Do you know who would step into your key roles tomorrow if someone left? For a lot of HR teams, the honest answer is "not really." Succession planning tends to stay on the someday list until a resignation or retirement forces the issue.
To help, we invited Melissa Kaspari to host a succession planning Ask Me Anything in PeopleOps Insiders, SSR's community for HR pros. Melissa is the founder of TrueNorth Talent Group and a former CHRO with more than 20 years of HR and executive leadership experience. She has worked across private equity-backed, multi-location and fast-changing organizations in construction, automotive, technology, retail and more.
Community members brought real situations, many of them submitted anonymously: founders who won't name a successor, controllers who hold every piece of institutional knowledge, and acquisitions that empty out the leadership team. Here's what Melissa told them.
Start Simple: You Don't Need Software to Begin
Asked about the biggest misconception organizations have about succession planning, Melissa didn't hesitate: people assume it's difficult and expensive. "It is not! You just need to get started with a simple Excel spreadsheet."
One member's team, a 200-person organization launching its first formal process in spring 2027, wanted lessons learned before they began. Melissa's advice was to resist overcomplicating it. The point is to understand where your biggest talent risks sit and where you need to start building coverage and readiness. Begin by identifying critical roles. "Not people," she stressed, "but critical roles."
Another member's leadership team agreed succession planning matters but wouldn't pay for software or consultants. Melissa has been in that spot herself. Her suggestion: find the one leader who supports the process, start the work with them, and build a spreadsheet with these columns:
- Critical role
- Business risk if unfilled
- Current incumbent
- Immediate successor
- Ready in 3–5 years
- Ready in 5+ years
- Next steps
The exercise should show leadership one of two things. Either there are no internal successors, and you need to start hiring with succession in mind, or there are successors who need a training plan to get ready.
Frame It As a Business Continuity Issue
A theme ran through nearly every answer: tie succession planning to business outcomes. "Learn to speak the language of the leadership team," Melissa said, and show how a critical role that goes unfilled affects the bottom line.
Community member Jenise Fuson echoed this. She noted that many organizations either don't talk seriously about succession until critical talent is about to leave, or they treat it as an annual check-the-box exercise. Calling it a business continuity issue, and putting a dollar figure on the risk, can be what finally opens the conversation with executives.
That framing matters most when the person who needs convincing is at the very top. One solo HR professional described a founder and CEO in his late 60s who says he'll retire "in a few years" but won't name a successor or set a timeline. How do you raise it without overstepping?
"Sometimes you have to overstep!" Melissa said. This is a conversation to have directly with the CEO, but timing matters. Pick a moment when he's open to it, because forcing it at the wrong time means hitting a brick wall. In the meantime, she likes to drop comments that plant the idea so the leader starts thinking about it, and to keep connecting the topic to business impact.
Plan for the Business You're Becoming, Not Just the One You Have
One member, Iris, asked a forward-looking question. As AI reshapes roles and skills-based talent practices spread, how do you evolve succession planning beyond replacing people in today's roles to building the capabilities and leadership pipelines the organization will need?
Melissa sees succession planning in phases. The first is business continuity: who steps in if someone "wins the lottery" tomorrow. The next looks at the organization's three-, five- and ten-year goals and builds talent pools around them.
AI is part of that conversation, she said, but it's not the starting point. Start with where you're taking the business and which skills it will need to get there.
The same foundation applies to talent you already have. Melissa calls identifying high-potential employees and critical talent one of the most important parts of succession planning. Look across your organization and ask what your bench strength really looks like, and whether you've named those people yet.
Identify Successors, Then Develop Them
Great at the job isn't the same as ready to lead
How can you tell whether someone is ready to lead versus simply being great at their current job? Melissa sees a common pattern: companies promote a strong individual contributor into a people leader role before they're ready, skip the training, and expect them to know what to do. "All we're doing is setting them up to fail."
The fix starts with asking who actually wants to lead people. Some employees want to stay on a technical track, "and that's okay." You can only plan well when you understand people's career aspirations.
Should you tell a high-potential employee she's in the plan?
One team had quietly identified the likely successor for their operations director. They worried that telling her would create expectations they couldn't guarantee, but that staying quiet might push her to take a promotion elsewhere.
Melissa's answer: "100% absolutely you should tell her!" But pair it with a real career development conversation. She may not want this path, so ask about her goals. Tell her you see future potential and outline what her development plan could look like, even if it's not fully mapped out yet. Make it clear that she owns her career, not the company. Melissa sees employees make the mistake of waiting for the company to tell them their next role "time and time again."
When a manager blocks growth
A member described a department head who keeps top employees from cross-team opportunities because they don't want to lose them. Melissa sees this as a broader leadership gap: not understanding the business value of developing talent and building bench strength. Holding people back just raises the odds they'll leave for a competitor who offers those opportunities.
