The Best Questions No One Asks Their Board Members

Excerpted from Chapter of 11 of the CEO Next Door by Elena Botelho & Kim Powell 

CEOs in their first two years feel especially vulnerable and eager to prove themselves. As a result, they often take a “report out” posture with the board: dutifully reporting results, summarizing actions completed and milestones met, and pedantically following up on board members’ suggestions. The very same CEOs who can effortlessly charm a customer and have built enviable relationships with their previous bosses seem to lose their mojo when dealing with the all-powerful board. Recall the lessons from Chapter 3, “Engage for Impact,” and Chapter 8, “Close the Deal.” They can be simply summarized as: “If you want to win people over, first understand who they are and what they care about.” Sounds simple enough? Yet it is too often forgotten in the anxiety-ridden first two years at the top.

Kim was recently called to Chicago to coach a CEO of a $75 million private equity–backed retailer whose lead director’s frustration was moving toward detonation. When she arrived, the CEO’s attitude was combative. As he saw it, he was hamstrung by a board of finance types who had no respect for the level of experimentation needed to achieve the desired growth. Kim listened to him for an hour while asking some basic questions about his plans for the business, his expectations for organic growth, and the like. He finished with an exasperated request: “Just tell me what to do to get this board off my back!”

So Kim asked a new question: “Have you ever tried to put yourself in the lead director’s head? Do you know how his broader portfolio is doing and how this business fits in?”

No, he admitted.

“Then let me tell you about your lead director. He’s young, just like you. This is one of his very first big investments. He’s proving himself, just like you. He has to work hard to get his investors to trust him with their capital. That’s how he invests in companies like yours. His partners want to see him driving this company and you to results. They want to know you’re not making haphazard bets. Numbers are his one and only opportunity to show that. Meanwhile, in an hour of talking about the business with me, you haven’t used a single number. You want him to be comfortable with risky moves? Then talk to him in a way that shows you appreciate where he’s coming from. You’ve got to speak spreadsheet to him, or you’re never going to earn the trust you need to be bold.”

Succeeding with your board (or with anyone else, for that matter) starts with understanding how their performance is measured and motivated. With that grounding, you also need to go beyond the numbers. Get to know your board members one-on-one and understand their context and their pressures, dreams, and fears. So often in problematic CEO-board relationships, the fundamental problem is a lack of shared context. Here you are, playing the highest-stakes game of your career, with a roomful of people you barely know. They feel the exact same way about you. You need them to trust you. Trust is built on alignment of interest, credibility, and familiarity. Underinvest in any of these three ingredients and the breaches in the relationship are sure to show up at a time when you need board support the most.

Susan Cameron, the former CEO and current board chair of Reynolds American Inc. (RAI), led the tobacco giant with a board of accomplished leaders—former House Speaker John Boehner, former Univar CEO John Zillmer, and Jerome Abelman, the general counsel for British American Tobacco, which during Susan’s tenure owned 42 percent of RAI, to name a few heavyweights. Susan describes having had supportive, productive relationships with them all, but not by accident: She invested in a one-on-one relationship with each member. Aside from regular conversations, she visited each of them in person every other year.

“I made an explicit gesture to go to them,” she says. “Doing it on their turf, they’re more comfortable,” she says. “It shows you value them.” From Susan’s point of view, every new CEO needs to set aside time to communicate directly with her board members as individuals, “so they get to know you and they understand your priorities and character. If nothing else, reaching out and discussing things with them will give them a level of comfort, and they will support you.” In other words, adding familiarity to the relationship can cement support, which could be the difference between whether they back or balk at your next strategic initiative.

Think of these meetings as your chance, at last, to interview them, albeit in a comfortable context that demonstrates respect. Your goal is to build a relationship and to establish the foundation for alignment and trust with the board. Here are some of the questions to ask your board members one-on-one within six months of your hiring:

What excites you the most about being on this board? With these questions, you’re looking for clues to their primary motivations: Relevance? Status? Stimulation? Compensation? Most board members genuinely want to add value, but understanding why can help you engage them more deeply.

How did you get connected with this board? The answer may lend insight about whether they’re likely to have an independent point of view or be beholden to a founder or investor.

Whom on the board do you talk with most often? This seemingly innocent question is a giant tell, often answering a key question: Who’s influencing whom? This question will help you understand the behind-the-scenes coalitions so that you can manage them and bring back-channel conversations into the light.

Where have you focused your time and efforts in the past? This question will help you understand the person’s competencies and also shed light on how (and how well) the board has functioned prior to your arrival.

Where and how would you like to engage in the future? This is an opportunity to proactively engage board members on issues where they feel they can add value. It will ease their doubts about how to participate and be useful and also give you a clearer picture of how much of their time and attention you’re likely to get.

What does success look like, for the company and for me as CEO, in one year? In three years? This is the start of many conversations you’ll have around expectations and strategy.

Invest in these relationships appropriately, and you should never have an iota of doubt about where you stand with your board. Regular one-on-ones are your chance to “connect the dots,” as Susan Cameron puts it, and make sure everyone’s belted in and along for the ride.

Note from Bob:  You can purchase “The CEO Next Door” today by clicking “HERE.”


Kim Rosenkoetter Powell and Elena Lytkina Botelho


Kim Powell is a Principal at ghSMART. She serves private equity and corporate clients in the areas of management assessment, leadership coaching and organizational change initiatives and advises their boards, executives, and investors on their most important leadership challenges.  Elena Botelho has been a Partner at ghSMART since 2007. She supports major corporate  and alternative investment clients globally, including Pfizer, Vanguard, AT&T, IBM, CHOP, Carlyle Group, Centerbridge, Berkshire, and many others.


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