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Listen to Your Customers, They’ll Guide What You Should Build

10 min read

At Tailwind we listen to our members and then we use their feedback to build our Pinterest and Instagram scheduling and analytics productsYesterday I was talking to a friend who is considering applying for a job here at Tailwind.  He asked me why I took the job of Director of Marketing and Growth back in July, and among the many things I told him was this….

Nearly every day somebody from Tailwind’s product development team talks at considerable length with one of our members, all of these conversations get written up, shared with the whole team on Slack (our instant messaging system), and they help us decide what features to build.  Around the office we call these “cust dev calls”, short for customer development calls, and they’re constant.

Why fight over what you think customers want?

My friend was impressed.  At his last job decisions about what features to build were considered too important to be made by anybody but the CEO, based on his considerable knowledge of the market.  In fact that was one of my friend’s biggest frustrations working there – that his ideas were never taken very seriously because his CEO always knew better than he did.  Or he thought he knew better.  The product my friend built there hasn’t found success yet.

Of course there are a group of people who know what your customers want even better than you or your well-informed CEO do, and those people are your customers.  So why not cut out the middleman, ask them what their biggest frustrations are, see what ideas they have to solve them; think carefully about the best product you could build to overcome those frustrations, and then build what it is your customers really want.

That’s what we try to do at Tailwind every day, and the effect that one discipline has had on our product over the years, on how our customers feel about us, and on our culture is flat-out remarkable.

A listening culture

Stephen Siu, User Experience Analyst

I remember the first customer development call that I sat in on with our User Experience Analyst, Stephen Siu.  I was taken aback by how little he talked and how intently he listened, by how nearly everything he said was a sincere question, a clarifying question, or a repeat question asked in a different way to probe deeper.

I was as just as impressed by what Stephen didn’t do in that call as by what he did do.  He never once got defensive, tried to justify a decision we’d made, or change a customer’s mind about something – no mean feat since we make a special effort to talk to users who leave Tailwind.  Nor did he judge them for what they said.  If they didn’t understand something in the tool, it was simply an opportunity for us to clarify it.

I was also impressed by the team’s response to Stephen’s copious notes: other developers, other teams, and the founders all weighed in to discuss the details.  EVERYONE was listening to our members just as intently as he was.

“None of us at Tailwind are professional bloggers or run businesses or agencies like our members do,” Stephen told me when I asked him why cust dev calls are so important, “Yet they depend on our product every day to build their business online.  Ultimately, we are working for our members so understanding their mindset goes a long way to informing both the big-picture and everyday decisions we make.”

For Tailwind customer development calls are a safe space (almost a sacred one) where people can tell us the truth about how we’re doing and where we could do better.  This kind of feedback can be hard to hear, and you definitely have to check your ego at the door, but if you can do that then customer development calls can be an incredibly useful tool in helping any business to improve their product, whatever that product may be.

What does it take to run a successful cust dev call?

Stephen suggests the following:

  • Before you setup the call, know exactly who you want to talk to and what you want to know
  • Assume you know nothing about why or how someone does something
  • Listen more than you talk
  • Ask the same open ended question 3 different ways; you’d be surprised how much new information comes out
  • Empathize and be genuinely interested in what they have to say

There are books you can read for a more thorough take on customer development and other fascinating startup tools.  “The Four Steps to the Epiphany” by Steve Blank (Step 1 is Customer Development), and The Entrepreneurs Guide to Customer Development come highly recommended by our co-founder and head of product, Alex Topiler.

Inclusion that extends all the way out to our members

Danny Maloney Tailwind
Tailwind CEO and Co-Founder, Danny Maloney

Tailwind’s founders Danny Maloney and Alex Topiler actually met at a Lean Startup meetup.  So it’s no accident that as a company we’re so committed to listening to our members.  Since the beginning our founders have espoused the principle of “validated learning” on which the Lean Startup movement is based.  In short – always be testing your hypotheses.  That means both listening to what customers say and watching how they behave and where they spend their money.

One of Tailwind’s cultural values is Inclusion.  In one of our cultural documents Danny says of Inclusion, “We are friends. We have each others’ back. We build things that empower the many. We believe everyone should be welcomed, regardless of what they look like, where they come from, who they love or what they believe.”

That inclusion extends to Tailwind members.  In cust dev calls our members are treated more like collaborators than customers: their opinion is valid and valued no matter what it is; we’re all working together to make the Tailwind product as good as it can be.

And it feels great.  I got our Product and Software Engineer Frankie Nwafili tell me about his experience with cust dev calls and learned that in one exceptional case we received a feature request from a member, built it, and told them it was live all in the same day!

