challenge. I often leave feeling I could have done more to interrogate a particular course of action or kick a project up to the next level if I’d asked what I really wanted to know.’

This need to not ‘rock the boat’ can be interpreted as a need to belong that was probably written in our DNA millions of years ago, says psychotherapist Sharon Martin, who notes that survival in prehistoric times was linked to inclusion in protective, supportive groups, without which there was a risk of starving to death or becoming prey for wild animals. As Martin notes, this fear programme around being ostracised can still run subconsciously underneath our decisions to speak out. She says, ‘It can feel risky and emotionally vulnerable to assert our needs or opinions, especially if we know they are different than other peoples’.

On top of that, while men are praised for their assertiveness or decisive opinions, a library of research shows that those same qualities can often be interpreted as aggressive, hostile or even unlikeable when expressed through women.

Certainly, ‘being a challenging voice in the room,’ is something that men are rarely accused of, or internalise as ‘difficult’ behaviour. Typically, males pushing back for clarity or inspiration are lauded as confident, passionate or disruptive, and seen as contributing value and conferred with characteristics such as ‘leadership potential’.

Women, however, may be labelled ‘difficult’ for behaviours and characteristics such as not ‘softening’ our perspective with an apology, asking questions that make people feel uncomfortable, or challenging an established conclusion. Conversely, ‘people pleasing’ behaviours—meeting other peoples’ needs and placating, rather than expressing our own opinions when they run contrary to others’, can often receive positive feedback. This, in turn, reinforces the idea that this is something women are ‘good at’ and what they therefore ‘should’ be bringing to the table.

It’s clear we need to revisit the messages society promotes about what our behaviours mean—and indeed how we define ‘difficult’ when applied to women.

Where to start with difficult decisions?

For many women, a crucial first base in redefining the idea of ‘difficult’ is in getting past the idea that to challenge or to disagree is not necessarily negative.

‘When I hear that people who spend significant amounts of time with one another don’t disagree, I wonder who is not speaking up and has become invisible,’ notes resilience coach Patricia Morgan. ‘Conflict is inevitable and a basically healthy aspect of most relationships.’

If you can reframe ‘being difficult’ as ‘engagement in a process’, it’s instantly clear why it’s important—not just for business success but when it comes to accelerating your own career. Being a constructive and strategic agitator makes you more visible within your team or company, highlighting your contribution and creating ownership in outcomes, as well as showing confidence, competence and leadership. Smart questioning arguably benefits everyone—creating better outcomes for projects and performance as well as amplifying your own voice. And while the questions may be positively uncomfortable, dialling up your ‘difficult’ doesn’t have to be.

‘My biggest worry is managing the impact on my working relationships,’ says Maya. ‘The occasionally robust challenge or awkward question might seem justified, but if I am constantly pushing back with questions—even if I feel it’s a positive thing to do—I worry that people will just see me as perpetually dissatisfied, disruptive or even negative.’

Asking questions in the right way signals that you’re engaging in a data-gathering or brainstorming exercise as opposed to veiled criticism. This necessitates being direct about what you want to know, as well as upfront and honest in why you are asking the question, and what answer you are looking for—as well as acknowledging other people’s expertise in the process.Approaching a challenge with a spirit of curiosity also helps open up the conversation. It turns an enquiry, no matter how pointed, into a chance to explore possibilities together, remembering that ‘difficult’ questions are ultimately difficult because they are seeking to find truth in a situation.

Of course, not every ‘difficult’ conversation or interaction will be met with a rousing sense of mutual opportunity or appreciated as a valuable contribution. ‘Difficult’ voices will inevitably create friction and that may mean coming up against others’ biases, egos or just plain disagreement. To minimise the potential for this kind of outcome, it’s crucial to consider how, where and when to optimise your approach. Deploying your most ‘difficult’ side at every opportunity can be as dangerous as staying quiet and flying under the radar. Get strategic and consider whether a meeting or a one-to-one may be the most suitable environment to ask certain questions, and at which point in a project or situation they will have the most positive or productive impact. Consider who is the best person to direct your questions at and intersperse your enquiries with positive observations or enthusiasm around moving forward to allow them to feel that they can come along with you—rather than feel pinned down or ambushed.

Ultimately, get the balance right and difficult questions can be the answer you’re looking for, opening up new possibilities and potential not only in the room, but in your career too.


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