When a mission-driven organization hires a CEO to lead significant change, the board takes on one of its most consequential responsibilities: creating the conditions for that leader to succeed. The board-CEO partnership is essential to strategic progress, and like any strong partnership, it depends on clear expectations, direct conversations, and mutual accountability. 

That’s the type of relationship that Cynthia Mills helps boards and CEOs build.

Defining this relationship is more important than ever as association and nonprofit business models face increasing pressure and many boards are supporting a change-agent CEO—sometimes also a first-time CEO—without a clear precedent to follow. Organizations expect their next CEO to consider new models, revamp long-standing programs, seek out unconventional audiences and alliances, and create alternative revenue streams, all while the external environment changes at a whiplash pace. 

We asked Cynthia what it takes to create a board-CEO partnership that can weather the demanding work of transformation. Her perspective is refreshingly straightforward and packed with concrete guidance developed through decades of hands-on experience. It’s easy to see why clients call her “The Board Whisperer.”  What follows are a few highlights from our conversation.

Think Continuum, Not Event

A former association CEO, board member, and now President & CEO of The Leaders’ Haven consultancy, Cynthia has been on all sides of the table. Her approach reframes executive performance management as something more practical than a once-a-year review. The most useful shift a board can make is to think of performance management as an ongoing conversation—about what the organization, board, members, staff, partners, and CEO need, and how everyone is going to work together to make it all happen.

Set expectations early. Make explicit agreements. Keep checking in. Those are the core elements of good communication, and they’re the foundation of effective executive performance management. 

The process should not begin and end with the formal annual review. 

“There has to be integration at every step, from board training, strategic design, search prep, and the search itself, to the CEO’s contract. Everything is linked. We need to do all of these things well, because they all feed into a good executive performance review process.”

Attention to each point on the continuum makes the next one more effective. When boards scope out this structure up front, the challenges that inevitably come with transformation become expected, planned for, and part of the work rather than cause for alarm.

➔ Scope Out the Structure Up Front

  • Reflective preparation by the board before the search.
  • A search process grounded in the leadership competencies most relevant to the position and the organization’s strategic priorities.
  • A CEO contract that spells out how reviews will work, when they’ll happen, and the cultural and operational agreements around how board-CEO work will be accomplished.
  • A transition document that defines performance expectations at 90 days, six months, and one year, with subsequent mutually agreed-upon annual performance goals aligned with the strategic framework.
  • An ongoing review process built around quarterly conversations, culminating in a formal annual evaluation and written review.

Define What Your Organization Needs

Before launching a search, Cynthia encourages boards to work through a few foundational questions, starting with what the organization needs from its next leader.

  • What does transformation mean for your organization? “Transformation” gets used so often that it can lose meaning without specific context. What will the new CEO be expected to build, fix, or reimagine? Is the goal brand reinvention, revenue diversification, operational turnaround, or some combination? The answer informs everything that follows, from the competencies the search firm vets to the CEO’s performance metrics.
  • What stage is your organization in? A founding organization, a growth-and-scale organization, or a mature organization each call for a different kind of leadership, with different expectations around risk and pace. Within that stage, also consider your context. One mature organization may have modern systems with a strong organizational structure. Another may have outdated technology and team structures that have become misaligned over time. Does your organization need someone to build on momentum right away, or someone to plod through first and then build, or a combination of both? The messages that the board will deliver publicly in support of the new CEO will also need to be carefully framed around this understanding to inform member and staff expectations, which impacts their perceptions of the CEO’s initial performance as well.
  • Given the stage of your organization and scope of transformation, what dynamics can you prepare for? Boards don’t have to guess here; transformation work has predictable stages. Cynthia has developed a model of the typical behaviors a board and CEO can expect to see across a five-year transformation. Boards can map this model against where the organization sits in its lifecycle to see where they intersect and what dynamics are likely to surface. Click here to download the full article, which details Cynthia’s key transition points model.

With consensus on these questions before the search begins, the board can spell out its vision in precise terms and evaluate candidates against it, rather than discovering misalignment months into the new CEO’s tenure.

“When we hit those rough moments in strategy and the slogging of building, we can go back and say, ‘We knew this was coming. Doing a transformation was going to hit this moment. So now we’re at that moment, and this is how we agreed to work together.’”

Define the Board’s Role, Too

The readiness work is also about the board itself and the way it intends to show up as a partner to the leader it hires.

  • What posture will the board take during the transformation? Cynthia strongly recommends that boards commit to developing alongside the CEO. That might mean attending CEO symposia, seeking out Exceptional Leaders events, and building regular learning time into the board agenda. Without these commitments, the board risks falling out of step with the very leader it asked to move the organization forward.
  • How will the board approach performance management? If a formal process isn’t yet in place, this is the moment to build at least the outline of one: how goals will be set, how often progress will be discussed, how the annual review will work, and where those commitments will be documented. The formal review serves as the written record of the board’s fiduciary responsibility, but it’s only one part of the process.

“Boards have to commit to learning so they can stay in step with a transformational leader. Otherwise, the transformational leader may leave them behind.”

