My First Year in a Leadership Role at Wrike
Moving up to a leadership role here at Wrike was both a challenging and exciting experience. I realized how everything was much simpler when I was only responsible for my own results. But as a leader, I gained the responsibility of helping my team achieve amazing results, too. I’m a big supporter of continuous self-education and have been reading a lot of books on management for a long time. However, there’s often a big gap between reading about something and understanding how to apply this knowledge to real-life situations.
In this article, I put together the most important insights I took from my first year in a leadership role at Wrike. I was aware of some of them in theory, but I never fully understood their importance and impact. They definitely fall into the “I wish I knew this in the beginning” category.
1. Prioritize prioritizing
I think it would be fair to say that we’ve all opened an email or Slack message to “quickly” go through updates only to realize we’ve been scrolling for an hour. And we’d be lucky to have even answered a third of them. We’ve also, at some point, just opened our work laptop when a colleague asks for quick sync, which of course turned into a lengthy conversation, and somehow it’s already evening. What do these situations have in common? We allowed external factors to affect our priorities, and instead of focusing on what’s important we just dealt with whatever was on the top of our to-do list.
It actually took me quite a long time to realize that even though I prepared daily to-do lists, there were still many items left pending by the end of the day. So I started a new routine: Before checking any communication channels like email or Slack, I put an exclamation point next to the most critical items on my daily to-do list. Then I scan through each email and ask whether or not it aligns with my top priorities.
Another thing I started doing is prioritizing key tasks related to my team. If there’s anything hindering my team from doing their work efficiently, I make sure that I dedicate enough time to address those problems.
2. Keep experimenting
Sometimes, new leaders deal with the fact that their organization already has established processes. This didn’t happen to me, however. At Wrike, we like to say with my manager that in the beginning, we were working in a “startup inside a startup.” There were no rules or guidelines — we had to create our own way of working, confirm that we were doing the right thing, and make sure that our targets were aligned with the global targets of the whole customer-facing team. That was (and still is) a big challenge, but boy, is it exciting! Experimenting had to become a constant part of what we do.
When we finally identified our direction, it was tempting to slow down and spend some time optimizing our processes, like tying up loose ends and clearly describing who should be doing what, when, and how. While we did spend some time on that, we decided that trying more processes and continuously challenging ourselves on whether or not we’re moving in the right direction was more important. Yes, many of our experiments failed. However, one of the principles of our customer-facing team is to “fail gloriously,” Meaning we shouldn’t be afraid of making mistakes as long as we learn from them, get up, and try something new.
3. Replicate success
The main goal of experimenting is to identify approaches and algorithms that work well. And once we find a potential solution, the next step is to check whether it was a flash in the pan or something that can be replicated. So this step can actually be part two of the experiment. There were plenty of cases when the first attempt proved to be efficient, but the second attempt was nowhere near as good. For example, when we delivered a webinar on how to adopt a new product successfully, the first round was a huge hit. We had a large number of attendees, a ton of questions during the Q&A section, and amazing feedback. Since we were excited about its success, we decided to deliver a follow-up webinar to expand on the topic and share more best practices. However, the second one didn’t generate the same level of engagement. It seemed that for those who were interested in the topic, only one webinar was enough.
Now, whenever we strike gold with any new initiative, we always ask ourselves, “Can this be replicated?” We give it another attempt, and if we’re successful a second time we ask, “Can this be scaled?”
In the past year, we identified several initiatives that passed both of these questions, which became an essential part of what we do. But we’re still not planning to stop experimenting, replicating, and scaling.
4. Automate it!
We performed a lot of work manually in the beginning, from creating detailed spreadsheets with lists of customers to prioritize our efforts, to sending way too many emails. And while these manual processes allowed us to identify the direction we wanted to move forward in, looking back now it’s clear that we should’ve started automating some of these processes much earlier. We were able to save an impressive amount of time by removing the manual, repetitive processes. After the first round of leveraging automation, our results improved by more than 100%!
However, I learned an important lesson about automating your processes: You need to quadruple-check your automation rules. One or two mistakes can cause a huge headache when you’re working manually, but when these mistakes are scaled due to automation, they can snowball into a disaster.
5. Let your team make their own mistakes
I always had a problem delegating and chose to do things myself whenever possible. This became a big problem when my team started growing quickly. I was able to help several team members from time to time, but at some point, my schedule was too packed. I recently read a book called “Procrastinate on Purpose” by Rory Vaden that reflected my own situation. Vaden states that we’re afraid to delegate because we don’t believe that our team can produce the same quality of work that we can. I couldn’t agree more. Yes, it’s unlikely that your team will do everything perfectly from their first attempt. But if you don’t let them make these mistakes, it’ll be much harder for them to learn how to do things the right way.
I remember what helped me stop worrying too much when delegating. I started asking myself, “What’s the worst thing that can happen if a team member makes a serious mistake?” Surprisingly, I felt a huge sense of relief when I realized that most of the time, there wasn’t anything that couldn’t be fixed. I felt better about and more confident in delegating, and now I’m a big fan.
6. Be mindful of your workload
This point closely relates to the first section about prioritization. It’s usually impossible to finish all of your work. As a matter of fact, it’s usually not possible to even finish most of your work. You’ll really be making decisions daily about what you’ll focus on and what you’ll deprioritize.
At Wrike, I finally learned how to say “no” to incoming work. It was much harder than I thought. We tend to underestimate the amount of time it takes to finish certain tasks, as well as how that time aligns with our priorities. For example, when asked if I could own an initiative that would only take 30 minutes per month, I agreed to take it on. It’s fine when you only have one of these kinds of tasks. But more and more “small” tasks started to emerge, and at some point, I calculated that all these “small” tasks combined took up an entire workday! One of our Wrike executives summarized it best: “When juggling with different activities, just like balls, the most important question is which balls am I willing to drop?”
I’ve only scratched the surface of the challenges that many other leaders face on a daily basis. However, it was (and still is!) fascinating to see how theoretical aspects of management and leadership can be applied to real-life scenarios, what’s working, and what’s not. I’m sure the list will grow quickly as I encounter and try to solve more challenges along the way.
