The art of getting people to open up
Elan Miller
The difference between a good project & great project lies in how you approach the problem. Whether you’re an operator or consultant, the journey to finding those insights often starts with interviewing key stakeholders to get their perspective before diving in.
Getting stakeholders to truly open up is the equivalent of a detective getting an early confession in their case — it changes the trajectory of the investigation.
If you can go below the surface to understand how stakeholders really feel over getting traditional soundbites you might hear in the press, you’ll not only get valuable signals for where to explore, but you’ll build their confidence in your ability to deliver on the solution.
Tl;dr There’s an art to getting people to open up — especially senior executives.
Here’s my 5-step framework to make it happen:
Set the stage
Warm them up
Open them up
Play therapist
Pass the baton
1. Set the stage
Don’t assume the person you’re interviewing knows why they’re talking to you. Oftentimes things get added to their calendar by an EA or producer, without sufficient context. Explain who you are, what you were brought into do, and share a high-level timeline to bring them up to speed in the first couple of minutes.
2. Warm them up
It’s important to let the person you’re interviewing ease into the conversation. Think of them like an Olympian, and help them warm up before asking them to run the 100M. Good warm up questions might dig into their role or something more project-specific like what success looks like. But whatever you do, don’t go for the jugular too early. Let them ease in before getting to the good stuff.
3. Open them up
At this point in the interview I like to give the person I’m speaking with a more interactive question to get them thinking in new & unexpected ways. It’s important to make your stakeholder extremely comfortable — i.e. “There are no right or wrong answers…let’s just play a game.”
One of my favorite games to play is the headline exercise.
“12 months from now, once we launch this initiative, what’s the dream headline?”
This is a fun way to get them to clarify their future vision & speak to desired impact, without directly asking them.
Some follow-ups:
“In what publication?”
Gets them to elaborate on their audience & where they want to tell their story.
“What metrics do you hope the article would cite in support of your headline?”
Gets them to speak to the metrics that matter & the kind of impact they aspire to make.
“If the journalist were to quote customers in this article regarding this initiative what would you hope they would say?”
Gets them to speak to the value proposition & key benefit.
“If the journalist were to interview the CEO or project lead at your company, what would you hope they would say?”
Gets them to speak to the impact they want to have.
Bottom line: The more fun and imaginative, the more people tend to open up. The more they open up, the more insight you get. And with more insight comes more firepower to solve the problem from a new angle.
Some other fun interactive exercises to run:
Start with why (made famous by Simon Sinek)
The 10 star experience (made famous by Airbnb)
Spectrum exercises (when you need them to pick a side)
4. Play therapist
Once stakeholders are all warmed up and you have them thinking about the problem in new and engaging ways, it’s time to ask the most sensitive question.
While this question will be specific to your project, a few of my favorites are:
“What’s a misconception about your brand that really pisses you off?”
“What do you believe that no one else believes?”
“Why hasn’t the initiative been successful in the past?”
If you ask these questions too early, without getting your stakeholder to open up, it will sink your interview (or land you a dud). Trust me — I’ve learned the hard way!
5. Pass the baton
As you wrap up your interview, it’s important to give your stakeholder the opportunity to raise anything you didn’t talk about.
I often ask…
“Is there anything we didn’t talk about today that you think could be relevant to us as we embark on this journey?”
It’s important to leave at least 5 - 10 minutes for them to answer this question (rather than sneaking it in with 30 seconds left) because it often tends to be the most insightful.
By asking this question, you give them the power to raise any key points or roadblocks they didn’t previously mention. More than half the time, executives save the best for last — opening up about things that are keeping them up at night or important organizational context that are critical to helping you solve the problem effectively. Ask this question and let them welcome you into their world.
Closing thoughts
Stakeholder interviews aren’t just about information gathering — they’re about giving you the ammunition you need to sell through your recommendation. Treat them as an opportunity to build a new relationship, make a good first impression, and give you a distinct advantage as you kickoff a new project.
Don’t just go through the motions — ask the right questions to get your confession.
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