Change-agent CEOs know what transformation requires, and they’re watching closely during interviews for signs that the board will back them when the time comes. They’ll ask about the board’s strategy, how goals will be set, and how the review process works and connects to organizational priorities. Top-performing CEOs are looking for a partner. A board that has done this work signals exactly that.

Put It All in Writing

If a board is serious about transformational leadership, the CEO contract should reflect that. In Cynthia’s experience, many contracts include a brief line noting that a performance evaluation will occur and little else. The board’s commitments should be outlined in far more detail. “The contract is setting up a relationship, not just an employment agreement.”

The contract should include what the bylaws say about the CEO position and details about the mutually agreed-upon performance management approach—a formal policy, timeline, and the elements that will serve as the primary basis for evaluation.

She also recommends the position description be attached as an addendum, along with an outline of how the board and CEO have agreed to work together, cultural expectations of the CEO’s leadership and the board-CEO partnership, and the specific behaviors each party has agreed to bring to the relationship. If the board has done this prep work, they’ll be prepared to have frank discussions with the new CEO during which both parties can offer strategies to handle each stage.

This level of detail in the contract also ensures continuity. Board composition will change over time, and a comprehensive contract helps new members understand and align with agreements already in place—not just about strategy and financial expectations but the dynamics of leadership. The contract is as much a record of strategic intent about the partnership as it is a legal document about compensation and benefits.

➔ Include These in the CEO’s Contract

  • Details about the mutually agreed-upon performance management approach. This includes a formal policy, timeline, and the elements that will serve as the primary basis for evaluation.
  • An outline of how the board and CEO have agreed to work together throughout the stages of transformation. This includes cultural expectations of the CEO’s leadership and the board-CEO partnership, and the specific behaviors each party has agreed to bring to the relationship.

Click here for sample board commitment statements for CEO contracts.

Check In Quarterly. Yes, Quarterly

Cynthia recommends that every board-CEO partnership begin with a transition document, which is a shared planning tool that outlines what success should look like in the CEO’s first 90 days, six months, and full year. Creating the document motivates the board to work through those complex questions before the hire is made and guards against vague or subjective performance expectations.

But its real value shows up after the CEO starts.

Cynthia recommends using the transition document as the basis for a standing agenda for board-CEO conversations held quarterly throughout the first two years. This practice dramatically changes the nature of the partnership. With regular, structured dialogue about initial expectations, what’s unfolding, and how to respond, there is space carved out for discussion—good and challenging. It removes the fear of difficult updates from either side, because it’s all part of the process.

“We are partners. And if we can’t sit together as adults and speak to each other about what is happening, then we are essentially agreeing not to have clear, transparent, open communication.”

For at least the first year, Cynthia encourages the full board to participate rather than delegating to an executive committee or a single board member. “I’ve seen too many situations where there is a difficult moment, and instead of everybody acknowledging the elephant in the room and having that adult conversation, it gets delegated to one board member to talk to the CEO. Too much gets lost there. We need to be able to say what we need to say in front of each other.”

Cynthia also encourages new CEOs to do their own assessments of the organization and bring them to the board during these meetings. What does the CEO now see that the board couldn’t before? What priorities should be revisited? What tradeoffs are needed as the work gets underway? The CEO should be explicit about their asks, whether that means recalibrating timelines, budget, and staffing needs, or clarifying what kind of board support will be most important in the months ahead.

With the transition document and the CEO’s assessments as touchpoints, these quarterly meetings create a habit of direct and productive conversation between the board and the CEO.

➔ Set a Standing Agenda Around Performance

  • Create a transition document outlining what success looks like in the first 90 days, six months, and full year. Reference it at every meeting.
  • Discuss progress and roadblocks. Normalize difficult or challenging topics as simply part of the ongoing process.
  • Don’t delegate the tough conversations. Get the full board involved.

The Plod Is Real. Plan for It

New CEOs hired for transformation often spend their first 18 to 24 months doing work that is less visible externally. Cynthia calls this the plodding phase—the rebuilding of systems, the modernizing of infrastructure, the reshaping of teams. The groundwork has to be laid before bigger changes have any chance of taking hold.

This phase is also where boards are most likely to lose confidence in the leader they just hired, especially if the CEO is following a long-tenured predecessor. The board’s temptation is to push for visible results early, to show members and stakeholders that things are moving. Cynthia cautions that chasing more visible initiatives too soon can undermine the rebuilding work, if that’s necessary. “We could do the big things now, but then we’d fall flat on our faces.”

Knowing this is likely to happen, the board and CEO can plan for it together, and the board should communicate about it externally. When members or stakeholders don’t see change right away, frustration tends to land on the CEO, even when the CEO is doing exactly the work the board hired them to do.

“If you don’t build this out, you’re setting up your new CEO to be a transitional CEO, not a transformational CEO.”

The board’s role in this phase is to make that work visible. That means telling stakeholders what the organization is doing, why the foundational work is critical, what the timeline looks like, and how they can engage in building what comes next. The CEO, in turn, can leverage their communication channels to do the same. Without doing so, constituents will make up their own stories about what is or isn’t happening, especially when they are invested in the outcome.

