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Five Questions Every Candidate Should Ask


Adapted from smorgasBoard

If you find yourself in front of a search committee, what are the key questions you want to be sure to raise?

Our suggested questions assume that you have done your homework. You have scoured the nonprofit's Web site, 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.

You've also read the other articles in our "Five Questions Every Search Committee Should Ask—Of Itself" and "Five Questions Every Search Committee Should Ask of Its Candidates." Your candidacy will profit from having anticipated the answers.

There are several questions, however, that should be of special interest to candidates. Here are our top five.

The Five Questions Every Candidate Should Ask

  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. 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.

    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. 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.

    Typically, we ask 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. 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.

    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!

    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. We recommend taking the discussion in steps, moving from the strategic to the tactical:

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

    If you listen well, questions on the definition of success will help accomplish several things:

    • First, they reinforce the importance of strategic alignment; that is, the alignment of the nonprofit's resources and leadership around the big goals.
    • Second, these questions reinforce your expectation of working in full partnership with the board.
    • 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, 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. There are at least two sorts of issues you want to know about: structural and cultural.

    Structural issues tend to respond to "What if?" sorts of questions: What if this donor goes away, what if this program exceeds 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?"

    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. (A Navy captain of our acquaintance used to say, "When the sailors stop complaining, I start worrying.") 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 break room 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.

  5. How can I add the most value? The organization you are interviewing with is already on a certain trajectory. This trend line is based on specific assumptions regarding direction and momentum, all of which are critical for you to understand. 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.

    Consequently, this question, like many of the others, deserves to be asked in stages. As a candidate, you first want to know what added value the board desires most from its next CEO. Second, 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. 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.


Sam Pettway, Kathy Bremer, Kim Anderson, and Margaret Reiser
© 2008, BoardWalk Consulting

Sam Pettway, Kathy Bremer, Kim Anderson, and Margaret Reiser are colleagues at BoardWalk Consulting, committed to "building strong foundations for nonprofits"® through executive search, board enrichment, and strategic facilitation.

Five Questions Every Search Committee Should Ask of Its Candidates


Adapted from smorgasBoard

Last month, we offered five questions every search committee should ask of itself, an exercise we recommend every search committee undertake at the very outset of any major executive search. This month, we focus on the more traditional issue of questions addressed to candidates.

A quick scan of the Internet yields literally millions of Web sites promoting suggested interview questions; we've seen lists as long as 800 "must" questions to ask. During our discussions with candidates over the years, however, we have found there are just a handful of questions that really matter.

All of us know of people who were hired for their competence only to be fired for their chemistry. In fact, very few senior executives fail because they cannot do the job; rather, they fail because they cannot do the job  here. Context is key—which is why we emphasize it in our questioning. The point is not "What makes you such a good leader?" but rather "What makes you such a good leader for us?"

The Five Questions Every Search Committee Should Ask of Its Candidates

  1. Why are you here?

    It is absolutely fair to ask candidates what brings them to the interview, what compels their interest, why  this opportunity and not that one has sparked their imagination. In so doing, you will learn a bit about motivation, shared values, and preparation, and you will establish (or reinforce) both the premise and the promise of the discussions you are about to have.

    A question as simple as "Why are you here?" will contribute to your understanding of a candidate's self-awareness, self-confidence, and inquisitiveness. Not coincidentally, it will also provide real-time evidence of a candidate's ability to address big issues succinctly.

  2. How will you make us proud(er)?

    When Shirley Franklin ran for Mayor of Atlanta in 2001, she captured her city's heart with a compelling slogan: "You make me Mayor, and I'll make you proud."

    To be sure, Atlanta had hit a low point in city governance before the 2001 elections—Mayor Franklin's predecessor is now in federal prison—but the concept has broad applicability to most CEO searches.

    This question does several things. It allows candidates to relate their strengths to the needs and goals they project on the organization, it promotes a discussion of core values, and it forces a focus on the longer-term issues of legacy, both the candidate's and the organization's.

    Equally important, this question can prompt a discussion of process—the ways in which your prospective CEO will deliver the reputation, the relationships, and the performance you seek.

  3. What will surprise us most about your leadership here?

    As we remind clients all the time, there are no perfect candidates. (Corollary: There are no perfect positions, either!) That is, every candidate under consideration represents some trade-off against an ideal.

    The trick is to understand the risks inherent in the trade-offs represented by a specific candidate. In our experience, the best candidates have a genuine appreciation for the risks at hand, and they are just as interested as you are in finding ways to mitigate those risks.

    The "surprises" question speaks to strengths and weaknesses, but it turns the conversation a slightly different way. You offer the candidate a way to bring up matters not addressed elsewhere in the conversation, and you encourage the candidate to personalize the response (rote answers won't work here).

    The insights gleaned can be both comforting and challenging. Inevitably, you will learn something that makes each candidate distinctive.

  4. What questions do you have?

    We are firmly convinced that you can learn every bit as much from candidates' questions as you will from their answers. Usually, candidates will weave their questions into the fabric of the discussion, but we still suggest you create a specific opening for questions about halfway through.

    Candidates who respond with probing, thoughtful, nuanced questions are likely to exhibit these same qualities in their leadership; candidates whose questions are dull, rote, irrelevant, or untimely may exhibit similar characteristics on the job. Through their questions, we have found, candidates demonstrate how they prepare, how they listen, and what they hold dear in subtle ways. We have seen interviews (and candidacies!) end prematurely because of the lack of good questions, and we have seen interest soar in response to prospects whose questions were especially provocative or illuminating.

    Don't wait until the end of the interview to invite a candidate's questions. Not only might you miss the opportunity to speak to issues important to your prospect but you will also miss the opportunity to phrase subsequent questions in ways that build on a candidate's concerns. Remember, you are recruiting a senior executive, not just screening applicants.

  5. What makes you interesting?

    When you hire a CEO, you get the whole person. An interesting, stimulating CEO with broad appeal and a balanced life will make a fundamentally more captivating colleague for you and the organization than will candidates for whom work is their sole outlet.

    In a recent set of interviews, the CEO search committee for an association we were working with stumbled onto the fact that the candidate they were speaking with had flown in the night before and spent the evening at a baseball game. Baseball and coaching, it turns out, were among this candidate's core passions outside of his work.

    The ensuing discussion about hobbies and diversions said volumes about the way in which the candidate made his leadership manifest. Time is every leader's scarcest commodity; pay attention to how your candidates use it. (P.S. The baseball-loving candidate started as CEO on August 1.)

Finding Out What Makes a Candidate Interesting

We don't favor questions that are convoluted, cute, or contrived. ("If you were an animal/a color/a car, which one would you be?") Rather, we like straightforward inquiries, such as:

  • "What do you do for fun?"
  • "How did you spend your last three Saturdays?"
  • "What magazines do you read?"
All of these are variations on a more fundamental question that you probably won't ask but likely is on everyone's mind: "Will we enjoy our time with you?"

Five Questions Every Search Committee Should Ask- Of Itself

Adapted from smorgasBoard

Since the founding of BoardWalk Consulting almost six years ago, we have had the privilege of working with literally hundreds of search committee members as clients grapple with their organizations' issues of leadership succession. From this fascinating mix of missions, personalities, recruitment challenges, and interview styles, we've developed two sets of key questions common to successful searches: