As a former HR Director turned Career & Leadership Strategist with over a decade of corporate experience, including leadership roles at PwC, Visa, and Microsoft (ABK), Cindy knows firsthand what it takes to navigate complex organisations and accelerate into senior positions. After realizing that climbing the corporate ladder was no longer enough without true alignment, she transformed her own trajectory by shifting from chasing the next title to designing a career that felt genuinely fulfilling.
Today, through The WIN, Cindy empowers high-achieving corporate women to redefine success on their own terms, build meaningful careers that work for them through every season, and create lasting impact. She is on a mission to ensure brilliant leaders no longer have to sacrifice what matters most to thrive in both work and life.
Invisible disengagement is rarely dramatic. It’s not someone walking out the door.
It’s much quieter than that. It’s when you’re still performing well, still delivering, still successful “on paper” but something inside you has switched off.
You stop speaking up in meetings unless you absolutely have to. You’re busy all day but nothing feels meaningful. You’re not excited by opportunities that used to energise you anymore. And you start counting down to the weekend on a Monday morning.
Most high-performing women miss this because they’re used to pushing through discomfort. But this is exactly where burnout starts, not when you collapse, but when you stay disconnected for too long.
I advise women to check in with these key questions: am I growing, am I being valued, am I actually enjoying what I’m doing and is this serving me where I am in this season?
If those answers are consistently “no”, don’t wait for exhaustion to force a change. That’s your early signal to step back and redesign before you break.
In my experience, a lot of women are still operating on autopilot where they’re climbing the ladder, chasing the next title, assuming progression equals success.
But I’ve worked with women who reached each “next step” and still felt completely misaligned.
If you already know the next promotion isn’t right for you, don’t take it just because it’s the obvious next step. You don’t have to keep climbing a ladder simply because you’ve already climbed this far or because you feel guilty where others think you should be happy to be
where you are.
Instead, get clear on what you want the next chapter of your career to give you. Maybe that’s more flexibility, more autonomy, different types of work, greater influence without managing a huge team, or even more space for life outside of work. Then work backwards from that.
The key here is being honest with yourself and sitting with discomfort especially when your answers show you that a different and unfamiliar path is needed.
Look at the skills, relationships, experiences and reputation you need to build to get there, and start using your current role to create them. That might mean taking on a different project, building relationships in another part of the business, moving sideways, exploring a different type of role, or creating a portfolio career.
That’s what career by design looks like: you decide where you’re going first, then make career moves that take you there.
During transitions, whether that’s returning from parental leave, a restructure, or stepping into a new role, the biggest mistake I see is women trying to compensate for uncertainty by working harder and increasing their hours.
But working longer hours doesn’t create career momentum. It just creates exhaustion. What actually protects your pipeline is being intentional about where your effort goes, not how much effort you put in.
One of the most effective strategies is to shift from reactive delivery to intentional influence (within the same working hours).
Practically, that looks like two key things:
First, define your non-negotiable impact zones. Instead of trying to do everything, identify the 2–3 areas where your work will most directly influence business outcomes or perception of your role. Everything else becomes “good enough, not perfect.”
Second, build a simple rhythm for building relationships and sharing key updates with your key stakeholders e.g. a weekly or bi-weekly update that clearly states what you delivered, why it matters, and what’s next. This keeps your impact visible and builds the right reputation
without constant overwork.
The key shift is that you don’t need more hours to stay visible. You need more intentional structure around the hours you already have.
Your career progression isn’t driven by how much you do. It’s driven by how clearly your contribution is understood in the moments that matter.
The most overlooked rule is this: perception carries more weight than performance.
Most women I speak to hate the idea of self-promotion and assume that if they do great work, it will naturally be recognised. But in reality, leadership decisions are comparative, not absolute.
People are being assessed against others in the room on visibility, perceived readiness, influence, and how clearly their impact is understood.
So self-advocacy isn’t about over-selling yourself. It’s about making sure your contribution is visible, understood, and remembered.
If you don’t shape that narrative continuously, someone else will or worse, it won’t exist at all in the rooms where decisions are made.
The first step is honesty without the ego or guilt attached to it. Strip it right back. Title, salary, expectations, what others think you “should” want.
Then ask yourself one simple question: if no one was watching, and if there were no consequences, would I still choose this?
That question is uncomfortable, but it’s also clarifying.
In my experience a lot of women aren’t stuck in their careers, they’re stuck in the identity they’ve built inside them.
Realignment starts the minute you stop defending the path you’re on and start telling yourself the truth about it.
The shift happens when you stop being known for what you deliver and start being known for how you think.
Execution is about doing the work well. Strategy is about shaping what work should be done in the first place.
So instead of just solving problems you’re given, reporting updates, and staying inside your lane, take a step back and start identifying patterns, making recommendations and connecting dots across the business.
Strategic leaders don’t just respond to priorities, they influence them.
In my experience, you don’t need to change who you are to build influence. You do need to be more intentional with how you show up.
Influence isn’t built in big networking moments. It’s built in small, consistent interactions over time.
The quickest way to do this is by identifying influential people because if you can win their trust, they’ll naturally recommend you to others which helps you build influence quicker. See where the lowest-hanging fruit is. Find commonality and use that as your in. Take the time to
get to know them. You can start with a coffee chat. Be curious, ask good questions and follow up. Share your thinking and look for opportunities to collaborate where your work naturally overlaps with theirs.
The goal isn’t to impress people, it’s to become familiar, trusted, and easy to work with.
You don’t need to be the loudest voice in the room. You just need to be someone people remember, respect, and want to bring into decisions.
One of the biggest misunderstandings is thinking promotions are decided in the performance review conversation.
In reality they’re usually decided long before. For example the list for July promotions would usually have been locked in Q4 prior or maybe even earlier depending on competitiveness.
By the time calibration happens, leaders are only validating decisions made months earlier comparing people across teams.
The key questions they’re asking to narrow in on their long and short lists are: who is already operating at the next level, who has clear impact, who has visibility, and who is the safest, strongest bet for the business right now.
That’s why waiting until review season to “tell your story” is too late.
The strongest cases are built 12-18 months in advance, depending on seniority, through consistent visibility, clear evidence of impact, and ongoing conversations about readiness. The women who progress aren’t just high performers. They’re the ones who’ve already positioned themselves as the obvious next choice before the room even meets.
The aim is to know the key decision-makers and ensure you’ve built high trust and a strong track record to get as many of them backing you as possible. Your goal isn’t to be the best-kept secret, it’s to be the best kept solution.
