Coffee with Rosie Gollancz

This week, we’re getting coffee with Rosie Gollancz. Rosie and I worked together at Big Health. After 5 years at Big Health — joining as employee no. 3 — Rosie is embarking on a new adventure!

Rosie drops so much gold in this interview — from advice for early employees to how to identify and get the role you want, and what inspired her to take her next leap.

How did you get into product management?

Like a lot of people in product management, I was doing the role long before I had the title.

I joined Big Health after completing my undergrad in Psychology, at a time when their first product, Sleepio, was just about to go into public beta. The job was originally titled ‘Users and Experience Manager’, and my mission was to grow the community component of the product from the ground up. As the human face of the product, my role was to interface directly with users, absorb their questions and suggestions, and communicate their needs back to the rest of the team (the CEO and our, then solo, engineer).

Being part of such a small team meant that I quickly gained hands-on experience of the full product cycle, from user research and data analysis, to prototyping and user testing, and, of course, tons of QA! I ended up absorbing more and more of the responsibilities of a PM and I loved it.

When you start out in a broad role it can take a while to discover exactly what you do and don’t want to be spending your time on. You have to figure out which of the small, sometimes subtle, aspects of your day-to-day life you want to form into a coherent role. Product Manager best represented that collection for me — the things I really wanted to be spending my days on. As the company grew, I was “officially” — and very happily — given the title of PM.

At the beginning, it might feel a little frantic and unfocused, but it’s so valuable to continually dive into the unknown.

What advice do you have for early employees?

Get comfortable being new at everything
I loved being part of such a small team — it meant that almost every day I was learning something new and getting involved in an unpredictable range of tasks. Be willing (and eager) to say yes to everything — at least once. At the beginning, it might feel a little frantic and unfocused, but it’s so valuable to continually dive into the unknown.

Product management, by its nature, has you switching between very different tasks multiple times a day, and communicating with people with different levels of knowledge and priorities. I think it could be tricky to be an early employee — and take on this kind of role — if you weren’t willing to be new at something all the time.

Being a PM is often not an exercise in being an expert, a lot of the time it’s being new and incredibly uncertain about things, but running with them.

Seek out experts
In a startup, it’s unlikely that there are going to be people who are experienced in many of the things you’re working on, so I’d recommend seeking out experts and mentors (outside the company) to learn from. I’ve been pleasantly surprised by how willing people are to share their expertise when you show them that you’ve spent time thinking about the topic, and that you’re interested and polite!

Be intentional
When you join a small startup, you are expected to be a Jack of all trades. This is great at the start, but there’s a risk that you continue to be seen as the Jack of all trades, and the master of none. As the team grows, people tend to occupy more focused roles, which may mean they absorb some of the things you’ve been working on. Make sure you figure out which parts of your role you want to retain, and speak up for them. If you want them to be yours, you have to make them yours — you don’t get what you don’t ask for!

Most of the time, you don’t even have the thing you’re afraid of losing, so you might as well go for it.

What advice do you have for identifying and getting the areas you want to own?

Keep track
Keep notes about what you’re spending your time on. A few weeks before one quarterly review, I started a Google doc and, at the end of each day, I noted down what I’d worked on. I went from struggling to recall what I’d been working on, to having a good sense of the things I’d achieved, what I’d enjoyed, and what I hadn’t. When the time came, this made it much easier to reflect and get a sense of the areas I wanted to own.

Speak up
A lot of this comes down to biting the bullet and making a solid case for what you want. I had an experience where I expressed an interest in a new role but I wasn’t nearly clear enough . By failing to explicitly say “I want this thing and here’s why I should get it” I failed to get a clear yes or no.

Do your research — come armed with reasons why you’re a good fit and how the change benefits the company. Most of the time, you don’t even have the thing you’re afraid of losing, so you might as well go for it. And, if you ask for something and you’re not given it, don’t take that as the final answer — start doing the job. It’s hard for you not to be “given it” once you’re already doing it!

I’d spent years hoping that my “passion” was going to strike me. I think a lot of people are waiting for that to happen — for “their thing” to appear in front of them.

After 5 years at Big Health, what’s next?

Over the past 5 years, I found that every time I got the opportunity to work on something more technical, it made me really happy! For a while I satisfied myself by learning SQL and dabbling with coding, but a few months ago I decided to take a bigger leap towards a more technical role.

I booked myself what I (somewhat jokingly) called a ‘Thought Retreat’ — an Airbnb in the hills in Berkeley — and spent a few days on my own hiking and hot tubbing, and thinking things over. When I was there, I read the book “You Are a Badass”, and I’m so grateful I did. In that short time, it helped clarify a few things that lead to me making the decision to quit my job of 5 years and take the next leap.

I’d spent years hoping that my “passion” was going to strike me. I think a lot of people are waiting for that to happen — for “their thing” to appear in front of them. The book spelt out that if you’re sitting back and waiting for that to happen, it is unlikely to do so. People create their passions, and often you have to get deep before something becomes a passion, and the only way you’re going to do that is to dive in head first. You’ve just got to go for it, and the bigger the leap, the more you stand to get from it.

Since moving to San Francisco, I’ve witnessed people taking a few months out to learn something really intensively and totally switch gears on their career. It felt like I’d hit a point in my life where, if I wanted to make a big change, this was a great time to do it. I decided on that trip that I was going to quit my job and take a coding bootcamp. I spent the next month learning what I needed to to pass the tech interview and…I got in! So I’m taking the next few months to build my engineering chops, and I’m feeling really excited about the opportunities that lie on the other side.

What do you consider the traits of a great PM?

1. Empathy — people often speak about empathy in the context of the user, and that’s super important, but it goes beyond that. You need empathy for the CEO who has investors to answer to, for salespeople who have to keep clients happy, for engineers juggling sparkly new features with years of technical debt. You have to assimilate a huge amount of information from all these stakeholders and move forward with the right things.
2. Curiosity — taking joy in seeking out the unknown. Identify problems and gaps and go nuts to solve them. Treat it like a game — ask yourself “how best do I solve this puzzle”, “who has experience in this”, “what’s the underlying job being done here?”.
3. Open-mindedness — this marries with curiosity really nicely, especially if you’ve worked on a product for a while. It can be easy to get stuck in what you know and assume that you know the right solution instinctively. Things change and evolve, and you have access to new information all the time, so you need to commit to being open to continually updating your assumptions.
4. Persuasiveness — sometimes you are the ultimate decision maker, at other times your job is to be the “shepherd and editor”. I found that description in Cracking the PM Interview — I think it’s a really nice way of looking at the role. You’re a guide for all these inputs, you have to attend to them, translate between them, and form them into a single, united path forward.

What books do you recommend to PMs?

• “You Are A Badass” — there is so much good stuff in this book. I found I had to adapt the language a little to really identify, but it’s made me more open-minded to this category of book and I want to consume more of them! We’ll see though, I might be cursing it in a few months! ;)
• “Cracking the PM Interview” — I read this recently and found it really helpful to clarify my conception of the PM role, and remind myself that I’m already doing it!
• “Algorithms to Live By” — many things I love in one book — psychology, computer science, logic, ethics — and how you can apply them in real life.
• “Learn to Program” — for a simple and very enjoyable introduction to programming (Ruby).

I left coffee with Rosie buzzing with inspiration (the kind of buzzing when you’ve had too much coffee!), and fire to go and be badass!

P.S. If you’re looking for a badass technical PM, hit Rosie up. She’s a superstar.

I started this series to learn from badass women and share those learnings with you. If you enjoyed this interview, please share it with others that might too :)