The #1 Success Habit: Listening Tours

This is an abbreviated version of the original article that appeared in the First Round Review called “The Habit Behind This Founder’s Fast Financings, Product Development and Book Deal” on September 20 2017. Written by the First Round team.

The night Adam Braun received his final term sheet for MissionU’s Series A investment he put his fundraise on hold. The round for his newly launched college alternative startup was oversubscribed in less than three weeks. Most founders dream of being in this situation, but Braun had more calls to make. Specifically, 23 more he’d place over the next 24 hours. He refused to make a decision until he heard what each carefully-selected person on his list had to say. These conversations are part of what Braun has coined a “listening tour.” These days, he activates one before every critical decision.

Braun embarked on his first listening tour as a recent grad, when he was deciding which first job he’d take out of school. Now, five listening tours later involving 80+ people, the practice has not only launched his career, but also companies. It’s helped him raise $30 million for his non-profit Pencils of Promise, which has built over 400 schools in developing nations, land his book The Promise of a Pencil on the New York Times and Wall Street Journal bestseller lists, and most recently, scale MissionU with partners like Spotify, Warby Parker and Casper.

Some readers may write this off as asking your network for advice. Don’t. These tours are structured processes, ranging from a week to six months, and require specific criteria and techniques to be followed.

In this exclusive interview, Braun breaks down exactly how he organizes his listening tours, including how he identifies who to meet and what to ask them. He walks through how to structure your process to not only make the decision at hand, but also to build lasting relationships with potential hires, partners, advisors and investors.

Why Listening Tours Are Different

First, let’s define it from the get-go:

• Listening tour | [lis–uh ning too r] | (noun): a structured allocation of time to question a carefully selected group of people with the belief that hearing their answers will provide critical clarity on the right decision to make.

As with any definition, it can be as helpful to define what it’s not. “It’s not a passive declaration that you will ask everyone the same one question or that you will set up a meeting with your advisors,” Braun says. “Nor is it like a customer visit, focus groups, a board of directors or corporate coach. There are distinctions from each of these practices.” Here they are:

• Meetings must be 1:1. There must be no risk of groupthink or passive participation. There are questions to work through and you must hear each person’s response to every question in-depth. Ideally every listening tour is in-person, but it’s not necessary. A phone call or video chat will suffice for those who’ve met and interacted with you before.

• It’s about processing, not presenting. A significant part of a leader’s job is to communicate information and channel it to the relevant groups. The beginning, middle and end point of listening tours is not about dispersing information in and of itself. It’s about discovering or sequencing information you hadn’t previously.

• People must welcome your context. You must be vulnerable, but that’s only part of the equation. It’s also what they do with it. Those on your listening tour must have the history, willingness and/or ability to suss out the key points and players in your situation. While he’s reached out cold to people before, most people who’ve been part of Braun’s listening tours are those he’s known personally or were one warm introduction away.

Before a listening tour, you truly don’t know the answer. You’re not begging the question — you’re in service of it.

So what decisions suit a listening tour? Braun uses the following lines of inquiry to determine when one is warranted:

• Is this the single most important decision I’ll make this year? If yes, he continues to the next question.

• Will it also have a transformational impact on my life and the well-being of my organization? If yes to that one, he asks himself the next question.

• Do I know with absolute conviction exactly what the best path forward is? If that answer is no, he makes time to engage in a listening tour.

The Anatomy of a Listening Tour

Startup culture rewards speed as a habit. In many respects, that’s golden advice. But not for listening tours, according to Braun, who’s seen the benefits of this deliberate, methodical practice. “Listening tours unfold, not unleash. You commit to a concrete, time-bound process where the jury is out until you meet with every person,” he says. “One conversation — one question even — can change everything.”

For example, prior to launching MissionU, Braun asked a person on his listening tour whether the program should be accredited or non-accredited. He said to Braun: “If you go the route of accreditation, you’re asking for somebody to out-innovate you.” That single comment dictated the foundation and future of MissionU as a college alternative. And that advice came from the 15th person he talked to on the listening tour.

All to say, listening tours take discipline, and that requires structure. Here’s how to run one:

Nail your timeframe.

