The Customer Success Pro Podcast
This is The Customer Success Pro Podcast, hosted by Anika Zubair. Customer Success is not a destination, but a a journey. Join me on this crazy CS journey as I chat to leaders, strategists and experts in customer success about their experiences and definitions of customer success and share with your their best practices on how to build and scale world class CS organization. Each interview will unlock tips, tricks and best practices to help scale your customer success career and company. I will dive into important and relevant topics to help spread knowledge about customer success in order to help companies put the customer at the center of their business. Because at the end of the day when customer are successful, so is the company.
Learn more at: thecustomersuccesspro.com
The Customer Success Pro Podcast
Building High-Performing CS Teams Without Playbooks with Courtney Balban
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In this episode of the Customer Success Pro Podcast, host Anika Zubair speaks with Courtney Balban, VP of Customer Success at Leadr, a manager enablement platform. They unpack how Courtney went from therapist to CS leader, why curiosity is a true superpower in customer conversations, and how her team runs a full cycle CS model without relying on rigid playbooks. Courtney shares how she teaches CSMs to sit in discomfort, separate noise from impact, and use deeper discovery to uncover real business problems instead of reacting to surface requests. They also dig into psychological safety, call coaching, leading managers through the teddy bear plus bulldozer balance, and the shift from retention first thinking to treating CS as a growth engine that speaks in outcomes and revenue language.
Chapters:
00:00 Introduction
06:55 Inside Leadr, full cycle CSMs and structuring the post-sale team
14:16 Cutting through the noise, activity versus impact and root cause thinking
23:10 Redefining customer value and building a team without rigid playbooks
30:32 Curiosity as a superpower
36:54 Why CSMs stop one question too early and how to go deeper without feeling salesy
42:19 Psychological safety, call coaching and how the team transformed
47:31 Leading leaders, big lessons learned
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Speaker 1 (00:00.396)
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Hello everyone, I'm your host Anika Zuber and welcome to the Customer Success Pro Podcast, your go-to space for real talk, expert advice and actionable insights in the world of customer success. I'm a CS executive leader, award-winning strategist, CS coach and customer success fanatic. I help CSMs and CS leaders build the skills and the confidence to become revenue driving pros and scale world-class CS teams.
So whether you're brand new to CS or a seasoned leader, this podcast is here to support your growth. Because customer success isn't a destination, it's a journey. And I'm here to be your guide and navigate every step of your journey. So join me every Wednesday where you'll get fresh CS tips, tricks, and strategies you can actually use. Some weeks I'll share my own insights and best practices from working in CS over the last 13 years
Speaker 1 (02:17.228)
And once a month, I'll bring on expert guests to dive into the most relevant and pressing topics in customer success today. So if you're ready to level up, hit subscribe on Apple Podcasts, Spotify, or wherever you tune in, and let's make your CS journey a little bit easier together.
Speaker 1 (02:41.038)
Today, I am joined by Courtney Belbin, VP of Customer Success at Leader, a manager enablement software built on the belief that leadership can be learned. At Leader, Courtney leads the strategy behind the entire customer experience team, driving impact across onboarding, retention, and expansion. Her work helps organizations turn people development into measurable business outcomes.
Before entering tech, Courtney spent a decade as a therapist, coach, and educator. She has a background that deeply shapes her leadership approach, blending operational rigor with empathy and clarity. And in this episode, we are diving into leading through curiosity and building a high performing CS team without playbooks. And we're going to explore how curiosity, structure, and human-centered leadership can transform the way a CS team performs.
So let's chat to Courtney. So welcome Courtney to the podcast. I'm so very excited to have this conversation with you today. For those of my listeners that don't know who you are, can you give us a little bit of a background as to who you are and share a bit more about how you went from being a therapist to a customer success leader and a little bit more about you and your team?
Absolutely. Well, thanks for having me. I've been so looking forward to our conversation. You're right. My path's been unconventional. I spent about a decade as a therapist. I worked mostly with young professionals and college students. And so that kind of early professional phase unlocked in me this interest in human potential. So essentially, why do some people thrive or succeed in certain environments and systems? And how do those arenas impact people?
when I stumbled into customer success, it really wasn't on my radar at all. I realized that it was essentially the same muscle, just a different industry. So I'm still helping people unlock capacity to grow and change, but now it's kind of at an organizational scale. So the skills were super transferable. know, in CS, we're still guiding people to like, you know, what do they really need, not just what they ask for. And so that's all just therapy in a different environment, which sounds...
Speaker 2 (05:00.898)
silly, but I've found it to be really true. I started as a CSM, which truly was the perfect entry point for me because I got to apply that kind of fresh therapeutic curiosity and relationship building directly with customers. So it felt very familiar. It felt very comfortable. I absolutely loved being in the trenches. I learned so much. I learned what actually drove customer outcomes versus kind of what do we assume drives them. So there was a lot of learnings in those early days as a CSM.
From there, I moved into managing a team of CSMs and then director level leadership, know, every day kind of living at the edge of my ability. So my capacity was constantly being stretched. And like you said, now as VP, I'm responsible for the entire customer success and services function at Leader. Leader is a manager enablement platform that helps organizations unlock better performance using AI powered leadership tools and frameworks and coaching. And so,
My team's responsible for everything post sales. So implementation, adoption, retention, expansion, all the things. We help organizations do more than just implement software with the services component. So our focus is on building healthier, high-performing teams. So that therapeutic foundation has been so helpful in every single role I've occupied because I've been able to leverage curiosity, pattern recognition, comfort with ambiguity.
in a way that's, I think has kind of become a little bit of a superpower for me and my team. So it's been a blast.
