Dear Board Chair,

After nearly two decades of working with nonprofit boards, executive directors, and CEOs, I have observed that leadership transitions often begin with a search.

Perhaps they should begin with a question.

Let me ask you one.

If your executive director resigned tomorrow, how would you know whether your organization was ready to hire their successor?

Not whether you could launch a search.

Not whether you could form a committee.

Not whether you could attract candidates.

But whether the organization itself was genuinely prepared for its next chapter of leadership.

The answer to that question may determine the success of your next executive far more than the search process itself.

When a leadership transition occurs, boards naturally focus on who comes next. That is understandable. The position is vacant. Stakeholders are asking questions. Staff members are looking for reassurance. Donors want confidence that the organization remains strong.

But before asking who should lead the organization next, should the board first ask whether it is prepared to welcome that leader?

How would you know whether your board is aligned around the organization's future direction?

Would every board member describe the organization's priorities for the next three to five years in the same way?

Would staff?

Would key funders?

Would your community partners?

And if the answers differ, what does that mean for the person who will eventually step into the executive role?

How would you know whether the challenges facing the organization are leadership challenges or organizational challenges?

If fundraising has plateaued, is that a leadership issue?

Or is it a systems issue?

If staff morale is struggling, is that because of leadership?

Or because difficult organizational decisions have been postponed for too long?

And how would you know whether the role itself has changed?

Perhaps the organization once needed a builder.

Today, does it need a strategist?

A fundraiser?

An operator?

A community ambassador?

A culture builder?

If the board has not yet answered those questions, how can it confidently evaluate candidates against them?

This raises another question.

When an executive departs, is the board's immediate responsibility to find the next leader?

Or is its responsibility to create the conditions that will allow the next leader to succeed?

Those are not necessarily the same thing.

Most boards understand the risks of moving too slowly.

But what are the risks of moving too quickly?

What happens when urgency is mistaken for readiness?

What happens when a search begins before the organization has clarified its priorities?

What happens when a new executive inherits unanswered questions instead of a clear roadmap?

And who should answer those questions? The board before the hire or the executive after the hire?

Consider another question.

If your next executive walked through the door six months from now, what would you want them to inherit?

Would you want them to spend their first year conducting assessments, addressing deferred issues, clarifying expectations, and rebuilding alignment?

Or would you want them to inherit a focused board, a stable staff team, and a shared understanding of where the organization is headed?

Which environment gives a new executive the greatest chance of success?

And which environment is more likely to attract exceptional candidates?

Perhaps the most important question of all is this:

What work needs to occur between one leader's departure and another leader's arrival?

Does the board need time to reflect on strategy?

Do organizational structures need evaluation?

Are there financial systems that require attention?

Are there difficult decisions everyone knows need to be made but no one has had the capacity to address?

Are there opportunities that have remained unexplored because leadership has been consumed by day-to-day operations?

And if that work needs to happen, who should lead it?

Should already stretched staff members assume additional responsibilities?

Should volunteer board members step into operational leadership?

Should the incoming executive inherit the responsibility for solving yesterday's problems while simultaneously trying to build tomorrow's vision?

Or is there another possibility?

What if the period between leaders is not merely a vacancy to fill?

What if it is a strategic opportunity?

An opportunity to assess.

An opportunity to stabilize.

An opportunity to align.

An opportunity to strengthen the organization before the next permanent leader arrives.

If that were true, what type of leadership would best serve the organization during that period?

Would it be someone focused on building a long-term legacy?

Or someone focused on preparing the organization for the person who will?

Interim leadership is not the right solution for every organization.

But perhaps the better question is not whether your organization needs an interim executive.

Perhaps the better question is whether your organization is ready for its next permanent leader.

And if the answer is not yet, what should happen next?

‍