A CEO’s relationship with the board of directors is built between board meetings, not in them.
In our decades of executive coaching with CEOs and their executive teams at Skyline G, one pattern shows up so reliably we can almost set a clock by it. Somewhere in the second or third year of a CEO’s tenure, they walk out of a board meeting and call us with some version of the same sentence: “I don’t think my board actually sees what I’m doing.”
The CEO is usually right. And it’s usually not the board’s fault.
Why the CEO–board relationship is lopsided by design
Here’s the structural problem. A CEO lives inside the business every day. Board directors see it for maybe six hours a quarter. Their read on the CEO gets formed in those few hours, and that read determines how much rope the CEO gets, how long they keep it, and whether they get to finish what they started. The CEO–board relationship is lopsided by design, and nobody teaches new CEOs how to manage it.
Why board trust matters more in 2026: record shareholder activism
In 2026, the cost of getting it wrong went up. Shareholder activism hit a new high: Lazard’s H1 2026 Review of Shareholder Activism counted 184 new activist campaigns globally in the first half of the year, up 20% year over year, with North America setting its own record at 94. Board change was an objective in 35% of those campaigns. When an activist investor shows up, the first thing they test is whether the board and the CEO are truly aligned or just politely coexisting. A board that trusts its CEO closes ranks. A board that has quietly lost confidence starts taking the activist’s calls.
So let’s talk about what CEOs who manage their boards well actually do differently. None of it is complicated. Most of it is just consistently ignored.
Why does the board meeting feel like a performance review?
CEOs experience board meetings as performance reviews because directors form most of their judgment about the CEO in those few hours each quarter. The fix is to build board trust between meetings, not in them. For most CEOs, treating the board meeting as the place to win the board over is the first mistake.
The CEOs we’ve watched build real trust with their boards treat the meeting as the place where the relationship gets scored, not where it gets built. The building happens in between.
One CEO we worked with, running a public company with about 4,000 employees, had a habit we now recommend to everyone. Every director got a standing call every five or six weeks. Fifteen minutes, no deck, three questions: What are you seeing? What’s worrying you? What would you want to know that I haven’t told you? She told us those director calls were the highest-leverage hours on her calendar, and it wasn’t close.
What those one-on-one director calls do is simple. They surface concerns while they’re still small. They let each director feel individually heard, which is a real human need even for people who run billion-dollar funds. And they mean nothing in the actual board meeting is a surprise.
That leads to the rule we give every CEO we coach: if a director learns something material for the first time in the board meeting, the CEO has already made a mistake. The board meeting is for decision, not discovery.
What should a CEO include in a board pre-read?
A CEO’s board pre-read should open with a two-page letter the CEO wrote personally, followed by supporting material organized so a director can go as deep as they want on any item. The board pre-read (also called the board book, board deck or board package) is the material sent to directors before a board meeting, and directors form their opinion of a CEO’s judgment from it. Most CEOs send far too much.
A 140-page board deck signals one of two things. Either the CEO doesn’t know what matters, or the CEO is burying something. Neither builds confidence.
The board pre-reads we’ve seen work share a shape. A two-page CEO letter at the front, in plain language: here’s where we are, here’s what’s working, here’s what isn’t, and here are the two or three decisions I need from you. Then the supporting material behind it, organized so a director can go as deep as they want on any item without being dragged through all of it.
Write the CEO letter yourself. Don’t let it get assembled by the chief of staff from function-head submissions. The board is trying to figure out how the CEO thinks, and that letter is the best window they’ll get.
How should a CEO deliver bad news to the board?
A CEO should deliver bad news to the board early and personally, ideally by calling the board chair before directors hear it from customers, press or each other. Nothing damages a CEO–board relationship faster than a director hearing something from a customer, a journalist, or another director before hearing it from the CEO. It doesn’t matter how small the issue is. What directors register isn’t the problem, it’s that the CEO didn’t tell them.
