What are the career questions ambitious mid-career leaders are dying to ask but rarely get the chance to? That’s exactly what we set out to answer in our latest Roundtable webinar. I sat down with two seasoned CHROs, Anna Petosa and Nicola Deall, for a candid, no-Teflon conversation about what it really takes to move from strong performer to credible next-level leader. No pat answers. No polished PR. Just real talk from people who sit at the table where these decisions get made. If you missed it, catch the full recording here.
The Game Changes — And No One Warns You
Marshall Goldsmith nailed it: what got you here won’t get you there. But here’s what I see play out in our programs every single time: the shift in what’s expected of you happens quietly and without a memo. Up until you hit that Director or VP threshold, you’ve been rewarded for getting things done. You delivered. You over-delivered. You were the person who made problems disappear. Then, almost overnight, the entire game changes. Now you’re being evaluated on something entirely different: Can you take others with you? Can you scale through people, or are you still the bottleneck?
What Anna and Nicola confirmed is that this shift is rarely communicated clearly by managers. Most high-potential leaders are left to figure it out on their own, often after momentum has already stalled. The leaders who make the leap cleanly are the ones who consciously let go of doing and lean hard into developing, elevating, and multiplying the people around them.
Feedback Won’t Find You — You Have to Go and Get It
As leaders rise, feedback gets rarer and more coded. The higher you go, the more people around you soften, sidestep, or simply go quiet. What our CHROs made crystal clear is this: if you’re waiting for your manager to give you a straight read on how you’re perceived, you’ll be waiting a long time.
The most intentional leaders build a deliberate ecosystem, mentors, coaches, trusted peers, and sounding boards, not as a nice-to-have, but as a career essential. And doing so doesn’t undermine your manager; it signals maturity and self-direction. Nicola made a point that stuck with me: it’s not about signalling that your leader is inadequate; it’s about owning your own growth. Frame it that way, and you shift the conversation entirely.
Courage Is the Career Skill No One Puts on a Resume
Here’s the truth I see consistently in our group coaching program The Roundtable for leaders and everywhere else: the career conversations that would change everything are the ones people never have. The conversation about what you need. The conversation about where you want to go. The conversation that requires you to say, clearly and without apology, “This is what I want and here’s how it aligns with what the organization needs.”
Both Anna and Nicola talked about the psychological safety challenge. Sometimes it’s not there with your direct manager. But the answer isn’t silence; it’s strategy. Lead with what you’re contributing. Name what you’re learning. Express your ambition as a shared opportunity, not a demand. And yes, it takes courage. But once high-potential leaders realize they have power, that their skills have real market value, the conversation gets easier. Self-awareness is the foundation. Courage is what turns that awareness into action.
The leaders who thrive in the next phase of their careers won’t just be the ones who work hardest — they’ll be the ones who are most intentional. Intentional about the shifts they need to make. Intentional about the feedback they seek. Intentional about the career conversations they’re willing to have. Leadership isn’t a solo act. And neither is growing into the leader you’re capable of becoming.
3 Ways to Keep the Conversation Going
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- Watch the full replay here and reflect on where the expectation shifts described in this session show up for you right now.
- Download The Roundtable 2026 Report on High Potential Leaders
- to explore what distinguishes leaders who sustain momentum from those who quietly plateau.
- Build your own leadership capacity in 2026: Registration is now open for our Spring The Roundtable for Leaders program. If you’re navigating increased scope, leading through change, or ready to move to the next level, book a meeting with Colleen to learn more.
Thank you to Anna and Nicola for an incredibly candid conversation. Be sure to join us on May 14 from 12 to 1 p.m. EST when author Dan Pontefract will be joining us on our Talent Talks series to talk about his new book The Future of Work is Grey.