I love that you use the word superpower as well because I think there's a lot of things in CS that we are superheroes with tons of superpowers, but I also think what you just said where CS and there like being a therapist are kind of cross-functional because I do agree. I think there's so many like lines of connection there. think that even when I think of all the customers I've spoken to and all the CSMs I've worked with, they're like, wow, like.
Speaker 1 (06:55.832)
Being a CSM sometimes is like being a therapist to your customers, but it's so true. There is a level of empathy, of understanding, of connecting, and all of this can be so directly tied to the work you've done before, which I know we're gonna dive in deeper to as well, but I love that you've said it. It is that. I think sometimes a lot of the work we do as a leader as well can be quite very closely tied to being a therapist. So I love that your background comes in that way. I've never...
had someone on the podcast that's come from being a therapist to a customer-sus leader. So I love that in CS we have such unique backgrounds that shape our entire industry. And I think it's what makes us even more powerful as an industry as well. But you started to talk a little bit more about the leader team. And I'd love to know a little bit more about the team. said everything post sales. That means so many things at so many organizations. Can you give us a better overview of exactly what the team is?
actually responsible for what you look like your customer base? What does that look like?
Yeah, so we primarily serve mid-market businesses and our focus is really on their management team. in our kind of post-sale team at Leader, we've got support representatives. we chat, email, phone support, all of that is closely connected because we work so directly with the end user in an interesting way, the end user being the manager. And then of course we have a CSM team and our CSMs are full cycle. That was actually an intentional choice we made about a year and a half ago.
was when we added services to our customer journey, that was a newer addition in the last about two years. For us, when we added that into our customer journey, we kind of watched points of friction for the customer explode. And so it was you're introducing 47 people into this one account and it created complexity where we didn't need it. We are not a heavily technical tool. And so we didn't need kind of all of these hands in the pie, if you will. That creates a lot.
Speaker 2 (08:52.404)
of that create the bigger issues, right? When we talk about CSM capacity and CSMs being the catchall and what are.
Yeah, it does. We end up being the hero in doing all of the bits.
Exactly. So there's a lot that we're kind of still unpacking and how do we structure that in a meaningful way. But our CSMs currently lead everything from implementation, you know, through retention expansion, so the full customer journey. We describe them kind of as the hub of the wheel and they're deploying the assets and resources that they need internally for the good of their customer. And then we have what we call Academy Coaches, which is our service delivery function. So we not only provide the manager enablement kind of AI powered software for leadership tools and frameworks,
but we also directly will one-to-one coach and train managers on management soft skills and what it looks like to grow kind of in their management competencies.
Got it. Love that. Also, again, I love that you said like full cycle CSM because I think it's really important to identify that as much as SAS is changing with AI, with the economics of the world and everything in between, I do think having that under one umbrella is extremely powerful. But also, like you said, there's no need to overcomplicate things. I think a few years ago,
Speaker 1 (10:03.906)
customer success was in a space where we were like, okay, you need to have this department and this sub department and this team running this and this team running that. And sometimes, again, that's just creating a very fractional customer journey and experience for every single customer. So I think it's really awesome that your team handles all that. But I think that's a lot too, at the same time, as much as I think it's really cool that your CSMs handle it all. I think it can be quite overwhelming.
which we are going to talk about and the skills and the team that you needed to hire to be able to have a full cycle CSM on your team. But before we jump into that, I kind of want to come back to your career trajectory again, because you're the first therapist or ex therapist I've had on the podcast. And now you're not only from CSM to CS leader, you're VP of customer success. What a trajectory. That's awesome.
I always like to ask my guests, what's next? Like, what is your CS career dream or ambition? I'm sure you're living it a bit, but I'm curious, what's kind of next for you?
Yeah, you kind of like led me into my point. This is such a tough question for me. I wish I had something like really ambitious and inspiring. But to your point, VP of customer success was never on any career bingo card for me. Working at a tech startup was never on my bingo card. You know, I used the language earlier of when I discovered customer success, I didn't know this was a thing. And so getting to kind of get a crash course in SaaS, in
customer success, even in just business as we've entered scaling and funding rounds and all the things that come with being part of a startup has been such a fun journey. But as I was thinking through this question, the thing that kind of is still popping up for me is learning what it looks like to build. Let me say it this way. I've seen what happens when we get the fundamentals right. And so even talking about like our CSMs kind of our capacity and so what do we do with that?
Speaker 2 (12:00.046)
I've seen what happens when our team can operate as a growth engine, not just as retention structure. And when our outcomes are tied to like real business impact and transformation, I think you unlock something really powerful. So in this role, it is kind of, I'm living it, but I'm betting that this focus I've had over the last three to five years on coaching and human development in this capacity, in this context, is gonna reap rewards as we...
head into some seasons of growth at Leader. And so both, I think, for our customers and for Leader. So I want to build a of a model where our managers aren't just using the platform. It's fundamentally changing how they lead. And even in our short conversation, you can see how that kind of is like right in the center of my Venn diagram. I think that's impacts it compounds. And it gets me really excited to stay a part of it. So I'm really driven to kind of prove out this.
theory, this concept at scale. We've not yet gotten to do that. We're still kind of living in like the white knuckling, again, startup phase. And so I want to show what's possible that when we combine this like human assisted technology with genuinely expert coaches and strategists in the CSM seat. So I think my background has taught me that, you know, transformation only really happens through
relationship and curiosity. So tech has its place, but it doesn't substitute for that kind of deep interpersonal work. And so that's the work that excites me even in customer success. So getting to kind of take what we've built here at Leader, kind of this hypothesis we had within our CS organization and get to see that scale as we grow is the thing that has me super excited.
