The struggles of a first-time manager — and what I’ve learnt along the way 😳

At the age of 27, I found myself in a position I had never been in before — leading a team of 8 people. Becoming a new manager involves endless challenges, from hiring to firing, meetings to messaging, facing hundreds of questions and uncertainties along the way.

While I still haven’t figured everything out, I have found that writing my thoughts down helps. So does seeing that my role models have experienced something more or less similar. In this article, I’ll share some insights from my own experience, what I have learnt so far, and what I would do differently.

Jumping into the management deep end 🏊🏼‍♀️

I joined productboard in 2018 as the very first member of the People Ops team. That’s right, the entire People Ops ‘department’ was me. I felt like a cheerleader for every single employee in the company, and especially for all the HR and hiring processes that we had to build from scratch.

Despite the obvious challenges of being a one-person team, I had so much fun those days. Coming from a corporate world to a startup with a flat structure, working with the company’s founders as well as the smartest, most empathetic developers, product managers, and designers — this was an absolute adventure.

I loved all these areas I could play with, be involved in, and learn about. With pleasure, I observed as my learning curve grew steeper and steeper. It was a joy and a thrill, but it was also hard. I got mentally exhausted trying to stay focused and do proper, thoughtful work.

It was difficult for me to admit that the way I was working was a) not scalable, b) not sustainable, and c) not healthy. I was working like crazy. I found sleep and even holidays boring. All I wanted to do was focus on anything productboard-related.

I knew there are only 24 hours in a day, but I wanted to deliver high-quality work, just like everyone else was. Around this time, I realized I needed to scale my team and the scope of my work. I needed to give away my lego. 😳

I am super grateful that the founders were on the same page. Actually, they pushed me to scale the People team. In hindsight, the only thing I would have done differently is hire people sooner.

Scaling the team 📈

First, I needed to figure out where we wanted to go as a People Ops team. Naturally, this was closely tied to where we wanted to go as a company. If the big picture is clear, then you can scale the architecture and processes, and then you can scale the team. You can determine both your growth strategy and the team road map.

To determine what each People Ops team member would focus on, we had to figure out what areas the People Ops Team influenced and then create a dedicated role for each area.

We realized that having one recruiter focusing on every single role across all locations was too slow and inefficient, so we decided to hire a recruiter per department and location. This way, each recruiter can also focus on other projects and deliver the best candidate experience.

Our team was changing month by month. From 2 people we grew to 3. A few months later, we were 6. A month later, 12. I remember an all-hands presentation where there were too many new faces to fit on a single slide. The old ways no longer worked. Every month I felt like I had an entirely new job.

Throughout this process, I remember asking myself: How do I grow a people team while ensuring that I’m on top of all the necessary day-to-day tasks — like interviewing candidates, onboarding new-starters, organizing meetings and community events, implementing tools, building scorecards, and focusing on productivity and the bigger picture?

To this day, the honest answer is: I don’t know. But one thing I have learnt is that you can only focus effectively on one project at a time. So you have to figure out what to prioritize at the very beginning (Something I’m afraid I didn’t do! 🤯).

With the team up to 12 people, our new Chief Marketing Officer, Tapan, recently told me: “Now you have to gain a macro view.” If I want to have one-on-one meetings with everyone, I won’t be able to focus on any other job, whether it be interviewing, hiring, strategizing, or supporting the team. There simply aren’t enough hours in the day.

Meetings 🤯

Our meetings and standups also had to change as we grew. In the early days, we had an agenda and a list of what we wanted to share weekly, calibration meetings with all the hiring managers, a sync with the CEO and CTO, plus weekly one-on-ones. But with all the actionable items resulting from these meetings, there wasn’t much time for anything else!

Going through everything on the list took about 30 minutes — and there were only two of us! Doing the same with 12 people would have taken the best part of a day. If we wanted to have a reliable forum where everyone could share their feedback, something had to change. But by the time I had come up with a new process, more people had joined the team. I learnt that the only way to stay effective in a fast-scaling team is to constantly change and adapt.

This point perfectly reflects the current situation: COVID 19. Since everyone on the team now has to work from home, we all have to adapt — and fast. Because we are all separated from one another, we constantly need to over-communicate everything and be there for each other at all times. We need to meet more frequently than ever before, to ensure that everyone is on track, has clear goals, and feels supported and part of a team.

Here’s a list of meetings we now run as a team of 12 …

• Recruitment standups with recruiting leads
• People Ops heads-up — a sync for the CZ team to see what everyone is working on and how they are feeling
• People Ops all hands — across both our CZ and US offices, facilitated by Jess.
• Debriefs — calibration with hiring managers, updates on hiring
• Retrospectives — after we finish a project or close a role, we look at what went well, what went wrong, and what we can do differently next time. This ensures that we are always improving our processes.

And with the coronavirus outbreak forcing the company to go fully remote, we’ve had to rethink the way we connect. Here are some of the meetings we now run as a team during self-isolation …

• 🕴🏻+ 📹 Standup meetings — I have heard that product teams and other companies have standup meetings more frequently. Instead of once per day, they do it twice or even three times a day.
• 👩‍❤️‍💋‍👩+ 📹 One-on-ones — I was thinking about having bi-weekly one-on-ones and then solving urgent status updates on a weekly basis with the whole team. This would keep one-on-ones free for more personal stuff. But since the team can no longer solve issues on an ad hoc basis by tapping me on the shoulder, running biweekly one-on-ones simply wasn’t possible.
• 🌮+ 📹 Virtual lunch breaks — We have regular, informal, virtual lunch breaks as a team, during which we talk about what’s happening in the world and how we’re all feeling. It’s a great chance to connect and boost morale.
• ☕️+ 📹 Virtual coffee corner — Our amazing Operations team twisted our Zoom room and now we have the “Corona Coffee Corner,” a virtual space where you can meet colleagues 24/7.
• 🏋🏻‍♂️+ 📹 Virtual working out — Juan, one of our backend engineers, leads a virtual workout 3 times a week to keep everyone in great shape. We even gamify the process of keeping fit with communal fitness challenges!

