In customer success, as in life, you can go through multiple transitions.  

A career transition can mean a multitude of things. It could mean moving into a leadership role i.e. going from a Customer Success Manager (CSM) to a Director of Customer Success within your organization. It could also mean joining an entirely different organization, like a startup, and starting a customer success function from scratch.

However, this article will instead examine how we adjust when we become CS leaders, specifically:

  • The best practices for how to move into an already-established team
  • The challenges you’ll need to overcome in your new leadership role

What does being a customer success leader mean?

I've had the fortune of being a CSM. I’ve also built a customer success organization from scratch, and in my last two roles as Director, I was able to build up an existing team. If you’re reading this article, chances are you’re deeply interested in customer success, and I have a feeling you’re going to be in a leadership position at some point.

Becoming a CS leader can mean a few different things. It can mean taking responsibility for either building an organization or growing an organization that already exists. We can address those responsibilities by thinking about transitions.

Now, as you’ll know if you’ve been through a leadership transition or moved into a different job, it can be complicated. However, they don’t have to be. We can take a few pointers and use them in any type of career transition that we go through.

A CSM’s transition from an individual contributor to manager
The transition from individual contributor to management isn’t exactly the simplest one; there are some fundamental shifts that you need to make when you go from dreaming about this career move to making it a reality.

Understand that a leadership transition can be stressful for all involved

Whether it’s your first time being promoted or your fifth, whenever you enter a new role and inherit a team, you inherit everything that comes along with it.

Whatever camaraderie, togetherness, or even infighting already exists is now yours to deal with. You’re inheriting individual contributors (ICs) i.e. your Customer Success Managers (CSMs) are individuals who work together in any way they can.

If there was a leadership vacuum before you came along – maybe the team used to be led by someone without much CS experience – you might find all kinds of ad-hoc processes. Everybody might be doing things their own way, without any standardization. But before we start building those processes, we need to put ourselves in the team’s shoes and try to understand what they’re feeling. This is key to succeeding in your new role.

When we create experience maps in customer success, we often think about what the customer is experiencing at each stage. We have to apply that same empathy to our team. The chances are, they’re worried about how you’ll see them. It takes emotional intelligence to lead a team successfully.

A lot of people work hard to build up a relationship with a particular leader, either business-wise or on a personal level. All of a sudden, that's ripped apart and someone new comes in, so people are bound to wonder how they’re going to build that relationship all over again.

They might also be worried that you’re going to force your will on them. We have to understand that whatever’s there, even if it's kind of piecemeal, has got the team to the point they’re at today. It’s not the best course of action to come in and say, “All of this is terrible. We're going to do it my way.”

That’s not how you build trust or respect. We have to make an effort to understand what's happening, how the organization got to this point, and then to grow from there.

How you’re demotivating your team and how to stop
Few things are as costly and disruptive as managers who kill motivation. It’s said that “people don’t leave jobs; they leave managers” and the stats back this up: 70% of an employee’s motivation is influenced by their manager, according to Gallup.

Your new team is also likely to be worried about whether their jobs are safe. They might think you want to rebuild the organization from the ground up with people you know. All these concerns are valid, and as CS leaders, we have to make sure that we recognize them.

Obviously, leaders have anxieties of their own. Are they going to like me? Are they going to understand my background? Are they going to listen to me? What type of relationship did they have with my predecessor?

But we have to put these concerns to one side and focus on our newly inherited team.

Say ‘no’ to blind leadership and earn your customer success team’s trust

Remember: trust is earned, not demanded.

You can't come in and say to your team members, “You have to trust me on this.” It doesn't work that way. Frankly, it’s an awful initiative and doesn’t demonstrate a shred of competency.

Think about any trusting relationship that you have experienced. Did you automatically trust that individual, or did they have to show you that they had your best interests in mind? That's what we have to do as customer success leaders, and we have to continue to do that.

The fastest way to lose your team's trust is to come in as their new leader, throw out everything that they've done, and try to impose your ideas without having observed what's going on already.

In the first 30 days of joining PublicInput, I kept meeting people, attending meetings and asking questions. I was learning about our customers, customer advocacy and what engagement looked like for them. I was gaining a better understanding of my team’s relationship with other departments such as marketing, sales, engineering, product, and support. I was learning first-hand how PublicInput views customer success.

But one of the hardest things I've ever had to do is not change things immediately. Word to the wise would be this: don’t get sucked into thinking solely of the short term. Coming in with a fresh pair of eyes, sure, I saw some things that could have been tweaked.

But first, I wanted to get an in-depth understanding of all the internal and external processes, and how they came to be. How did we get to this? How were customer health scores calculated? What have our current customer retention strategies been?

