You can’t handle the truth!

Steve Blank, Eric Reis and many others encourage founders to “get out of the building” and talk to users, prospects, and customers. Most of us do that at the beginning of the startup journey – but how do you keep it up in month eight or year five? If you’re at a big company, how often are you talking to your key constituencies?

We launched our first product a few months ago targeting business travelers who work for small and medium-sized companies and book their own flights and hotel rooms.

A few weeks ago, I realized that it had been three months since I’d spoken to a customer. I felt like an idiot.

So, I cleared my calendar and setup a few dozen calls to get back to the founding principles of our business, remind myself of the challenges, and see how we’re doing at actually solving them. My interviews with our customers typically run 20-30 minutes and while I always benefit there are plenty of cringe-worthy moments.

I always start by asking each customer about themselves and their needs, not about us and our performance. It’s helpful to learn where your customers are coming from. It also puts customers in a comfort zone to talk about themselves a bit first. After all, that’s what they’re experts on.

Our customers have a surprisingly wide range of reasons for traveling for business. There are about as many rationales and circumstances for flying to London or Cleveland as there are industries and markets. And, nearly every traveler views buying travel through a different lens, and has different priorities. One common thread I hear over and over: no business traveler is happy with the way they buy business travel (let alone the travel itself!)

When I get to the heart of a customer interview, I try to focus on asking open ended questions.

Why’d you try Upside in the first place? How’d you hear about us? What resonated for you? Why did you buy from us? Would anything prevent you from buying again?

I’m always prepared to get an earful. Some answers make me feel all warm and fuzzy. Other responses scare the crap out of me. But it’s all valuable.

The second major lesson I learned from talking to our customers: business travelers are sharply divided over how much they care about specific issues like saving their company money versus racking up loyalty points for themselves. (The two goals don’t always go together.)

Sure, every business traveler wants great value and they generally hate to overpay. But different customers define value in different ways. One more reason why we have to be thoughtful about how we explain our proposition.

Customers I’m speaking to make it clear that they want to believe that a new company can offer them awesome benefits. But they have been burned so many times -- especially on business travel -- that they suffer from an understandable skepticism about a new company that promises big improvements.

We know we have to work even harder to earn our customers’ trust, especially when we’re making that crucial first impression with an advertisement or a marketing offer.

One more invaluable lesson we’re learning from our customers: pay attention to the “dog that didn’t bark in the night.” Obviously, if you talk to people who buy your product (especially repeat buyers), you’re mostly going to hear good reviews...even outstanding reviews.

But what about all those people who didn’t buy? The silent, unreachable, potential customers? The fish that got away? Sometimes you can learn more from them, than from your biggest fans.

One way we route around that is by asking customers a few questions about what they say to others.

Did you tell someone else about our product? If so, how did you explain it to them? What was their reaction?

It may be second-hand information, but it beats a loud silence.

We know we’ve got a giant market in the business travel space and customers with real pain points, but after a bunch of customer interviews I know we’ve got work to do. . . but am confident we’ll get there.

In order to keep the learning going (and in an attempt to avoid making the same mistake twice) I've setup a recurring block on my calendar to conduct 15 to 20 interviews every few weeks. What's your strategy for keeping up with your customers and market?

If you’d like to check out Upside for yourself, InMail me on LinkedIn and I’ll hook you up with a promo code for your next trip. And if you do try our product, I’d love to talk to you about your experience.

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