How to Prepare Your Second-in-Command for Executive Leadership
Leadership Series | Guidance for executives looking to cultivate, shape, and elevate emerging leaders from within.
I’ve seen it happen more than a few times:
A respected leader prepares to step down, confident they have a strong internal successor ready to take the reins. This senior staff member has been a steady presence for years… someone talented, committed to the mission, and trusted by the team.
But for one reason or another, once the recruitment process begins, something doesn’t line up. The board hesitates. They don’t share the outgoing leader’s confidence… and ultimately, choose to look externally.
The question isn’t why the internal candidate wasn’t ready but why the board didn’t see it.
So if you’re an executive fortunate enough to have a strong second-in-command or emerging internal talent you believe could one day step into your role, now is the time to start preparing the ground. It will take more than just titles and talk… You will need to connect the dots: help your senior staff member build critical relationships, gain visibility, and develop a leadership narrative that allows the Board to see what you already do.
Below are practical things I’ve done in my career, or have seen done by my peers, to ready and elevate internal leadership talent.
1. Give Them Boardroom Visibility
Your internal leader can’t earn the confidence of the board if the board hasn’t had an opportunity to see them lead (feels like a no-duh, right?). This exposure is critical to building the familiarity and trust needed for a successful succession. When your emerging leader has the opportunity to speak in the boardroom, sharing their vision, insights, and achievements, board members begin to associate them not only with competence, but with authority.
To be clear, it’s not about making an artificial showcase: It’s about finding authentic opportunities for them to shine.
Some practical ways to build board visibility include:
Invite them to present key updates or strategic reports at board meetings. that highlight their ownership and judgment.
Assign them to a board committee or task force, especially one within their area of expertise.
Include them in board retreats or strategic planning sessions, giving them space to contribute ideas, problem-solve collaboratively, build rapport, and demonstrate critical thinking.
Find them high-impact assignments that have real, bottom line impact and benefit from collaboration with board members.
2. Strengthen Their Executive Communication
Visibility alone isn’t enough. Once your emerging leader has a seat at the table, they need to be able to communicate at that level. Many emerging leaders are exceptional operators with their teams but struggle to make the jump when speaking with the board. They often communicate at the wrong altitude, getting too detailed or tactical, which can leave the board questioning their strategic capability in the long term.
Your role is to help your staff adapt their communication to the executive context, where clarity, brevity, and strategic framing matter most. The goal is to help them shift from explaining the work to articulating the impact.
Practical ways to build this skill:
Coach them to lead with impact and insight, not information. Shift them from reporting on what happened to what it means for the organization? Push them to frame their communications around impact: what changed, why it matters, and what’s next. Remind them they don’t need to explain everything that happened.
Never let them go in cold. Have them practice presentations with you or work through key discussions together. Resist giving feedback in the moment. Instead, debrief afterward on what landed, what didn’t, and how their presentation could be stronger.
Be radically candid with your feedback. They can’t grow without hearing the truth about where they’re over-explaining or under-communicating, or where their communication tics might be getting in the way of being heard.
Model and Mentor. Take time to narrate your own thought process when preparing for meetings so they can see how you translate complexity into clarity. Explain why you choose to include or omit certain information, and how you decide what truly matters for the audience. Let them know more than just what you communicated, but how you thought about it. This is where real executive judgment can be taught.
3. Build Strategic Exposure and Judgment
One of the biggest gaps I see in emerging leaders is limited experience (and opportunity) to make decisions with real stakes. In many small or mid-sized organizations, even strong senior leaders spend most of their time managing operations rather than navigating larger conversations on financial trade-offs, risk response, and competing strategic priorities. As a result, they may not have had the chance to build the muscle that true executive judgment requires.
Strategic thinking and emotional steadiness are developed through real-time interfacing with complexity, not through reading a book or observation. Emerging leaders need to see how hard calls are made, how competing priorities are balanced, how relationships are managed under pressure–and then given the opportunity to do it themselves. Help your senior staffer build this skill by:
Including them in strategic meetings, even if just as an observer at first. If possible, let them sit in on negotiations, crisis responses, or organizational challenges so they can see real decision-making under pressure.
Pulling them into decision-making. Have them in the room for budget reviews or annual planning, particularly when board collaboration is involved. Ask for their opinion. Carve out time to explain your reasoning afterward, even briefly, to reveal how decisions are shaped.
Inviting them into your thought process. Share how you approach trade-offs, assess risks, and interpret board dynamics. Exposure to how you think, not just what you decide, builds their strategic instincts.
Coaching them on stakeholder dynamics. Many internal successors stumble not on ability but on relationships. Help them understand unspoken power structures, personalities, and institutional history so they can navigate confidently.
4. Create Personal Connections
In the case of executive leadership, perception is as important as performance. A potential successor can be talented, capable, and trusted internally, yet if they feel like a stranger to key stakeholders they will never make the leap. Finding opportunities for your senior staffer to build authentic relationships with board members, funders, and strategic partners will allow others to see their leadership firsthand and develop confidence in their character and judgment long before a transition is on the table. You could try these:
Facilitate introductions intentionally. Set up informal coffees, joint calls, or small-group meetings with board members or major funders, especially if there is common ground or shared work. Give them context beforehand so they can speak comfortably and authentically.
Share visibility. Bring them along to donor visits, partnership discussions, or community events where they can represent the organization and demonstrate leadership presence.
Encourage external representation. Let them attend conferences, serve on panels, or participate in collaborations that naturally expand their network and credibility.
Signal endorsement publicly. When appropriate, mention their work in external conversations or acknowledge their leadership in group settings. Your confidence in them helps others see it too.
5. Succession as Long-Term Leadership Development
You need to think of succession planning as a long-term development process, not just a short-term contingency plan. You and the Board should aim for more than identifying who could step in; you should be actively growing their readiness and broadening their exposure over time That shift… from crisis management and replacement planning to capability building… is what turns succession into a true strategic advantage.
A few tactical things to consider adding to your succession planning process:
Executive Skills Matrix & Assessment. Create a defined skills matrix for executive capabilities paired with an assessment tool to track senior staff progress and guide targeted professional development during their performance reviews.
Annual Board Succession Conversation. A standing yearly discussion with board officers about your senior leadership team. This is not about performance management but perception management and gaining meaningful feedback on how the board perceives current talent.
An Open Conversation With Your Board About Your Eventual Departure …including your perspective on internal talent, who is growing, and where the real potential lies.
A Living, Continuously Updated Plan. This isn’t a set it and forget it exercise. An organization needs a dynamic document, regularly reviewed and refreshed as leaders grow and organizational needs evolve.
Final Thoughts
There is a tremendous amount of invisible leadership inside organizations. Talent that gets overlooked during transitions not because of a lack of ability, but because they’ve never had the opportunity to demonstrate their capacity before it mattered.
Your second-in-command can’t just be a name on a chart you quietly hope will rise to the occasion. You need to stretch them strategically, relationally, and intellectually. Put them in the rooms where judgment is shaped. Give them visibility long before they need it. Help them build the relationships that will create the confidence needed to make the leap.
If you do this early and consistently, the board won’t need convincing. They’ll already see what you see: a capable, credible leader who’s ready when it matters most.