Hey You, Product Manager?—?Shut Up and Listen

I landed my first Product Manager job over a decade ago by making the transition from Software Engineering. Only one startup was bold enough to even interview such an unproven quantity. I remember prepping the week before, pulling my best fake-it-till-you-make-it moves and superficially researching PM skills online so I wouldn’t come across like a complete fool during the interview. A decade ago, everything online stressed the importance of “communication skills”. A decade later, everything still does.

This makes sense because Product Managers must in fact have great “communication skills” to succeed. But that’s obvious enough to be the equivalent of “Don’t Be A Crook” and broad enough to be not very actionable. After watching many PMs work over the years, not to mention the hundreds of interviews Square conducts every year, I realized that the better way to help PMs communicate well was to decompose this broad topic into its underlying building blocks.

More importantly, I also realized that the most overlooked of these building blocks is also one of the most foundational — Listening. “Communication skills” are frequently misunderstood as “articulate in group settings” — how many terrible LinkedIn profile photos have you seen of a PM type dude holding a microphone in front of an audience? But that’s nearly as superficial as focusing on Kim Kardashian’s fame while forgetting about her history of charitable good works. Oh wait, scratch that analogy. But you get the idea.

Why?

A lot of the PM job, much like the people manager job, is about synthesizing diverse strands of information from customers, engineers, designers, sales and support. It is about then using that understanding to form hypotheses and convictions. Finally, it is about evangelizing these to internal stakeholders, sometimes in the face of passive inertia or even active resistance. So the ball is set rolling by listening well to synthesize — as Stephen Covey says, “Seek First to Understand”. It is impossible to be elite without.

More specifically, a PM must be able to:

• quickly get to the core of what the other person is saying when collecting information while also adapting to their communication quirks. Ramblers, slow talkers, super taciturn, shy, overly verbose, fast talkers, interrupters, overly joyous and total wet blankets — ya gotta handle it all
• know when to peel the layers of the onion to go deep and when to switch gears to go broad
• turn that mushy mess of “stuff” from different people into hypotheses and convictions
• repeat the exercise all over again when getting buy-in because Engineers are not mushrooms (feed ’em shit and keep ’em in the dark — get it?) and will correctly push back the minute they sense bullshit being shoveled in their direction.

This is much harder than it sounds. And here is the more insidious part — the people that struggle with this become victims of misinterpretation in both directions. People that give them information feel not heard or cut off and may in the future even hesitate to engage, and their own decision-making and judgment can suffer since their convictions and hypotheses are sometimes built on a rickety foundation.

It is possible to improve at this. But it is hard as hell. I’ve been trying for years and I still struggle often. Anyone who says they have this nailed is either on their way to becoming President (apparently Slick Willie was quite the great listener) or, well, they’re lying to themselves.

Over years of trial and error, I developed a few practices to listen better. I first labeled these “best practices” but that would make a mockery of how hard it is to be “the best” at listening. So I renamed them suck-less practices. Here are my five suck-less practices:

Do The Prep: Honest Abe Lincoln spent four hours sharpening the axe and only two cutting the tree. Our #WeakSauce arms will do neither, but at least we can prep to listen better. To the annoyance of people around me, I love asking for prep docs ahead of meetings so I can prepare ahead. Here’s why — if everyone has the same information when they walk in, everyone keeps up. It’s terrible being in a meeting where you don’t understand half of what’s being said — that “I’ve been here for 2 years but this meeting reminds me of my first week” feeling. It’s impossible to listen deeply when that happens — prep is the only way we have a shot. Personally, I like batch-prepping for all meetings the night before with a focused 15–30 minutes to scan all background material and to jot down my questions and comments. I confess I’ll blow a day from time to time and feel 5% worse about myself the next day. 15 minutes the night before to feel 5% better?! No-brainer trade.

Pocket your damn phone: Seriously. Pocket your phone. The biggest obstacle to listening is distractions. As The WSJ said in an excellent piece about listening:

“Even before the age of digital distractions, people could remember only about 10% of what was said in a face-to-face conversation after a brief distraction, according to a 1987 study that remains a key gauge of conversational recall”.

