5 Questions Candidates Should Ask During the Search Process

Congratulations. You are a finalist for what looks like a terrific CEO role. Do your homework before your interview with the search committee. Then, make sure you have these insightful questions at the ready, says Sam Pettway of BoardWalk Consulting. 

May 16, 2019 – There has been much discussion about the key questions to be addressed a search for a new CEO, but what about from the candidates’ side and the questions they should ask during the executive search process. “If you find yourself in front of a search committee, what are the key questions you want to be sure to raise?” asks Sam Pettway, founding director of BoardWalk Consulting, in a recent report.

“Our suggested questions assume that you have done your homework,” he said. “You have scoured the non-profit’s website, you have digested the 990, you have read a solid sample of their published materials (annual reports, solicitation letters, program reviews and the like). You know the backgrounds, bios and interconnections of the search committee members, and you’ve studied key stakeholders, constituencies and competitors.”

Thus prepared, there are several matters that should be of special interest to candidates. Mr. Pettway offered BoardWalk Consulting’s top five questions:

1. What do you like best about the incumbent?

This first question may feel like a softball, but it offers a nonthreatening way for you to steer the conversation into what might be delicate territory. “There are several reasons to ask about your potential predecessor,” Mr. Pettway said. “You will learn a good deal about the culture and values the organization holds dear. You will develop a picture of the deficiencies or gaps the board hopes to correct with its next CEO. You may begin to sense how comfortably the board moves from conflict to consensus.”

“Even a CEO whose performance has been disappointing will have admirable qualities and key supporters, and our experience suggests that search committees welcome the opportunity to say nice things about someone they may have just nudged out or even fired,” he said. “If the CEO you would be succeeding is highly regarded or leaving after a long tenure of treasured service, you will get an earful about things you will not want to mess up. Here, candidates would do well to follow that part of the Hippocratic Oath usually paraphrased as ‘First, do no harm.’”

2. What unfinished business would I inherit?

Even the most beloved CEOs don’t get everything right. “After all, the reason balance sheets balance is that every asset has an offsetting liability.” Mr. Pettway said. “In a wide-ranging discussion, search committees inevitably drop lots of subtle clues about priorities left unaddressed, issues unresolved and goals unachieved. Your goal is to make sure you don’t mistake subtlety for unimportance.”


Sam Pettway is the founding director of BoardWalk Consulting, a firm committed to Finding leaders that matter for missions that matter. Over his career in executive search, he has worked with hundreds of board members and leadership teams with entities ranging from start-ups to mature multinationals in both the corporate and nonprofit sectors. Since founding BoardWalk in 2002, he has served clients as varied as international relief agencies, national foundations, regional trade associations and local agencies in dozens of markets.


Typically, Mr. Pettway said, BoardWalk Consulting asks a similar question of incumbent CEOs at the outset of a search for their successor. “The best and most self-aware of the lot are quite secure talking about their unfinished business, and the incumbent CEO’s viewpoint can be enormously useful,” he said. “Even so, the board’s perspective is the one you want to be sure to capture at this stage, since that’s who you will be working for.”

3. How will we define success?

“It is critical for you and the search committee (and, ultimately, the full board) to have as much clarity as possible around expectations,” said Mr. Pettway. “If you and your new board have not set out expectations with some degree of specificity, then you cannot be held accountable for missing those expectations, right? Wrong,” he said. “In our view, shortfall in performance is rarely about competence and often about expectations. The trick is to convert expectations from a hidden agenda to an open agenda.” Mr. Pettway suggested taking the discussion in steps, moving from the strategic to the tactical:

  • What do we need to have accomplished together five years from now?
  • What three or four things do we need to achieve, resolve or demonstrate by this time next year?
  • What needs to be addressed right away?

If you listen well, Mr. Pettway said, questions on the definition of success will serve several purposes:

  • First, they reinforce the importance of strategic alignment; that is, the alignment of the non-profit’s resources and leadership around the big goals.
  • Second, these questions reinforce your expectation of working in full partnershipwith the board.

Related: 10 Ways Business Leaders Can Improve Their Appeal to Candidates

  • Third, despite a few requests to the contrary, you really cannot address every priority all the time (although juggling is a much-appreciated skill). Ideally, priorities flow from the strategic plan. Priority-setting is a key responsibility of the CEO, but it’s far easier to set priorities if you’re working in tandem with the board.

4. Where are the potholes?

Both you and the organization will be charting new maps and setting new directions, said Mr. Pettway, even if everyone swears your principal challenge is to maintain the strength and momentum that greet you upon arrival (rarely the real case, incidentally). “To be maximally effective, you want to arm yourself with as much knowledge as possible about the hurdles and potholes you might face,” he said.

At least two sorts of issues are critical to know about: structural and cultural, said Mr. Pettway.


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Structural issues tend to respond to “What if?” sorts of questions: What if this donor goes away? What if this program exceeds the goal? What if these assumptions are off by 20 percent? The structural potholes can be somewhat arcane, as in “Which footnote to the financial statements concerns you the most?”

Related: How to Increase the Odds of a Successful Hire

The cultural issues tend to be about people, heritage and legacy. Every organization has its operating norms and protocols. You want to know which issues/styles/approaches everyone takes for granted—especially if the existing norms and protocols represent barriers to progress.

Even if change is exactly what the board is after, the body can still reject the transplant. If you hear some version of “That’s not the way we do things here,” you may be simply stirring things up in a healthy way. If you hear it more than once or from more than one quarter, you may be at risk. According to an Army friend of ours, “If you’re a step ahead of the troops, you’re a leader. If you’re a mile ahead, you’re a martyr!”

There are several ways to get at these cultural norms: What issues have other senior hires stumbled up against? What gets applauded in the hallways? What’s being talked about in the breakroom and in the parking lot? “The more you understand these topics and the culture that promotes them, the sooner you will develop a map that your new colleagues can embrace,” said Mr. Pettway.

5. How can I add the most value?

The organization you are interviewing with is already on a certain trajectory. “This trendline is based on specific assumptions regarding direction and momentum, all of which are critical for you to understand,” Mr. Pettway said. “Even more critical, we suggest, is the need to understand how the exceptional candidate—hopefully, that’s you—can add real value beyond that available from the merely well qualified.”

Related: Recruiters Beware: Treat Candidates Better or Risk Steering Them Away as Future Employees and Customers

“Consequently, this question, like many of the others, deserves to be asked in stages,” Mr. Pettway said. “As a candidate, you first want to know what added value the board desires most from its next CEO. Secondly, as you develop a deeper understanding of the organization, its opportunities and its challenges, you want to confirm for the search committee—and for yourself—that the special assets you offer are in fact of real value in this particular circumstance.”

Every encounter you have with the search committee and its fellow board members helps set a precedent for the way you will deal with each other once you’re the CEO. “The value of questions from a candidate can be exceptional, and they provide an excellent way for a superior contender to stand out from a slate,” Mr. Pettway said. “If you complement these thought-starters with your own research, life experience and natural curiosity, you can be assured of a provocative, informative and rewarding discussion—and a subsequent interview.”

Contributed by Scott A. Scanlon, Editor-in-Chief; Dale M. Zupsansky, Managing Editor; Stephen Sawicki, Managing Editor; and Andrew W. Mitchell, Managing Editor – Hunt Scanlon Media

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