I didn't know our customers when I arrived, and I didn't know what health meant for them. I didn't know what level of usage was good or what level of recording of activities was bad. I needed to understand all of that and more.

The team was great, they answered all the questions I had – they even offered input, and they listened to my thoughts and suggestions.

How to lead a customer success team through a management transition
While starting a new role is exciting and poses a fresh bank of possibilities, it’s not always an enviable position when you step into someone else’s shoes. This is especially true when you’ve got to build new relationships with your predecessor’s team.

So, for your first 30 days as a customer success leader, just learn. Don't touch anything. You can search for info, you can look in the CRM (customer relationship management). But more importantly, you need to listen to and observe your team members, and the wider processes in your new company.

Once you’ve nailed this, it will result in your customer relationships will become healthier. A reassured, content team will have a positive impact on customer experience in the long term.

What to focus on in your new leadership role

There are a few things I think that you should focus on when you inherit a team. First and foremost are the people, your direct reports.

It’s super important to take the time to understand where each team member is coming from. What’s their experience? What’s their background? What are their challenges? What are their strengths? What are their worries?

We need to know all of this as CS leaders. To build trust at a team level, we have to build trust on an individual level as well.

When someone applies to a company, everybody looks at their resumé, but when you come in and there's a team already there, people often don't look at their background. Maybe they glance at LinkedIn, but they don't look deep into the experience of the individual and how they may contribute to your vision. That's a huge mistake.

Generally speaking, when you're a customer success leader, you're not necessarily working in the weeds, in the thick of it. Some Directors of Customer Success adopt a hands-on approach, and I get that. These Directors have their own accounts, their own customers, who they're responsible for. But the vast majority of the work is carried out by their CSMs (the individual contributors).

If you’re in a leadership position, you need to understand them and let them know that you’re there in service to them, not the other way around.

Leadership and customer success
In this episode of CS Connect, Microsoft’s Customer Success Strategist, Vish Walia, digs into the magnetic topic of leadership in customer success. He’s joined by leadership expert and CS enthusiast, Nils Vinje.

Years ago, I had a manager who asked our team, “What do you think I do? The big stuff or the small stuff?” We looked around, knowing it was a trick question but not knowing which side the trick was on. Almost everybody said, “You do the big stuff. You’re the big-timer and you get the big money.” That’s what most of us think of senior management, right?

He said, “No, I do the small stuff. You all do the big stuff – you make the money. Small stuff gets in your way and stops you from being able to do your work – it's my job to get that out of the way. That's the small stuff. I have to make sure that you have everything that you need to do the job you were hired to do, while you all do the big stuff and talk to customers.”

That stuck with me. It's actually the CSMs who do the big stuff. A leader’s job is about decision making, but also making sure the rest of the team has what they need – the motivation, the tools, the processes, and the overall vision of what we need to do for our customers. If they have that, we can help them grow, and then the good stuff can happen

You also want to focus on processes. Take a step back and look at what's happening. What does engagement look like? What does engagement mean to your customers? If it's a technical product, do your CSMs have the technical knowledge they need? If it’s more adoption-based, what does engagement mean?

Understand your process, understand your playbooks, and understand what's there and what's missing. That way, when you're talking about how to improve, you're armed with the knowledge of what's already there.

Understanding accounts is another extremely important piece. You should know how many accounts there are and how many each CSM looks after. You should know the annual recurring revenue (ARR) of everyone's book of business. You should understand your segments. You should understand who's doing what so that you can start to tweak the CS function where necessary.

NRR (net revenue retention) is the single most important metric that has come forward in the last year or so, and it’s related to churn. You need to have a clear picture of both of these metrics and what’s driving them. You should understand as much as you can why customers are leaving, so you need to dig in, talk to your CSMs, and look at the data. You could even have conversations with a couple of customers that have recently churned.

Finally, you need to focus on evangelizing your vision for CS, your next move. The whole time you’re learning about the CS function you’ve inherited, you need to think about how it aligns with your overarching vision. Communicate that vision to your stakeholders and your leadership team, the Vice President of Customer Success or CEO – whoever you report to. Make sure everybody understands customer success is not the same as customer support.

The first 90 days in your new leadership role

At this point, you know what you need to do in your first 30 days as the new leader of an existing CS function: learn and observe.

But within the first 90 days (from day 31 through 90), you should talk about what you observed. Talk about team structure and the processes that need tweaking. It’s time to discuss with your new team the quick wins you can have as well as the actions that will lead to longer-term success. Maybe that's hiring more people or perhaps that's fine-tuning your customer segmentation, but above all, do something that makes it happen.

Everyone wants to see results, so in your first 90 days, make something happen. Help people improve, get some certifications started, or get some playbooks up and running. If you can get that stuff moving, you'll be very successful in your new leadership role.

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