I think something you just said was really, really important to highlight, which is customer success has always been seen in a retention phase. going back to my first leadership role in 2015, it's so true. I was always told like, make sure we don't lose any customers. Like don't like manage churn. Don't lose anything. That's what your job is as a CS leader and what you're supposed to enable your team with. But you're so right. I do think the next stage of customer success is growth. I do think
Speaker 1 (14:16.652)
CS and the entire post sales teams at SaaS organizations are truly the real growth engine within companies, especially now when it's so much more expensive to close a new customer. It's so much trickier to keep a customer. You have to focus on making sure they see value and grow over time. But that, I think, is just putting an immense amount of pressure on customer success teams.
that pressure continues to build and we continue to be like, okay, there's AI now, there's all these other things and whether it's AI, whether it's like profitability, whether it's growth, upsells, you name it, there's all this noise, let's call it, that's happening within customer success. And a lot of leaders and a lot of CS professionals are being pulled in every direction. And I know the theme of our talk today is really around cutting through all of the noise in customer success. And I'm sure you have your
therapist hat on as I say this, but what does that actually mean to you as a customer success leader?
Yeah, I think it's about knowing the difference between activity and impact. Even as you were listing off those things, you know, like I felt my blood pressure rising, like, yep, those are all things that if I were to look at my to-do list or the, you know, our meeting agendas, it's like, those are the things we're talking through. And I think whether you're a CS leader or a CSM, we can drown in the number of requests or pings, know, trainings, feature fix. It all feels so urgent. And I think it all comes from
and large, they're well-meaning people with their own priorities. You how many times have I slacked a CSM, something that felt really urgent to me, that it's just noise in their world. And so I think it's about figuring out that busyness isn't the same thing as effectiveness. And there's kind of this ruthless process that you have to start to work to avoid spending all day responding to noise and then therefore not move the needle on what actually matters. You know, so I think it's about
Speaker 2 (16:17.166)
anchoring our activity in impact. So back to the core outcome we exist to solve for. So if you're a CSM, it's back to the impact for the customer. As your SPS leader, it's both the customer and the business. You have to get ruthlessly clear about what is moving the needle versus what is ultimately just the tyranny of the urgent. to your point, I think it's very therapist of me to say, but I think a big part of it is teaching and learning emotional regulation.
ESM's in particular come to mind, especially when they're new to the field. I can viscerally remember this feeling where you have this tendency to jump when someone says jump. A customer asks you how while you're jumping.
at how high to jump basically.
Speaker 2 (17:03.232)
And there's this immediate anxiety, and if that word kind of has its own negative connotation, this immediate drive to even while in tension, fix it right now. But we have to learn how to kind of sit and be curious as our first instinct to regulate that drive to immediately react. I think that's really critical because when you pause, maybe even breathe, depending on your environment, and really ask like, what's going on here?
what is the root cause here that we're dealing with instead of just instinct? think you do cut through a lot of noise. You stop treating symptoms and you start solving real problems, which is really just pattern recognition, seeing what's one off versus what's systemic. Because I don't think there's any world where we don't have one off things we need to get through. We don't have the luxury of being like, well, that's not connected to a root cause, so I don't have to do that.
But I think the power is in the regulation and the pattern recognition, the naming of it, because we're then able to start to track that over time and begin to name what is noise and what is not. And so that's where that idea of curiosity is the superpower. I think when you approach any noise of any kind, customer-wise, internal, whatever it looks like for you, with a regulated patient curiosity, instead of that
I think it might be baked into all of us and see us like that solver fixer instinct that reactivity you give yourself a chance to identify what actually matters and what maybe needs reprioritize, deprioritize and what is just truly a distraction.
Yeah, I love that. But it's so true though. I say this a lot, sometimes in CS we end up getting a little bit lazy because it's so much easier to track activity than it is to track impact. But as we know and as we've been discussing, impact is so much more powerful, but sometimes you do really need to cut through the noise to hit the impact because
Speaker 1 (19:05.226)
As you said, there's a Slack message or there's a training request or there's some sort of bug or feature fix or whatever it is that's ending up on our desk that ends up being quite a distractor. But I think a lot of us know that we shouldn't be actually focusing on these things. But because it's the easy thing to focus on, our brain is naturally moving towards, OK, let me just check this off the to-do list because it's done. And then I feel
a hit of dopamine and I feel really, really good about it. And I'm like, yay, I've been a great CS professional today, but did I actually drive impact? And I know everyone I work with in a coaching capacity, but I know a lot of people listening to this podcast are probably thinking, I know I shouldn't be doing activities. I know I should be doing impact, but how do you actually decide what truly deserves your focus and what truly is driving impact? Because we can say all these fluffy, beautiful things.
But how do you actually get to that point of like, this is impact and this is just noise?
Yeah, this is a tough, tough question, right? I think this is one of those things that is more like a muscle that you build over time as opposed to a black and white answer, but it's really important that we wrestle with that on a regular basis. So the first thing I would say is that we need to look for leverage. So in any given kind of pile of demands or of requests, what is the thing that will create compounding impact?
So as opposed to just a one-off fix. that requires to your point, especially if you're, well, if you're a CSM or a CS leader, you have so many things going on that realistically are top priorities, right? It's that little like, which of these should I get rid of? It's priorities. And you're like, yes, like they're both. You don't get to choose. But is there anything that just came at me or is on my list today that has compounding impact? That is.
