7 Questions To Ask First | npENGAGE

7 Questions To Ask First

By on Oct 31, 2011


A third (33%) of nonprofit executives take over from someone who was fired or forced to resign, according to the 2011 Daring to Lead report, which surveyed 3000 nonprofit executive directors earlier this year.  The easiest way to avoid getting the boot yourself is to avoid taking a leadership job at a dysfunctional organization in the first place.

Ramping in public is hard enough  – meeting & leading the team, taking inventory of a community of supporters, revitalizing relationships that may have wilted  – without finding yourself facing unexpected infrastructure failures. The

Daring to Lead report finds that a full 55% of your peer executives name technology as a “depleting” aspect of their job (it would have been the most depleting of all options surveyed, if not for the joys of HR – like evaluating and hiring/firing staff). As someone interviewing for a top job, how can you detect warning signs of organizational system decay *before* your professional credibility is on the line? It doesn’t have to be a “buyer beware” situation, after all.

You wouldn’t buy a home without insisting on a thorough inspection of things like plumbing and wiring first. The best time to negotiate budget for needed repairs is before you’re holding the keys to a fixer-upper.

It was once my day job to visit worldwide facilities and – within 2-3 days – determine and document whether a given organization had the necessary systems in place to meet their commitments in an ongoing way – no hiccups, no excuses. I was helping pick suppliers for Motorola and Dell, and I got to really live with my decisions, because the winning facilities would be mine to manage for years to come. I knew my brand – both mine personally, and my employer’s – would be blamed for any failures.

So leaning on that background, as well as my more recent decade in nonprofit technology, I offer the following interview questions that an interviewee can ask of a hiring organization, to determine whether a given group is where you should place a career bet.

The Seven Questions

1. Do you have a documented succession plan? Can I see it?

  • This should seem quite natural to ask. You’re in dialogue because succession has become reality. If it wasn’t anticpated, why not? If they can’t/won’t produce a plan, or if the plan doesn’t make sense, ask follow-up questions.
  • 34% of nonprofit executives will depart within 2 years, yet only 17% of organizations have a documented succession plan.  Given group A or B, choose to work for the group that had the tough conversations & planned ahead, or plan to spend a lot of your time teaching staff & board members about long-term sustainability.
  • BONUS POINTS: Should be given to a potential employer that has an automated succession plan – one that can be triggered quickly during a time of upheaval (assigning out critical tasks to key staff & board members, for instance) or an automated onboarding plan (which will ensure that key introductions, reviews, visits and trainings get scheduled in the best order). Modern databases can help organizations take these inevitable situations in stride.

2. Please name the systems in place to accomplish the following tasks, and include main go-to person for that task, indicating whether staff, volunteer, contractor, or outside firm, etc.

  • This inventory – and any deficiency therein – will be your portfolio if you take this job. Note what’s left blank, what has multiple answers, and what’s “unassigned.” Follow-up questions might be
    • Are there plans to train someone on this common function?
    • Are there plans to select a system for that?
    • Common functions:
      • Office functions
      • Telephones & voicemail
      • Computer & printer networking
      • Staff email
      • Staff & resource calendar
      • Accounting & payroll
      • Outcomes management
      • Supporter record keeping
      • Grant fundraising and foundations
      • Volunteers
      • Events & attendees
      • Partner organizations
      • Public officials
      • Corporations
      • Media contacts
      • Website, blog updates and other social media
      • eCommerce, online transactions
      • Mass email communications
  • You do yourself – and your potential employer – a disservice if you don’t ask for this up front. Daring to Lead found that 70+% of your peers find communicating with the public, the board, donors, foundations, and partners to be “energizing”, yet more than half of your peers described the technologies that are supposed to help accomplish those things to be “depleting”. Know up front whether you’ll be traveling light (with a manageable number of systems that work and play well with others, & provide a holistic picture without double-entry, etc.), or whether you’ll be leading a team that’s limping along with 30 piecemeal tools cobbled together (and never in sync). Or know where your potential employer has no track record at all.
  • BONUS POINTS: Should be given to a potential employer that has an automated system back-up plan for irreplaceable data like supporter records and website content. If you ask when the last back-ups were performed, and who triggered them to occur (Was it personality driven? Or process driven?), you’ll get a pretty good idea of whether your own personal investment of time and talent could be derailed in the blink of an eye. Modern systems should provide automated off-site, multiple-redundancy back-ups.

3. What data is provided to the board about fundraising (and on what frequency)?

  • Daring to Lead’s findings indicate that you have a 44% chance of interviewing with an organization whose board can’t come together – as a united front – and say that each board member supports the cause enough to hand over personal funds.  Before you accept a job offer, you deserve to know if the board has your back. If nobody’s even tracking that information, be prepared to be in “start-up” mode, with all the long hours and frequent diving-catch plays this mode entails.
  • If the board isn’t regularly shown their own contribution to fundraising (whether count of prospects identified, tally of thank-you calls made, or a table of each board member with the total sum of “soft credits” they’ve earned year-to-date), then it’s going to be a major culture change for them if you intend to set expectations high (and I hope you will!).
  • Daring to Lead found that many executives doubt they can influence their boards’ performance. This blows my mind. The report’s writers emphasize only 4 calls-to-action at the end of the 2011 report, and “Recognition by executives of their own important role in helping to improve the performance of the board” is a recommended action.
  • BONUS POINTS: Should be given if an organization is fully transparent with their board members regarding fundraising, to the point where board members rightly feel they are part of the team that is sustaining the organization financially. Modern fundraising tools can automatically send dashboards (like the one here) of real-time data to board members’ inboxes. Because you can’t change performance without showing that you’re measuring it.