Again, this comes back to good communication: set expectations early, make explicit agreements, keep checking in.

Share the “why” behind the work and be transparent about what’s happening and when. This protects the CEO, builds stakeholder investment in the transformation, and reinforces that the plodding phase is part of the plan, not a sign that something has stalled.

Do the Formal Review, and Do It Right

The formal review and written evaluation are still essential. It’s where the conversations, agreements, and check-ins of the previous year come together. It’s as valuable for long-tenured CEOs as for those in their first year, and regardless of how much trust the board and CEO have built, it should never be skipped. “You don’t get to skip your fiduciary responsibility just because you trust the CEO. Because one day the CEO will leave. If you start skipping good fiduciary practices now, then in seven years you’ll be out of practice, and you will have lost most of the board members who experienced doing it well.”

So commit to doing the review on time, every year. In Cynthia’s experience, a missing review can also create uncertainty and lead an outperforming CEO to wonder whether the board is dissatisfied or considering a change, even if that’s nowhere near the case.

“If it’s a 95% knocked-it-out-of-the-park performance review, for crying out loud, spend 95% of your time talking about that—and ask how the board can help the CEO keep replicating it!”

➔ Tips for Getting the Formal Review Right

  • Gather written feedback from the full board. Written responses from multiple board members often reveal valuable patterns for the CEO. A single comment may not stand out on its own, but collectively, written feedback can show the CEO where expectations could be clarified or shifted. They are also highly valuable in identifying areas that point to additional board development needed, board orientation revision, or a shift in communicating essential data & information to the board.
  • Match the tone to the performance. Cynthia emphasizes that boards should think about how the CEO will receive the feedback and what you want to reinforce. If the CEO has had a strong year, the review should be primarily positive keeping areas for improvement in the right proportion.
  • Inquire, don’t accuse. Before raising a concern, boards should ask questions to make sure their perception is accurate. Explore the topic with the CEO, ask what factors are at play, get their take on the situation. Then you can decide if it needs to be formally addressed, and how to do so productively. If a perception is simply out of whack, what was missed in communication or understanding that would have informed the board better?

Mutual Investment Makes It Work

The board-CEO relationship works when both parties take responsibility for making it work. The board’s job is to set the new CEO up for success—preparing before the search, partnering with a trusted firm to run it, communicating transparently with candidates during the interview process, and setting a performance management framework that works well for both sides.

Once in place, the CEO’s job is to set the board up for success in return—removing barriers, providing strategic context, and giving the board the support it needs to make good, timely strategic decisions. That includes the performance management process itself.

Cynthia frames this as a practical reality of the job. “Like it or not, if a CEO wants a great performance review process, they have to take charge of it. That doesn’t absolve the board of their responsibility to participate, but it does mean the CEO sends the policy, bylaws, position description, performance review instrument, CEO self-evaluation; reminds them of deadlines; creates an anonymous method for results compilation, and supports the committee chair the way they would any other committee.”

That mutual investment is what makes the partnership work. None of what Cynthia describes is complicated. But it does take the willingness to decide, together and in advance, how the partnership will operate when the work gets hard. The patterns you establish at the beginning of any relationship tend to last for the duration. It’s worth starting this one off right.

“Remember that the purpose of a review is to have the best possible partnership-forming conversation that you can have. It’s not solely about ‘board oversight of the CEO.’ It’s about advancing the partnership by having an open conversation about the achievement of the strategy for the organization.”

About Cynthia Mills, Certified Master Coach, FASAE, CAE, CPC, CCRC

Cynthia Mills founded The Leaders’ Haven to help leaders & teams go beyond business as usual & continuously transform, so they can fulfill their true calling & exceed the expectations of the people they serve.™ The consultancy partners with clients to align for impact & leverage results through strategy, governance, and leadership.

The Leaders’ Haven serves associations, tax-exempt organizations, corporations, small, privately held, and family-owned businesses, and faith-based communities as a business strategist, board consultant, facilitator, leadership development catalyst, business & executive coach, succession planning & search sherpa, change leadership guide, and speaker.

Nicknamed by clients “The Board Whisperer™,” “Chief Experience Weaver™,” and “The Lamaze Coach for Boards™,” Cynthia relishes transformational journeys and loves that moment when everyone sees their potential and commits!

Cynthia holds an MA from the University of York, England, as a Rotary International Ambassador Scholar and a dual BA from Queens College as a Presidential Scholar. She is a member of the Association of Charlotte Area Consultants (ACAC), International Coaching Federation (ICF), International Coaching Council (ICC), American Society of Association Executives (ASAE), Association Executives of North Carolina (AENC), Professional Woman Network (PWN) & the PWN International Advisory Board. She was awarded Honorary Lifetime Membership in the Georgia Society of Association Executives (GSAE) and is a Lifetime Member of Strathmore Who’s Who Worldwide, which honored her as the Professional of the Year for Consulting, Coaching, and Professional Developme

Email Cynthia or find her on LinkedIn.

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