Speaker 2 (20:59.352)
connected to a root cause or is a repeated need that I'm facing or my customers are facing. And so when I'm working with my team and we're facing this like, uh-oh, red alert, the noise is everywhere, it comes down to kind of two questions that can have a lot of variations. And the first is what we've been talking about. Does this solve a root problem or is it a symptom? That doesn't mean if it's just a symptom that we won't solve it, but it goes back to the power of naming it. Because if you look at your list and it's everything's a symptom,
Something is wrong, right? And then secondly, similarly, but worded differently is does this meaningfully move retention, expansion, customer value? So what is this connected to? This is where I think to your point, we can get kind of lazy because we could make a case for everything being important for retention or customer value. So we've got to make sure that our definitions are right. So like when we say retention, what does it take to retain a customer?
its outcomes, its value, it's not always customer happiness. so knowing their business enough to know that this one-off request that we said is a symptom, does this move the needle on their outcomes? Yes or no. And it might be yes, but we need to know that. And then same thing with expansion and then customer value is a very broad term. And so making sure that we're clear on what our definitions are so that we can meaningfully answer that. So really what we're doing here is we're using
It's essentially a version of the Eisenhower matrix, right? Like urgent versus important. Those things are tension a lot, but I think naming which is which allows you to identify those patterns that are tripping you up over time. So if you try to just kind of reinvent the wheel immediately, I think you'll get lost as opposed to saying, let me first start to assess the work I'm doing. What is a symptom and what is a root cause?
Again, there are certainly times when I think the one-off fix is the right choice, but the pattern naming is what's really important. And when we start to have that lens, I think we can make better decisions. All of that said, if you don't know the root challenge or the through line or the outcomes, all of that can be really difficult.
Speaker 1 (23:10.594)
It is. And I think that sometimes it's really difficult even for our CS teams to figure out what customer value or customer outcomes actually is. Like you said, customer value can mean a million different things. It can be interpreted differently depending on the segment, depending on the type of customer you actually have. And I really feel for CSMs today because in a world of customer success, two, three, five, eight years ago,
seeing product usage or seeing the product being used heavily meant that customer was receiving value. But unfortunately in 2025 and I'm sure into 2026, customer usage does not directly mean customer value. And coming back to your point, sometimes teams can be very uncomfortable with that. They just don't understand where to even connect the dots of like, okay, is my...
activity that I'm doing with my customer actually shaping or resulting in customer value or customer outcome. And I think that, you know, when we talked before and you've said it too, it's like your teams have to really sit in discomfort and that's how you've actually been able to help them become more strategic. So can you tell us a little bit more about what that means for your team and like how they're able to get to customer outcomes and value?
while sitting in discomfort. I loved when you used that terminology before.
Yeah, there was a season and I like even looking back, I cringe a little bit at it, but I think the heart behind it was good. But there was a season where all I talked about was this is an art, not a science. This is an art, not a science. And there's truth to that. And also like we can measure ROI. So again, as a young CS leader, I was learning. But when I first joined the team, leaned CSM lean very heavily on structure to feel safe. So they wanted playbooks, they wanted scripts, they wanted the right answers, they wanted measurable milestones.
Speaker 2 (25:06.926)
Hear me, in a maturing CS org, none of those things are wrong or bad. They have their place, but we had a team of high performers in an early stage startup who wanted to succeed. Structure feels safe, so I get it. But what was happening was we were over relying on scripts or playbooking, and I think that can make CSMs robotic and reactive. And so the first thing I wanted to do was build their confidence and judgment.
before layering on that structure. And so that's kind of what we've been talking about, right? It's like, I can ask, is this a root cause or not question, but have I built that judgment muscle yet? And so I needed to learn to read a situation, ask really great questions, pivot or adapt based on the answers that they heard as opposed to just saying, okay, great. And then asking their next question, right? Listening to hear as opposed to prepping for the next question. So I think playbooks should enable great
thinking, not replace it. And if you add them too soon and we had, they became crutches. And so once they had that foundation, we can start talking about layering and frameworks that support the thinking rather than replace it. I give all that context or preface to say, getting them comfortable to sit in that was the hardest part. And it was hard for me too.
Yeah, I bet. We're all, our brains like comfort. Our brains like to know, I'm just thinking, I love my checklist right in front of me. I'm like, I feel really good when I check everything off my checklist. again, our human, like our innate desire is to survive, right? Like we're just trying to live and survive and that means staying safe. And our brain wants to protect ourselves all the time. Yet you're having to train yourself and your team to sit in discomfort and ask those tough questions.
of your customers, which is just not normal in any sense of the word.
Speaker 2 (26:56.364)
No, and again, to our whole point of the conversation, meanwhile, other demands and requests.
Yes, there's everything else on your plate too.
Yes. So yeah, we practiced a lot. We tried very, very hard to start to normalize discomfort in our work. So we'd openly say things like, as a CS leadership team, I don't know the answer. Let's figure it out. Small things, big things. So again, none of this is like, wow, what a profound idea. But it was, we went into every single interaction saying, where can we normalize ambiguity? Where can we normalize discomfort? And so,
We often resisted the urge to solve things for CSMs. So as opposed to saying, here's your next step or here's what I'm seeing, it was a lot of modeling of curiosity first before sharing a perspective. So what are you hearing underneath of that? Or what's your take of what they're, you know, we work with management teams. So, you know, when we're talking about management dysfunction or unhealthy patterns, what are you seeing in that there? And so, you know, we also changed how we did, we call them value reviews, but QBRs.
customer call prep. For a season, we eliminated pre-built decks and started with, they had a series of questions they had to answer as part of their call prep. Like, what is the customer's desired outcome here? Does this conversation get them closer? If so, yes, then define a win for the customer today. What do you need to learn from them today? So we were building the conversation direction as opposed to giving them something to talk through. Wow. It was really hard.