Listening tours range from one week to six months, depending on the urgency of the decision and one’s time to organize the tour. On average, they run between one to three months. Of course, each person will have her own business context to consider but, here’s a rule of thumb: the long-term ramifications of a decision should be directly correlated to the length of the listening tour.

There are occasions when a decision needs to be fast-tracked and speed listening tours are necessary, such as when term sheets are about to expire. That’s why Braun delayed closing MissionU’s Series A to conduct an expedited listening tour where he completed 23 calls in 17 hours. “On one of the calls, a founder within an investor’s portfolio shared how even during tough times, the investor stepped up to support the company,” says Braun. “It’s easy to imagine how great an investor can be when things are going well, but it’s not until you talk to people who’ve seen how a fund operates when things aren’t perfect that you gain real value. The conversation convinced me that this investor would have our back through good and bad. It’s not something I would’ve known without a listening tour.”

In this vein, nailing the duration of your listening tour means taking two main factors into account: scope and urgency. Here’s are three questions that Braun asks himself to calibrate the right amount of time — not too short or too long — for his listening tours:

• What’s the deadline by which I need to make a final decision? If there isn’t an external forcing function, set a mental deadline that serves as one.

• Who are the best people in my extended network from which to solicit feedback? Note the “essential” people, those who will bring outsized value and weight in their feedback. Chat with each one before the choice is made.

• How long will it take to connect with them? Consider several options, but it needs to be live (phone, video chat, in-person), not asynchronous (email).

A major component to designing a successful listening tour is setting expectations with the rest of your team or company. “I understand that, to many, this may seem like an unreasonable amount of time to be away from your team. But it’s not a sabbatical — it’s in immediate service to the company,” says Braun. “But that’s why being candid and clear about the tour and its purpose is critical. In my experience, anytime I’ve been leading a company or holding a full-time job, my listening tours are short, concentrated experiences between a day and two weeks — versus, say, two months. Tell your leadership team that you’re embarking on a listening tour that’ll require the majority of your time over the next day, week or weeks. Don’t check your phone or email during those meetings — you must honor that time for them to respect it.”

Source and set your list of people.

A listening tour is not emailing the closest people in your network with a question or asking three investors for their opinion. It is a tightly curated list of people who fulfill certain criteria. For example, the day after incorporating MissionU, Braun brainstormed a list of 12 people. They embodied specific traits that could be summarized as follows: high-integrity individuals who he knows personally, trusts and who are building or have recently been involved in building a company valued at $200M or more. This criteria is meant to be inspirational and aspirational

Next, create a list. It need not be fancy, just comprehensive. Braun writes lists of everyone he knows — from college to his work with the United Nations Special Envoy for Global Education — to ensure he’s casting the widest net possible. Most professional or social platforms allow you to export your network — this can be a good starting point from which to add and remove.

Don’t limit your list to people you’ve known for years, either. The listening tour is a unique opportunity to transform weak ties into strong ones. “You create a family-like dynamic when you tell someone: ‘I’m facing one of the most important decisions of my life and I’d really value your advice,’” Braun says. “Right away, they have to think, ‘Wow, this person really values what I think and we’ve only met once.’ Some of my best relationships have evolved this way, like Adam Grant who I reached out to for advice on how to launch a book and has since become a friend who consistently provides me with thoughtful advice whenever asked.”

Structure and start your outreach.

Once you compile your list, draft and queue up a brief, personal email for each person. It’s less important to provide a ton of context in a long missive — and often counterproductive. “The thing people get wrong asking for someone’s time is they try to justify it with a long email,” says Braun. “Before your start, you create the feeling that whatever you’re asking for is going to be onerous. Include everything you need in three lines or less.” Here’s an example from Braun’s fundraise:

Hi XXX,

A few months ago you suggested that when I was ready to raise capital I should touch base to hear your thoughts on how to best run the process. Considering the team is assembled and we’re going to start the raise in [INSERT MONTH], I’d love to get together to to get your thoughts and guidance.

Feel free to cc an admin if it’s easiest. I’m flexible next Monday, Thursday and Friday. I’ll also send through the deck beforehand.

Thanks!

Adam

There are a few key points to highlight here:

• Prioritize words like advice, insight and guidance. Even if you have a close relationship with this person, you need to demonstrate that you are coming from a vulnerable place and respect their opinion.

