The Value of Mentoring for Product Leaders

Adam Thomas loves to mentor – he jokes that in the multiverse where there’s a million different versions of yourself, “in 40% of them, I would be a teacher”. “I just get a huge kick out of it. I love seeing people understand things, seeing the lights come on.”

Adam’s career has seen him progress from system architect and programmer jobs straight out of university to his last full-time role as Director of Product at repricer tool business Informed.co He’s focused on developing internal tools and artificial intelligence throughout his working life, and his mentors have been hugely important to him. But it was a poor experience with one of his first managers that was instrumental in shaping his career and his leadership style. He explains: “I think everybody has a manager at the beginning of their career who tells them what not to do, and how not to behave and who pretty much exists as an anti pattern for however the rest of your career is going to be. I had that manager very early in my career, he didn’t really care about anything other than his numbers. The guy was brilliant – I still think of some of the things I’ve seen him do and how good he is – but the whole people thing misses him. I told myself I never wanted to be that kind of corporate climber.”

Why Early Experiences Count

However Adam can easily name three other managers whose support and influence have helped him to further his career and grow his skillset. One of them was that corporate climber’s boss – in contrast, someone who mentored Adam in the early days. “He was hugely influential, really teaching me the ropes about company policies, being an executive sponsor for my wacky ideas, as you might call them. He would walk me through how to present, how to get my ideas across in a boardroom or a big conference room. We’re still in touch, I talked to him about a month ago.”

Adam’s next mentor was a boss from his time as a system architect at financial services company DTCC. “He had a reputation for being hard to work with, but that was only because he expected good work,” he says. And he taught Adam a lot of product management skills that he’s taken into his leadership roles – how to understand what customers want, how to talk to a user, software development lifecycles. “He’d say ‘don’t do it the lazy way. Don’t look at emails. Go where they are. Sit down with them and ask them questions, talk to them, get to know them’.”

Lastly, Adam talks about Chris Butler (who’s now at Facebook), someone he worked with at software design and development studio Philosophie. He refers to the company as his product management finishing school, as working there equipped him with many of the product leadership skills he continues to find very valuable. He explains: “It put me through a lot of projects. Chris really helped me hone my strategic thinking, giving me exercises and putting me in places where I’d have to think about the long-term future of a company that I wasn’t a part of. He really taught me how to do product strategy, how to manoeuvre in rooms where you have low power, how to facilitate. So Philosophie was my finishing school and Chris was and still is someone who’s really important to me and to the way I think.”

Adam still considers Chris his mentor today. He firmly believes that it’s critical to have a mentor at every stage of your career. “Pathfinding is easier when you can see other paths,” he says, “what I mean is that having someone who has gone through some of your struggles and picked a direction can help you to find yours.” He adds that product leadership can be lonely, and product leaders have to make decisions for people who don’t have – and can never have – the same context. It’s therefore enormously helpful to be able to refer to someone who understands your context and who can ask the right questions and verify that your decision making is sound. Adam says: “As you get more senior, your conversations with your mentor shift more into the meta, the science of it all – at least that’s what happened to me. No more talk about what to put on a roadmap, now we talk about why a roadmap even exists. Less talk about people themselves, more about the type of person, and how to help more people at scale.”

He’s between roles at the moment  – he took a career break at the end of last year when his father became ill, and then the pandemic struck – but he still has found the time and motivation to mentor other product managers during lockdown. He explains: “I found out during the Covid outbreak that my neighbour is a product manager – and it’s turned into a bit of a mentor/mentee relationship. She’s also one of the leads for a black product manager group, so through her I’ve met a whole bunch of people who needed advice.”

Taking the Process Seriously

Acting as a mentor has been integral to many of Adam’s past roles. But he points out that many companies pay just lip service to mentoring schemes. He says: “Every new company that you onboard will say find yourself a mentor, so-and-so is looking to be your mentor, and it’s all nonsense. You can’t be a mentor without being proactive.”

Being an effective mentor means paying attention to your mentee, and one easy place to start is to increase the cadence of your meetings. Adam thinks this should be once a month as a minimum, and probably every two weeks. You should also structure your conversations, don’t just meet up for a coffee and a chat. You need to build a programme around your mentee, he says: “What do they want? How are you alike? How can you help them navigate their problems? You should challenge them to come to you with problems and ideas. They should be able to bring you a structured problem that you can deal with. Critique is a huge part of mentorship. You’re not there to be their friend, though you might like to be. I want my mentee to get better at what they do, that’s the main thing I want out of their relationship with me.”

Adam says he’s had a few mentoring relationships that he considers big successes, but one in particular stands out. He says his mentee was a product person, but he didn’t know it. He was a natural communicator, he didn’t necessarily have the hard skills he needed, but he got interesting jobs in spite of that. “I told him when his job at the last startup he worked for fizzled out ‘go and work for a bigger shop, be a cog in a wheel for a while’. I told him that if he kept going to startups he’d never have a boss who would really be able to teach him.” Bigger organisations have more support and a structured approach, Adam reasoned, and working for one would help his mentee to understand process and politics – because dealing with people in a larger organisation who don’t know you and just expect results is very different from a startup environment.