Speaker 1 (28:31.36)
makes very hard though, because I think again, like a business review or value review or whatever you're calling it, it's not meant to be a presentation. I do think if you're going in with the slide deck, great, you have talking points, but that's all it should be. It should not be like a professor student relationship where I'm just talking at you. It is a conversation and you do have to ask uncomfortable questions. You have to ask open-ended questions. You have to make sure it's a back and forth because you have to make sure that the customer is
receiving and sharing the value add from this conversation. Sometimes a pre-built deck, to your point, is only going to limit someone and box them into what they absolutely have to say. I know a playbook, listen, a playbook and a script got me to where I am today. It really helps. I had nothing bad to say about them, but they shouldn't be your crutch. They should be something that you are using as a tool, but not something that you have to read off word per word.
to be able to deliver value to your customers, which is really, I'm sure, uncomfortable for your CSMs. And I know that you like to use curiosity a lot. You mentioned it earlier on in this call as well. How did you get them to be curious about this? How did you get them curious about the day-to-day, the building of a QBR deck, the asking open-ended questions? All of these are truly what it takes to be strategic, but sometimes we don't realize that in our day-to-day.
hustle and grind. So how did you start to coach this into the day to day with your team?
Yeah, I think this is great because again, we've used this word a lot, but I do think it is kind of like the superpower at the center of a lot of things CSMs are great at. We had to do two things. First was, to your point, rewire their thinking. And then the second was begin to train the actual frameworks that they could run. So I did a couple of things. First, we started framing challenges as fun. It is so silly, but you know that there's like a saying or a teaching around nervousness and excited or the same somatic feeling in your body.
Speaker 2 (30:32.686)
They're just different depending on what you call them. So I started to apply that same principle to ambiguity. So when there was a problem or discomfort or a customer call, we were going into kind of feeling like we didn't have what we needed. I probably got felt really silly or seemed really silly to them for a while, but we would reframe like, this is fun. We get to get closer to figuring out what their root cause is. And so maybe it only worked for me, but that was a subtle shift.
that we started to make was instead of going, don't know what I'm doing in this call or I don't know what I'm supposed to ask, it was, this is a fun opportunity. Secondly, we started talking about, can't, you're a high performer. So we've talked, I've mentioned that. Like these were people who wanted to be successful in their roles, we all do. And so when I started to help them see that it wasn't the playbooks that were helping them be successful, it was really great, curious questions that helped them learn what they needed to be successful.
Suddenly the push for curiosity wasn't the enemy of their success anymore. It was the key to their success, which then is what made them hungry for, now train me on this. Train me how to ask good questions, how to follow up, how to active listen. And so I had to convince them that it was for their good and their customers' good. And then they were open to the training, as opposed to giving them a training, which is just another playbook.
Yeah, I love that. But I also love that you use curiosity as a superpower. Like, I think it really is, and I do think it's an underrated skill because sometimes you just have to dig that much deeper to get to what a customer outcome is or how to deliver value. But I do think it's underused in customer success as well. And I think that if you live in the discomfort like we talked about earlier, you have to be curious to get out of that discomfort. You have to ask hard-hitting discovery questions, which
Again, another very important part of customer success that I don't think has talked about enough actually, but can you give an example of when your team actually started to use curiosity to start to turn situations around? Because it's all well and good to say, be curious, ask open-ended questions, go have a good conversation with your customer that's strategic. But on this podcast and in general, I like to be tactical and practical. And I always like to ask, like, how did your team
Speaker 1 (32:51.72)
actually use curiosity to turn situations around or to help themselves or help their customers.
Yep. So we had a top 10 customer who we have, I've mentioned it, we're a management enablement platform. So part of what we do is performance management tooling. And we had a customer, one of our top 10, who was particularly interested in a feature we did not have in our performance reviews module. So if you've worked anywhere for a while, you know that there are a million ways to do performance reviews, right? And so people have a million different philosophies. And so it wasn't surprising that we didn't have a feature or functionality they were looking for.
And we've run into these before. And historically, the conversation would have been, I will pass that on to our product team, right? I will pass that on to our product team. Or, worst case scenario, make a promise that we couldn't keep. But in general, it's usually, that's great feedback, I can pass that on. And instead, this CSM turned to curiosity and started pulling at, why is that your performance review preferred method? Tell me about what that provides for you. Tell me about the insight that gains for you.
What do you do with that information as an HR team? And so they got really curious about how that particular feature would serve the business as opposed to, yes, we can pass it on to the product team and we may or may not build it. And what was so interesting was we ended up being able to solve the problem with a feature that already existed about 80 % of the way. And then the other 20%, we were able to expedite into development really quickly because business impact was clear. And so the customer felt heard.
They obviously adopted it more deeply. They were able to expand their contract, all of the things we want to see, right, in kind of a perfect scenario, but it was because she asked three or four more questions. So it not only impacted the account for us, right, retaining it, but it solved an actual problem for them that they thought they knew what they needed. We could solve for it differently. And so otherwise we would have slapped a quick solution on it or...
Speaker 2 (34:53.323)
miss the mark entirely and let it sit in some development queue that unconnected to a meaningful business outcome.
All right, just a quick pause from the podcast. If you want to feel more confident in customer conversations and stop getting stuck when a customer pushes back, I have something that's going to help you immediately. It's my Objection Handling Playbook, and it's a practical guide that gives you clear scripts, frameworks, and examples so you know exactly what to say when customer objection comes up.
