Blog Webinars and Podcasts

Mastering CS – Candid Leader Insights – Con Cirillo | Ep 1 Podcast

November 1, 2023 29 minutes read

Summary points:

Welcome to Mastering CS – Candid Leader Insights, an interview series where our Head of Marketing, Irina Cismas, chats with some of the most influential customer success leaders in the industry. In this episode, she’s joined by Con Cirillo, the Director of Lifecycle Marketing at Funnel and an advisor for investment groups and companies. Con has over 15 years of experience in customer success, marketing, and sales, and in this episode, he shares his insights on how to build and lead a successful CS team.

In this interview, you’ll learn:

  • How Con uses the 30-60-90 day framework to onboard new CSMs and help them learn the product, the story, and the customers.
  • How to avoid common mistakes and misconceptions that CSMs might have, such as being too reactive, too passive, or too salesy.
  • How to tackle the challenges and trends that CSMs face in a fast-moving and competitive landscape, such as customer churn, retention, and advocacy.
  • How Con hires and develops a strong CS team that has the right mindset and skills, such as curiosity, coachability, and ownership.

If you want to hear Con’s detailed insights and tips for customer success, watch the podcast below. You won’t regret it!

Key insights and takeaways for CSMs based on the interview:

  • Use the 30-60-90 day framework to ramp up as a new CSM: This framework can help you learn the product, the story, and the customers in the first 30 days, engage with customers and execute on the role in the next 30 days, and add value and be proactive in the last 30 days. This way, you can build a solid foundation and confidence for your role.
  • Avoid common misconceptions and mistakes in the CS world: Some of these are relying too much on internal documentation, rushing into execution without building a foundation, or not being open-minded and curious about new trends and technologies. Instead, you should learn from your mistakes, have a growth mindset, and seek feedback and coaching.
  • Keep up with trends and tech that are relevant to your customers and your product: You can do this by looking for signals that are meaningful to your customers and your product, being an anthropologist within your company and outside, and being transparent and communicative with customers about new features or changes. This way, you can stay ahead of the curve and deliver value to your customers.
  • Hire and build a cohesive CS team with intangible skills: Some of the intangible skills that Con looks for when hiring CSMs are curiosity, coachability, ownership, and passion. He also builds cohesion and unity within his team by telling stories that give purpose and direction to his team members. He also handles situations where he is not on the same page with a customer or a colleague by sitting side by side with them and framing it as “us versus the problem”.

Podcast Transcript:


Con Cirillo 00:37
Hi! How are you?

Irina Cismas 00:39
I’m fine. Thanks. It’s great to finally meet you, even if it’s virtually.

Con Cirillo 00:44
Likewise, I’ve heard great things. And I’m excited to do this.

Irina 00:48
Thank you. Thank you so much for taking the time to join me today. Yeah. When I envisioned the Mastering CS – Candid Leader Insights,his is how the series is called, I picture it just like this a casual chat between professionals, almost as we were having a cup of coffee, relaxed and real. So this is all this is all about. Sound

Con Cirillo 01:15
Audio, visual wise, coming through okay?

Irina Cismas 01:19
I guess so. Yeah. All good. It will be approved by Mike. So. Okay, we can go ahead. So to kick start our discussion, and speaking about the journeys, I want to ask you, if you had to capture your journey into CS leadership in just three words, what would they be?

Con Cirillo 01:48
“Completely by accident” would be the phrase I use. I certainly did not set out in my career to necessarily become a leader that works with CS. I mean, I think growing up, I wanted to be a firefighter or something more common like that. So my journey to this has certainly been by accident, but a delightful one.

The 30-60-90 day framework as a new CSM

Initial focus – first 30 days

Irina Cismas 02:10
Speaking of beginnings, and by all means, when I was little, I wanted to be a guest. This was my desired job, because everybody was treated nice and we had the cool kids so that I want to be a guest. But speaking of beginning, this year, my daughter transitioned to a new kindergarten. And there was a mix of excitement, eagerness, and a little bit of unknown for her. And I was thinking that it’s kind of like the journey of a new CSM. And reflecting on that, either from your experience or someone you’ve observed ,who you’ve been working with, what do you think should be the initial focus for a new CSM in their 30 days?

Con Cirillo 02:56
The most important thing for a CSM and this is I think true for every person joining a company is to learn the space, learn the product, learn how it works, learn how your customers think about it, a lot of the more tactical stuff of when did we do EBRs. And how do we think about outreach, right?

Like there’s all the mechanical things that those can come with time you can teach somebody how to do those things, or when to click the button. But that mindset and that curiosity of “do I want to learn about how this all works?”. And like “why do we as a company exist?” If I’m a CSM in my first 30 days, that’s the question I’m ultimately going to try to answer. And it’s one where the journey is the destination, I don’t know that you’re necessarily going to find one single answer to that question, but just trying to immerse yourself in what the product is that you sell, or what the thing is that you do. The sooner you build an appreciation for that as a foundation, everything else starts to be easier because you have a strong background to build on.

60 day mark – what’s next?

Irina Cismas 04:02
And moving past that first month, as they move towards the 60 day mark, what’s the next big step or shift you believe they should focus on?

Con Cirillo 04:13

I would start to say that’s when you think about starting to engage the customers that you are serving and your book of business or the role you’re going to be doing more on an execution day to day level, starting to understand who your customers are, right? And what’s the context like. How are each of them using the product or your solution in different ways and there’s probably going to be some overlap and some themes and trends that you can pull out which is great. And a lot of them might have like edge cases or some extra history that trying to learn how to empathize and catch up to where they are in the relationship relative to your company that will serve you well to.

