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Mastering CS – Canding Leader Insights – Ep 12 – Laura Litton

January 30, 2024 28 minutes read

Summary points:

In our new episode of the Mastering CS – Candid Leader Insights podcast, Irina Cismas, Custify’s Head of Marketing sat down with Laura Litton, Director of Success at LiveSchool.

Let’s discover Laura’s journey in customer success and her insights for customer success managers.

What you’ll learn:

  • How customer success looks in the education sector
  • Challenges in CS teams
  • How to choose the right CS tools
  • How to build a successful CS team
  • Common mistakes in CS
  • CS predictions for 2024

Key insights and takeaways for CSMs based on the interview:

CS in education: Whether as a teacher, instructional coach, or in a success-oriented position, the need to understand and meet the diverse needs of students, teachers, and school leaders is paramount. This approach involves recognizing individual differences, adjusting teaching or coaching strategies accordingly, and building trust. The goal is to simplify and effectively address challenges, allowing educators to focus on the broader needs of their students and staff.

Overcoming challenges in CS teams: Successful leadership, as exemplified in experiences with Screencastify and LiveSchool, involves fostering open communication, actively listening, understanding individual needs, and adapting strategies accordingly. The narrative particularly emphasizes the value of giving team members the opportunity to express themselves, even in uncomfortable situations, and responding to their specific needs, such as providing autonomy to demonstrate trust. This approach mirrors the individualized attention required in teaching, where understanding and catering to the unique needs of each student is crucial.

Building a CS team in education: Laura, with a background in education and education technology, emphasizes the importance of recruiting individuals with classroom and school leadership experience for roles in fast-paced education technology startups. Such candidates are valued for their empathy, adaptability, project ownership, and passion for problem-solving, particularly in addressing challenges faced by educators. Additionally, Laura seeks candidates who are comfortable with data analysis and have technological proficiency, essential in a startup environment focused on educational partnerships.

Handling rough times: To address this high-stress period, Laura emphasizes the importance of supporting and motivating the team. Strategies include sending food items to team members to help them recharge, offering individual praise and thank yous, using platforms like Thanks and Spoonful of Comfort for small gifts, and giving company shoutouts in Slack to acknowledge experimentation and new solutions.

Podcast transcript

Education and customer success

Irina 00:04
Laura, you have an extensive background in education from teaching and coaching to leading in the educational tech space. I’m curious how your experience as a teacher influenced your approach and perspective in your CS career.

Laura 00:18
How? Well, I think as a teacher, you know, you’re constantly faced with many students who have not the same expectation, or understanding or even needs of what they need moving forward. And your job is always to be really empathetic to what they’re bringing into school every day. So we really adaptable to all the things that they need, and the ways that you’re trying to move them from where they are to where they can get to. And then you need to really clearly communicate what it is that you’re trying to get across, and also understand what they are trying to tell you.

And so I think, you know, more than anything else, as a teacher, you realize that you can’t try the same thing with all of your students and expect that it will work since they are all different human beings, and we’re all different human beings. And then I was also an instructional coach. And so as a coach, I think I learned this even more is that all of the teachers that you’re working with have very unique needs. And so to meet all of those needs, you’ve heard this from many other teachers, I know, you tried to address all the different learning styles, right? All the challenges that they’re presenting, you’re just constantly being adaptive around the methods that you’re using, the way that you’re communicating the modalities through as you’re communicating, you just want to make sure that everyone that you’re working with feels really confident and comfortable with whatever material it is that you’re trying to share with them.

And then as I joined the success side, it felt really similar. So I’m basically just a coach now on the other side, and I really have to seek to understand all the different varied needs that all of the people I work with, usually still teachers and school leaders need to adapt any strategies that I think might help and communicate really effectively. And so you know, every once in a while, I’ll start a conversation. And I’ll realize that this is not going the way that we want it to neither of us is understanding each other. And so I need to pivot, you know, my strategy, my style, the way that I’m understanding what their issues might be so that I can help them reach their goals.

And really, as I work with more and more, both educators and school leaders, I realized that they just want to build and maintain that trust with their students or with their staff. And so my role is just to find, you know, like, what is it that you are trying to influence in your school? What is the culture you’re trying to build? What are the goals that you have? And how can the specific tool that I’m working with help you address that goal, but the approach is actually really similar. And the perspective is really helpful in that you understand how difficult it is to focus on any one thing. When you are a teacher, since you’re constantly thinking of the other 36 students or the other 50 teachers, and undecided, I tried to just make that really simple so that I can help you address this challenge we can, we can tackle this one together. And that frees up the rest of your day to address all of the things that your kids and your teachers need from you.

