Two Questions To Ask During Hiring Reference Checks Instead Of “Where Can They Improve?” Be Specific About Situations & Create a Permission Structure for Honesty

I LOVE doing reference checks — on founders we are hoping to support and key hires into their teams. On-sheet (provided by the individual) and back-channel are both valuable in their own ways. Don’t incorrectly write off the ‘candidate supplied references’ thinking that it’s worthless to speak with people who have been prepped or likely to be positive. Sometimes you just need to ask better questions. Here are two that I’ve found to be expecially useful.

businessman on a phone call writing notes on a pad, digital art [DALL-E]
  1. “If a colleague of [name] didn’t want to work with them again, what reasons could you imagine them giving for this decision?”

Rather than just ask generally about “strengths and opportunities” or “when are they at their best vs when do they struggle,” you want to always try and ground the reference in someone’s actual lived experiences. Additionally, creating a permission structure to talk about how *others* have reacted to the candidate gives the reference a chance to provide observations without having to own the opinions themselves.

You can use the answer to this question in two ways. First to identify behaviors and styles that might be situational and to consider whether the hiring org and new role are well-suited given these past experiences. Second, to test self-awareness by asking the candidate this same question and comparing the results. Are they aligned with what their on-sheet reference told you? If not, guide the discussion over to the specific feedback and gauge openness to hearing it, potential defensiveness and so on. In my mind a great reference call will not just assist in the hire/no hire decision, but aid you in making that person successful once they start by getting a sense of where and how they might need coaching.

2. “One of my responsibilities is to help [name] be a great CEO. Where do you think they might need some guidance or support? How do they like to receive feedback?”

Many of the founders we back are first-time CEOs, and some of these folks are stepping into that title as first-time managers. That doesn’t give us pause — we love ambitious people who take the responsibility of leadership seriously. Where they’ll need to develop to be successful — and how their natural instincts/previous work prepared them for this next step — is really valuable context for our relationship with them.

The tendency when probing on this area is to ask a version of “Do you think [name] will be a good CEO and why?” That’s fine, you’re likely to get a list of strengths that this individual has displayed in previous jobs. But again, similar to the example in #1, I believe in a more specific framing: where is this person going to need help and how can we provide this support in a way that’s effective for them? Armed with this information we’re going to be in this founder’s corner from Day One, trying to build trust, keeping an eye open for their blind spots, and getting them feedback in the manner they appreciate (the whole ‘effective communication is not about speaking but about being heard’).

Framing the question in this positive way also establishes advocacy and a growth mindset, not judgment and fixed notion of what the CEO may, or may not, be capable of. And it’s consistent with Homebrew’s mission/brand promise.