• Convey flexibility. “The one thing I always do is request that the conversations are in person if at all possible,” says Braun. “Aside from that, work around people’s schedules and make it clear that you value their time. Show, not tell this, too. If asked for dates and times when you’re free, don’t give fewer than three options if possible.”

• Find neutral ground. While some people may ask to meet at their office, when possible, Braun suggests getting together outside of the work environment to minimize distractions and create an informal feel. To be convenient for them, that may be a coffee shop near their work — or even a nearby park. Choose a place where you’ll be undisturbed.

Once you’ve got your template set, send them. Ideally, on the same day. “Since you’re trying to speak with everyone in the allotted timeframe, sending in a batch gives them — and you — the most time to respond and set a time,” says Braun. “However, if you’re in the early stages of building your network, start with the people you are most confident will meet you. Then, if needed, reference one or two of the conversations you’ve already had to increase the likelihood of others responding.”

Compose your questions — in three tiers.

A set of questions is the engine for any listening tour. Braun breaks his process into three steps:

• Research. Spend significant time reading articles, books and websites to get as smart as you can on the topic on which you’re asking. Listen to podcasts of those who have achieved a successful outcome in the space you’re pursuing and lean on that collective set of information to identify what the key variables and levers to success are.

• Relate. You must cover each question, but not each one is equal. “When I create my list of 12-15 questions, three to four questions separate from the bunch as the most critical. I know this because, if needed, I can often nest three to five other questions underneath them,” says Braun. “When I draft the questions, I’ll star the ones that are the most critical three to four. These, taken together, answer the highest level question to be answered: the one that addresses head-on the obstacle to making a decision. This tiering may evolve as conversations happen, but stack your questions the best you can to prepare.”

• Recite. The physical act of having researched and written down questions gets them ingrained. Adam still takes a list of questions with him to check-off each one during a conversation, but when asked about them years later, his recall is precise. “It’s like learning your lines for a play. The more you take them to memory, the more you can focus around your emotion when asking them — as well as others’ emotion,” says Braun. “It gives you license to pick up signals from the person across from you that you may miss staring at your notebook.”

Active Listening is Disciplined and Structured

Your listening tour is as much about what you ask as how you ask. Over 11 years, Braun has refined the most effective strategies to extract the most out of meetings. Here’s how:

Engineer a student/teacher dynamic.

The secret to a successful listening tour is vulnerability. From your first email, you are admitting that you need guidance to make the right decision. Follow that same thread in your interview. “Your objective is to gain as much knowledge as you can from the person you are with,” says Braun. “Listen with the intent to learn. As soon as you find yourself debating or interjecting, stop. Aside from asking questions, you shouldn’t be speaking very much at all.”

Braun brings a notebook to every meeting with his questions listed so he can check them off and take notes. “It creates an environment that mirrors a college lecture. They’re telling you everything they know about a particular subject and you’re writing it down. It causes them to think very deeply because their observations are being captured and considered,” says Braun. “The mere act of writing in someone’s presence shows acknowledgment and a weight of importance to each word spoken.”

The only path forward is saying you don’t know the path forward. Say it, mean it: “I need your help to get there.”

Watch the clock. Pace your agenda.

To get through each question requires strict time management. Instead of calculating your time per question, consider Braun’s templated agenda to stay on track:

• 5 minutes: Thank the person. Share context that the person doesn’t already have. Emphasize that you’re learning to make a critical decision. Assure them this is one of many meetings, following a structured process to achieve an intended outcome.

• 40 minutes: Move through your question list as deliberately as you can. It’s natural that most meetings will center on a few questions, but guide the conversation forward. Give a heads up before jumping in that you don’t want to interrupt, but will watch pace.

• 15 minutes: Save your three to four most important questions until last. “ It’s common to want to ask your most pressing questions first to guarantee they’re answered, but people need to warm up. And that takes having a better grasp of the context and key variables before delivering a truly thoughtful response.

Take one of Braun’s top three questions for MissionU’s fundraise: Who is the ideal investor for us? “If you ask a question like this at the start of a conversation, you’re going to hear about the best investors on paper. You don’t want the best investors on paper. You want the best investors for you,” he says. “When you ask it at the end, they evaluate your business model and existing relationships first. And so are better positioned to answer the question from the standpoint of: ‘Based on my understanding, here is who I think you should target.’”