Irina 03:03
The question I have now comes from my perspective as a parent, one who is deeply invested in finding the best educational environment for her child as the writer of success advice, but how does your work in Customer Success contribute to shaping a positive school culture and influencing student behavior?

Laura 03:21
Yeah, I think we all want to know that the schools that our students or our children are attending are safe places where hopefully there’s an element of fun and excitement and our kids want to go to school every day. And that they feel like it’s a place where they are challenged to continue learning, but rewarded for doing the right thing. And so my focus is really just empowering educators to recognize and reward those students when they do the things that we want them to do. So you can imagine like you’re a teacher, and you really want your students to collaborate well together, or you want them to jump in and be really helpful to one another.

So what my role is now from a LiveSchool perspective is to reach out to the educators to find out those things that they want to encourage amongst their students, help them create that rubric of the things that they’re looking for in their kids, and then make it very transparent to the students and to the families that this is what we’re looking for. And then they give points to those students who are demonstrating collaboration, right, who are working together, really helpfully, who are sharing ideas with each other who are jumping in to help their peers.

And so as the teacher is positively reinforced, they’re calling out, they’re praising them. They’re saying thank you. And they’re giving them these points, that reinforcement that encourages the other students to also start collaborating, some of them or maybe for the very first time, right, they may have never collaborated before, but they see that their fellow student is doing it and getting praised for it. So they want to do that as well. And that then continues to cultivate this really supportive atmosphere that we are all here to help one another. So we’re building up that safe space where we can all come to school and to try new things and know that we’re going to get that support from other students as well as our teacher.

And then one step further that I think is particularly helpful about having a digital tool is that we facilitate that communication between everything that you’re doing as an educator, your students, and your students, families. So now the families are also seeing a report or they’re getting those notifications that they’re seeing when their children are creating that collaborative environment when they’re sharing when they’re helping others. And they get to have that essentially, like weekly report that says, Here are all the great ways that your kid was a really awesome superstar in school this week. And all that’s fine focus on all that, you know, positive behaviors and celebrating that. And so when I was in the classroom, right, I would try my best to make those positive phone calls home, right? I know that like Nefertiti was doing an amazing job. And so I’d call up her mom, and I’d say, oh, my gosh, she’s a blessing in my classroom, I really appreciate her. But I did that maybe, you know, once a month, because I was so focused on all the other elements of classroom management. Now, I basically get to help teachers share all of the really great things that their kids are doing with their families every day. So instead of it just being something where that mom hears from me once a month, she can now see every single day how, you know, well, Nefertiti is doing in class. And so I basically just get to sit here and help educators to celebrate all the positive things that are happening and hopefully make it so that you know, parents, like you get to see the really great things that your kids are doing, as opposed to wondering what happens in school every day? And are they doing the right thing?

Irina 06:37
Yeah, I think this is reassurance and the fact that the kid is spending basically 70 or 80% of its time in the schools with all the schedules that they have. You want to know they’re in a safe environment in an environment that appreciates them and emphasizes their unique value. So it sounds, I would say, reassuring and it gives a parent that peace of mind that their child is okay.

Laura 07:12
Yeah. And you get to celebrate it at home using very similar language, right? So you’re like, “Thank you for being collaborative today.” And I, as an educator or a school leader, appreciate you using the same language with your kids that we’re practicing in school every day.

Joining a new CS organization

Irina 07:25
Now, I want to ask you about beginnings when you first joined Liveschool, and also sticking back to your started Screencastify. How did you kick things off? How did you tackle the early challenges in these different settings? Did you have a different game plan for each word? How do you start when you’re joining a new CS organization?

Laura 07:49
Yeah, well, so it is so funny to think back. But Screencastify was way more chaotic than LiveSchool. So when I first started at Screencastify, it was February 27, 2020. And I remember this very clearly, because I went into the office like normal on that day, my first day of onboarding was to receive a computer, we had like a company wiki, where I was reading about all the different departments and what we had done and what we were focusing on. But on the second day, all of Hong Kong had decided that its schools needed to be closed for COVID. And then over that weekend, most of the schools in Europe had closed.

