What CS Leaders Should Know (But Their Teams Aren’t Telling Them)

April 5, 2022

ESG Customer Success

Category: Customer Success Resources


Customer Success leaders are doing their best. They care, and they want to do right by their company and their team. That intention goes a long way! But let’s be honest – CS leaders are no different than any other leaders, in that they don’t always get it right. It’s just a fact of life and business that sometimes, despite all the good intentions in the world, leaders can get it wrong.

We’re lucky enough to connect with CS leaders every day, so we know firsthand that they will do just about anything they can to get it right – especially when it comes to their teams. The CS leaders we work with are some of the most caring, genuine, generous people we know. And they deeply want to do right by those they lead and support.

So, we hope this paper will help you do just that! We spoke with individual contributors who hold titles (or have in the past) like Enterprise CSM, CS Operations Manager, Gainsight Administrator, CS Program Manager, Digital CSM, and Manager or Team Lead of CS.

Sound like some of the roles on your team? That’s the idea! We wanted to get their perspectives about what leaders in their lives and careers, be it past, present, or future, should know. What they should really know, that chances are, their teams aren’t telling them to their faces.

These individuals were incredibly generous in sharing their honest thoughts with us, so out of respect for their privacy, we won’t be naming any names in this article. We will use their own words rather than paraphrasing or reframing the perspective, because we think their opinions are the ones we all really need to hear.

The “things leaders should know” fell into four categories:

  1. Engagement
  2. Communication and ego
  3. Autonomy and trust
  4. Professional development and recognition

Weighty topics, indeed! Some of which can be difficult to discuss. But they’re important, so let’s try, shall we?


Rising stars in the CS profession want to work for leaders who are actively and genuinely engaged with them and their work. They want leaders who care about what they’re working on, proactively engage with them on accounts and projects, and aren’t completing an activity or having a conversation just to check a box. “When [they’re] halfway [involved], it feels more frustrating, as they are very reactive or aren’t up to speed, which wastes my time and theirs,” explained one CS Operations Manager we spoke with.

They also want leaders who lead from the front by working alongside the team, understand what it’s like to be in their shoes, and make a concerted effort to stay involved and in the know about the status of current initiatives. They want you to be really in it with them, so you’re well-positioned to provide educated direction, rather than offhand and perhaps ill-informed suggestions. Another CS Operations Manager told us she “prefers when [she] can think of [her] manager as a mentor and an extension of the team” because “strong leadership is highly involved.” Factors like active involvement, engagement, and mentorship help team members to feel truly supported by their leaders.

Perhaps our favorite theme from my many conversations on this topic was the desire for leaders who demonstrate their caring by listening to understand and act as a support system by making themselves available when their team needs them. Listening to understand, rather than simply waiting for your turn to speak, is an underrated leadership skill, in our humble opinion. Finding the balance of when to speak up and when to simply absorb the information you’re receiving is something that many leaders struggle with. So, it really resonated with us when several of those we spoke with made comments like “I appreciate when my manager listens to me describe an experience with a customer, a problem I’m having, and/or a possible solution, and turns it into strategic approach that can be presented.”

This is especially interesting because, yes, this statement indicates that listening is critical to what this individual is looking for from a leader. But not listening alone. Listening, processing, and then strategizing to move forward. Now, this same sequence of listen, process, strategize may not be right for all scenarios, of course. Perhaps an individual may simply want a leader to hear them get something off their chest, even if they’ve already determined the right path forward, or want to determine that path on their own after the conversation. That’s okay, too! Asking your team members what they’re looking for during a specific conversation can be a great tool here – do you just want me to be an ear? Do you want me to listen, and then help you problem solve? Or is it something else entirely?

When leaders ask questions like that, it can also open up a door for your team members to come to you with their questions. By making yourself available when your team has questions, particularly those they may be hesitant to ask or those they may feel are “stupid questions” (which, by the way, don’t exist in our book), you’re signaling to them that a free flow of communication, including whatever questions each of you may have for the other, is safe and welcome.

