How to ask the hard questions

Let me introduce myself. I am that person behind you in line at Target who asks your opinion of the shampoo you’re buying (apologies, but I am interested). And the gal shifting a bit closer to your private museum group to ask your guide a question or two (c’mon, doesn’t it deepen your experience?). And the shopper grilling sales associates about business models and the seamlessness of offline and online business (cue nervous smiles, shifty eyes). I am, and have always been, naturally nosy.

Yet despite this healthy dose of chutzpah, early in my career as a group facilitator, a client took me aside, mid-focus group, and told me that I seemed, “afraid to ask the hard questions.” Yikes. Absolutely not. I denied the charge and proceeded to run the rest of the group like a matador in the bullfight of her life. But, later, mulling over his words, I admitted to myself that I was afraid – to probe deeper, to hurt feelings, to disturb comfort zones, to offend.

After many, varied, interview experiences over the years – during which I’ve spoken to people about issues that range from the happily benign (skincare and beverage choice) to the hyper-intimate (vulnerability at work and mortality) – I’ve honed some technique and working principles to help me dive headfirst into prickly situations. Now, we don’t all interview people for a living, but most of us must ask questions, sometimes awkward ones, to improve our proposal, our project, our position. The better we are at asking the hard questions, the more nuanced the answers. So….

Get comfortable with the uncomfortable. Both you and your interviewee might be incredibly open in connecting, and sharing.  You may be thoroughly prepared with your discussion outline and objectives and contingency plans. But, for you to do this right, you will need to tread in awkward territory. To go in with the mindset that you can control discomfort only sets the stage to curb the unpredictable, and thus any serendipity that might ensue. Not worth it.  Don’t spend your time trying to make the conversation feel normal, or right. Rather, spend that energy making it feel real. Way better ROI. A good interview can chisel away at your biases – but you must be ready to be cracked open.

 Show your feelings. Yes, this flies in the face of the social science rule book. But listen, if you are a sentient being, it is a fact that talking about illness, or a patient dying, or someone feeling vulnerable at work, will make you feel. This only reveals that you are human, not a bad interviewer. How you express your feelings while staying on track reveals your skill. I have cried with interviewees, and then apologized afterwards. I have shared their awe at tales of dismissive doctors, and then asked how they would have done it differently. Sure, I have exposed some of my self here, but in these cases, I feel it’s important to reveal my humanity. I feel confident enough in my capabilities that I can maneuver around any of my over-sharing.

Know when to shut up. In my many years of interviewing – across subjects, cultures, and countries – it’s clear that people want to share.  A dynamic conversation doesn’t mean that you, the interviewer, should do the talking. You should listen, and probe at the right moment. And you need to let those moments appear, in their own time. Use silence the way you work a muscle – sometimes you flex, sometimes you let it go. In moments of silence, take a breath and let your interviewee fill it with their stories. A good ramble is a tapestry of thoughts, ruminations, and unvarnished truths. This is what you want.

Then again, don’t be afraid to put words in their mouths. Beware. I am now going to trot out a concept that has been somewhat worn thin: employ empathy. But stay with me, because there is a there there. Don’t just attune to what that person is going through (which is somewhat transporting). I’m asking you to go method with your empathy. Imagine when you have been in a situation like theirs, and sit there for a while, in it, feeling it. Perhaps we’ve not been cancer patients, or hemophiliacs, but we’ve all had moments of joy, vulnerability, despair, and delight. So when you ask how they felt in a particular moment, let them talk first, then suggest another emotional option (e.g., did it feel like XXX, or maybe more like YYY?) Emotions are complicated and fast-moving. People can’t always locate, articulate, or deconstruct them. Many need a verbal springboard against which to react. I know I’ve done my job well when someone I’m talking to says, “no, actually, it’s not like any of your options, it’s more like ZZZ.” Ahh, yes, of course it is.

And when words fail, use imagery. Again, people don’t always know how to shape what they feel. For those times, share a collection of evocative imagery (I use images pulled from magazines) and ask them to choose a picture(s) that represents the experience. Inevitably, a visual will spark a thought out of which you and your respondent can make meaning.

On a micro level, an interview creates an opportunity to understand one’s category or business challenge. On a macro level, an interview opens opportunity to stretch the confines of yourself – your perspectives, comfort zones, and biases. In our increasingly atomized and echo-chambered lives – this is a rare gift. Make the most out of it.