And so even though I was going to come in to go in person to conduct case studies in Chicago public schools that were using Screencastify, and prove out the efficacy of, you know, using Screencastify, to create webcam recordings or screen recordings and how that helped improve student achievement. All of those initial plans just went right out the window, because we could see the writing on the wall that COVID was definitely spreading, and it was going to come to the US and all of the schools were going to close at a moment’s notice. So we decided to completely scrap the idea about going and doing case studies.

And instead, they kind of made an initial COVID Taskforce. And they said, Laura, we want you to learn as much as you can about the impact of COVID and remote learning and education. What’s happening, what are some best practices, what are educators doing? What are school leaders doing? And so it really, you know, just became like, okay, what are ways that I can find this information since it hadn’t hit the US yet. So I joined different Facebook groups of like tech leaders in schools who are trying to figure out everything. And then I put together a webinar of educators from schools that were using Screencastify across the world where their schools had already closed, so that they could share some learnings about how they were using things like videos and screen recordings to stay connected to their kids and to create lessons, you know, overnight for everything that was going to be required of them when they went to remote learning. And so when I started at Screencastify we had maybe you know, like 45 I’ve different schools and districts that were in place that were using Screencastify. And over those next three months, that would just ballooned to, like 4500. And so we didn’t have a success team when I first started. And we had to kind of create everything from scratch.

Now at LiveSchool, very different, right? They had a really great team in place. They knew exactly why their schools and districts were using LiveSchool, they had great relationships with the teachers. So instead of creating things from scratch, I brought everybody together so that I could learn from them. And I wanted to ask them to make transparent to me, like, what makes the team special? What do they care about? How do they make big decisions in this team so that I’m not coming in and doing things dramatically differently? And I’m able to, you know, hear what’s been working well for them? And what is the history then? What are some of the accomplishments that they’ve made them really proud? What is their experience been since joining since LiveSchool had been around for a lot longer? It had been something that I had bought from my school back in the day. So I had known of its existence for a lot longer time as Screencastify. And what were some of the biggest challenges that the team has faced?

And then we dived into, you know, what do our partner schools really value? So what is it about the LiveSchool mission that brings every team member in? And that brings every educator in? What, you know, testimonials? Do we have that show that people like using LiveSchool and find that helpful in their schools? And, you know, why do they choose to use it? So what convinces them to stay with LiveSchool? What, if anything, has prevented them from achieving their goals with LiveSchool in the past? So it’s essentially a series of different listening sessions with my new team, and then documented all of this shared everything that I heard from them, verify that that’s what they meant. And then I had to meet with each of them individually, now that I had a bigger picture of the team. I was like, Okay, tell me about you. Right. So what do you like to see when you come to work? And how often should we be meeting? Or how often should the team be meeting? And when I want to say that I appreciate the work that you’re doing? Do you want that to be done publicly or privately? And, you know, what do you really want to do next, with your career with your opportunities that LiveSchool? What do you think that the organization should take on? So instead of it being a kind of chaotic environment, where I was just learning as much as I could individually, this became much more of learning about the team that’s in place, and what’s going to motivate them to be really successful moving forward with a new leader in place, right? I don’t want to disrupt things before I find out what is happening, what is going well, and how can I help fit into the culture that they already have in place?

Team and client connections

Irina 12:51
While you were accelerating into your journey at Liveschool or Screencastify how did you go about strengthening your team and client connections? Was your approach different in this towards school culture?

Laura 13:09
Again, yes, they absolutely were so different from each other. So Screencastify, right, had all of these individual educators who were choosing to bring Screencastify to their classroom. So we were a freemium model, where the largest number of all of our educators were just really gung ho about getting video creation in their hands. And they wanted to share videos with their students and with their students’ families, right, that was before COVID happened.

That was the story of who a traditional Screencastify educator was. But then, because of remote learning being thrust upon all of these schools and districts, thousands of them decided, oh, we need a tool to help our teachers connect with their students and with their students’ families, let’s get Screencastify put in place for everybody. And so overnight, it became a top-down decision. That’s, you know, I would say, needed a success team to help those district-level leaders and those school-level leaders have a vision and a goal for what they wanted to accomplish by putting Screencastify in place, right? Like, how are we going to implement this? Was every teacher expected to start with this tomorrow? Right? There was no time if we remember that case, it was right like March 8th, and that was a Wednesday and we just needed to jump in and do things. We wanted to put success in place to make sure that, school and district leaders could see who was creating videos, because when Screencastify was originally created, it was only going to give the statistics to the individual teacher, there was nothing to group them all together and answer school leaders’ questions about which of their teachers were creating videos.