4. Show me the data that proves that a program activity undertaken within [insert appropriate time period – I’d suggest six weeks] produced a community benefit.

  • You’re probably getting the gist by now, thinking of this as a light “audit” of what the organization knows & documents about its usage of donor funding to produce change.
  • I’d urge you to “drill down” and ask to see the source document that shows a specific outcome, whether it is a legal document showing that a piece of land was conserved, or a stack of surveys indicating that students now know how to report bullying. Then ask to see how the data about this outcome is documented in a systematic way: on which report would this outcome show up?
  • BONUS POINTS: Should be given if the organization can identify 2 new types of information, or new attributes, that have been added to the outcome measurement system within the past year. This means they are actually using the system, and that they know how to adapt to change. Modern systems were designed to be flexible, because providers know that the pace of change isn’t slowing down anytime soon.

5. Where are the records for staff and board professional development trainings on [insert industry-specific topic]? Can I spot-check the attendees at the most recent training on that topic?

  • Take your knowledge of a trend impacting the intended employer’s industry, and find out whether investments are being made (and tracked!) in developing staff to cope with (or extract additional value from!) this trend. Need topic ideas? Just look at the workshop session titles for 1 or 2 recent conferences for organizations like this. Topic examples might be “electronic medical records” or “bullying on social media.“ This isn’t intended to be a gotcha question, and if the topic you pick hasn’t been addressed, let them explain their rationale & suggest a topic that was found to be more pressing. But then *check the date & attendees* for the most recent training on that topic. Lack of training investment tells a story. Missing records tell a story. If half the staff has turned-over since the last time a critical training was offered, that tells a story, too.
  • BONUS POINTS : Should be given if upcoming trainings and topics are already scheduled for individual staff, indicating a true learning organization.  Modern systems should allow teams to assign future tasks, like trip reports and cross-training sessions, to any staff or board member – ensuring you get the most out of every investment in developing your team.

6. Over the past 6 months, highlight the items on the board meeting agendas that were initiated by staff, as opposed to board members. How could you tell who initiated what?

  • Daring to Lead finds that “many executives still struggle to define the return on investment (ROI) of board-related activity.” If there’s not already a culture of the board helping executive staff make strategic decisions, you’ll have to fight that battle. If the board assembles their agendas thoughtfully and deliberately, there should already be a process for gathering input from staff.  You’ll learn a lot about how things really get done at an organization when you see how the sausage is made.
  • BONUS POINTS: Should be given if processes are in place that both document and automate workflows when submission-approvals cycles are required.  Nobody will have to dig through a predecessor’s old email archive if business takes place in systems instead of via post-it notes or carrier pidgeon. Modern systems don’t require a programmer to configure, letting teams define and tweak their own reportable approval processes, keeping everyone aligned and informed.

7. What board candidates have been identified, and what interactions have been logged while cultivating these individual candidates over the past year?

  • The recruitment of good bosses has never been more important than it is now, with time-tested financial models seeming to topple over night, rapid geo-political and technological changes, and the retirement of the nation’s largest-ever generation. “The biggest angst is finding board members,” as an ED states in the Daring to Lead report. With it often taking 18-36 months to secure a sought-after candidate, you cannot afford to start from a blank page.  Scanning a list of potential candidates & familiarizing yourself with how they were identified, what their skillsets are, their giving capacity, and their engagement level will give you an excellent read on the organization’s high-level fitness for the next 12-24 months.
  • BONUS POINTS: Should be given if candidate records have at least a year’s worth of historical data regarding ALL involvement – not just giving & event attendance – and if the next six month’s worth of “what’s next” cultivation tasks are documented & assigned with due dates. Modern systems facilitate automation of the moves you will make while doing the delicate courtship dance of recruitment with in-demand board members. You’ll be ever-so-glad to have some of the next few months’ worth of strategic moves already in the pipeline.

Now go forth and secure a position where you’ll really be able to deliver the impact you’re capable of. If you think any of these questions are inappropriate for a serious executive candidate to ask, I invite you to chime in and explain why you won’t need that information within a few weeks, if not days, into your new gig.

A few notes:

  • This checklist does NOT address immediate financial solvency of the organization. Daring to Lead found 46% of executives reported cash reserves of less than 3 months, so do not neglect to do serious digging on that topic. If you are a CFO, perform financial audits for nonprofits, or you’ve seen a good list of financial questions to ask, *please reply to this post with a link!*
  • I’d never say to ignore your instincts. Just know that *informed* instincts are better predictors of your near-term future.

Yes, daring to lead does at some point require a leap of faith. (“Jump off a cliff with me” is the West Wing quote that comes to mind…) There will always be uncertainty & fear, and, as the Daring to Lead report found, significant loneliness – reported by 70% of executives! – at the top. No organization you join will be a sure thing.

I’m just saying to inspect the safety net for human-sized holes before you take to any given trapeze. Because when you fall – and we all do, whether a critical support link in the chain fails, the roof caves in, or someone greased the bar – we need you to be able to get back on your feet, climb back up, and lead on.  If you find big holes in the net prior to taking a job, be sure you get buy-in – and budget! – to replace or repair the net before you fly too high.


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