Adam’s mentee ended up working at Mastercard. “He didn’t like it at the beginning but I noticed our conversations very quickly got a lot more nuanced. His questions got better. He started understanding data better, how to present his points better, because if he didn’t he couldn’t get the resources he needed. In six months he levelled up tremendously, and he got somewhere he wouldn’t have if he’d gone to another startup. His skills as a product person have grown exponentially.”

He tells a story of another successful mentoring relationship. He was at #mtpcon San Francisco last year, checking Slack, and one of his analysts sent him a document. She’d spent four years in customer success and really wanted to move into product. Her documents hadn’t really told anyone anything, and weren’t clear. “But this time she sent me a document that said these are the outcomes I’m looking for, and I thought ‘you’re finally getting it’. I almost felt like crying. When I arrived, folks didn’t take her seriously, but by the time I left – she’d become a powerhouse, taking on her own projects with way more confidence and ownership.”

Qualities of a Good Mentor

What qualities does he feel a good mentor needs to have? Many of them are skills that a good leader also needs to possess. Patience is an obvious one, says Adam, and some self-awareness because “you should know that you were where your mentee is at one point, and you thought you knew it all”. Empathy is also a crucial quality, as is curiosity: “I hate when somebody claims to be a mentor, but it’s just them shouting at somebody, it’s not a two-way conversation.” Adam adds that his Mastercard mentee has equally taught him a lot about how to bring people together and how to be warm, because those are his natural skills.

What’s next for Adam? With some friends he had planned to start a consultancy focused on product strategy for smaller companies, their plans were well advanced but the pandemic has put paid to them. So he’s talking to potential employers at the moment. “I’m waiting for something interesting, but every time I see something I think might be interesting I run into a hiring process that’s horrific,” he says. He feels that the product recruitment process “over-indexes” on the wrong things. “They over-index on things like artifact creation – so you make good looking artifacts – and how fast you can get things done. But product is a very empathetic and relational job. It’s about how you talk to people, how you herd cats, how you make decisions.”

If the product hiring process looks to tick the wrong boxes, it’s partly because recruitment is often farmed out to HR teams who don’t necessarily understand what’s required, says Adam. But it’s also because “there aren’t a lot of product managers”. He explains: “By that I mean that there are very few product managers who have worked for a product manager who has trained them. They’ve never got to be an apprentice under someone, at least in earnest. The ones that have are few and far between.”

If you’ve never seen work done in a different way, then you end up thinking everything is new. Adam adds: “It ends up being a lot of folks just guessing. They read articles on Medium and they end up trying to mimic the engineering process, or looking at what design does, and trying to mash it all together. There’s no real hiring protocol. The biggest companies like Google or Facebook have their own specific processes, but otherwise no one really knows how to hire for product.”

Hiring processes aside, what kind of products is he particularly interested in? “I really enjoy talking to customers and throwing out ugly products just to see how people work with them or make things happen. But with everything going digital and remote post Covid, I’ve become really interested in the streaming and rights worlds. I’m interested in understanding who makes the choices, how creators make a living, how to make it more fair, how to give people the data they need to make better decisions on all sides.”

Whatever his next leadership role, mentoring will be a part of it –  Adam adds there are strong links between the interpersonal skills he’s developed through mentoring and his leadership style. Mentoring has taught him to be more patient, he says, and to learn different styles of communication. “When I was younger, my mother used to say ‘Adam, you act like the world owes you something’. In some respects, this arrogance has helped me go places, stomping into rooms, sometimes as the only black man in the room or company  – it’s one of the reasons I’m being profiled here. However, I needed to temper it. Through mentoring I was forced to see other perspectives and slow down and be more open. I had to get out of myself and that has made me a far better leader.”

The Benefit of Mentoring for Leaders

He also strongly believes that product leaders should take mentoring seriously, because it teaches them to be better leaders. It may be voluntary, and you may not be incentivised to do it, but mentoring forces you to slow down and make time for someone else, and leads to different perspectives that help you see the world as it is. Says Adam: “Don’t use it as a photo op. Don’t use it to feel better about yourself. And definitely don’t waste someone else’s time.”

Mentoring has changed the way Adam approaches product leadership in several ways.

It’s led him to ensure he always sets clear standards. “You’ll be surprised what folks can do if you set clear expectations,” he says. “This lesson alone has changed how I lead teams, because I spend far more time communicating expectations and searching for alignment.”

He always makes sure people have the resources they need: “When you give people opportunities, most folks will flourish. You shouldn’t be afraid to make that connection. As a leader, this translates into how I work with other disciplines. I’m much more open to giving opportunities and sharing resources with other teams, without expectation.”

Finally, he finds it’s important to remember to respect boundaries. He adds: “Don’t push too hard. I’ve got much better at setting rules and holding firm. That’s super helpful in product management.”