And we needed to answer all of these brand-new video recorders’ inbound questions. So for example, when I started we had something like 15 or 20 questions that would come in from all of our teacher users in a month. That was February of 2020. By March of 2020, we were getting 8000 inbound questions. And we needed to make sure we had all of those in, we needed to be sure they all got an answer, because there’s nothing worse than knowing a teacher is frustrated and not able to connect with their kids, because they’re waiting on an answer from you. And so we also didn’t have any experience in working with district leaders from an organizational perspective. So I just invited them all to chat, I just asked if we could take 15 to 20 minutes. So I could pick their brains and ask them what kind of help they would need and what kind of help their teachers would need in their school leaders. And so those initial conversations with our earliest adopting districts really helped them shape how we would implement Screencastify across all of the other thousands of schools and districts.

Whereas at LiveSchool, my team already had this extensive history of working with partners, they already knew what their goals were, and what the vision was, and they already knew how we were implementing LiveSchool across many different schools. So I was able to then pick my teammates’ brains, I still reached out to as many of our school level leaders and our educators as possible just to hear it straight from them. And I’ve heard so many people call this a listening tour. And I absolutely agree that it is crucial.

So you need to hear it from as many of your different partners as possible. Why did they decide to bring LiveSchool to their school? What are they hoping to accomplish? What’s been really difficult for them? What do they hope to do next. And so pretty immediately, I also began asking my entire team to record all of our calls with partners, so that we could share all those learnings as often as possible internally to the rest of the team. Because it’s one thing, if someone from my team says, “Oh, my gosh, this school needs to have this new feature, we absolutely need to make it possible for them to be able to do this thing.” But it’s another and more powerful to be able to show that pain on the school leader’s face when they can’t accomplish something that they’re trying to do yet, by grabbing that snippet of that conversation and sharing it with our product team. So drastically different approaches. But in both cases, right, you need to talk to the humans that are choosing to buy the tool that you’re working with, and hear it from them. Whether you’re doing that for the first time for an organization, or you’re getting to pick the brain of your teammates first and then still go on that listening tour.

Challenges in CS team

Irina 17:38
Speaking of plans, let’s talk about challenges. What are the common challenges you face when joining different CS teams? And how did you overcome those?

Laura 17:49

Yeah, I mean, I think this is probably true for everyone that’s ever walked into a school as well. But every team just has different dynamics. Right. So I was recently on a webinar, and I heard Kristi Faltorusso say this, but every place you walk into will be so different. And that is just absolutely true. The way that they’re operating, the way that they’re making decisions, the challenges that they’re facing, right. So I was able to build some of the things for the Screencastify success team that I’ve been able to reference again, at LiveSchool, but I had to seriously adapt it based off of what the unique circumstances are for my new team, right? It can’t just copy and paste or pull everything over from one organization to another.

And so I think the best way to overcome this challenge that every team has a very unique dynamic is that you have to foster that culture of really open communication as quickly as you can. You have to ask everyone questions, you have to actively listen to what they’re telling you, you have to ask them to expound upon what they’re thinking. And you have to use that really well-intentioned teacher wait time to just sit in uncomfortable silence until they fill in the gaps with all the things that you couldn’t know unless they told you.

And everyone needs something different from their manager. So I was so appreciative of my teammates at Screencastify, who were really bold and told me when I was failing them as a manager. Like, I had a support team member who once asked if we could read “Radical Candor” as a book group. And then after we finished, she challenged me to provide her with more autonomy, so that she could try new things. And I could demonstrate that I trusted in her. So still really proud of Molly for doing that. But I think it’s just so crucial to make sure that you’re hearing people, that you’re giving them the opportunity to tell you things, and that you’re recognizing how every human being, just like when you’re a teacher and every student is different, is very much true as an adult. All of your team members are going to need different things from you.

Gaining actionable insights

Irina 19:50
What do you think are the biggest obstacles in gaining actionable insights for CS?