Now, inside, you will learn how to respond when a customer says they have no budget. You'll also learn how to confidently redirect when they say they need more time. And of course, we're going to talk in the guide about how to move the conversation forward when a stakeholder goes completely silent. The guide also covers how to uncover the real reason behind an objection so you can address it
properly and move forward with your customer. Plus, in the guide, as you do in many of my guides, you get plug and play scripts that you can use on the very next call with your customers. If you want to grab the Objection Handling Playbook guide, you can go ahead and download it right now. All you have to do is go to thecustomersuccesspro.com forward slash resources. That's thecustomersuccesspro.com
I will link it down in the show notes of this episode. All right, let's get back into the podcast. I love that, but I really, really love that they dug a little bit deeper and asked those questions. I was just nodding my head and smiling as you were saying like, why do do it this way? Or what does this actually earn for you in your performance review? why is it that you want like asking those open-ended curious questions?
Speaker 1 (36:54.964)
are so fundamental in customer success. But I don't know if it's like brainwashing or again, how we've ended up being in customer success for years. But unfortunately, I find that most CS professionals don't want to ask the question. They almost stop one question short of what real discovery and real unlock can be when it comes to speaking to a customer. I think it's because we're people pleasers. That's my little take on it. And I think we just want to be like the
all-knowing, all-helpful customer success manager to all our customers, which there is a time and place for that. I'm not saying be rude to customers at all, but I do think that sometimes we stop one step short and we end up selling ourselves short as well. And I think CS professionals and the ones I work with as well, they don't want to go deeper because they feel like they're being too pushy or too salesy.
And I'm saying that in air quotes because I do think discovery is a customer skill, not a sales skill, but it is underserved in customer success. So I am curious, you let them start asking these questions, but how? Like I'm sure there's leaders listening to this podcast saying, yes, I want my team to start asking these great discovery questions, but how did you get them to do it without feeling too salesy or too pushy?
Yeah. If I've heard it once, I've heard it a thousand times, right? It feels invasive. It feels like they told me what they want to tell me. And I think we have to first of all reframe that exactly what you said. Curiosity is about service. It's about getting them the actual solutions they need. It's not about selling them something they don't. And so when we stop too early in our discovery, we're actually leaving customers in their own pain points.
Yes, we're not helping. We're actually causing more pain.
Speaker 2 (38:46.7)
Yes, exactly. So it's about teaching the difference, think, between it's a style difference, interrogation versus exploration or curiosity.
I love that. That's a great interrogation versus exploration. love that because I also say like we are guides. We're meant to guide them to their next step and if you're not exploring properly, you're not going to be able to guide them. These are great words. love that. Sorry I interrupted you.
Great, but you're exactly right. Interrogation, right? It's, we've all felt it. It's rapid fire questions that feel like a checklist. Exploration is one good question. Actively listening to the answer, which is also a skill, right? I mentioned it, I kind of like drove by it earlier, which was active listening is not nodding along and mm-hmming and then saying, great, thank you.
That's not everyone thinks it's like listening and I'm like you should listen regardless, but actively is participating in the conversation
I'm things I'm noticing things you're saying and then asking a follow up based on what you heard. So one of the ways I helped my team feel more comfortable with this was giving them permission to ask permission. So what I mean by that is they share something that you know is a thread that needs pulled on saying something like, hey, I'd love to understand more about that if you're out for it. Or hey, do you mind if I ask a slightly deeper question or I ask a little bit more about that?
Speaker 2 (40:02.7)
I think you kind of coach them to looking for doors. So moment in that conversation where a customer might hint at something deeper that kind of sends off your spidey senses. So like if a customer says, you know, we're busy right now, we hear that a lot, right? HR teams, that sort of thing. We've got a lot going on. A CSM, a way you can kind of stick your foot in that door is by saying like, yeah, what's top priority for you today? What's your priority for you guys right now? What's on the whiteboard? What's the number one thing on the whiteboard you wish you could get rid of?
one question alone can kind of stick your foot in the door that now they want to be heard. Customers want to be heard. They want the money they spent on your solution to actually impact their business. If you don't ask questions about their business, you can't deliver solutions. And so when they start to feel permission to soften the question, but also see, hey, you can't be helpful without this, I think it can start to unlock some things.
I love that you said permission as well. And I think you mentioned it earlier where your team does lots of role playing, lots of moments where they're actually able to try it and make mistakes and be in a safe environment where it's okay to try it. I think sometimes in customer success, maybe because it's the pressure of the world and technology right now where it's like, if I make one wrong move, I'm going to be fired or laid off or I'm never going to get that promotion.
I think as leaders, it's a very important part of the role to make sure your team feels safe to try and to make mistakes because even if you hired a seasoned customer success manager that's a veteran in the space, we all make mistakes as humans and you need to learn from them and the ability to feel safe and really...
give yourself the permission to try something new, like try tougher discovery questions without feeling pushy, you're never going to actually learn from them if you don't try them. So I think it's really awesome that you call it out, that your team feels safe and has the permission to try, which I think, again, opens the door to so much more and the ability to be strategic, the ability to drive outcomes comes from that initial part, which is like, I feel safe and I have the permission to even just
Speaker 1 (42:19.188)
actively listen and have a conversation with my customer. And that creates a huge shift in my mind. It moves us away from that activity that we were talking about at the top of this conversation into actual outcomes and driving revenue and growth for your customers. But I'm sure this made a huge shift for your team too. Like moving from activity to moving to outcomes, I'm sure there was like your team morale change when they were able to be more open and
discuss these things, but I'm sure the way your team works now is so different. Can you speak to like what it was like, the impact you've seen before having this kind of open permission space to really focus on customer outcomes to like now and what you guys are doing at the moment.
Yeah, so like I said, we kind of were very afraid of failure when I started with this team. And so we were working through that consistently. so even you hit the nail on the head, even before we could introduce, you know, FiveWise frameworks or any kind of curiosity driven frameworks, we had to create psychological safety, which meant freedom to fail. I had to do a lot as a leader of publicizing my own failures to say, here's where I messed up or here's a clip from a customer call that did not go so well.
