Building confidence in your career story: 7 questions that transform how senior executives present themselves
There's a curious paradox I encounter regularly in my work with senior executives. They are demonstrably successful in their careers – many have progressed in tough corporate environments, are entrepreneurial, lead international teams and deliver in really challenging situations. Yet when it comes to articulating their own value, they falter. They struggle to move beyond listing responsibilities to telling the compelling stories that make them memorable candidates.
The challenge isn't simply self-consciousness, or a reluctance to oversell or sound inauthentic. More often, it's that people don't recognise the qualities that make them who they are as being genuinely valuable. Yet it's crucial when creating a compelling CV to go beyond ticking off a list of skills and responsibilities if you want to show what you’ve really accomplished.
The confidence gap
Many of my clients confuse what they're accountable for with what they've actually achieved. They think in terms of "I'm responsible for all this," but that weight of responsibility, while significant, doesn’t set them apart – all it really expresses is “this is what I’m supposed to do”. Lots of other people might share similar responsibilities. What makes you unique is how you manage that responsibility and what you do beyond the basic requirements.
The truth is, your career stories are your differentiator. Nobody has walked in your shoes, even if they've held the same roles in the same organisations. Your particular connections, challenges, and responses create a narrative that belongs only to you.
The 7 questions that change everything
These are the questions I ask my clients that consistently unlock their most compelling career stories. These aren't just CV-building exercises - they're tools for understanding your own value and building genuine confidence in your professional narrative.
1. What did you actually spend your time doing, and why did it matter?
This isn't about listing achievements from a performance review. It's about understanding the real purpose behind your work and who benefited. When you can clearly articulate not just what you did, but why it mattered, you transform from task-executor to value-creator.
2. What obstacles did you face, and how exactly did you overcome them?
Every role comes with challenges, but how you identify, understand, and navigate them reveals your problem-solving approach. I often find clients chuckle when I ask about the reality versus the sanitised version of their experience. Those authentic moments of difficulty and resolution make people credible and interesting.
3. What did you walk into from week one, and how did it differ from your expectations?
The gap between what you expected and what you found often reveals your adaptability, judgment and initiative. I worked with someone appointed to a business that was struggling and ultimately failed – he was initially concerned this would reflect badly on him. Through our conversations, we discovered he'd preserved livelihoods and supply chain relationships far longer than anyone expected, met regulatory requirements and ensured a professionally and compassionately managed business closure. He learned more in that experience than at any other point in his career.
4. What were the core objectives you were given, and how did they evolve?
Organisations change, priorities shift, and roles adapt. How you responded to these changes – whether you drove them or adapted to them – demonstrates your strategic thinking and flexibility.
5. What was your actual impact? What did you alter, stop, or start that created real benefit?
This is where many professionals undersell themselves. They focus on what they were supposed to do rather than what they changed. Your impact might be transformational, but it could also be incremental improvements that accumulated into something significant.
6. What did you genuinely enjoy, and what do you never want to do again?
Just because you're good at something doesn't mean you should keep doing it. I've worked with people who assumed their proven capabilities should dictate their next moves, but they lacked the confidence to change course toward work that energised them.
7. What's your superpower – the thing you do that others don't necessarily see?
This is often something unseen that you know you do well, but don't announce or perhaps even realise because to you it’s intuitive or comes naturally. It might be your ability to relate to people at all organisational levels, your talent for thinking through unintended consequences, or your skill at asking the right questions without seeming confrontational. These hidden strengths often become your most valuable differentiators.
The power of authentic storytelling
When you can answer these questions with specific examples, something remarkable happens. You develop genuine confidence because you're not trying to be someone else – you're clearly articulating who you already are and what you've actually accomplished.
I once worked with a lawyer who, through his children's sports activities, had volunteered with an ambulance service after his own child was injured and he realised no one was on hand to help. We explored this experience alongside his legal career, and he ultimately moved away from the profession and became a paramedic. Sometimes life takes you down routes you never anticipated, but only if you're willing to examine what truly drives you.
Why this matters more than ever
In our current landscape, where Artificial Intelligence can generate jazzy templates and match keywords to job specifications, authentic storytelling becomes even more valuable. Technology can produce generic responses tied to role requirements, but it cannot capture the context of your experience, your individual behaviour, or your genuine impact.
The most sophisticated AI cannot ask you the right questions about your career, help you process the answers, or give you the confidence that comes from truly understanding your own value. There's no substitute for the human touch in uncovering what makes you uniquely qualified and genuinely fulfilled in your work.
Your next step
Whatever document you're creating – whether it's a CV, LinkedIn profile, or interview preparation – the foundation should be these authentic stories. They transform you from a list of responsibilities into a compelling candidate with a clear narrative about how you can create value in your next role.
The goal isn't to create something that looks different from everyone else's CV. It's to create content that's authentically different because it reflects your unique experience, genuine strengths and makes you memorable.
If you think you might benefit from some help uncovering and articulating your career story, I'd be happy to discuss how we might work together. As a first step, we can spend 15 minutes or so to talk through what you're looking to achieve and how I might be able to help - and if my approach isn't right for you, I'll always say that too. Sometimes the most valuable thing is simply starting the conversation. You can email me here.