We’ve seen this play out the hard way more than once. A CEO knew in week six that the quarter was soft. He decided to wait for the final numbers so he could present a plan alongside the problem. Reasonable instinct. By the time the board meeting came, two directors had already heard it from a large customer. He kept his job, but the question one director asked in the hallway afterward (“What else don’t we know?”) followed him for the next eighteen months.
The counterintuitive part is that early bad news builds board trust rather than eroding it. A CEO who calls the board chair on a Tuesday to say “we’re going to miss, here’s why, here’s what I’m doing about it this week” is demonstrating exactly the judgment the board is paying for. A CEO who waits until the numbers are final and then presents them with a spin is demonstrating the opposite.
The 2026 shareholder activism numbers make this practical rather than philosophical. Activist investors win when they can tell the board a story it hasn’t heard. If the directors already know every weakness in the business because the CEO has been walking them through it for two years, there’s no story left to tell.
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Can a CEO disagree with the board and keep its confidence?
A CEO can disagree with the board and keep its confidence by engaging the concern openly in the meeting, doing the work offline, and returning with a reasoned position and a request for support. Most CEOs get this wrong in one of two directions.
Some CEOs fold too fast. They agree in the room, then slow-walk the decision afterward. Directors notice, and they never quite forgive it. Other CEOs dig in publicly and turn a strategic disagreement into a test of authority, which the board will win every time. It’s the board’s job to win it.
The CEOs who handle board disagreement well do something slower. In the meeting, they engage with the concern out loud: “I hear this, and I want to make sure I understand it fully before I respond.” Then they take it offline, do the actual work, and come back with a position and the reasoning behind it. “I’ve thought hard about this and I still believe X. Here’s what would change my mind. I’m asking for your support.”
Directors can live with being overruled by a CEO who has clearly taken their view seriously. Directors cannot live with being managed.
How should a CEO work with an activist-appointed director?
A CEO should give an activist-appointed director more access than other directors, not less: invite them into operating reviews and let them see the business at close range. A settlement director (also called an activist-appointed director) is a board member seated under a settlement agreement between the company and an activist investor, usually to avoid a proxy fight. More boards now have one. It’s tempting to treat that person as the activist’s representative. In our experience, that’s a mistake.
Once someone is on the board, their fiduciary duty runs to the company and its shareholders, not to the activist fund that nominated them, and most settlement directors take that duty seriously. The productive move is to over-communicate with them specifically. More access, not less. Invite them into the operating reviews. Let them see the business at close range.
Activist-appointed directors who feel stonewalled report back that the CEO is hiding something. Activist-appointed directors who feel included tend, over a few quarters, to become some of the CEO’s most useful allies, because they’ve done the homework and can vouch for it.
What should a CEO do when the board chair is the problem?
When the board chair is the problem, a CEO should keep every commitment and a record of it, build direct relationships with every other director, and raise the concern early with the lead independent director or the governance committee chair. A strained relationship with the board chair is the hardest board situation any CEO faces, and we’ve coached through several. Sometimes it’s a founder-chair who can’t let go. Sometimes a former CEO who sees every change as a verdict on their era. Sometimes just a relationship that curdled.
There’s no clever tactic for a difficult board chair. There is discipline.
Keep every commitment, and keep a record. When trust is thin, a paper trail of “said we would, and did” is the only argument that works. Build direct relationships with every other director so the chair isn’t the only channel through which they see the CEO. And have one honest conversation, early, with the lead independent director or the governance committee chair. The lead independent director is the independent board member who leads the other directors when the chair is not independent, and part of that role is exactly this kind of conversation: “I’m concerned the working relationship with the chair isn’t serving the company. I’d value your counsel.” That isn’t going around anyone. That’s using the corporate governance structure the way it was designed.
We’d add one more thing, because it’s the part CEOs least want to hear: be honest with yourself about the possibility that the chair is right. Sometimes the friction is a signal, not an obstacle.
What happens in the executive session, and how does the board evaluate the CEO?
The executive session is the part of the board meeting where the independent directors meet without the CEO or other management, and it is where the board’s real read on the CEO gets spoken out loud. Most public-company boards hold one at every meeting. For a CEO, the executive session is the single most anxiety-producing twenty minutes on the calendar, because it’s the one room in the company they can’t be in.