Laura 19:57
I mean, especially if you’re in really small EdTech companies like I’ve been, knowing who your current paying partners are is one of the biggest issues. So having the data that you need is going to be the biggest obstacle, right? Like, where is everyone located, who made the decision to decide to buy something. And keeping all of that knowledge as you will undoubtedly shift from one customer resource management tool to another is going to be a big one. But then once you know who your partners are, then knowing why they bought is important. I think so many speak to this, that like the sales team will have a conversation to be able to pull up pain points, to be able to pull out goals. But are they sharing that information with the success team? Can we capture that in our CRM? Can we track whether we’re delivering towards it? Right? Am I able to talk to every new partner that comes in and ask them what they’re hoping to accomplish?

And then finally, maybe this isn’t true everywhere, but definitely in the small startups that I started at, being able to showcase the value that partner schools and district leaders are getting out of a tool is crucial. They need some sort of data visualization that shows the fidelity with which it is being used across all of their different educators. They need to be able to see that they are using the different tools in different ways and that those ways are having an impact on their students. Because at the end of the day, we’re in this space so that they can positively influence student outcomes and family outcomes in their school community. But being able to show that has been quite tricky. So I’ve done as much as, you know, like, lean into writing SQL queries in BigQuery, so that I can power Google Data Studio to make data visualizations for people. I will say that now that there are tools like ChatGPT, and all those things, it might make that process way more accessible to non-computer science people. I had that background, so that was a little bit easier to walk into. But usually, it’s just like trying to figure out who your partners are, why they decided to buy, and how you can show them that they’ve gotten value from your tool.

Choosing the right CS tools

Irina 22:13
Thinking about students, how crucial is choosing the right tools and technology for CS Success?

Laura 22:19

Ha, I’ve had so many really fun conversations with people where we just walk through our CS tech stack. But I personally think that the tools can only come after you’ve figured out what is the information and the processes that you need. So to get started with, even when we had so many unique partners, we wrote almost everything in just our Google Docs, and calendar, and sheets, and slides, that meet and we used Slack to communicate with one another. And it wasn’t until we stood up any kind of process that we decided we needed to start bringing in a tool.

So for example, we knew that trying to schedule something back and forth with different school leaders who had a lot of change in their day, we had a lot of changes in our day, we needed something that would, you know, cut that process down. So that would be why we would bring in like a calendaring tool like Calendly. And we knew that in having all these conversations that we were recording with our partners, we needed something that would shorten them to just kind of quick snippets that we could then share with the product team or with the sales team. So we brought in a conversational tool, you know, like a Chorus.

And then we knew that we needed something that could schedule sequences, right, because every partner needs to learn things at a different time, and you don’t want to dump it all on them on the first day. So we wanted to drip out specific information based off of triggers that they had taken in the product. And so we brought on, you know, like a sequencing tool like a Mixmax.

Now me personally, I still have yet to implement an actual CRM platform. And I know that there are lots of, you know, CRM organizations that would be horrified by that. But I think that there’s a little bit more sophistication that we need to do in terms of all the learning from the initial experiments that we’re running before all those bells and whistles and honestly simplification that the CRM platform would bring would help us. And so while we’re working with a smaller budget, maybe than some of our larger other partners in CS might be working with, we’re still kind of focusing on let’s find the right process. And then we can look at ways to bring in a tool to help us automate it.

Building the CS team

Irina 24:26
We talked about beginnings, processes, laying down the foundations, and then we talked about tools. Now I want to speak about building teams. When you are building your team, are there certain qualities that immediately stand out to you as essential?

Laura 24:44

I’ve done quite a bit of recruiting in my time since we have had to scale up teams really quickly. And obviously, I am completely biased, having come from the classroom, having come from the school side, and now working in education technology that serves the same educators. But I am basically always looking for someone that has previous classroom experience, and a big bonus if they’ve had some school leadership experience as well, because I know that they will already be empathetic, they’ll have that really strong sense of adaptability, they will own every project that is given to them. And they just have this passion for problem-solving, especially all of the problems that the educators that they’re working with are facing.