Solving the big frustrations

Alex Topiler Tailwind
Alex Topiler, Co-Founder and Head of Product

At its core, customer development is more than just listening to your customers wishes and building what they think we should build. When it comes down to it, what we really strive for the conversations to reveal, and what we’re trying to understand more deeply than anything else is: what are the biggest problems and frustrations our members are dealing with on a day-to-day basis? Why are these things frustrating? Why do they put themselves through these frustration? And what would it enable them to do if those problems didn’t exist?

As our other co-founder put it, “If people are willing to go to great lengths for something, it must be important.  And the real key is understanding what they’re actually chasing after. Often times, the most pronounced frustrations and most time-consuming tasks are the biggest opportunities to create products that actually make the biggest difference in people’s lives. When someone is willing to put themselves through so much pain to achieve something, think about how important that payoff is for them! Imagine having a 2-hour commute to work each day through horrible traffic. Now imagine someone offering you an 8-minute helicopter ride instead. That’s the kind of opportunities and results we’re on the lookout for in every conversation.”

How customers feel when you really understand them

The feel-goods aren’t just reserved for our engineers.  Being listened to does wonderful things to our customers too.  I hear it time and again from them – that they told us how our product could be better, we listened, we made the change, and then, more often than not, they say the “love” word.  Which we can’t get enough of hearing!

Here’s how Tailwind member Tracy van Overbeek from put it:

Tracy Van Overbeek and the This Grandma is Fun Team
Tailwind Member, Tracy Van Overbeek and the team

“One of the things I struggled with was I wanted to see just Pins from one person in my Tailwind Communities feed and it was hard to do that, there wasn’t a way. And that was a change that you put in. I loved that.  It speaks volumes about a company who values its customers and our opinions. It creates a real feeling of loyalty with me. The fact that you guys do that is outstanding.

Over the past six months, she’s seen all three of the requests that she made to improve Tailwind Communities get implemented.  (In case you’re wondering she asked for: filtering for Pins from one Tailwind Community Member, not showing Pins in a Community that she’s already Pinned, and bringing back share counts for Community Admins).

“I’ve noticed sometimes you haven’t been able to make the changes, but communicated back and forth, you’ve explained why and the benefit of doing it vs. not doing it so that I get it, I understand. A lot of times I’ll hear – its not something we can do now. I’ve actually seen items like that that you did get to later though. It showed up down the road. You didn’t just listen and then forget about it. I think that’s rare. That’s a big plus to being a Tailwind customer.”

The birth of Tailwind’s Marketing Customer Development Calls

And where did I pull that last quote from?  From the notes of a marketing cust dev call of course!  I’ve been so impressed with the process that I’ve started conducting cust dev calls myself.  I talk to our members about how we’re doing with our marketing, what conferences we should attend and what content they’d like to see us make for our blog and social media.

What to Pin in December in the run up to Christmas and Thanksgiving based on the most popular Pins from Tailwind members published last December across the 11 most popular Pinterest categoriesWe got the idea for our successful “What to Pin When” series of blog posts and Facebook Lives from a marketing customer development call.   Here’s the note I made during that call with Cerys Parker from  I’d asked her what content she’d like to see Tailwind produce:

“What you should be Pinning if you niche is whatever, travel say.  What topics are coming up, what is popular, what sizes of Pin are popular, what keywords etc.”

It was a request that was echoed by Kim Vij in a later call.  She said:

“Every once in a while Pinterest talks about what’s popular on Pinterest at the moment. Do more of that because they don’t do it enough of it.”

In that spirit I’d love to hear from you in the comments about what content and marketing of ours you like, what you don’t like, and what you’d like us to blog about in the future.

Tacos and Kudos

At Tailwind we like to thank teammates as publicly as possible when they do something awesome.

I thought it might give you a fun peak into what it’s like to work at Tailwind if I shared some chatter from our “kudos” Slack channel.  I’d just gotten off the phone with Tracy Van Overbeek (see her comments above) and I wanted to let our developers know how amazing I think they are by showering them in tacos (rewards anyone on the team can give out which can be redeemed for lunch dates with colleagues.  You can only give out five a day, so I ran out before I could give one to every developer).

Warning – I do swear at the start of this – sorry!  I wasn’t thinking the world would see it…

slack taco kudos channel chatter 1

And then later I clarified a little:

slack taco kudos channel chatter

Yup – I know.  They’re a fun bunch.  Tacos and pineapples flying all over the place.

Join the debate

Comment below, or check out some of the great discussion this blog generated on HackerNews

Join the Tailwind Team

If you’re interested in joining the Tailwind team in New York City, Oklahoma City, or remote, check out our open positions now.


David is Tailwind’s Director of Marketing and Growth. He is a former journalist who wrote for The Times and The Financial Times, a marketing agency co-founder, founder of Confluence digital marketing conference, father of two, and early morning writer. He grew up on The Isle of Wight in England and lives in Oklahoma City.