The CEOs who handle executive sessions well do two things. First, they ask the board chair or lead independent director for a debrief immediately afterward, and they make clear they want the unvarnished version. A CEO who only hears the polished summary learns nothing. Second, they treat whatever comes back as data, not a verdict. If the same concern surfaces two sessions in a row, that’s a signal the between-meeting work described above isn’t landing, and it’s often the point at which a CEO brings in leadership coaching to work on it with someone outside the boardroom.
The board’s formal CEO evaluation works the same way, just on an annual clock. Usually the compensation committee or the nominating and governance committee runs it, often with input from every director and sometimes from the CEO’s direct reports. The CEOs who get the most out of it do their own self-assessment first, in writing, and share it with the committee before the board’s version arrives. That does two things: it shows the board the CEO sees the same gaps they do, and it means the conversation is about the plan rather than the diagnosis.
Both the executive session and the CEO evaluation feed the board’s thinking on CEO succession planning, which every well-run board does continuously whether or not the CEO is told. A CEO who engages with succession openly, naming internal candidates and investing in their leadership development, signals confidence. A CEO who avoids the topic signals the opposite.
CEO board management checklist: six strategies to start this quarter
These six CEO board management strategies are the ones we’d put on any CEO’s calendar this quarter.
- Hold a recurring one-on-one with each director. Fifteen minutes every five or six weeks. No deck. Three questions: What are you seeing? What’s worrying you? What would you want to know that I haven’t told you?
- Rewrite the board pre-read so it opens with a two-page CEO letter. Write it yourself.
- Deliver the bad news you’ve been holding. Identify the one item you’ve been saving for the “right moment” and call the board chair this week.
- Bring the activist-appointed director inside. If there’s a settlement director on the board, invite them to the next operating review.
- Ask for the executive session debrief, and share a written self-assessment before the CEO evaluation. Treat both as data.
- If the board chair relationship is strained, book the conversation with the lead independent director before you need it.
The principle underneath all of it
Directors extend trust to a CEO in proportion to how well they believe they understand the business and the person running it. Every strategy above is a way of increasing that understanding.
CEOs who treat the board of directors as an audience to be managed eventually get found out. CEOs who treat the board as a group of smart people to be kept honestly informed get something rarer than approval. They get the benefit of the doubt, and in a year with record shareholder activism, that’s the most valuable thing a board can give a CEO.
Build the board relationship before you need it. Tell the board first. Disagree in the open. And write the letter yourself.
Want help building this kind of board relationship? Skyline G’s executive coaches have worked with CEOs and executive teams at hundreds of companies, from start-ups to the Fortune 500. Schedule a conversation about what we can do for your company.
About the authors
Thuy Sindell, PhD is Co-Founder and President of the Coaching Division at Skyline G (Skyline Group International), where she leads a global network of 120+ executive coaches, facilitators and consultants. An executive coach since 1998, she has personally coached senior executives at Apple, Google, Microsoft, Meta, Netflix, LinkedIn, Charles Schwab and Johnson & Johnson, and is rated the #1 coach at two Magnificent 7 companies. She holds a PhD in Organizational Psychology from Alliant International University, founded two software start-ups (Hit the Ground Running, acquired by Kenexa/IBM, and Knowledge Genie), and is co-author of four books on leadership and career performance, including Hidden Strengths (Berrett-Koehler, 2015). A TEDx speaker, she has been featured in Forbes, Fortune, CNN, NBC, The Washington Post and Psychology Today. LinkedIn · Full bio
Milo Sindell, MS is Co-Founder, Managing Partner and President of the Coaching Scaled Division at Skyline G, where he drives strategic direction, the product roadmap and the ECx coaching platform. He holds an MS in Organization Development from Pepperdine University, was previously a senior consultant at Intel and Sun Microsystems in strategy, change management and leadership development, and co-founded Hit the Ground Running, an employee performance software company acquired by Kenexa (now IBM) in 2010. He is co-author of four books on leadership and employee performance. LinkedIn · Full bio