Servant leadership — the team always comes first 🦸🏻‍♀️

This is something that resonates with me endlessly. I have a great role model in one of my favorite managers, Cori, who led a massive remote team across different time zones. The first thing she did each morning after waking up was to check that everyone is doing ok.

I want to be a servant for everyone in my team. I want to help them be successful in everything they do. I want to enable them and encourage them to reach further and realise their potential. In fact, this is what all our leaders at productboard aim for. Take Toni, our amazing Head of QA, who had this to say on the notion of servant leadership:

“I always think about it in the context of this graph with the 4 quadrants. For me, removing blockers for my team, be it work-related or even personal if I can help, is always in the Urgent and Important quadrant. So it comes first, ahead of almost anything else.

Also, I like to think about productivity at the team level, not just the individual. So even if I can’t personally help right away, there may be someone else who can. Sometimes all that’s needed is a bit of coordination to get things going, and in the end we’re productive as a team. Even if someone had to sacrifice a bit of their time to help, the net gain is still positive.

At this point, the team is so used to helping each other that sometimes the problems are already solved by the time I find out about them! This also ties in well with being a servant leader, as you prioritize helping your team. However, you are also responsible for giving guidance and direction, so you need to find the right balance here.”

1-to-1s and Growth Plans 🌱

I remember running my very first 1-to-1, and it was hilarious. I also remember all my own 1-to-1s with my ex-managers. I desperately wanted to talk about my uncertainty and imposter syndrome, about where I wanted to grow, what I wanted to really focus on, how I could learn this or that, but there was usually zero time for this.

Theoretically, I knew that 1-to-1s are supposed to be time dedicated to your direct report. Time just for them. And it’s fully up to them how they want to use it — and whether they want to use it at all. They can have an agenda ready and share it with you prior to the meeting. They can go through projects they lead and drive, ask for feedback, and discuss the courses and conferences they want to attend.

But I learnt that most of the time, I usually go through status updates — where we are with specific candidates, how the pipeline looks, what events we are organizing, who we are sourcing, etc.

Realizing this, I knew I needed to take the initiative here and save at least 10 minutes per 1-to-1 to focus solely on the person’s mood, wellbeing, and growth plan. For this, we started playing with a card deck that comes with the book Help Them Grow or Watch Them Go.

I have found that radical candor is the best approach when it comes to communication. I lead honest conversations with my teammates and ask for feedback directly in one-on-ones. Informal conversations are also important, as that’s where we build trust. Ultimately, it’s about doing, not saying. If you want people to feel comfortable sharing stuff with you, you need to act in a way that deserves their trust.

Delegator or micromanager? Balancing two extremes ☝🏼

While I am trying not to be either extreme, knowing when to delegate and when to dive in yourself is one of the toughest parts of management.

If I step back too much, I’m the absentee manager who doesn’t get their hands dirty when the team needs it most. And given the number of projects I have on my plate beyond people management, it could seem like I’m not really coaching everyone in the same way.

On the other hand, I know that if I get too involved, for example by asking my amazing reports to run every decision by me, I would be perceived as a micromanager and control freak. If I need to give my opinion on everything my team is working on, there’s definitely something wrong. By doing this, I’m showing them that I don’t fully trust them. I’m not letting them learn by doing.

I think that self-reflection and empathy helps here, as does asking your team members for feedback. Do they think you are too hands-on or not enough? Always emphasize that you welcome opinions, whether positive or negative, and reward people who express them. Let your team know that it is totally OK if anyone disagrees with you. Ask them: if you were me, what would you do in this situation?

Constant context switching 📺

This is another battlefield for me. I felt so overwhelmed by back to back meetings, each one about something completely different. I’d be jumping from a calibration meeting to one about our new careers page, trying desperately to switch focus from one idea to the other, while in the meantime receiving 34 slack messages and 10 emails about 44 completely different topics.

There’s really no obvious fix for this problem. Sometimes you just have to roll with it. What helps me is to go through my calendar each evening and prepare myself mentally for each item for the next day.

One hack we use is “speedy meetings,” where instead of scheduling a 1-hour meeting, you schedule it for just 50 minutes. Likewise, half-hour meetings become 20 minutes. The ten minutes you save at the end allows each participant to prepare mentally for the next one, or to go get themselves a refreshment. What’s more, having less time helps you run meetings more efficiently!

Another idea is having “No Meeting Wednesdays,” which allow everyone across the company to get some much-needed focus. Companies like Figma and Lattice have already introduced this initiative.

And finally, a bit of gratitude 🙏🏼

I admit that my experience of management has been one long and challenging learning curve. I sometimes feel like I’m not experienced, empathetic, or patient enough. But despite the constant challenges, I feel super lucky to have leaders who believe in me and a team that always helps me strive for better.

I am so fortunate to be surrounded by people who are my daily inspiration. I am also tremendously grateful to have our VP People, Jessica. She has been a great source of support for us all, especially during this difficult time. I am super happy to have someone at productboard who can help us get through this together.

Love note 💌

Thank you, team! And thank you productboard! And thank you Nick Edwards, for being our amazing addition to the team. He helped me with this article and provided with his honest feedback. So much love and health to everyone!