So I also realized that because I’ve always worked in really small and quick-moving startups, I’m basically looking for people who aren’t afraid to crunch data, right, because all we have is a whole bunch of data about each of our partners. And we need to figure out who to reach out to next. They have to be fairly tech-adept because we’re going to move quickly, we’re going to try new things, we’re going to make sure that we can be the experts for all the educators we’re working with. And they really have to have just a fabulous presence online, since the vast majority of the relationships that we build with schools are going to be in a digital setting. So they basically have to come in and have a really strong conversation with me about how they’re able to analyze data, and then share it in a non-techie way. So using all of our layman’s terms, with all the educators that we work with.

Irina 26:16
Why do you think it makes the what’s the difference between a good CSM and a great CSM?

Laura 26:26
Sure, well, I think that there are so many really excellent CSMs and CS teams out there that are building relationships with their partners, escalating the issues that arise, intuitively solving the problems raised by the people that they’re working with, and meeting the challenges that their partners say need to be solved for, right. But the difference between all of those good CSMs and CS teams, and the great ones, is that they’re finding that the discovery process, which was originally created by, you know, your sales or your growth partners, continues throughout the life of the partnership. They’re going to always multithread, find new points of contact, capture all those testimonials, and all the different use cases, so that not only are they acting as a great product expert about the tool that they’re working with, but also as this really great consultant from a pedagogical standpoint of what the school needs and what the educators need. And they’re helping connect the tool to the teaching and learning that’s taking place, right. It’s not just about crunching numbers in this product; it’s about making sure that your kids are achieving more.

They’re also excellent at synthesizing multiple people’s experiences, so that when they say, “Hey, this is an issue that needs to be addressed,” it’s because it’s grounded in data from so many great examples from the people that they work with. And then finally, when they create a solution that fixes the problem for one of their partners, they share that. They share it internally to the other team members so that everybody’s like, “That would work really well for my partner too,” or externally so that other people in this product’s community are able to benefit. But they’re essentially acting as that guide to other CSMs and to other CS teams, so that everybody benefits.

Irina 28:16
How do you keep everyone on the same page and maintain a cohesive team environment?

Laura 28:26

I think one of the most crucial things here is that you do find time to meet together, especially since we’re so isolated, my team is fully remote. So, for example, as a leadership team, we meet every Monday. So that made sense then for as a success team, we meet every Tuesday. So we could use all the learnings from all of the different departments that we’re meeting with from a leadership team, in order to set our goals for the week, check in, reflect on what’s happened. And we’ve changed that cadence in terms of how often we meet, whether it’s multiple times a week, or fewer times a week in our busiest seasons, to really make sure that this is what the team finds to be most helpful. But essentially, right now, we meet once a week to cover everything from, “How was the weekend?” Right? So always starting with a temperature check about what are you excited by outside of work? What makes you human being that you want to share with us?

And then from a revenue standpoint, where are we now, where were we at this point last year? What’s our target? How are we doing any new business? Right? So who are our new partners that we need to onboard to make sure it gets started? Who are returning partners? What wins took place this week? What red flags and warning signs are like fires that need to get pulled out? Or issues that are popping up? What are some big bugs that are being requested that we need to prioritize? What are some project updates that we’re focusing on? So we also individually have projects that we’re pursuing, experiments that we’re running, how are things going, are we stuck at all? And then finally, just kind of open-ended ideas, concepts, suggestions we want to throw out to one another. Any upcoming PTO that we want to make sure we’re maneuvering around to take care of each other.

So we do that once a week. And then I meet with each team member individually. So we can go through how they’re doing, how they’re feeling, anything that they would like to highlight, or ask for help on, any projects that they’re specifically working on that I can provide some guidance or some help to. Every Friday, we go through specifically what our partners have helped us learn for this week. So what are all the really great insights that we’ve had from them that we want to share with others? What questions or blockers did they raise that we still have? And then support, we also meet separately on Friday to go through all the inbound questions that we had. What did we learn? How do we want to turn those into things we can share with others? Where are we still blocked? Or what questions do they have?

And then throughout the week, right, we’re very much open to just having all kinds of impromptu conversations. So we love to jump into like Slack huddles so that you can just share information very quickly, send messages to each other, we’ll throw ad hoc meetings onto each other’s calendars, we’ll do things like quarterly retros, to plan out our goals and figure out from a project perspective how things are going, we’ll meet with other teams so that we can see the new features that are going to be released, or talk to them about the sales process, whatever the case might be.

