Sixth Work Anniversary — anecdotes and lessons

This month I am celebrating my sixth anniversary at Pipedrive. I never imagined I’d be in the same company for that long. Let me share here with you some of the anecdotes and lessons learned during this time.

So, how did you two meet?

A job is a relationship. After my marriage, I deem this the second most important relationship to have. All because of the amount of time I have to spend dong it, being in it, thinking about it. When I met the team at Pipedrive (a team that has changed in size, people, form, and location many times in these six years) I was not actively looking for a job. I needed one but I had given up on the traditional active way of looking for one because it was not yielding the results I was after. Hence I decided to take it as a relationship: I would first work on myself, enjoy the ride and stay open to building connections organically and purposefully, nurturing the valuable ones and letting the others pass me by, not trying to force anything in the process.

When I stepped into their P80 office in Tallinn for the first time I was volunteering for Tech Sisters. They were the hosts of a meet-up we were organizing. Their name said nothing to me, but their atmosphere captivated me immediately. People I didn’t know approached me to say hello and asked what I was doing around. They made me feel welcome. Their office didn’t look friendly and open. It was friendly and open. They asked if I was looking for a job, which I wasn’t.

A couple of hours into the event my mating signals started going off. The Head of Product (one of the co-founders) who would become my first manager there, had given a relaxed intro and mentioned a few job openings, one of them for a product manager. As the event developed, my positive energy was growing. Some of my friends were giving talks about their work with smart textiles, or in the European Space Agency, and others had come to listen to the presentations. This was all exciting in itself. So all my happy hormones were high for all the reasons.

Later, when we were mingling, I asked a few more details from the recruiter about the job, and she told me that while they didn’t have an ad out there yet outlining the details, they’d be happy to take in my application if I was OK with just the verbal description. That same night I came home to put my CV in order, prepare a letter and send both over. That was February 2015, and after a round of 5 interviews with 7 different people, I stepped into my first day of work on Monday 30 of March 2015. The rest is history. Now let me share with you some pieces of that history.

A couple of vanity metrics:

• The Pipedrive team has grown about 10 times since I joined, when we were around 70 people with one main office in Tallinn, and a smaller one in the US. We are now over 700 employees, located in 10 offices around 8 different countries
• Our customer base has grown from a bit less than 30K in 2015 to 95K paying customers today
• I have had 6 jobs, 3 of those in the last year, and all of them within product

A few lessons

If you read some of my previous posts you might notice a trend on the topics I touch: reflection and learning, introspection and growth, relationships. These lessons have all a bit of some or all those topics. Keep reading if they are your cup of tea.

It is not so much whether you say yes, no or maybe. Clarity is what truly matters.

Saying no is a difficult but very important emotional and social skill. We all have limited time. We all have limited energy. We all have limited support. When we don’t learn to say no, we may be committing ourselves to failure. As a product manager this is crucial in delivering the things you truly trust will add value to both customers and business, at the risk of missing out on another set of possibilities. In terms of doing product work I learned this skill very well from my first manager at Pipedrive. We still even use a slack emoji reaction which is an icon of his face when answering no to certain questions or requests.

But honestly, this skill is important beyond any job. Because when we say yes to anything in life, we are at the same time saying no to an infinite set of trips, encounters, events, opportunities, accidents… The fact that our time is limited makes it all so. And even if resources are ample, saying yes to everything can result in poor outcomes, low return on investment, loss of trust, burnout.

But if you change perspectives you might notice that saying no is as hard as saying yes. It is, after all, just another face of the same cube with 5 nos, and 1 yes. What I have learned however, is that saying maybe can also have dire consequences. Let me exemplify: in at least one of those six job changes I mentioned above, I should have said no to what was in offer. People who believed in me offered me to take on jobs that I didn’t think I could. I didn’t say no. I said maybe. I said “let me think about it”. I left the door open. I even wrote down the skills I thought were needed for the job, and mapped myself against them. The map looked fine, if one only looked at the skills. But there was something else missing: bandwidth. While I said yes with my mouth, in my mind I was saying maybe. My warning signs were erupting. Something was out of place, but I was not clear about what it was so I attributed it to fear of the new and the unknown. It turns out that going from having x responsibilities to having 10x responsibilities requires a very different set of skills even if the type of work is the same, and while some people can handle it, I am sure that most will do better if they grow gradually into that volume of work. I am more of the organic, slow type of grower. This half baked yes resulted in me doubting my good relationship with my employer. I ended up quitting the role, taking a longer-than-usual break and resetting my very depleted batteries and my very confused identity.

