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Michael Sippey has been shipping software since that meant literally shipping software. “We used to have a field in our CRM to indicate whether the customer needed 5¼-inch floppies or 3½-inch floppies,” he says. It was the early 90s — and the process and structure of product management was still being invented, often on the job. Sippey was an English Lit major in his first job ever at financial services software maker Advent, when he was plucked from the marketing team and given a chance to shape a product.

So he had to get scrappy fast. With help from some excellent mentors, he learned perhaps the most important lesson of product management: You have to do the groundwork yourself. A lot of things have changed since then — Sippey is now a leader in the field, most recently VP of Product for Twitter, and the internet has reimagined software development — but some things remain the same. If you want valuable, actionable product input, there’s no substitute for sitting down with your customers and prospects to truly understand their problems.

At First Round’s recent CEO Summit, Sippey shared the one most important rule and three steps for gathering powerful customer feedback that can make all the difference for your product roadmap. Reminding everyone that they can’t build great things in a vacuum, he recalled a time from early in his career when meeting with customers kept him from barreling down a very wrong path. These lessons he learned over a decade ago are still immediately relevant to founders and product leaders today.

The No. 1 most important rule: You must speak to your customers every day.

At Advent, Sippey lucked into great bosses who saw his potential and wanted to develop it. First, they trained him on the key habits they saw in successful leaders. “The most vital one that they taught me was this: Talk to at least one customer a day. My boss was adamant about this,” says Sippey.

And talk to customers he did. He got on the phone at least once a day to connect with people who were using the products he managed, and sat in on support calls for a couple of hours each week. He went out on a few sales calls a month, too, to learn how customers were thinking about and using the products.

Before long, a common refrain emerged from these conversations. In brief, customers needed a software solution for transaction reconciliation. And Sippey had an idea for a product that would fit the bill. “I was gung ho, super excited. We were going to make it really, really easy for people to do stuff,” he says. “So I started to write, because I thought that the job of a product manager was to write a market requirements document (or MRD). I ended up with a huge document describing every single function and feature that the product should include.”

Armed with an MRD of impressive thud weight, he met with his boss. “She leafed through it, and just said, ‘All right, you need to go talk to Frank.’”

The Frank in question was Frank Robinson, an Advent board member and pioneer in what he dubbed “market validation,” now more commonly known as customer development. Frank gave Sippey the advice that would transform how he thought about product management. “He said, ‘Okay, stop. Rewind. Tell me about the problem you’re solving.’”

Sippey did, explaining all the calls and customer interactions he’d been having. “Frank said, ‘That’s pretty good, but you don’t really know what problem you’re solving yet. You don’t really understand the customer at all.’” The framework for being a good product manager was there — the customer engagement was strong and necessary — he just happened to be asking the wrong questions and not making the most of his time with people.

So Frank set about teaching Sippey how to validate the market for his product idea. What emerged are the three key lessons that have since guided him through great success at Six Apart, Say Media and Twitter — and that every startup should put into practice today.

Lesson One: Set up at least 30 meetings, or you won’t have a good product.

“This directive has stuck with me for 22 years now,” says Sippey.

Get customers on the phone and line up 30 meetings with the point people you will be selling to at each company. Talk to them about their problem and describe what you’re potentially building to solve it. Do this before you write a single line of code.

Back to the Advent anecdote: Sippey had already been on the phone with many of his customers, of course, so he knew who to call. And after about three weeks, he had his 30 meetings set up — then it was time to build some slides. “Basically, I’ve used the same deck ever since,” he says.

It’s a simple formula that works for leading nearly any customer feedback session:

5 Minutes: Introductions.

30 Minutes: We think you have this problem.

10 Minutes: Here’s how we’re thinking of solving the problem.

10 Minutes: Feedback and next steps.

As you’re asking each company how they solve the problem in question, don’t hesitate to drill down into specifics. You might even ask if you can bring in the people who actually do the work where the problem exists (designers, engineers, salespeople, etc.), and see what their process looks like when they’re doing it. You’re there to learn as much as you can about the reality of the company in the day-to-day.

When it’s time to ask for feedback on this interaction, Sippey recommends keeping it simple. Don’t ask for a grade on your presentation or some nebulous rating. One of his favorite tricks is to frame your question in baseball terms:

Did you hit a home run or a base hit?

“That lets people be creative. One time, we had someone say, ‘Well it was a single, but the pitcher is really slow with his throw to first so you could probably steal second.’”