But making sure that all of that is wrapped up in how are things going from a cadence perspective, I don’t want to have more meetings than are necessary. And so we constantly review like, do we have too many meetings on the calendar? And where can we start to cut those back to give more working time for everybody that’s trying to help out as many partners as they can?
How to handle rough times

Irina 31:35
Everything encounters its share of challenges, especially in customer success. Can you talk about how you handle tough situations? And how do you motivate your team during these times?

Laura 31:46

Yeah, so I’m assuming that anyone else in education technology knows that back-to-school season is just really, really tough, right? Every single one of your school partners is trying to get started at the exact same time with new teachers who don’t know how to work with whatever system it is that you’re working with yet, and returning teachers who have blissfully forgotten how to do things while they’ve taken some time to do professional development or connect with their families over their summers. So it’s all kind of a gale force every back-to-school season, and I rely a lot on food to fuel my team. So sending them little food items in the mail to make sure that they’re able to recharge, I give a lot of individual praise, and thank yous, both to everyone on my team and to all the teams that we collaborate with.

I’ll send my own team small gifts like that, you know, thanks is a great platform, or spoonful of comfort. I’ll give company shoutouts in Slack to really promote all of the experimentation that they’re doing, or new solutions that they’ve found. And then just constantly remind them on any call that we’re on that we are all doing the absolute best that we can, while maintaining our wits about us and acting in a humane way. Because at the end of the day, if we get completely drained, we won’t be the best partners for all of our educators who might be having really tough days of their own. So we have to make sure that we’re taking that deep breath, that we’re taking those moments away to recoup, relax, and refresh, and come back to offer all the support that we can to all of our partners.

Common mistakes in CS

Irina 33:26
What are some typical mistakes that often lead to failure or underperformance? And more importantly, how do we fix those issues?

Laura 33:38

Yeah, I think one of the first challenges is like analysis paralysis, right? You are given so many pieces of data about the partners that you work with, that you’re often not sure where to start. Like, should I start with the people who are using the product the least? And try to get them to use it more? Should I start with the ones that are using it the most and have conversations with them about why it’s working well? Should I start in the middle and just try to move them more towards having more extensive usage? It can be a complete cacophony of voices in your head, but also what you see out there online in terms of advice. And so, you know, I would suggest choosing one, starting there, and making that decision, and then explaining to everyone why you’re making that decision and carefully tracking how it goes. So I like to think of everything in success as an experiment, right? You’re trying to move the needle, you’re trying to help people, you’re trying to influence. You’re trying to help through change management with different partners. And you really just have to start somewhere. And then make sure that as you’re applying the learnings from that experiment to the next one, that you’re constantly failing forward, right? I think that’s a big one, is that people are afraid of making a mistake at all. And that analysis paralysis that’s in place is going to be the biggest mistake of them all.

And I think a second one that often leads to failure is assuming that you know everything, right. So I think a lot of times, especially if you’re from education, and you’re working in education technology, or if you feel like you are the subject matter expert, and you’re walking in to provide that subject matter expertise… I am no longer a teacher, I am no longer a school leader. And the experience of leading a school and teaching in a classroom changes constantly. I never taught through COVID, for example, so I cannot pretend to assume that I understand the challenges that our educators are facing right now. Right in this world where the students had remote learning for one or two or two and a half years, it’s just vastly different from my own experience. So you always have to assume or approach each new experiment, or each new conversation with a kind of beginner’s mindset, and find out as much as you can about what makes this person tick, and what are the problems that are happening in their classroom, or what’s really important to this school. Because even though you’ve implemented your tool with thousands of people, you’ve never done this implementation at this school.

So I think between making sure that you start somewhere, but that you always check your assumptions, those will be the two biggest ways of ensuring that you can get past some of the typical mistakes that lead to failure.

Learning from mistakes

Irina 36:20
I am a strong believer that the best lessons are coming from the ones are coming from the ones that we make because of those mistakes. So I want to ask you, what is the latest mistake you’ve made in your CS role that’s turned into a valuable learning experience?

Laura 36:40
Absolutely right. I’ve got to share my own losses on this one. I was trying to help a group of schools turn on a feature where they would share automatic updates with all of their family members. And so, you have to get family members to sign up for these updates, and then you have to click a button to turn it on in LiveSchool, right? My CEO is going to love this. But I essentially way overdid it. So, I created this three-touch email sequence, I had a Loom video of me explaining why this would be helpful and how to turn it on. I offered my calendar if they wanted to chat about it, I also offered to turn it on for them. And I sent out that sequence to like 25 schools that had more than 500 families signed up. And out of those 25 schools, I got exactly one response that was like, “Sure.” So I was like, “Wow, I don’t know what I did wrong here. It seems like they’ve got a lot of really invested family members. Seems like the school is taking the time to get everybody signed up. Where did I go wrong in trying to show how to get started?”