At my return, I still had not learned the lesson. I said yes to yet again other opportunities that were a mismatch for me. This time it was not bandwidth, it was a misalignment with my goals. Just because you can do something well doesn’t mean it’s the right thing for you to be doing full time. I bake delicious salted caramel chip chocolate cookies. You don’t see me opening a cookie shop, do you? I did these jobs well, and I enjoyed them, but they were taking me away from what I liked doing the most: product management at its full, not partially.

As much as I pride myself on being a reflective learner, I did not manage to arrive at this lesson on my own. I relied on others. A big thank you is in order to the organization who has embedded a set of personal coaches who we can turn to for psychological support. It was through a couple of these coach sessions that I learned my problem was that, while I could easily say yes or no to roadmap items, and research tasks, and meetings, I was terrible at saying no to job offers. So when a new opportunity came around the corner, I asked to be given a bit of time to think about it (two months, exactly). Within that time I planned a full day off just to reflect, read, write and research on the topics that were troubling my professional identity, and I landed on a clear answer. Fast forward to today, and I could not be happier. Of course there are challenges and problems and conflicts I have to deal with, but they match my interests, my skills and the bandwidth I have to tackle them. There is also plenty of room for growing and learning new things, but at my own manageable pace.

The lesson is not about going around giving yeses and nos like free candy. Having learned to give clear answers did not come with giving them too easily. We don’t always have enough data to make informed decisions nor the clarity to make confident ones. When possible we must take the time no to let it pass by, but to actively seek clarity. And when no data is available or no time can be taken, we should at least be clear about the risks we are taking when saying yes or no to something, and be ready to deal with the consequences those risks can have for ourselves and for those around us.

Note: I am still seeing that coach every 2–3 months to check-in on myself, I keep a journal to look at my emotions from the distance, and I talk to friends. All of these help me rebalance.

Being genuinely open to diversity requires empathy and adaptability.

Product Management is a job in which you can only succeed by working collaboratively with a vast array of people in different functions and roles. The complexity of the product you work with is reflected in the organization (or is it the other way around?). The more complex your product or organization, the more complex the sets of people and teams you have to work with.

Add to that a successful hiring process in which a colorful mix of nationalities, levels of experience and personalities are brought in together and you have a truly diverse environment to work with. To illustrate it, imagine a team with a Brazilian PM, an Indian designer, a Russian engineer, an Estonian data analyst, an American copywriter, and a German illustrator; all between the ages of 21 and 53; practicing hinduism, catholicism, with some agnostics and other atheists; some who have never left their hometown and others who have lived in 7 different countries across 3 continents; all in a range of personalities from gamer introverts, car-racing ambiverts, and music writer extroverts.

That is the environment I work in, and it has been like this even when we were 10x less people than we are today. From the beginning, many of my behaviours have been put to the test in these conditions. As an example, while one of my strong skills is being an open communicator, with initiative and charisma, this skill is not helpful if I am working with a deeply analytical introvert who prefers small groups to articulate his ideas or who one who needs times to get her thoughts sorted out before sharing them. As a hiring manager participating in recruitment and as a product manager being involved in meetings from strategic planning through design explorations all the way to testing sessions, my experiences have taught me a lot about how to see the value a person adds even if they communicate in a style different from my preferred ones. I have gone from saying no to someone based on my “gut feeling” to saying yes to a person because they demonstrate skills, knowledge and effectively complete a task without them matching my taste in Netflix shows or my views on politics. I have been able to do this by systematically involving a diverse group of people in the process, putting an as objectively as possible set of criterias around the decision, and learning to manage my subjective reactions. I have had to learn to balance gut feeling (which is just experience) with more detailed and careful analysis.

To give you a couple of additional examples, I have learned to be comfortable with 10–15 seconds of silence in a meeting after asking a question (try to count in your head… that can get too long for most of us). I have learned that the fact that someone has a need for status and recognition, does not mean they are false and arrogant. They just have different psychological needs. I have learned that just because someone has potential does not mean they will develop it, or just because someone has proven experience will they succeed at every other resembling challenge you throw at them if circumstances in their lives have changed.

All of this requires not that I stop being myself, or that I try to change who others are, but that I learn to relate to others and tune into them, while at the same time respecting and managing my own values, beliefs and emotions. I am not a social success wherever you put me nor am I an always-effective negotiator, but I can confidently say I am able to work with many different people in different environments in an effective and honest way, regardless of our differences.

