The Unintentional Career of John Cutler [Mind the Product]

Multiple hat wearer. Prod dev nut. This is John Cutler’s online bio.

He’s someone you’ll certainly have come across if you’re at all interested in any of the discussion around the thinking and theory behind product management. He writes, he tweets, he regularly speaks at conferences, and with 31,000 Twitter followers (not to mention 26,000 followers to his Medium blog), he’s a prolific and consistent voice in the study and development of the product management craft.

Currently, John is the product evangelist at San Francisco product analytics software developer Amplitude. He’s been there for just over a year and says his role is somewhat different from what most people imagine a product evangelist does. By this he means that he doesn’t spend his time directly advocating for Amplitude products: “Although I think we have an amazing product, my role focuses on the surrounding systems and ‘culture’.”

Instead, he works on showing people that they need to make the shift from thinking about data as something to snack on or pull out to make a point, to making measurement and evidence an integral part a product team. “It means thinking about roadmapping, team structure, how you plan, all sorts of things in product that have a big impact on how the team interacts with measurement and analytics.” It also means that product teams need to constantly be asking themselves the following: “Are we learning, are we reducing uncertainty, are we exploring new opportunities, what does the evidence say, how can we learn more?”

An Evangelist’s Working Week

With all these things to cover, there’s a lot of variety in John’s day-to-day work. “Most of my work is external facing,” he says. “So far this week I’ve had eight coaching calls with non-customers, two coaching calls with customers, and one conference in San Francisco for B2B product managers.

“Earlier today, I was speaking to someone in a team of two who described themselves as product ops. I was learning more about how the company works and how data and measurement could be integrated into their approach.”

A week before, John was speaking at a conference in Las Vegas (he’ll be speaking at MTP Engage Manchester in February too) – his work involves a constant chop and change of activity. “I’m speaking at conferences, doing coaching calls, writing blog posts – I’ve also just finished a book for the company that took three months to write – that’s what I’m up to day-to-day.”

Being a Trusted Expert

At Amplitude, John is the only product evangelist, but he says the company has an internal mantra which is “to be the trusted expert”. “It’s a mission that everyone in the company takes seriously. Everyone in the company strives to be a trusted expert and it’s one of the things I love about working there.”

And while he truly does love the work, John admits it can be challenging. He puts pressure on himself to make sure he does a good job in demonstrating Amplitude’s vision for how product teams should operate. “I talk to so many teams that I’m past being surprised, I think I’ve seen 95% of situations. But it’s a challenge to communicate different ways of working to people without threatening them. It’s a very subtle thing. I can’t be prescriptive, they’re not paying me. We’ve done a couple of experiments where I’ve worked with our professional services teams, but in general the businesses I speak to are not paying me. I do this to learn and to help them.”

He says he’s found a book by Ed Schein called Helping: How to Offer, Give, and Receive Help, about the power dynamics in trying to help people, to have been especially useful in building relationships. “Every relationship where you help people initially has a power differential. Who has the power? Is it me communicating best practices or is it them inviting me in because they’re a prospective customer?”

He knows that if he feels he’s got a product or organisation problem worked out, it can be a sign that he’s seeing things that don’t exist. He says you can go into an extremely successful company and believe that your mental model for how a successful company works maps on to what you see. For example, if you believe strongly psychological safety you will attribute company success to psychological safety. But that’s often one factor of many in a successful company.

My Role is a Product

Ironically, John isn’t part of the teams that develop Amplitude’s products. So, as someone who lives and breathes product management and product thinking, how does he find playing a supporting role? “I enjoy product. I’ve enjoyed working in UX research, in startups, so I imagine what I’m doing for Amplitude as a product. Let’s think of products as a differentiated delivery mechanism of some value exchange. For example, if I’m doing lots of one-on-one coaching sessions then I would view this as research and ask myself how can I scale this delivery? I do love being on a team, it’s one of the things I love most about product development. Now I’m in a looser team across marketing, but I think about what I’m doing as a product.”