And so, my CEO suggested, “Why don’t you just take everything that you did and pare it down to two sentences, right? One that says, ‘Here’s the number of families who you have signed up,’ and we’ll turn it on for you, just say, ‘Sure.'” And I tried that. And wouldn’t you know, 12 out of 25 people responded almost immediately saying, “Yes, please do that for me.” And so, this is probably unsurprising to all of you out there that work with very busy professionals. But my big takeaways were less is more. So if I can give them the exact information that they need, so that it fits on their cell phone as they’re going from classroom to classroom, or, you know, hopping into the car at the end of the day, with as few words as possible, it’s going to send the message home.

And then, can I partner that with an ask of, “Can I help you do this?” or “Can I do this for you?” Something that gives them an easy opportunity to say, “Yes, please take care of that for me,” or “Yes, please take that off my plate.” Right? So I think, as I’m now looking at all the other experiments where I’m reaching out trying to drive usage or make sure that I’m able to help them achieve the goals that they want to achieve, I’m constantly thinking through, “How can I shorten this copy? So, how can I get it down to 250 words or less?” And then, “What’s a key metric that would be the reason they should do something, right? Like, what would drive this decision? And how can I help them achieve that?” So that’s my most recent mistake: trying to overload someone with information where they are not going to be able to read it, they’re not going to have the time, or be able to watch the video. How can I truncate it and make it easier for them?

CS predictions for 2024

Irina 39:25
As we wrap up, I’d love to hear your thoughts on the future. What are your predictions for the customer success industries? Are there any trends or changes you foresee that we should all be keeping an eye on?

Laura 39:39
I am probably not the first person to say that I think we’re going to see a whole bunch more of AI-powered customer insights. So whether you’re recording a call and grabbing all of the insights from there, or you’re kind of searching through all of the emails that you’ve had with somebody, or any other way in which you’re engaging with your partners, I hope that we will be able to take the learnings that are coming out of each of those conversations or interactions, and create even more personalized customer journeys for them. So therefore enhancing all of that proactive support that we can provide them, because we’re using basically predictive analytics about where we think their journey will go next, based off of all the other partners who we’ve been trying to help. We’re trying to make this as clear as possible, and we’re trying to make sure every one of the partners we work with is successful. So I know that I’ve seen more and more people moving this way, and I think that’s a great thing for us.

I would also double down on the humans on our team. And the really human-centric approaches that we’re taking to build and maintain that trust with each of our partners are going to be so crucial, right? At the end of the day, you want to know that someone has heard you, has understood your pain, and is there to help provide a solution to the issue that you’re raising, because you haven’t figured it out yet, and you’re looking for a little bit of help. So even as we rely more and more on AI insights, and all of the things that are coming out that we can summarize across everybody, there’s still going to be a need for, and we should still rely on, the really great thinking power that each of us has, and each of our team members have, to make that interaction with all of our partners as personalized as possible, and making sure that, you know, they’re feeling that trust, they’re feeling heard, and that they’re being successful.

Irina 41:30
Laura, it was a pleasure talking to you today. And thank you for taking the time to share with us so many great advices, you shared your personal experience. And I really I really enjoyed. And because it’s almost ended the year, I want to wish you happy holidays!

Laura 41:56
Thank you so much. It was awesome getting to dive into these questions with you. And I hope that there are success leaders everywhere out there that are following your advice as well. I think this is the time for all of us to reflect on what’s gone really well. What we want to improve on and then giving ourselves the space to take some time away so we can improve on them because you need a lot of energy to do that. So thank you and happy holidays. I hope that your 2024 if it doesn’t come with a bunch of resolutions, at least comes with some energy to be able to tackle whatever you wanted to.

Nicoleta Niculescu

Written by Nicoleta Niculescu

Nicoleta Niculescu is the Content Marketing Specialist at Custify. With over 6 years of experience, she likes to write about innovative tech products and B2B marketing. Besides writing, Nicoleta enjoys painting and reading thrillers.

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