10%! I am horrified at how often I’ve glanced at my phone for some mindless notification. Like a drug addict unable to control themselves until the (dopamine) hit is delivered, the phone runs roughshod over all rationality. I know you know the feeling. Since most people are terrible at multitasking, it’s mostly impossible to listen well while multitasking. I’d rather be five mins late to a meeting so I can “manage the addiction” and then give them a solid 25 instead of a semi-distracted 30. Controlling the phone — because let’s face it, most of the time the damn thing controls me — is really key.

Ask good followup questions: The room at Square was filled with 40 people and the goal was for the CEO and his team to get detailed input on where things were going well in the company, where improvements were needed, what next year’s corporate strategy should be. Any such large meeting with a broad and complex topic has very high lunatics-overrunning-the-asylum potential. And yet, my boss applied the 5 Whys framework as the starting point for the conversation and made it orderly and productive. She also made a fan out of me. As Wikipedia suggests, the “primary goal of the technique is to determine the root cause of a defect or problem by repeating the question “Why?”. Each answer forms the basis of the next question”. Personally, I like using the informal equivalent in 1:1s or even groups. Over years of doing 1:1s, I found that the first statement on a topic of discussion is frequently the outermost Russian doll. Asking good followup questions helps unpack the situation — certainly the multiple Whys but also “I don’t understand X, explain more”, “Is that an assumption or is that provable with data?”, “Why not?”, “How?”. It’s usually the third or fourth followup that yields the most insightful nugget. Not knowing how to ask good questions compromises listening by feeding incomplete or even inaccurate information. Dig. Probe. Follow up.

Provide in-flight recaps: Another simple practice — re-creating the situation at hand in your own words is super helpful for better listening and recollection. Once I’ve gotten the insight I’m looking for, I’ll quickly recap for the other person to make sure I understand the issue and to confirm that I didn’t misinterpret them. I’m shocked at how often I get slightly corrected by them. Once I’ve corrected myself, we can proceed until the next time I stop to recap. I know this sounds as annoying — some jackass constantly parroting your words back when all you want to do is scroll through your Instagram feed — but practice helps avoid parroting. A simple “Can I summarize what I just heard you say?” goes a long way. With enough practice, it’s possible to do this without looking like a tool.

Take good notes: A PM and I sat across from each other in a 1:1 and I asked them how things were going on the 3 action items we had discussed the prior week. They, in turn, asked me what the action items were in the first place. I felt like an idiot because I had forgotten what exactly I had asked them to do since neither of us had taken notes. So we had to retrace our conversation from scratch, much like you do when you forget your keys and have to walk the prior path to find them. The larger point is that I would be #1 on the “We need to shitcan these mediocre people” list in no time if I went to ~15 meetings a week and didn’t take notes down in most of them. Good notes are king. Of course, good is subjective and the ideal format that works for you is too. I’ve worked with effective colleagues who are constantly scribbling chicken scratch into a dog-eared notebook that looks like it’s seen better days when it was brand new…in 1805. More power to them. Tom Tunguz of Redpoint shares a great pointer to Bullet Journal — looks like a real commitment to get good at it but more power to those determined masochists too. As for me — I type bullet points with near-complete sentences as fast as possible into Evernote. Notes remind me to re-ask followup questions I didn’t get an answer to last time. They build a searchable archive for past unresolved threads. They help with prep. Most importantly, they improve listening and recollection by providing an extension to your distracted brain.

This is not an exhaustive list by any means, nor is it a surefire pathway to elite listening. For example, Meditation is a powerful tool that helps with listening and so much more. Being observant enough to understand body language and adapt to it matters too. But these five suck-less practices can provide a good-enough upgrade — think of them like the reliable Honda you bought after ditching your unreliable jalopy.

The Mercedes can wait. Until then, keep listening and keep seeking, first, to understand.