Nonprofit Interview Red Flags and Where to Find Them


Published by on June 9, 2024

It was my third week in a new job. Normally that‘s the “honeymoon period” and already I was thinking about divorce. A few awkward things had made me tilt my head on the first day but I told myself: you’re new here, you need to settle in and get the lay of the land. (I had recently left a disaster of a situation and was feeling raw about nonprofit life.)

In that third week, sitting in a staff meeting, one of my colleagues announced she was leaving. It wasn’t a huge shock—I knew this already—but she was the third person to quit since I arrived. Immediately after, in the same meeting, another colleague raised his hand, stood up, and choking back tears announced he also was leaving. The entire room went silent.

Like a scene from The Office, I pictured myself looking into an imaginary camera and saying, “What have I done…”

The car ride home that night was filled with many internal monologues. I consider myself a good judge of character and situations, but clearly I had missed some glaring red flags. How? Were they there and I didn’t see them? Did I ask the wrong questions? Did the CEO simply sell me a bill of goods?

I thought back to my interviews and realized the signs were there all along. And if you’re in the process of interviewing maybe you can learn from my mistakes.

It’s time in time with your time*

You’ve probably heard some version of the adage: being on time costs you nothing. The further I go in my career the more value I place on the importance of being timely. Some of the worst professional experiences I’ve had involved issues with time—and keeping to it—and the organization mentioned above was no exception.

Planning my initial interviews took rounds of going back-and-forth because things kept getting scheduled and then canceled. I shouldn’t have been surprised when this issue continued after I was hired. My boss missed or was late for more than half our standing meetings.

If you notice wonkiness with time and schedules from the outset, you should be moderately concerned. Of course, emergencies happen, but there’s a chasm between legitimate reasons and poor excuses.


A bit more on the issue of time


In the experience above, the window between my job application and receiving an offer went unusually fast—that is, once the interviews finally got scheduled and done.

In our sector this process is typically overly cumbersome… and glacial. When it happened so rapidly I saw it as a positive sign. In hindsight that was a mistake. Career expert Madeleine Burry has a perfect explanation of why we should be skeptical of on-the-spot job offers, saying, “Unless the company is very small, it’s odd for there not to be some sort of internal conversation that takes place before a job offer.”

If you ask your prospective future nonprofit employer about their timeline, listen for specifics. “We will hold three rounds of interviews, and depending on the candidates, we expect to have someone in place within six weeks.” Responses like that are thoughtful and precise. On the other hand, “When we find the right person” is pure hope, and you can’t run an organization on hope.

What is the rate of change?


At a 100-person organization, four people leaving in one month may not be a major issue. But the nonprofit above was fairly small—four departures was a quarter of its staff.

Some might find it inappropriate to ask about the rate of transitions during an interview but I think it’s perfectly logical. If organizations can ask us about our past, by way of checking references, we can ask them to air some of their laundry. Ask about the specific role for which you’re applying. Is this a new position? If not, what happened to the person who held it previously? Inquire also about the team you’d be joining. Ask about the size, dynamics, average tenure, and what others say about roles (or the organization) when they depart.

I believe the responses to these questions—or lack thereof—can be insightful. If they don’t settle right with you, your gut might be telling you something.

Read the room and read it deeply

Much like in dating, there’s a lot to glean from “getting to know you” conversations like interviews. You’ll try to pay attention to the subtleties of body language and what people say… and what they don’t say. When you’re sitting across the table (or on Zoom) really trust what you’re interpreting in those interactions.

In my situation, the CEO fully owned the discussion and only prescribed the questions their employees were allowed to ask me. I misread that as confidence when in reality, it was pure dominance—and this spilled into the work once I was hired.

In the same way, I failed to read the room and notice the other employees’ expressions. Employee retention-ist Debbie Cohen cautions, if an exhausted, non-optimistic team is part of the interviews, those feelings may spill over onto the candidate, which can be a big problem during the recruitment process.


Experience is a quirky thing. It often teaches us what not to do, but we don’t always listen. Hopefully my mistakes can be a teachable opportunity for those of you on the job hunt.

Other than sleeping, you’ll spend more hours of your life working than any other activity. Deciding where you spend those hours is no small decision. Before you dive into that next professional adventure make sure you’re doing it thoughtfully with both feet planted firmly in reality.

Job hunting can be a pain in the ass. The less you have to do it, the better.

* Fantastic song by the fantastic band, Yes


Evan Wildstein is a Hiver and nonprofiteer with twenty years of experience in fundraising, strategy, and operations.
In addition to his work in social impact, Wildstein has coached organizations on board development and talent growth, commissioned operas, and produced learning initiatives. He is the author of recently released book, The Nonprofiteer’s Fundraising Field Guide: 30 Practical Ways to Boost Philanthropy Through Servant-Leadership.

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