6 Things I Learned from my First Year as a Senior Leader

Exactly a year ago I was promoted to director of account development at Wrike. Somewhere in the back of my head, I understood that it was a senior leadership role, but at the time I was so busy with what was going on, I never had a chance to pause and think of what this role entails. The project I have been building with my team — hybrid sales & customer success motion for the SMB segment of Wrike customers — grew into a company-wide initiative. The whole segment was now served in the hybrid format and to scale quickly and effectively a lot of work had to be done. After about 3 quarters the dust started to settle and I slowly began realizing that I was now in a different role. Yes, it did have similarities to what I was doing previously, but only to a certain extent. Now, when we’re about to close the first “official” year of the account development management motion, I took a little time to reflect on the things that have changed for me since I started in the new role. That said, I would like to share the 6 things I learned from my first year as a director here at Wrike.

Your initiatives need to impact a lot of people to make a difference

As an individual contributor, you have full control over your result. You either hit the target or you don’t. If you implement any new approach and it is effective then probably you’re doing the right thing. On the manager level, a key objective is to serve the team taking into account individual strengths and leveraging them to their fullest potential. The support provided can also be in an ad-hoc format and different types of initiatives can be launched to help the team member. On the director level, the game changes one more time. Not only do you need to come up with ideas that have the potential to improve the results, but the impact of those ideas needs to be noticeable on the whole team’s level. An idea that could improve the work of one team member is still good — but it would be reasonable to delegate the implementation of such an idea to the line manager and focus on larger initiatives. As a result, when I’m brainstorming on how I can serve my team better I have an additional filter through which I drag all the ideas — could this, at least — in theory — make a difference for the whole group or, at least for a large part of it. If the answer is no, then I would probably ask the managers to run this idea as a pilot project with one or several individual contributors and focus on other areas.

Decisions need to be data-driven

Obviously, it’s not the case that I wasn’t looking at the data when making decisions previously, but in my current role, it became even more important. Any change in what we do and how we do it needs to be justified by performing, at least, a high-level analysis. For example, we may consider trying a new communication channel for prospecting. Before making the first step, we analyze what would good look like. How many customers need to be engaged per day/week/month to call it a success? What trend would be an indicator that everything is going well versus whether any change is required? How are we going to measure the results and where? These and many other questions rely on data on also on educated guesses that we have to make regularly. It’s important not to overdo the analysis — otherwise, there’s a risk of decision paralysis. However, getting a good enough volume of data before beginning a new project can increase the probability of success dramatically.

It’s important to fight the desire to help everyone yourself

One of the first mistakes I made when I moved to the director role and started managing managers was basically disregarding the whole idea. Instead of allowing them to make their own mistakes and learn from them, I felt a strong urge to jump in myself wherever help was needed and assist individual contributors (ICs). While yes, the problems did get resolved, such an approach was far from effective in the long term. ICs need to trust their managers and be able to rely on them — otherwise, the whole concept of line managers would be questioned. Also, me helping ICs directly created confusion for them regarding who they were actually reporting to. While I still have 1:1 meetings with ICs every now and then, the managers are (and should be) the main go-to persons whenever any questions or problems emerge. And I, as a result, have more time available to focus on strategic activities that would make a positive impact on the whole team.

Operating in ambiguity is a new norm

I sometimes reflect on the old days when I was a sales rep or a customer success manager. When I’m reminiscing that time it seems so easy — I had my book, KPIs, targets to hit, and ambiguity was not a common word in my vocabulary. As I shifted into the leadership role and started making a vertical career I quickly realized how many unknowns the leaders have to deal with. No one knows the right answers — one has to review the data, make educated guesses, build the minimum viable product (MVP) test it, understand that it’s a failure, rebuild it again and again, and finally understand that you’re on the right track, and then scale. And there can be many iterations of “understand that it’s a failure” and “rebuild it again” before you get to success. At the same time as a senior leader one needs to provide as much clarity as possible both to ICs and line managers. They need to have an understanding of the key priorities, what success looks like, what’s the best way to get there, and many many other questions. That said being able to thrive in ambiguity and constant change is a key skill for a senior leader.

You have to be the beacon of light in tough situations

There are many situations leaders have no direct impact on that create a lot of stress and ambiguity for the team. Even in my relatively short 6-year tenure at Wrike the company has gone through multiple acquisitions and leadership change. When such change is taking place team members start to worry what impact they’re going to have on them. Concerns vary from big (e.g. are there going to be any layoffs) to small and mid-sized (e.g. are the books of business going to change? Are there any changes coming with the tech stack that is currently used? etc.). It is the role of the senior leader to work with these concerns, address them and find the right words even in situations where not all answers are available. My approach always was and still is the same — stay positive and help the team to deliver business outcomes. Since the nature of the hybrid work our team is performing is quite specific — we’re responsible for both sales target and retention target — my narrative was pretty straightforward: we’re responsible for two mission-critical functions for our business: generating new revenue and retaining existing one. So as long as we do our work well, it would be very unlikely that any change would impact us. Obviously, there are business scenarios when any team may be at risk — but it’s always a game of probability. And it is in our power to reduce the probability of any negative change to a minimum. I also have a habit of avoiding the “everything is great” narrative. I’ve seen more than one case when such a narrative was perceived by the team members as fake and unconvincing and the only outcome was a decreased trust in the leadership. However, I draw a thick line between stating that everything is great and maintaining an optimistic mindset searching every day for new ways to perform the work better and deliver outstanding results. “What else can we do to be successful in our roles?” is the key question that I ask myself and the team members over and over again. And I have to say that this spirit of innovation and entrepreneurship can be quite contagious.

Be yourself and remain authentic

One of the first things I noticed in the director role was a certain change of behavior and attitude of the team members. Those who have known me for a long time didn’t demonstrate much of a change, but newer team members were noticeably choosing their words carefully and avoided proactively expressing their opinions. From the early days of the role, I started pushing for a change. I emphasized over and over again that each rep was much closer to the customers than I was (since I was finally pushed to give away my book of business) and that it was very likely that their perspective regarding certain situations, dynamics, and more was way more objective than mine. I also asked the experienced reps to continue being vocal about the challenges as well as about things that, in their opinion, weren’t working well. Over time this approach led to amazing results. Team members openly share their suggestions, and concerns since they know that both myself and my leadership team would take the time to thoroughly review them.

Please don’t get me wrong — I’m not saying that every single concern or suggestion leads to change — there are many situations where for quite objective reasons change is not possible at the moment (e.g. when it makes sense for the rep but contradicts with what’s right for the business). But I strongly believe that the understanding that the feedback is welcome and would be taken into account contributed well to the atmosphere of trust that we’ve been building from day one. I’ve heard more than once “Artem, you’re a very straightforward person!”. I completely agree with that statement and intend to continue being that person. If something is wrong — I will never sugarcoat it and will be very direct about it. If something is right or someone deserves praise — I will make sure that the person is aware that he or she is doing an awesome job. This may be perceived from the outside as a too-blunt approach. But I believe that being sincere in all types of situations helps to build trust with the team and trust is something that I value a lot.

These were probably the main insights I got from my first year in the senior leadership role. Can’t wait to see what the next year is going to bring!