This is also the time to ask customers whether they’d be willing to beta test for you. And don’t be afraid to ask how much they’d ultimately be willing to pay for the solution you proposed — just be ready to ride out an uncomfortable silence. “It’s essentially a game of chicken. But eventually someone will say, ‘Well, we’ve got two full-time employees doing this thing that sort of solves the problem and they cost this much. We probably don’t want to do it on a license basis, we probably want to do it on a monthly basis.’ Then you can start to unpack how they feel about cost.”

The last question Sippey always asks is one of his favorites: “If you had $100 for our development budget how would you spend it? There’s always someone who thinks, ‘Wait a minute, this product only costs $100 to make?’ No. You’re asking them to imagine a pie totaling $100. How would they allocate those development resources for your team?”

This can be another powerful way to open the floodgates and get customers’ honest reactions — even if those reactions aren’t what you want to hear. “We had one customer say, ‘Well, I’d spend about $10 of your budget on this product that we talked about and $90 of your budget fixing the bugs in your existing product.’ Hearing something like that is always fun,” Sippey says.

When it comes to soliciting constructive criticism, you need to be receptive to things you didn’t expect to hear — that’s usually where success lies.

Sippey recalls another market validation experience, this time for a new digital jukebox product he worked on for a while following Advent. “The idea was that we were going to sell it to bar owners directly. They were going to be able to make more money from their jukeboxes, and it would be easier for them because they wouldn’t have to buy CDs,” he says. “We went and talked to bar owners, and told them, ‘Hey, we have this amazing product. Do we have a problem to solve here?’ And they were like, ‘Nope.’”

Turns out that while those bar owners liked the idea, they weren’t the buyers the team should have been speaking to. Jukeboxes are generally owned and operated by third-party distributors. That product still went to market — just with the benefit of knowing who the actual buyer was. “We learned that we were completely wrong in the initial assumption about who our target customer was," says Sippey. "We were only able to do that because we got in the van and talked to people.”

Lesson Two: Get in the van.

In the age of Google Hangouts, this is probably a metaphor for you today. For Sippey, it was once quite literal. “We really did rent a passenger van,” he says, again recalling his rookie tenure at Advent. Because as Frank was quick to explain, you can’t build an innovative solution on your own. “He told me, ‘You’ve got to have your lead engineer, your lead QA person, your lead support person, and the sales person with you at all of these meetings.’”

We’re going to get in the van, and we’re going to go do this.

There’s enormous value to getting all the key players face-to-face with customers and hearing them describe the problem you’re about to tackle. “You really want the whole team to understand the three fundamental questions around building products: What problems are we solving? Who are we solving them for? How are we going to measure success?” Sippey says.

Equally important — whether literally or metaphorically — is getting that same team back in the van when the meeting is over. “Score each meeting right away,” Sippey says. Some important points that you’ll want to record while they’re fresh in your mind include:

The key thing is that we did this as a team. You get much better at your pitch after the first five meetings. After the first 10, you start to see patterns. After 20, you really understand segmentation of the market. After 30, you have a really good understanding of what it is that you actually need to go build.

Incidentally, that transaction-reconciliation solution Sippey was developing for Advent? 20 years later, it’s still one of the company’s core products.

But if you don’t have a whole gang of department heads to carpool with, that doesn’t mean you can skip this step. Sippey is working on a new product right now; the team is currently just him and a co-founder. Still, as soon as he ends a Hangout session (his van is virtual now, too), he spends time processing the takeaways. “I transcribe everything. And whether my co-founder is on the call or not, I always debrief with him: This is what we learned. These are the things that customers care about,” he says.

Lesson Three: Focus on their problem, not selling your solution.

At the end of the day, the things that customers care about should be your guiding all of your requirements. After all, your success will depend on addressing their needs — not developing the slickest interface or most buzzworthy concept. Take another look at Sippey’s formula for the meeting slide deck. He spends more than half the time discussing the problem, and only 10 minutes on his proposed solution. This is very purposeful.

Sippey admits that things don’t always go according to plan. “When I look back on my career, I’ve made a lot of mistakes in product planning and development. A lot of them,” he says. “The common thread, though, is that we spent too much time thinking about features, and not enough time thinking about the problems that we’re trying to solve.”

We are in love with our solutions. We’re in love with our products. But that’s missing the point.

“The point is that we’re supposed to be solving a problem for people, and understanding that problem on a really fundamental level,” says Sippey. “Only then can you create a product that actually resonates with the market, and a business that can scale beyond any one feature.”

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