3 Interview Questions I Wish We'd Retire or Rewrite Already

Hiring is a two-way street. Period. This is not up for debate if it's done well. The best interviews feel like conversations, not pop quizzes. And with that in mind, there are 3 questions I passionately believe need to be sanitized from any future efforts to find your next great employee. You ready? Here we go.

"What’s your 5-year plan? or Where do you hope to be in 5 years?”

Oh, I’m so glad you asked. Because obviously, the answer is you, dear potential employer. This job. This team. Forever and always... right? Except, well, how would I know yet? The most honest answer is something like: “I’d love to grow here—if the culture, leadership, and mission feel aligned once I’m in the driver’s seat.” But wow, has that ever landed awkwardly in the past when I was bold enough to be truly honest during an interview. Something employers purport to crave, but only if it matches their unspoken, unknown anticipations.

Maybe it’s time we stop pretending this question uncovers real insight. Asking folks to pledge a certain portion of pre-allegiance feels less like you want to know me better and more like I need to love you on our first date. And worse, if their honesty doesn't match your goals of retention and longevity, who would we blame for that? Its just unrealistic and classically unfair.

Honestly, the best thing you could do it talk about your employee engagement, supplemental trainings, retention efforts, benefits, and how often folks at your organization are promoted and/or rewarded for their work AND THEN ask "So, do you feel like this is a place you might want to be at for 5 years? Does our efforts and culture of retention and promotion feel like a place you could really plant your professional flag? What really sticks out to you concerning your own professional goals?"

“What kind of work culture do you thrive in?”

Respectfully: no. Much like the prior question in question, you tell me about your culture—what it’s really like to work there, not just what’s on the About page—and then I’ll let you know if that sounds like a match or my reaction to that environment. Otherwise, it’s like asking me to name my dream dinner when maybe all you’ve got is a decades-old frozen lasagna in the fridge.

Because often this question seems to be a kind of unintended pass/fail test. Oh, did my expressed needs not match your workplace culture? Bully for you to quickly rule me out, I guess, but bummer for me to even have needs that seem unreal, unrealistic, or something you're unable to meet.

Want to fix this one? Give me context, not a trick question. Like the 5-year question, give me something specific and tangible to respond to about your real or intended culture, instead of asking me to be functionally philosophical in front of a real case study, like I don't know... your very organization, for example? The one I applied to. The very one that is interviewing me this very moment for a real job in a real setting with real people and actual culture to highlight.

“How do you handle complex situations?”

Complex how? Like, an underperforming teammate? Or someone stealing credit for your work? Or… experiencing systemic inequity baked into an organization's leadership, specifically prohibiting me from success? Because, as you might now realize, the answer varies dramatically based on me, my experiences, an organization's situation, environment, and their culture. But look, it's not lost on me why you're asking.

So, better yet: tell me about a real challenge you’ve faced at your organization or as a team, and then ask me about how I’d show up or react in that moment. Maybe I'd blend in really well around here, or maybe I'd bring something fresh and new to the table. Oh hell, maybe I'd do the very same thing the people before me did that you disliked. But at least you'd know. And honestly, in the theoretical landscape of an interview, maybe you'd realize the options are not as dynamic as you'd once thought before now that it's a discussion point vs. a real-world situation.

And either way, you won't really know if we're not discussing real-world examples based on what's been experienced or can be anticipated at your organization. And you won't truly get a real feel -- in what is ultimately a litmus-based environment in the first place -- if you're not grounding your questions in reality, instead of the explicitly prior-experienced or theoretical. You are a real organization. I am a real person. This interview should be grounded in that reality, not just a strange place to pontificate theory or regurgitate my resume.

Well, ok. That's it. This is the post. These are terrible questions with well-intended goals. And thankfully, there are so many other, better, more effective questions to consider. But unless you're going to re-frame them to match a real reality? Let's please lower these into the ground and say goodbye, tearful or otherwise.

Ben

PS: I'm a recent search expert and long-time nonprofit leader in the midst of his own active job search. What I'm trying to express is that I'm the professionally poignant kind of active participant in this process and have lots of opinions. And sure, while it's not relevant to this article, yes, I do love alliteration.