Leadership in CS: mistakes and learnings from my own experience

Laryssa D'Alama
Customer Success Stories
7 min readMay 20, 2020

“What is it like to run a CS team?”. “What are the main challenges?”. “How complex is it to manage dozens of CSMs?”. “What are the barriers you face along the way?”. These are examples of questions I frequently hear from people from the market and also colleagues who want to know more about leadership in Customer Success. The high interest on this subject is due to the fact CS is still not that common in the Brazilian market, and secondly, because I’ve been running CS teams for 6 years, leading a considerably big team (currently about 60 people).

I’m completely conscious I still have a lot to learn about leadership and Customer Success — who doesn’t? But I also know that some things I’ve already faced can help others find shortcuts in their own experiences, especially who is starting at CS and first-time leader. That’s why I decided to share some learnings and mistakes I made and that I consider helped me be a stronger CS leader for my teams and for the company I work at (RD Station). Hope some of them can help you out. ;)

Being authentic

It’s common to think you should look like someone else to be a leader — but what does it mean? In the book Unusually Excellent (highly recommended!), Jon Hamm says the best leaders he knows are just themselves. And they bring their unique characteristics into business. This not only makes you feel comfortable but also allows others to really see who you are. When you are not comfortable, pretending to be something different, it creates a barrier to trust as people can’t see who you really are — and they feel it.

Find your own way to be a leader — and remember your way is unique! At the beginning of my career as a leader, I was 100% focused on copying others. I don’t think it’s wrong when you have good things to learn from experienced people (mirroring is good!), but after some time I cottoned on to the fact we must balance mirroring good practices with using our own characteristics. During all these years, I learned how to bring my own personality into my leadership role — like giving others funny nicknames (Leozito, Yorrita, Rafita etc), discussing animes (japanese cartoons) with CSMs and making really bad jokes to my direct team. This not only lets your day be lighter, but makes others see you as what you really are: a human like them.

Focus on people, and then on results

Once I heard: “With great results you’ll have happy people”. Years after, I’m sure the right quote should be: With happy people you’ll have great results. I like to say a Customer Success leader is the CSM of your own team. Let me explain: we must guarantee our clients (team members) are reaching success (their professional development) through having their barriers removed (constant feedback, assistance in their routines) and showing the right steps to succeed. The better we act to ensure someone is on the right path to success, the more satisfied and the longer they’ll stay in our companies. Team turnover is “churn”. People getting promoted is “expansion”. And happy CSMs are advocates of our company, helping to bring new talents and strengthening the company value in the market.

Show the road ahead — and make the team be part of it
“Where are we now?”. “What are the next steps our team should be taking?”. “And why?”. In CS, we are always evolving. There is always something else we can try to increase the results, even when we already have good ones. And the best way to take the upcoming steps is building the path together along with your team. Here I can tell you about a mistake I made in the past.

At the beginning of 2017, I was running the Onboarding teams of RD, and I was very excited to show to my teams the projects we would execute during that year. The challenges seemed to be well known and the prioritization was perfect (in my opinion), but after presenting everything to the team, the surprise came: some people didn’t buy into it. Talking to them, I realized some important things we could do regarding their operational routine — which would impact positively the customers — were not mapped. And that is because I was not in the operation and I didn’t listen to them properly before planning the next year. That was a very important learning for me, and after that me and the team leaders started having some sessions to build together some ideas I could use to the upcoming department plannings.

It doesn’t mean we will be able to listen and accept everybody’s opinion, especially in big teams, but it is important to capture the main pains and ideas the team has. Sometimes they can be even better than yours. Additionally, every time you have the chance, be transparent with numbers, challenges and future plans. This makes the team feel more comfortable by knowing where we are now and what is about to come.

Keep the purpose alive

We all know it is not easy to daily deal with customers desires and needs. Especially when there is a bug to fix, a financial mistake to be corrected, a demotivation due to bad strategies using your solution and so on. Sometimes it is stressful. And this can make a CSM think: “What am I doing here? What is the purpose of it all?”. If your team starts to feel tired of their routine, they can leave you. And they will only think about leaving the position when they don’t see the noble purpose of their jobs, if they don’t see the huge impact they cause by helping others.

At RD, we keep our mission alive every month, repeating the mission aloud in the CS monthly meeting. Our mission? “Empower customers and partners in the Digital Marketing democratization”. And why is it so important? Easy: to remember why we wake up everyday to go work. To remember during very demanding days the power of what we do in every small action. It is powerful. Keeping the purpose alive makes your team go further in their CS careers.

Be close and accessible

Who doesn’t want to be listened to? To feel important, represented and close to their leaders? I believe everybody does. Knowing you have a voice and the leadership wants to hear from you is one of the most essential things the new employees care about. And not only it: as I told you before, knowing what happens in your team’s operation is crucial to help you make better decisions about the present and the future, impacting customers and the company.

At RD, leaders are expected to have recurrent 1–1 meetings with their direct team members. In my case, I not only have bi-weekly 1–1s with my direct team (team leaders), but I also have 2 slots/week opened for skip-level 1–1s with CSMs. In these meetings, I like to hear more than talk, letting the content of the meeting be chosen by them. I like to hear what they are thinking about the company and their jobs, as well as to know if they have opinions about specific subjects and their plans for the future. Hierarchy is a natural obstacle, and these meetings help to break it. Everybody wins when we are together and aligned.

Being frank is better than firing someone

We normally see difficult conversations as something bad (giving feedback due to poor performance, for instance), but the right way of seeing it is as an opportunity of letting the other know what we think. It is an opportunity for change. To help other people grow. And this is completely fair and powerful.

What makes the difference is “how” we do it: using the right words, and showing the others we care about them. I like the Radical Candor approach from Kim Scott, in which she believes the key to success is balancing between challenging someone and expressing how you care about them.

Source: radicalcandor.com

Another important thing they say is: if you don’t know how to say something, say it anyway. It is better to ask for apologies about the way you talked than not giving someone the opportunity of knowing something important. Firing someone should never be a surprise for your team, as, ideally, you give them recurrent feedback. Having difficult conversations in order to make people involved is better than firing them in the future because I chose to be in silence in the past. And it is also very grateful when you see people improving after a good conversation. This makes you feel like a great, amazing leader.

Really help others go further: who will be the next you?

A great leader can be measured by the number of team members succeeding in their careers. I believe this is the most important role of a leader: developing others. Making people fly. Because when they succeed, they go further. And when they go further, so your company goes further (remember again: happy people make great results).

Don’t forget that you also want to keep evolving in your own career. And for this, you need to have successors able to replace you when you are ready to accept new challenges. I’ll give you two examples of mine:
1) when we decided to split the direct-customers and partner onboarding teams and
2) in my rotation from onboarding team to CS team.

In both situations, it was crucial for me to have prepared professionals to replace me — otherwise I wouldn’t be able to move forward. Fortunately, I am always preparing my team leaders to become managers like me, and on these two occasions I had the pleasure of promoting team leaders as managers (Manu and Bruno — great professionals!). Seeing promotions like these is surely one of the best moments for a leader.

Hope you liked the tips above. And let me know if you agree with them, and also if you have another point to add. Hope you succeed in your career!

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Laryssa D'Alama
Customer Success Stories

Customer Success Senior Manager @resdigitais #CustomerSuccess #CustomerOnboarding