This lesson is, of course, not just provided by this job experience alone but by all the social interactions I live through. That said, this still remains an important chunk of all of them, as this is is the job I have been in the longest and it represents so far 1/3 of my working life so far.

It is not the comfort zone if there’s still a good balance of challenges and benefits

For the past three work anniversaries I have taken a break to ask myself if I am getting too comfortable. After all, I am a millennial who grew up surrounded by videos and articles of motivational speakers shouting at me: get out of your comfort zone!

I also work in an industry with high employee turnover (at least last time I checked), and each of those years has been “the longest I have ever been at a job”.

Many of the issues I dislike at work I find in other places because they are always about people. However, there is a great match in values among the people we’ve hired throughout the years which has allowed to balance our differences and keep the usual human conflicts to a healthy level. This has been the main reason to stay around this long. But in the process I have also been able to see my work and my skills evolve in a way I wouldn’t have had I not had the patience and dedication to see them through.

Six years combined with a lot of change (read the numbers above again as a reminder) have given me a combination of experiences equivalent to changing workplaces (new faces, new objectives, new offices, new locations and another host of variations and exponential changes). All without changing the market in which we are neither the customers we serve. Details of how we approach them, yes. New markets, larger customer base, diversity of users, yes. But not the essence of them.

This means I have been able to see our product evolve and get stuck. Succeed and fail. I have seen our customer base transform. Relationship with departments born, stale or die. I have seen new departments being created, and I have even designed new roles.

I have also seen some decisions we have made or left pending which have brought both good and bad results down the line. Just when we thought that was not an issue any longer…

And no, I am not comfortable. I still get scared in the face of new challenges. I still get excited and frustrated. I still find obstacles along the rides I can smoothly drive thanks to experience. But I also find new rides. I always see there is much more to learn and grow and try than what I know. And I never feel like a day is anything like the previous one.

The lesson for me here has been that if I move from place to place, I might just encounter myself with the same problems, run away from them instead of learning how to handle them, and end up giving up on humanity. But by having stayed long enough I have been able to see my impact and that of others, I have been able to learn from mistakes which results can only be seen with time, and I have learned that many truly valuable things take time to develop. Like a bonsai. Like my marriage. Like the friendships I have built in this place and previous ones.

I won’t be here forever, but for now, I will keep on declining those kind Linkedin offers, and then I will leave, before the challenge and fun start fading away.

It is all is about people, and people are both beautiful and difficult.

There are many hard skills I have developed these past six years. Yet the most powerful are all about people.

What I said above about diversity and adaptability? Product management is a lot about that.

A great product manager has to be able to sit and analyze vast amounts of customer feedback and make sense of product data without getting lost in insignificant details. This requires to have patience, curiosity, and interest to interpret the needs behind the feedback, the emotions in it, and how they relate to data. There is people behind those two things: customer feedback is an obvious one, but it may not be obvious for all that product data is all about users behaviour.

This product manager needs also to look at business data and match the previous one with this one. And guess what? There are also people behind those business numbers. Investors and managers with expectations and responsibilities that keep them awake at night (in stress) or get them out of bed in the morning (in excitement).

That same product manager analyzing all that data has to be able to make conclusions and present them in a way that grasps the attention of her colleagues to be able to drive action from those insights. This requires to tune into people. It requires being able to disagree and challenge, but also to disagree and commit.

Next, that product manager will sit with a designer passionately explaining details of flows, behaviors, pixels and colors that combined solve the problems brought up by the insights. The product manager will have to graciously match the thinking of her colleague without necessarily having all the vocabulary or technical understanding of the designers crafts, yet with the humility to respect and trust her colleague, but the confidence and ownership to highlight possible risks or mismatches with customers or business reality.

The same story will have to repeat itself with the engineers, and the analysts, with the researchers and sales people. It will be all about people. From product discovery through product delivery. From strategizing through execution. From celebrating wins to learning from losses. People will be the reason to make it or break it all along the way.

In these six years, it has all been about the people. I am proud to be part of the story that has grown a strong product team. Smart, dedicated, curious and passionate professionals. I have learned from some and taught some others, and I hope I can keep on doing it for a bit longer…

Happy Anniversary to us, Pipedrive! 🎉

Maria 🌺

Originally published at https://marialasprilla.wordpress.com on March 23, 2021.