The hardest conversation in succession planning isn’t about capability gaps or financial modeling. It’s about acknowledging that the skills that made someone valuable in their current role may not translate to leadership.
As CPO at PBO Advisory, I’ve had to navigate this reality while leading our succession planning work. It requires honesty, empathy, and a willingness to separate contribution from potential.
Because here’s what I’ve learned: succession planning isn’t just about filling roles. It’s about preserving what makes your organization distinctive while building capacity for what comes next.
The Tenure Trap
Most organizations default to promoting based on tenure. It feels fair. It rewards loyalty. And it avoids the uncomfortable conversation about whether long-serving employees are actually ready for executive leadership.
But tenure and readiness are not the same thing.
When we mapped talent at PBO, we found several team members who had been with us for years, contributed significantly to client work, and were deeply respected. But when we assessed them against executive leadership requirements, gaps emerged:
- Strategic thinking that connects functional expertise to business outcomes
- Financial acumen to manage P&L responsibility
- People leadership that builds and retains teams
- Change leadership that guides organizations through transformation
These capabilities don’t automatically develop through tenure. They require intentional development, targeted experience, and often, a mindset shift from individual contributor to enterprise leader.
The uncomfortable truth? Some of our most tenured team members weren’t the right fit for next-level leadership. Not because they lacked value, but because executive leadership requires different capabilities than technical excellence.
What Succession Planning Actually Requires
After leading PBO’s succession planning work, I can tell you that effective succession planning requires three things most organizations skip:
- Honest Capability Assessment
You need to assess people against future requirements, not current performance. This means evaluating strategic thinking, financial literacy, people leadership, and change capability with the same rigor you apply to technical skills.
At PBO, we created a comprehensive assessment framework:
- Ready now: Can assume executive role within 3 months
- Ready in 12-18 months with targeted development
- External hire required due to capability gaps or timeline constraints
This clarity allowed us to make intentional development investments rather than hoping people would grow into roles organically.
- Development That Goes Beyond Training
Leadership development isn’t about sending people to workshops. It’s about systematic capability building through:
- Executive coaching that addresses mindset shifts
- Stretch assignments that build strategic thinking
- Financial exposure that creates P&L literacy
- Board exposure that develops enterprise perspective
- Mentor relationships with current executives
And here’s what most organizations miss: this takes time. Even high-potential leaders need 12-24 months of intentional development before they’re ready for executive roles. If you’re waiting until someone leaves to start developing their replacement, you’re already 18 months behind.
- Culture Preservation Alongside Capability Building
This is where many succession plans fail. They focus exclusively on skills and capabilities while ignoring culture fit.
You can hire external talent with impressive resumes. But can you hire someone who embodies your values, understands your client relationships, navigates your internal dynamics, and maintains the culture that makes your organization distinctive?
At PBO, we’ve had to balance building new capabilities with preserving what makes us PBO:
- Client-first orientation that guides every decision
- Integrated thinking that connects finance, operations, and people
- Transparency and trust that define how we work together
- Long-term relationships over transactional engagements
These aren’t skills you can train. They’re cultural qualities that require careful assessment and intentional reinforcement.
The Conversations No One Wants to Have
Leading succession planning has required me to have conversations I wish I could avoid:
Telling a long-tenured employee that they’re not ready for the next level. Explaining that contribution and leadership potential are different things. Being clear about development timelines when someone wants to move faster than they’re ready for.
These conversations are hard. But I’ve learned that clarity is kindness.
Stringing people along with vague promises serves no one. Being honest about readiness, gaps, and timelines creates respect even when the message is difficult. And creating transparent development paths gives people agency over their growth rather than leaving them guessing.
What Success Looks Like
A year into PBO’s succession planning work, I’m seeing the impact:
Our high-potential leaders are getting executive coaching, board exposure, and strategic projects that are accelerating their development. They’re not waiting for someone to leave. They’re being built up now.
We’ve identified capability gaps early enough to address them through targeted development rather than crisis hiring. This gives us options instead of forcing suboptimal decisions.
And perhaps most importantly, we’ve created transparency about how leadership decisions are made. People understand what executive leadership requires, what their development path looks like, and what timeline is realistic.
Succession planning isn’t just about filling roles when people leave. It’s about building an organization where leadership continuity is baked into culture, development is systematic, and everyone understands what growth looks like.
That’s the difference between reactive crisis management and strategic succession planning. And it’s what separates organizations that scale from organizations that stall.
Nicole Devine
CPO, PBO Advisory Group
[email protected]
(858) 622-1681
Is your organization developing the right leaders for the next round?
PBO Advisory Group helps companies build honest talent assessments, intentional development paths, and succession plans that preserve culture while preparing for the future. Let’s start the conversation.
Articles & Podcast on Succession Planning
Francesca San Diego, CEO | Succession Planning as Strategic Renewal | Why I’m Planning My Own Transition
Jennifer Rebis, CFO | The Financial Architecture of Succession Planning | Why Most Organizations Underestimate the True Cost
PBO Leadership Team | Succession Planning That Actually Works | Integrating Finance, Operations, and People Strategy
PBO Leadership Team | Beyond the C-Suite | Why Succession Planning Isn’t Just for Executives
