Leading Product Teams: Piyum Samaraweera
Leading Product Teams is a series where I speak to people about their experiences leading teams of product managers. I’m intentionally talking to both people who recently had their first management experience, as well as those that have been at it for a long time, to pull out meaningful insights to help others improve and move up in their careers. I worked with Piyum when I first joined the team at Carbonite and eventually reported to him before he left the company. He is presently the CPO at FieldRoutes.
How did you get your start in product management?
Thompson Financial in 2000. We were delivering full-text research digitally to Wall Street. The product function already existed, and I led a tech support function. Based on my customer conversations, I was constantly telling the head of product that the product should do X, so he suggested that I apply for a job.
When did you first lead a team of product managers?
We were building a team to extend the Research Direct product to new customers. The PM we hired targeted that opportunity. We figured out different personas, although they weren’t called that at the time. We wanted to have discrete PMs building towards each of those personas, so I asked to build a small team to focus on the opportunity.
What was different managing PMs vs other teams?
There wasn’t a notion of best practice(s) for product management or even what you’d call a software development lifecycle. Each product manager worked differently with their teams. They weren’t doing agile; XP was one of the precursors to agile. We knew enough to have product people to bridge the gap between customer needs and execution in engineering. Still, there weren’t a lot of resources available that explained how actually to do that. We just had to figure a lot out on the proverbial fly.
I did a lot of reading, and there was some content, but it was tough to figure out how to implement it in practice. I remember reading somewhere, “write the story on a [index] card,” but they didn’t explain why or how this was supposed to help. It was a lot of trial and error. I will say one thing that made us maybe more effective back then - we spent more time talking to engineers, trying to reach a shared understanding.
You can throw agile and scrum out the window; it’s really about the conversation. Back then, the conversation was all we had. We were doing big specs upfront when I first started, but eventually, we started breaking things down and talking more.
What were some specific challenges you faced managing product managers?
Put aside the people management issues for a moment, if you had a one on one with someone and you knew there was an issue, you didn’t really have frameworks to draw on to address the issue or coach people through it. If things popped up in the development process we didn’t have a ready list of ways to de-risk the project. It was a lot of trial and error and conversations with engineering. Looking back, I think in general we were being very myopic about building small pieces of the software or a particular feature, rather than a larger repeatable workflow.
What do you look for in IC hires today? What have you seen as indicators of success?
Some things are foundational, like communications skills and the ability to consume large amounts of data. There’s confidence, which is tough to mine for in an interview process. The person needs to be OK with ambiguity. Work ethic is vital. Good PMs tend to work harder than many other functions as they often act as the hub. The big one for me is empathy. It makes the PM successful, and like confidence, it is hard to test for in the interview process.
How do you run interviews to have the best chance of getting good candidates?
Having everyone with assigned roles and questions to ask is critical. It's too easy to have everyone asking in the same area and not realize it. The other essential thing is to have a broad cross-section of the organization involved in the interview process. When candidates are talking with other product managers or development, they tend to dive into the weeds of the process. When I include someone from sales, marketing, operations, or customer success, it is a very different conversation. It's good to put them outside their comfort zone and see how they handle themselves with people and personalities they'll need to work with daily. Another good idea is meeting them outside the formal interview process. Have coffee with them. How do they act in a "non-interview" environment?
What are the additional skills required to lead other product managers beyond the IC skillset?
The word human comes to mind, but that's a loaded term. There's a level of caring and commitment to their employees that has to be there genuinely. You want to find people who realize their success depends on their team's success and put a ton of effort into their people as a result. That's a shift that ICs don't always make when they move into management. It's been them versus the world for so long it's hard to make the mental switch. You also have to be OK with your team being successful and getting lots of kudos, and you may or may not get any recognition for their success. Again, it's a shift from how it works when you are an IC. Lastly, the most successful managers make personal connections with their people. They're not always your friend, and you may not always see eye to eye, but you understand them as a human.
What do you see as the most common failure mode for people in their first product jobs?
People think they have the title GM when they show up, and it gives them the ability to run roughshod over others, make decisions in a vacuum, and make decisions without bringing people along. In my opinion, that’s the most common problem. I walked into Intuit from Thomson and did precisely that. I executed everything they asked me to, and my first performance review was poor. My manager told me, “you’re not going to make it here; your brand is awful. You’re just stepping on people to get stuff done.”
What’s the most common thing that holds people back from moving to higher PM roles?
I think it's confidence and the willingness to make decisions on a larger scale. I think you can coach and pump their tires a bit, but it has to be within them that they have to be willing to take it on. Historically and still today, we, humans, are still very averse to failure. That keeps many people from wanting to take on the next biggest thing, making the critical decision.
What feedback do you have on the profile of an excellent Product Manager?
Beyond the skills we talked about, it is for the PM to understand the filters and perceptions. To understand their unconscious biases, not only for the good of their offering and product for how they hire and manage their teams or interact with their peers.
As an example, I was listening to this Podcast about how Amazon had built this AI candidate screening tool, and it turned out to have baked in biases because of the data set they used. Given the way the whole business is going (AI), I think product managers need to be much more aware of potential biases in the way products are built.
Overall I agree, I like this.
[PRODUCT LEADERS] You can view the Profile of an Excellent Product Manager here. With everyone I interview I’m looking for honest feedback on the profile so that I can fine tune it over time. I’d love to hear from you as well. Please feel free to reach out if you’d like to discuss the profile or anything else.
Key Takeaways from Piyum’s Experience Leading Product Teams
Insights
The value of the conversation within the core team has been slightly lost to so many electronic tools. Remember to actually have really conversations with your team about what you are building and why.
Many things matter in hiring, but for Piyum, focusing on whether the candidate shows that they can be empathic, both with customers and with co-workers is a primary indicator of future success in the role
The most successful people managers are the ones that can make the mental switch away from personal achievement and recognition to focusing on the success of their team
The ability to identify and remove bias will become more crucial for product managers over time. Not only for their own decision making, but as we build more AI/ML tools that decide for us - we need to know what biases we may be building into the system.