Can you give me feedback? So modeling what that looked like. We did a lot of call coaching where I was affirming all the things they were doing really well in addition to the opportunity that they had to improve so that they could see this wasn't about catching you doing something wrong. This is about kind of fanning the flame of the skillset you have to make you excellent in the way we both want you to be. And so I couldn't even introduce any of that, like when it comes to team morale until they felt safe to try it.
And so that was big. That was from me. That was from people higher in the org than me. That was C-suite. Like if they're going on the road with a CSM talking through, how can we make sure we create psychological safety, even if this goes sideways, we had to build that foundation of trust. So first, we're very scared to mess up, which is tough from a team morale perspective in a startup environment. Again, lots of things flying at you all the time. Team morale was low.
Speaker 2 (44:32.066)
You might even say that when I start to introduce this concept, it dips a little bit, because it feels like more.
It feels so hard. It's so, again, you're getting out of that safe checklist brain of like, stay safe, stay where you know, rather than doing something that's uncomfortable.
But over time, I think what they started to feel was confidence in the internal team that, these people are in my corner and we're not a team of individual contributors or a group of individual contributors who all happen to sit beside each other. We are a work, like a team that works together to help each other succeed. So once we started to see that process change on the other side of it, I think what's really cool is that both from customers and internally,
CSMs are viewed like trusted advisors. And so it actually changed the way everyone else perceives CSMs, which changes how they show up and changes morale, right? They feel way less burnout from checking boxes because they get to solve real problems.
They have to solve the problem. They have to see that this, this was a problem and I made it a solution.
Speaker 2 (45:35.702)
Exactly. And so they're energized by that. We've seen lower turnover because the work they're doing actually feels meaningful instead of impossible. So they're viewed as this, like I said, strategic partner, both from clients and then also internally. And so we've subtly stopped being the catch-all team that customer success can so easily become. They're considered essential to the company's success, which increases morale. We are having fun together.
solving these problems and learning from each other. And it's really cool given where we started.
Yeah, I love that. We're not task monkeys. And AI is going to replace that anyways, any day these days. But I love that you guys are feeling like you're doing something tangible and that tangible is you can see the result because you're watching the change happen, which is amazing. And I love that you called out that you were honest and open and transparent as a leader and you were sharing your failures. I think a lot of times leaders don't feel that they should share failures. But I mean, come on, guys, we're all human.
Like at end of the day, your team needs to realize that you're not this up in this ivory tower doing everything perfectly. And I think a lot of times what you said, like call coaching, allowing the space for your team to really see what happens and transform themselves into these better strategic partners. You need to call it out. Like I wasn't perfect. I'm far from perfect even today. But I think that a lot of times as leaders, we do need to give our team that space to grow, but also
the ability to give them things that are gonna be able to transform them into those strategic leaders, which sometimes, again, tasks are not gonna do that. It's gonna be the icky middle, which is like the hard questions or the uncomfortable conversations or screwing up in front of really big customer. Because some of my biggest learnings in my entire career is when I have royally messed up in front of a big customer and you would never see me do it again.
Speaker 1 (47:31.842)
We do have to give our teams permission to do that. And yeah, I just, love that you were able to be open and honest with them. And on that, have there been actually some big lessons that you've learned along the way? Because you've now managed managers and an environment like yours, which seems like it's growing, which is great, but I'm sure there have been some tough lessons that you've learned along the way as a leader.
Yeah, yes. Like where to begin, right? In particular, leading leaders is a totally different muscle. In any kind of leadership position, whether you're leading individual contributors or managers, your job isn't to have all the answers. And in a leader of leaders situation, your job is this really interesting kind of blend of needing to create clarity and capacity for your people.
at leader, but also personally, I'm a strong believer that the middle manager is the hardest job you have pressure from.
Yeah, you've gotta manage up and down and everything in between.
It was so hard. And so it's almost impossible, again, to use our theme, to cut through the noise in a way that your priorities aren't always at odds. And so as I was learning to lead leaders, it took a lot of failure to learn what it looked like to fight for their capacity and constantly reinforce clarity. so asking tough questions with them, things like when they're stuck, hey, what's the story you're telling yourself about this problem?
Speaker 2 (49:02.882)
You know, like where are you personally stuck so that we can unlock some of your brain's capacity to get where you need to go? We're transferable skills, but man, the lessons to, the path to getting there, to creating clarity without overly, being overly rigid was really hard. They need clear vision and guardrails. They don't, but they need autonomy. And so that is a tension point that is really hard, right? Like I could be a,
a heady bear of a manager, because manager, right, where it's like, is about making you feel good and making sure you have everything you need. Or it could be a bulldozer. Here's what's required of you. Here's where we're going. Here's the objectives. The reality is we call it internally, like you need to be a heady bear driving a bulldozer.
particularly implausible, but that's the job of any leader, but particularly of a manager of managers. And so it's been an ongoing lesson of where shoot, my rigidity held them back here. They needed more autonomy. And then on the other side, know, my giving them autonomy here was actually incredibly unhelpful. They needed me to lead with a heavier hand and that is something that only came with reps.
It is kind of my muscle. You have to learn how to give them the freedom in space while still giving them the structure, which again, very different to leading ICs.
Yep. And so it goes back to your point. Vulnerability is what scaled that. Like vulnerability is what allowed me to put a bow on those lessons and continue to grow from them. Hey, here's what happened in that scenario. Do you have feedback for me? And they always do. And it's usually pretty good. Hey, yeah, you're right. I was way overly rigid in that and that actually held you back. Here's what I want to do different next time. We're building trust even though we're not performing perfectly. And that went a long way. So that teddy bear bulldozer tension has
Speaker 2 (50:50.284)
has been and continues to be a challenge that I'm learning to navigate.