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  1. Avatar
    Dan Lovejoy

    Poor @willus and his taco disability. 🙁

    Such a great post, David. One thing I would add, and I’m sure Stephen understands better than I, is that you can’t JUST listen. When you’re doing generative research, sometimes you also have to watch your customers’ behavior to really understand the task. Sometimes customers don’t understand what they need. They ask for a feature that they think they want, but that solution won’t really solve the actual problem. I’ve seen this over and over again when we “gather requirements” once and go away to try to build something.

    Maybe, though, this does not apply in the case of Tailwind’s apps. It could be that the use cases are so well-defined and the contexts are so deeply understood that deep listening and interviews are sufficient. I would bet, though, that if you really went in a new direction, you’d need to do some observation.

    Kudos to you all for listening and making your customers’ lives better!

    • Avatar

      Thanks Dan,

      Don’t worry too much about Will. He gets plenty of Tacos.

      So glad you read this. Great thoughts. Listening is the right place to start, I suppose. We do also watch what members do here at Tailwind – in fact a great follow up post could be something on how to clean through the data you gather and make sensible decisions based on it. A big part of that (that I observe here, at least) seems to be really thinking about the feedback you get, and watching how your customers actually behave, as well as what they say they’re going to do.

      An example from our marketing team is the “What to Pin When” posts we put out. People said they wanted it, but will they actually consistently take time out of their lives to consume it? If the engagement goes down rather than up we’ll have to reconsider the wisdom of the series.

      Where it gets really messy it seems are those big intuitive advances that nobody could have told you they wanted, but that are much loved. How do you generate those reliably?

      • Avatar
        Dan Lovejoy

        With regard to your final question – I believe that a lot of that breakthrough insight comes from engagement with the customer.

        First, table stakes – of course – you’ve got to have really GREAT people doing the research and product work. They have to be open-minded and thoughtful, not defensive, inquisitive, caring — all the things you described in your post.

        But I would argue that they have to get out in the field and shadow the customer. Watch them work. Ride in the car with them. Follow them to the printer. Ask questions along the way. Really understand the job, the context, the players, the motivations, the goals, and the workflow. (And there are probably a million other ways to categorize these – this is not a canonical list.)

        When I was working on electric vehicles, there were multiple times I ran across EVs parked in prime EV parking spots, not plugged in. This never would have occurred to me unless I had seen it with my own eyes. I would never have asked an EV owner this question. Did this lead to some great breakthrough? No, but it helped me understand how EV owners behave.

        The other part that I think you’ve got down cold is just trying stuff. Just throw it out and learn from it. Because when they put their cursor or their finger on it, they’ll tell you what is or isn’t working. (When you can get past, “I like this,” or “I don’t like that,” which is where so many of these conversations end in other companies.)

        Thanks for the discussion. Good stuff.

  2. Avatar
    Adrian G

    I think that’s an awesome strategy. I had a Cust Dev Call a while back with Stephen and Francis and you’re right, they are great listeners. They were really enthusiastic about the feedback and suggestions I was giving them and they asked a lot of great follow-up questions. Not many companies really listen to their users.

    • Avatar
      David Christopher

      I’m glad you got to experience that Adrian, and that you feel the same way about it that I do. I’m sure your feedback was helpful!

  3. Avatar

    Speaking of what the customer wants…I’ve found it time consuming to see a pin I like, click on tailwind, pick all the boards I want it to go to, set an interval and the types of slots I want it to go in, click to post to facebook or twitter (which still isn’t working for me yet) then click on schedule…or more future steps if I schedule later. It’s faster just to “pin” straight to the boards I want. I know the key feature of tailwind is posting at optimal time slots, but I’m not feeling like I’m saving any time when I’m using tailwind. Is there a way to have a custom “default” setting so I can get pins scheduled with 1 click? Is there an ITTT that automatically sends my new posts to tailwind? Thanks for anything you can help me with!

    • Avatar

      Hi Wendy,

      It sounds like board lists might help with your process. You can learn about them here.

      You may also find it slightly faster to add all the pins to drafts, use add board to all, then choose the intervals but don’t hit schedule yet. Once all drafts are ready then click the schedule all button at the bottom of drafts page.

      As an official Pinterest partner we’re committed to adhering to Pinterest’s Terms of Service. When it comes to more automated scheduling we’re careful not to do anything that might get our member’s accounts flagged or penalized in any way, but we’re always looking for new ways to save time whilst keeping accounts safe, so thank you for your ideas.

      We really appreciate the feedback and I’ve passed it on to the appropriate folks here at Tailwind to see what can be done.

      The quickest way to get some help with the facebook and twitter click to post would be by emailing – help at tailwindapp dot com with your issue.

      Also I’m not aware of any ITTT integrations with Tailwind, unfortunately, but that’s a great idea!

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