“What’s a Win for You?”

7 minutes, 3 links

Holloway Editione1.1.1

Updated September 14, 2022
Stop Asking Questions

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Timothy Sykes was at it again.

Looking at him through my webcam, I could see the winning smile of a man who expected to get the better of any conversation.

I asked him about his work ethic, and he managed to turn it into a pitch. “I have a DVD called Penny Stocking where I teach people … And not surprisingly, my real-time stock trade alert service is fifty times more popular than this DVD that would actually teach them to do it on their own.”

I asked him how he started blogging. “Wall Street Warriors,” he said. “It’s a hit TV show now in fourteen countries, so I was in that show, in five to six episodes of season one.” Then he artfully mentioned his book, telling me, “People were emailing me what they wanted to know. So I wrote a book called An American Hedge Fund.”

Honestly, I was in awe of how skilled he was at pushing his products, but I couldn’t spend 60 minutes like that. I interviewed Tim because he quickly turned a blog into a $45K-per-month revenue machine, which he then used to fund a collection of finance software and marketplace sites. Mixergy had become both a passion and a content business, so I wanted to learn how he got people to his site and how he monetized his content.

My audience wanted to learn too. That’s why they listened. Not to hear him plug his products.

After Tim’s interview, I leaned back in my chair and tried to figure out how to stop situations like this. They happened often. And most interviewees weren’t even as deft at self-promotion as Tim, leading to even more awkward interviews. Most were like jackhammers, hoping that determined repetition would help them break through. Heavy-handed promotion would ruin my podcast the way it ruined many other podcasts.

I wasn’t mad. As an entrepreneur myself, I understood. When you run a company, you have big responsibilities. If you don’t sell, you don’t eat. And if you have a team, their families don’t eat either.

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That’s when I realized something. They were pushing their goals out of desperation. To tell them “don’t pitch” would be like saying “don’t eat.” What if I could assure them they’d get what they needed? If they knew their goals would be met, couldn’t they chill out and enjoy being interviewed?

I tried something new while preparing for an interview. Before recording, I asked my guest, “What’s a win for you?” That did it. Asking someone about their goals reassured them that I cared about their needs and that I’d work with them to reach those goals.

A typical example of this happened when I talked with Adam Jackson, who founded multiple companies, including MarketSquare, the local shopping site he sold to Intuit. When we connected, he had a serious look on his face and seemed to be distracted. I asked him, “What’s a win for you?” He looked taken aback by the question. He smiled. Then he said, “You know, I feel like it already is a win because you asked that.”

Adam told me he wanted to talk about how he disagreed with the way funding works in Silicon Valley. That was unexpected. He raised $23M for his latest startup, Braintrust, the talent marketplace. I came into the conversation thinking he was a typical Valley fundraiser, but he wanted to argue against the system that I assumed he mastered. He also said he likes to get “outside the box a little bit,” meaning he wanted a loosely structured conversation. Another blow to my plan, which was to take him through a hero’s journey outline, a technique you’ll learn about in the sections on interview structures.

No problem. I quickly scribbled notes about what he said at the top of my interview doc. After I introduced him, I set him up to verbally punch the fundraising process and talk about the problems he had raising money. It was illuminating to see how much trouble he had because his business plan had a unique twist: he gave financial upside to participants of his marketplace. Once we talked about that, he was more than happy to give me what I was after—the chronological story of how he built and sold multiple companies.

If I hadn’t asked about his needs, he might have gone along with my approach, but there would have been an underlying tension in the conversation that I couldn’t have understood.

Most guests don’t have a clear answer to “what’s a win for you?” Sometimes their marketing team has recommended they do the interview. Sometimes they just accept the interview request because they like me. They don’t have a goal or agenda. That’s fine too. When I ask the question, even if they don’t have a specific answer, they know I care about them and they trust that I have their interest in mind, even as I pursue my own interview goals.

Now I start most of my calls with some version of “what’s a win for you?” Variations on that question include:

  • What’s your #1 goal for this interview?

  • What would make your team happy to hear us talk about?

  • Why did you agree to do this interview?

  • How can I make this interview as useful for you as it will be for me and my listeners?

Try it. You’ll see that if you show interest in your interviewee’s goals, they’ll help you hit your own goals.

Listen: “What’s a Win for You?”

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Join the Resistance6 minutes, 2 links

Get Guarded People to Open Up

I wasn’t being a jerk when I pushed Jason Fried to tell me about his failures. I acknowledged and admired how he bootstrapped Basecamp into a project management tool that was bringing in millions of dollars a year in profits.

Still, I wanted to hear about his failures. I learn a lot about growing a business by understanding how people overcome failures. But if I’m honest, I was also hoping to see that he was like me: a human being with failures I could relate to.

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