My superpower isn’t knowing, it’s exploring.
One of my favourite types of exploration is the interview. It’s a chance to go deep with someone in an area I usually know the surface version of: them and their experiences. It’s also one of my favourite ways to gain new understanding. Which I then get to share back to clients and readers.
I was a creative strategist in the ad world for many years of my career and that’s where I discovered this particular superpower. The official title was Planner and the expectation of the role was knowing. The planner is often the person in the room who is expected to have the answers. To questions of strategy, to questions of business impact, to questions about the creative work itself sometimes. Clients expect it and so too do our agency peers.
I was good at having answers in the moment, at understanding the full context of the work and the client business need. Because it was my job. But I was actually better at saying three words that often gave people in the room pause. “I don’t know.”
The world of advertising is one with a lot of egos. Big talent and also, unfortunately, big egos. The constant push for awards and accolades over client results has left the industry in a state of disrepair as clients find new ways to connect with customers beyond traditional ads. It’s a world that, like so much of modern life, expects certainty and confidence. And knowing. Not knowing for some reason is frowned upon. Yet uncertainty is one of the few guarantees in life. We can hope and we can plan, but we can’t know for sure until we go out into the world experience it and see what comes of our effort.
But I started my career as a journalist, and in that world the expectation is that we don’t know. That’s where we start and the work itself is about seeking understanding. It’s exploration. It’s asking “why?” and “how?” and starting from a place of not knowing. The journalist who goes into a story thinking they know they answers are often the most dangerous and irresponsible. The same is true of planners. I spoke to a class of ad school students and this was the idea I wanted to impress upon them most.
In a world that demands we know and show up certain I want to encourage you to challenge that cultural expectation. In your work and in your life. Instead, I want you to get better at asking questions, because the other part of my bold statement of ignorance was always, “let me find out.” And the way I found out was usually by asking questions. I’ve shared before that I am a professional question asker and have encouraged you to lean into asking questions as well. I thought I’d share with you five tips I picked up over my career that have helped me become a great interviewer and explorer.
I hope these help you feel confident in not knowing and in your ability to find out. So here they are:
Five tips for better interviews and greater understanding.
Leverage the most powerful question in the culture: Why? All the other “w’s” are great, but this is the one that gets to the heart of things. You don’t have to use the exact word, but the point is to follow up answers with a question that allows you to go deeper. “What makes you say that?” is a good one or “help me understand that a bit more.”
Keep it open ended. Ask questions that can’t be answered with just a yes or no. That means literally start your sentences with who, what, where, when, why, or how. Never “is” or “did.” It forces the person to think about and explain things to you.
Stay curious. Yes, you have your questions prepared (I hope—add prepare in advance to your mental list if it’s not on there) but don’t let those questions dictate where the conversation goes, if your subject says something interesting or gets a light in their eye, ask them more about it. Be open to letting the conversation take you to unexpected new places. The person you’re interviewing is the expert on whatever topic, let them lead the way some of the time (with guidance from you of course).
Don’t forget it’s a conversation not an interrogation. Meet people where they are--it’s your job to ensure they feel comfortable. You’ll get better answers if the person you’re speaking to feels at ease, feels seen, and feels as though you care about what they have to say. So make sure they know that. I often start interviews by telling people they’re the experts and I’m there to learn from them.
Always leave room at the end for them to add anything that might not have come up in your questions
*Bonus: Always follow up with WHY?*
There’s nothing wrong with not knowing. In fact, it can be a super power—something that helps you stand out from the crowd of people faking it until they make it. It takes a bit of courage and vulnerability but is often worth it. If you’ve ever been in a situation where you were expected to know the answers but weren’t quite sure what they were, share in the comments and let us know what you did. Do you have any go to questions or approaches for seeking understanding? I’d love to hear those too. In the meantime, stay curious.
A Story Well Told
One of my favourite TV shows right now is Insecure on HBO. Created by Issa Rae who became famous for the amazing and hilarious web series The Mis-Adventures of Awkward Black Girl, Insecure is a lens into the love and life of modern 30-somethings in California. Every episode makes me want to move to L.A. and spend the rest of my days figuring out life and love with a crew of friends while being hilarious and listening to amazing music. One of my favourite characters (they’re all my favourite) is played by Natasha Rothwell. In this interview, Rothwell talks about her own evolution as a storyteller and actor on the show. Check it out and let me know what you think.