Coffee with Jessica Barnett

This week, we’re grabbing coffee with Jessica Barnett. Jessica is a Product Manager at Trello, with a contagious passion for improving processes!

Check out Jessica’s posts on questions to ask in a PM interview, and how to create a resume that gets you an interview.

How did you get into product management?

When I look back now, I can see a perfect progression throughout my career. At every step, I was learning things that make me better at my job today, but I didn’t take a very direct path. I didn’t set out to become a product manager, and I basically stumbled into technology.

I ended up with several designer and developer friends and I was fascinated by the cool things they were working on. I was doing operations for an insurance startup at the time, a completely different universe. As we chatted about our jobs, they’d mostly vent about how miserable they were. While they loved their actual work designing and building things, they were in classically dysfunctional agencies. The sales team pulled together crazy, half-baked proposals with fixed rates and set due dates. Once signed, the account team would toss the specs over the wall to the “creative team” and demand a speedy delivery. As I dug deeper, I became convinced I could improve these communication and process problems, and have fun doing it.

So, with no tangible experience whatsoever, I founded a web development agency working with some of those designers and developers. It was awesome, and a tremendous learning experience! I had to figure out the entire universe of running a web agency very rapidly, not just technology, design, and user experience, but also how to manage clients, hire a staff, write contracts and proposals, and so much more.

I also did a bit of consulting on web strategy, social media, and process development. I eventually realized that what I love most is product, not business management. So I moved to an agency where I focused on the product side — that confirmed how much I loved being able to focus on one product and wrap my whole mind into it. For the last several years, I’ve worked on product teams in technology companies and that’s where I’ve definitely found my calling.

It’s interesting to think about the things I did long before that were directly product related too. I was a theater geek in high school and directing was my favorite part . I loved pulling everything together to bring a story to life, often 100+ actors, singers, dancers, carpenters, designers, publicists. In hindsight, I was basically doing everything that I’m doing today when I was 15.

Being vulnerable and open to feedback from smart people is immensely valuable, and I believe one of the most valuable things we can do in our life.

Where does your passion for improving processes come from?

My love of process improvement definitely shows in my style of product management today. As a kid, I loved puzzles, Legos, and organizing. For as long as I can remember, I’ve found myself saying, “There must be a better way.” When I see messes, inefficiencies, people getting frustrated with work, or things moving too slowly, that immediately triggers my desire jump in and fix things.

What I’ve really had to work on is how I communicate about the problems I’m trying to solve. I’ve had to overcome my instinct to just take over and instead channel that passion into constructive questions I can pose to a team. That’s a skill I’ll be practicing for the rest of my life!

As PM’s, we interact with so many different groups of people; if you just walk in and tear down what they’re doing or how they’re doing it, you’ll not only miss out on learning a ton, but you’ll also burn those bridges super quickly.

How did you start work on being a better communicator?

I’ve always been direct and rather aggressive but I’ve spent years studying communication and working to improve the way I communicate. Results definitely matter, but the way you get results matters too.

Two of the most helpful things I practice are:

  • Always assume people are trying hard and have good intentions.
  • When that breaks down, ask questions. From a good heart, be curious about what’s going on.

As PM’s, we interact with so many different groups of people; if you just walk in and tear down what they’re doing or how they’re doing it, you’ll not only miss out on learning a ton, but you’ll also burn those bridges super quickly.

Instead, I think, “This team is amazing and trying their absolute hardest, so let’s find out what they think is going on and how we can work together to make things even better.” That approach has served me really, really well.

I took an amazing Creative Problem Solving course in college where our instructor encouraged us to use specific strategies to communicate. They included:

  • Praise first (before providing any other thoughts, especially potentially critical or negative feedback)
  • Frame concerns as questions
  • Use “yes, and” instead of “but”
  • Don’t shoot down people’s ideas and instead create separate spaces in the conversation to brainstorm openly, and then converge back down to a specific idea

I’ve reached out to great communicators and asked for their advice and feedback a lot. Being vulnerable and open to feedback from smart people is immensely valuable, and I believe one of the most valuable things we can do in our life. I’m very thankful for those willing to share their wisdom.

Anyone can find a job that makes them happy and fulfilled. You shouldn’t give up.

How do you think about career advancement?

I think a lot about how to find a job that you love and how to advance your career. Friends joke that I’m their “career coach.”

So many people are really unhappy in their career and don’t think they can do better. I totally disagree. Anyone can find a job that makes them happy and fulfilled. You shouldn’t give up.

Always keep an eye on industry news and trends. An awareness of what’s going on in your particular role is very handy (networking and an occasional job search are helpful). Even when you’re happy, stay open to new opportunities. Interviewing is an important skill to develop. You don’t want your first interview in years to be for your dream job when you’ve been unemployed for a few months. Interview enough that you feel comfortable and confident. The easiest time to find a new job is when you already have one.

I actually think interviewing is a great way to hone in on exactly what you want. A couple of years ago, I was ready to move on from a job but didn’t really know what I wanted. The process of interviewing with a few companies was incredibly helpful. From that, I figured out great questions to ask along the way.

What books do you recommend to PM’s?

I’ve recently read several books about starting a new role. My favorite was “The First 90 Days.”

I also highly recommend Scrum, Don’t Make Me Think, Rocket Surgery Made Easy, Mindset, Beyond Reason, and Cracking the PM Interview.

What do you consider the traits of a great PM?

  1. A love of learning. Being a PM requires constant learning. If you don’t enjoy it, I think you’ll get burned out pretty quickly.
  2. Insatiable curiosity (and never taking things at face-value). Always dig deep to understand root causes: why something is happening, why was a feature requested, what’s causing the problem, what were their goals? The more that you can practice having an open-minded curiosity about everything, the better.
  3. A love of working with people. The more you want to collaborate and communicate with others and find solutions to problems together, the happier you and those you work with will be.
  4. Bravery. So much of product management requires a ton of bravery. Especially when you’re starting out in your career, you’re talking to older people who can be very intimidating. Whether that’s your clients, customers, co-workers, you can’t be afraid to push forward, to speak your mind, and to question the status quo.
  5. Wanting to constantly improve. The nature of doing product is working with so many different types of people, and there will be improvements to the product and process all the time. Be comfortable with never being “finished”.
  6. The ability to break down things simply. To be able to take a huge, complex thing and break it down into small, manageable pieces that can be easily digested. To create a structure to the way that you communicate, and figure out the right information to convey when. That’s a skill you’ll use constantly.

I left coffee with Jessica inspired by her work to become a better communicator and PM. We also share an obsession for improving processes and will be geeking out on that together over more coffees :). Thanks for grabbing coffee, Jessica!

And thank you for reading — I’d love to hear your thoughts on this series on Twitter or in the comments below.

Thirsty for more? I got you :)