Your last question is meant not to trigger the last word, but the first word for future conversations.

Braun’s final question is always: Is there one person you really respect and think I should also be speaking to about this? “Many of the most instrumental people I’ve met for the first time are because of asking this question on listening tours,” says Braun. “Half of the time people will give you an answer and offer to connect you themselves. On my listening tour defining the MissionU product, Jeff Raider [co-founder of Harry’s and Warby Parker] suggested I connect with Joey Zwillinger [co-founder of Allbirds], who has become a great friend and highly endorsed the branding agency Red Antler that we later worked with to build the entire MissionU brand identity. Without Jeff introducing me to Joey, MissionU would look completely different today.”

Because listening tour meetings are so dense, there will be times when you feel as if you have all of the information you need to make a decision. Don’t fall into this trap. Default to completing the tour. Braun takes it a step further and doesn’t think about his decision formally until he has spoken to everyone. “The goal of the tour is to learn as much as you can in an allocated period of time. It is not to make a decision,” he says. “If you spend your meeting deliberating on the decision — even in your own head as the other person speaks — you’ll not only miss formation, but the entire purpose.”

The listening tour is a listening tour — not a deciding tour. Making a choice at the wrong time can eliminate options.

Make your decision only once the tour’s complete.

At the end of the listening tour, Braun dedicates 4-5 hours to review his notes, typically over 1-3 days as his notes from listening tours can be upwards of 50 pages. Most times, after reviewing his notes, he’ll have a sense of where the consensus is on the major decision. “At this stage I recommend two practices: long, solo walks and handwriting your thoughts. Walks help clear the distractions of a nonstop flood of email and social media,” says Braun. “As for handwriting thoughts, I’ll write unstructured journal entries to activate my ‘subconscious listener.’ I find that, when I handwrite a journal entry — specifically with the expectation that no one will ever read it — I tap into the voice of that listener. That’s my gut, my intuition. That’s the voice to follow.”

The outcome of both of these practices is not to suss out the consensus from those on the listening tour — but to find your inner voice while in acknowledgment of that consensus. “Sometimes, you’ll agree with the consensus. Other times, you’ll completely disagree. But it’s not about consensus. That’s a critical tenet of listening tours. Again, it’s not about consensus. It’s about what your gut tells you after you understand where the consensus lies. It’s how the context shifts after you’ve shared it with those you trust.”

Circle back to close the loop.

It’s basic manners to follow-up with those you’ve met — both to thank them and share the outcome of your process. Most will send a mass email or perhaps a customized templated email. Braun will typically leans away from group updates, and toward a more personal quick text. “It’s informational, but not long. Something like: ‘Hey, I just wanted to let you know that this where I landed on the decision. I can’t thank you enough for all of your insights. I hugely appreciate you. If I can ever help you in any way going forward, please just say the word.’ That’s it,” says Braun. “If your intent is to seed and build a long-term relationship, you don’t need to deliver a long report. But more an authentic recognition for their time and support, and an intent to reciprocate.”

Bringing It All Together

There are step-by-step guides for the perfect sales hiring process, replicable blueprints for onboarding and detailed outlines for product prototyping. But when it comes to something as basic as listening to make decisions, people dismiss any concrete regimen. But don’t make that mistake: give the structured, time-bound process of a listening tour a try. First, determine if the decision is worth the investment. Nail your timeframe and prime your team so they can support your pursuit. Source your list of people according to specific criteria and trigger your outreach. Compose your questions in three tiers — and work through each one, for everyone. Circle back in the same way you met: 1:1. Then get distance to process your notes and make the decision solo.

“VCs aim to make decisions that’ll have a high return on their initial investment. I wouldn’t have categorized them together at first, but I’ve come to expect listening tours to perform similarly — I want a high return on that time, both belonging to those on the list and me. That means that how we spend that time should not only serve the decision at hand, but the future decisions we might share with each other,” says Braun. “Over the long term, that starts to manifest as advisors for your company, future board members — and ideally, advocates for your mission and movement. This structured way of investing in decisions leads to many more good choices to make. That’s really what you hope to line up as a founder.”