Insights into nonprofit leadership & governance

Five questions every candidate should ask

December 15, 2018  

For the past few months in this space, we have enjoyed sparking discussion of key questions to be addressed in the context of a search for a new CEO. Our first article highlighted “Five questions every search committee should ask—of itself.”1 Our second article covered “Five questions every search committee should ask—of its candidates).”

This month, it’s the candidate’s turn. 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 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.

You’ve also read the other articles in our “FiveQuestions” series. If the organization is aBoardWalk client, the search committee will certainly have asked these and similar questions; if not, your candidacy will still profit from having anticipated the answers.

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

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 theHippocratic 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?

As we have noted in previous writings, 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, 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:

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%? 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. 3 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.

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. 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. 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.

In summary, here are the five questions we believe every candidate should ask:

1. What do you like best about the incumbent?

2. What unfinished business would I inherit?

3. How will we define success?

4. Where are the potholes?

5. How can I add the most value?

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.

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