She recommends starting with a direct conversation to understand the resistance. The manager may fear losing a strong performer, worry about backfilling the role, or feel insecure about their own position. Once you know the concern, you can address it while reinforcing that developing talent is part of every leader's job.
Handle the Hard Conversations Head-on
The passed-over number two
A sales team's longtime number two assumes he's next in line, but leadership chose someone else. How should they tell him, and can they stop him from walking out with key client relationships?
Melissa answered this one live on video. First, sit down with him and have a candid conversation about why he wasn't chosen and what you'll do to help him get to the level he needs to reach. Choosing someone else without that conversation will leave him angry and upset, and chances are he'll leave and take those relationships with him.
On the client question, she turned it back to the company: do you have an agreement or non-solicit in place that would prevent that? Those are the documents to review now.
When succession is a family decision
In a family business, the owner wants his son to take over, even though the son has limited experience and several senior employees are clearly more qualified. What's HR's role?
Melissa acknowledged the family dynamics make this hard and said it calls for an open conversation about the son's readiness. One option is for a more senior employee to take the role while training and mentoring the son to step in later. The son could also rotate through different roles to learn the whole business, which, she noted, would give him more credibility with employees.
Small Teams, Flat Structures and External Hires
No deep bench? Plan for coverage instead
Smaller companies don't need a ready replacement for every role, Melissa said. The goal is to reduce dependence on any one person and create realistic coverage options. Three ways to get there:
- Cross-train people on important processes.
- Use outside fractional workers to fill gaps.
- Plan your next hire with succession in mind.
Fix the structure first, or start planning now?
A 60-person company has almost no middle management, and everyone reports to one of three executives. Is succession planning realistic, or does the org structure need to change first?
Before touching the structure, Melissa suggests getting clear on the company's strategic goals. Is growth expected through acquisitions or new locations? Do the executives have clear responsibilities and decision-making authority, or is overlap creating confusion? Those answers show what structure the business needs now and as it grows. Once that's clear, "succession planning absolutely makes sense!"
When nobody internal is ready
One team had identified its critical roles but found that for at least half of them, no internal candidate was close to ready. When do you stop developing internal talent and plan an external hire?
Melissa first praised them for building an internal pipeline with employees who want to grow. If some roles need more experience than anyone has today, it's time to go external, and that's not a bad thing. Just make sure the new hire fits your culture. A more experienced external hire can also be a great mentor to the people you're developing.
When the Risk is Already Here
Three leaders leaving after a PE acquisition
One member's company was just acquired by a private equity firm. Three of its five senior leaders are expected to leave within 18 months, and the new owners want a succession plan in 90 days.
"First of all, just breathe," Melissa said. Start with the three expected departures and work backward from what the business needs to protect. The 90-day deliverable should be a credible transition plan with clear coverage, successor options and actions to close the gaps.
With three of five senior leaders leaving, she would treat this as one coordinated leadership transition. The timing and overlap of the departures matter as much as the individual replacements. Questions to answer:
- Will the departing leaders support the transition?
- Is there a training plan for each identified successor?
- How will you communicate the changes, both those already made and those still coming, to the rest of the company?
"Transparency is very important," she added.
One person holds all the knowledge
A company's controller has been there 22 years and is the only one who understands its financial systems. Nothing is documented, and she resists training anyone because she sees it as a sign she's being replaced.
Melissa called this an immediate business continuity risk that needs to be raised directly with the controller and executive leadership. No company can afford to have all its financial system knowledge in one person. Her priorities:
- Document critical processes.
- Cross-train a qualified backup.
- Evaluate whether responsibilities should be split or an additional hire is needed.
Who Owns Sucession Planning, and How to Tell It's Not Working
Who should own succession planning: HR, executive leadership, department heads or some combination? Melissa's answer is a combination. HR should guide the conversation, with executives, department heads and other key stakeholders contributing. Leaders share responsibility for developing talent and preparing employees for what's next.
That shared ownership is also how you can tell whether the process is healthy. Melissa's early warning signs:
- Leaders can name potential successors but can't explain what they're doing to prepare them.
- A vacancy sets off a mad hiring scramble.
- One person is the obvious successor for several roles.
- HR owns the process and is expected to handle all the follow-up.
The Bottom Line: Just Start
If there's one takeaway from the hour, it's that succession planning doesn't have to be big, expensive or perfect. List your critical roles, be honest about who could step in, talk openly with the people involved and tie it all back to business risk.
A huge thank you to Melissa Kaspari for sharing her expertise, and to every member who brought a question. You can find Melissa and TrueNorth Talent Group at truenorthtg.com.
Want to join conversations like this one? PeopleOps Insiders is SSR's free community for HR pros. Members trade advice, ask questions anonymously and get access to expert Office Hours sessions like this one.