Yeah, I love that. And I think your career at Leader has been exceptional. I think it's awesome that you came in as a CSM. You were able to really home grow the team, but also your entire career trajectory and just go from CSM to VP of customer success, which is amazing. And I know a lot of people listening are thinking, how do I do that too? But if you had to start over today and you were back to being a CSM all over again and you know everything that you know today and everything we've discussed, would there be anything that you do differently as a CS Leader?
Yeah, I'd be a lot louder. So what I mean by that is that, you know, I may have mentioned it, but a couple of years ago, we actually shifted our value proposition as a company or our market positioning. And a large portion of the motivation behind that was what CS had identified in our customer base as it related to the problems we actually solved. So we were making assumptions about how leader impacted organizations in its early startup days. And through looking at actual customer data, realized
we're not moving the needle there at all. Here's the actual impact we're making. And all of that information lived with me and my team. And instead, it got buried in noise because we were rattling off feature requests not tied to outcomes. We were chasing down tasks. We were the catch-all department, all of those things. Whereas if I had amplified those patterns in customer voices sooner, both as a CSM and then as a manager of CSMs, I think
would have got further faster as a company, but also as a CS team. We would have built the structures and the processes that supported what we were actually seeing instead of just kind of chasing our tail and wasting time.
Speaker 1 (52:36.654)
Yeah, and I think that's a really good tip, by the way, and reminder to us all. I remember when I first stepped into my first executive role, I realized that I needed to challenge the norm more. And I think that's what you're trying to say. It's not necessarily just saying loud things and just being obnoxious, but it's like making sure you are heard and your points are heard and that things are valid. And I think sometimes in CS, we don't do that often enough, even though we have all this information, literally the companies.
lifeblood, which is customers. And it's just sometimes you need to be more thorough, more direct, more impactful with what you share and what you say across the board. And I love that you think in that way too, because I think if you are truly trying to be an executive leader, you do have to challenge, you do have to come in and be impactful and you have to be louder for lack of better way of saying it.
If we are loud about all the wrong things, we just add to the noise.
I can not rethink. I love that. I love that.
We pull that food out, now people want to listen to us.
Speaker 1 (53:39.052)
Yeah, amazing, amazing. Well, Courtney, we can keep talking for ages, I'm sure. But it is point of the podcast where I like to challenge all of my guests with the quick fire questions where you have to answer the next few questions in a sentence or less. Are you ready? Amazing. Okay, my first question for you is if you could predict the future of customer success, what do you think CS will focus on next year?
I am.
Speaker 2 (54:04.812)
Yeah, clearer value articulation, you connected to outcomes and revenues. CS will speak ROI language more proficiently.
Yes, I love that. Love that. It's like my love language. Like, let's make sure we're measuring outcomes for our customers. I love that. Okay, next question is which app or software do you use every day or every week? It can be on your phone. It can be on your laptop. Can be CS related or not?
Yeah, Claude projects. So it has allowed me to make better use of small pockets of time because I don't have to re-ramp my brain into what I was where I just left off. So it's been an efficiency game changer.
Love that, love that. And if you could change one thing about customer success, what would it be?
Yeah, how do I want to say this? Revenue leaders would stop treating it like a support function.
Speaker 1 (54:55.138)
Yeah, yes, we're all growth and revenue leaders. We're not a support function. Great answer. Okay, next question is what is one cool or new thing that you've been doing or prompting AI for? And this can be again business or personal related. Yeah.
So this is a little bit of a plug for a leader, but genuinely genuine. Leader has changed the game in how effective my meetings are. So right now in every single meeting I run, I get coaching as a leader on how effectively I communicated, how effectively did I run that meeting, and 10 out of 10 times I am getting better as a result. So it has been unbelievably helpful.
love that. know Gong and Fathom do that for customer calls. like live coaches you like you're talking too much or this is what you should have said differently. And so that's really cool that Leader does that for a leadership kind of feedback. That's awesome. Amazing. And my last question to you is who should be my next podcast guest?
I love this question. I think in light of our conversation today, Nigel Hammond, he's one of the founders over at Forsight, which is a startup that's doing some pretty cool work around the way. Of I love Forsight. So I think he'd be a great fit.
Bye!
Speaker 1 (56:09.76)
Amazing. That's a great suggestion. love the TV at Foresight. So thanks for suggesting that. Courtney, thank you so, so much for this insightful and honest and transparent conversation. I loved every second of it. If my listeners want to learn more from you or get in touch because they have more questions, what's the best way to get in touch with you?
Yeah, so you can find me on LinkedIn. You know, like all of us, we're all hanging out over there pretty often. So you can find me, Courtney Balbin, and all the leader brandings everywhere, so you'll know it's me.
Amazing. Thank you so much Courtney. I really appreciated your time.
thank you so much. Appreciate you.
Thanks for tuning in to the Customer Success Pro Podcast. I hope you picked up something valuable to take back to your team.
Speaker 1 (56:52.512)
If you enjoyed this episode, would mean the world to me if you took just 10 seconds to leave a review on Apple or Spotify. It helps more CS pros like yourself discover the show and creating new episodes takes a lot of work. So leaving a nice review keeps me motivated to keep creating. And don't forget to hit subscribe on Apple, Spotify, YouTube, or wherever you listen to podcast episodes. I drop a new episode every Wednesday packed with practical tips. And if
you've got a topic you'd love for me to cover or want to be a guest on my show, send me a message. All the details are in the show notes. I'd love to hear from you. And hey, if this episode helped you, share it with a fellow CSM or CS leader. Remember, sharing is caring. Cheers to your CS journey and I'll catch you next week for our next episode.