Despite John’s clear passion for product, his career actually came about by accident. He dropped out of college – “I couldn’t focus on that stuff” he says, and then spent a few years as a musician. He plays bass guitar, piano and writes songs. “I got paid to be a musician and to tour for a couple of years. I didn’t get paid much for it, but it was a privilege, an amazing experience. I could wake up and think about music every day and most musicians don’t get to experience that.” These days, he says, his musical endeavours are limited to playing the ukulele with his 20-month old son.

He’s worked as a game developer at Simon and Schuster, as a producer at Nickelodeon, and had a variety of product roles at companies like Pendo and Zendesk, all interspersed with periods of consulting. “I’m a train wreck of career decisions, nothing has been intentional,” John says. He adds that he always felt he was doing a decent job as a product manager, but would get “get hung up on the systems surrounding product in general at the company”. Then he’d become distracted and/or bored. “Again and again I would see situations where just a small amount of recalibrating of how strategy was communicated, or how things operated, or small adjustment in the relationship between with CTO and the CPO could have had a far-reaching impact across the company. If those things didn’t change, I would get distracted.” He says he gets obsessed by organisation design, how communication happens and how people are aligned.

Becoming Intentional

If nothing in John’s career has been intentional to date, then it’s something he’s trying to change now. “It’s almost like I have lots of jobs – I have this external persona, the Amplitude job, I’m a parent, and I have to take care of myself. It can get overwhelming. Maybe I’ll figure out the next step soon.” He counts himself extremely fortunate that he’s been able to do what he wanted to do and then been able to move on to something else when it stopped being exciting or he felt he was getting burned out. “I have to remind myself how lucky I am.”

About that external persona then: John’s strong voice and online presence developed because he found that writing about problems helped him to think them through.  “But only 10 people were reading the posts back then,” he says.

“It’s only relatively recently that a lot of people have been reading them. I write as a way to work through ideas and concepts, and that’s why you see me revisiting my ideas.” He’s adamant that he’s not a thought leader, but “more of a thought fast follower or a second thought leader”. “I’d say I’m an observer of dysfunction – I was called a poet of dysfunction on Twitter the other day. I’m the one who says ‘why are we doing this?’ and I can’t move on until I understand the big picture.”

He comments that there are some personalities in product management who think about what they do as a business – they’ve made boundaries, he says, something he’s never done. As a result, he can look on his Twitter account at the weekend and find there are 30 DMs asking his advice on some aspect of product, so he feels he needs to rethink the way he communicates, or he risks burning out. He adds: “I think you have to think about scaling yourself out. It’s a core product manager trait, you can’t be the one making the decisions, you can’t be the one to write the Jira tickets all the time. You have to think about how to empower everyone around you.”

Managing Your Product Career

So what would be his advice for anyone thinking about their product management career? “I could have really thought through what would put a smile on my face and get me excited,” he explains. “My mistake was that there were times when I was bored and I didn’t have a smile on my face.”

He thinks that people can get stuck in organisations and then take on the dysfunction of the organisation. They get stressed about it, but often they don’t consider that the real problem is that they’re not stimulated. John thinks people should analyse what they enjoy doing when they search for guidance: “I doodle for fun, I always draw. I enjoy communicating, I must enjoy communicating ideas on Twitter, and I like the idea of teaching and helping people improve their situation. I like helping people and sharing knowledge and I’ve been able to slip into that as a career full-time.”

There are good reasons why John calls himself a multiple hat wearer. Happily, teaching, helping people to improve their situation, and sharing knowledge are all essential parts of the daily nine-to-five for John as Amplitude’s product evangelist. It’s a role that means he can keep studying his pet passions of organisation design, communication, and how people are aligned – and keep informing and educating us about them too, through his blogs, tweets and public speaking. Be sure to see what he has to say at MTP Engage Manchester in February 2020!

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Source: Mind the Product https://www.mindtheproduct.com/the-unintentional-career-of-john-cutler/