Communication and ego

Now, we realize that these two topics may not immediately seem as though they should be clumped together into one theme. But we think as you keep reading, you’ll understand why we did so. In fact, in reviewing the feedback from all the CS pros who spoke with us, we were surprised to see how many times they tied communication and ego together. These concepts also brought to mind the recent paper written by ESG’s Sheik Ayube and our friend Anita Toth on understanding personality types and communication styles for executive comms. Perhaps there’s something to thinking about this in the reverse as well. But that could be another paper unto itself, so we’ll save that topic for another time.

The first thing that made us wonder if these two were connected was when we heard from a former CSM, “I can’t stand when managers get on our one-on-one and ask ‘What’s going on? Need anything from me?’ without a clear meeting agenda.” Now, the no-agenda part is clearly not awesome communication, but where does the ego come in, exactly? Perhaps from a manager’s point of view, it doesn’t. But we suspect that from the other side, the CSM coming into a one-on-one could interpret the lack of agenda and general question as their manager ‘speaking down to them.’

This was just a hunch, so we continued on in our conversations, where we heard additional comments like “I wish my former VP of CS had known that you praise in public, critique in private.” This kind of behavior from an executive would certainly elicit a feeling of embarrassment or feeling less-than. Again, perhaps indicating that the leader was doing so in order to make themselves look or feel more important.

And then, it was simply spelled out for us, when we spoke with one CS pro who told us “I can’t stand when leaders lack self-awareness, humility, or desire to improve, or focus only on title and their own career growth. I appreciate when my manager communicates openly, transparently, and consistently.” So, there you have it! Communication and ego. Need one, need to lose the other.

Autonomy and trust

Unlike the last, this category did not bring us a lot of surprises in our research and conversations. But it’s one that, in general, leaders are still not great at. And not because they don’t want to be. But simply because humans like to be in control, and even when we know we should give up that control, it’s really stinking hard to do.

We stopped counting how many times we heard the word ‘micromanage’ with a negative connotation after about a half dozen. Seems like a no-brainer, right? Don’t do it! But easier said than done. We’ve all heard professionals in every possible industry talk about the detriment of micromanaging. It’s a waste of the leader’s time, their employee’s time, and pretty much makes everyone miserable. Instead, we should trust employees to do the jobs we hired them to do, enabling and encouraging them to take active ownership of tasks and projects and to make decisions based on their knowledge and experience.

But what we heard from these CS professionals is that while that is indeed extremely important, it, in fact, goes beyond just ‘not micromanaging,’ to making “better use of skills, experience, and time.” For example, one former CSM told us “I appreciate when my manager recognizes that I am a high-performer and allows me to high-perform by being there to remove the orange barrels, not put more of them in front of me.” Another told us, “I can’t stand when leaders act like managers.”

Read that again. “I can’t stand when leaders act like managers.” Those are powerful words! That’s a far way from just ‘not micromanaging,’ don’t you think? It speaks to the cultivation of the next generation of CS leaders, whom it is our responsibility to nurture and inspire. How can we remove the things in their way and let them run, full speed ahead?

Professional development and recognition

This is, in a way, a continuation of the discussion of cultivating the next generation, and is, of course, part of any good leader’s repertoire. Leaders mentor, coach, and develop our teams, provide them training and certifications, proctor feedback and brainstorming sessions, the list goes on. Sure, leaders do all this so team members can be good at their current jobs, but more importantly, so they can be ready for what’s next. Hopefully what’s next is still at your company, and perhaps even still under your leadership. But even if it’s not, it’s simply the right thing to do.

Frontline CS professionals want leaders who “seek to understand what motivates [them].” Does that ring a bell? Perhaps along the same lines of listening to understand? Now let’s go beyond just listening to what they’re saying, to listening for clues about their motivating factors, or *gasp* even asking them what motivates them most. For some it’s money, others private or public recognition or praise, and for others still, it’s little surprises like sending them a $5 Starbucks gift card or their favorite candy (which, of course, you know offhand), simply because they’re doing a great job.

These leaders of tomorrow also want to work for and learn from those who “provide constructive feedback and useful criticism to help [them] improve,” and perhaps most importantly, those who “recognize and evangelize [their] work and its impact for the company.” And they want these things regardless of the formal professional development planning processes of your company.

So, what?

You don’t have to take our word for it, but please do take the word of these smart up and comers in the CS space. Pick one thing in this article that you could do just a little bit better at and start working at it. Even if they themselves don’t end up on your team one day, we can all but guarantee that someone who thinks just like them will.

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