I don’t think it’s a expectation that customers will have. You’re going to know the ins and outs, and you’re going to be totally caught up on the relationship in the first 60 days or even six months. But showing that you care and showing that you’re trying to figure out everything that’s gotten you to the point and them to the point that they’re at, the sooner you try to understand that once you have that foundational knowledge of what you do, right, how is someone using it? And how have they gotten here? To me, that’s step two, right? And then you start to build more confidence and be more comfortable with starting to add value to them. But I think you have to learn where they are and how they got there.

Milestones to reach in the 90 days mark

Irina Cismas 05:37
You mentioned step two. So now I’m going to ask you about step three, because I want to provide to our audience that 30-60-90 days blend, hence the questions. So when we are reaching the 90th day, what’s the milestones or accomplishments would they be looking for to make sure that they are on track, and they are moving the needle for the business that they were hired in?

Con Cirillo 06:07
Starting to do, I’d say that that’s where the training wheels should start to come off. And that third months, maybe they’re actually having customer facing calls themselves, or maybe they are starting to look proactively and listen, oh, we have a new feature coming out that I’m hearing about in marketing, oh, I think this customer might benefit from it. So getting those gears turning, and you’re spending the first couple of months like catching up to present day. But I’d say 60 to 90 days that’s in that third month, where you’d hope to start to see the gears turning forward, seeing them execute on some things by themselves and just a more really start to settle into what the role is going to look like.

The thing that I feel separates good CSM from great CSMs in that time, is again, are they starting to connect dots and look at other things happening in the business and almost interpreting and inferring? “Oh, I think this might solve a problem that one of my customers has”.

People who can start to be on offense and are comfortable kind of looking for what comes next. To me that’s that’s a sign of someone who’s really ramping quickly. And if it takes someone a little bit longer to get there, that’s reasonable, too. But that hunger has to be there. And by that third month, it should be pretty clear if somebody’s comfortable and going to be comfortable serving the customers they are in the space that they’re in.

Misconceptions during the first few weeks as a new CSM

Irina Cismas 07:35
I’ve somehow always found that sometimes the biggest growth comes from those little hiccups or misconceptions we have early on. Are there any common ones you’ve noticed CSM might have in this initial phase?

Con Cirillo 07:53
Yeah, there is all of the internal documentation, your CRM, there might be a written down history or a narration of why a customer came to you and why they picked you over someone else. And that information may be accurate to the time. But if that customer has been with you for two years, their business has changed, their use cases have changed, the people using the tool have probably changed. So it is important to lean on all of the documentation and all of the stuff that tells the story that exists before you get there. And keep an open mind and actively listen to your customers to try to understand read between the lines.

So maybe what’s changed since then, or have there been assumptions that others in the business have made about, “oh, they’re really just looking to solve the x, but maybe you hear them mention y or z”. So it is certainly a good to spend your time doing your homework on the things that are written down. And have some of that extra space and keep an open mind to the things that you can hear about your customers because you have a fresh set of eyes and a fresh perspective that frankly, no one else in your company has, which is a great advantage.

So being able to listen and actively kind of shape your own story a little bit and understand your own color and flavor on how you think about your customers and what they’re doing. That’s something where if a great CSM pushes themselves to be more open minded like that, you see that payoff.

How and what to prioritize in the first three months

Irina Cismas 09:28
You mentioned earlier about a lot of documentation. And I know that every time when you start in a new company, there’s a lot of information that you need to absorb. And I often find myself overwhelmed of the information. How do you prioritize everyone in the role of a CSM, which from my perspective, is in the central of everything and has multiple stakeholders that he needs to serve. From where do you start in your first three months?

Con Cirillo 10:03
Yeah, the first place to start is the product, the sooner you build that product knowledge and that just underpinning appreciation for what it is, what you do all that. To me, the sooner you build that the better. And the more that compounds and pays off and every other day that goes by. So I would start with I want to be in the product.

And if I’m a new CSM, I want to really learn how this product works. I want to learn what doesn’t work about it and just try to immerse myself in this tool, so that when I go to talk to anybody, I actually can empathize a bit more with the things that they’re trying to get done.

Once I have that foundational product knowledge, I do think getting the story. Okay, what’s the story we’re telling here? What’s the narrative, what’s from a product marketing side, or from a sales side, like help a new CSM kind of immerse themselves in that story. Because then anything they do and talk to customers about, you can start to view it through that lens, okay, I get tired of using the tool in this way. But the problem they’re really trying to solve is this other thing, right? That may be hard to quantify maybe more of an emotional pain. So foundational learn how to use the product, technical knowledge, then more of the storytelling piece is kind of part two.

And then part three, that’s when I’m probably going more into like the CRM or looking at the onboarding tools that are using so I can really learn my specific book of business. But if you try to learn that too fast, and you just start saying okay, customer X is doing this and customer wise doing that, you know, they’re renewing next month, you can get by with that stuff. But that’s pretty surface level, there’s really this deeper appreciation that starting with how do I use this tool? How do I think about this story in this company, doing those two things first, and then spending time in your CRM or really learning the tactical piece of what you’re doing? To me that’s a good way to ramp.

Aligning with other teams

Irina Cismas 12:00
That’s very interesting, because usually there are a lot of articles that say CSMs should align with sales. And based on the talk that you made, the way I read it, is first is product, then it’s a combination of Product and Marketing. And last but not least it’s the moment in which I go deeper into the handover between sales and customer success and very interesting top you made.

Con Cirillo 12:37
Might be a little bit of controversial, but that’s probably not the most common way to do it. I just have found across all of the companies that I’ve joined in any capacity. Some of the ones where I’ve been the most successful are the ones where I spent the most time learning the product and learning the positioning and the story first. And I know there have been cases and speaking from my own experience, where I rushed into like, “Okay, I just want to go do the job and create value and do all of the tactical things that were on the job description”. And I have found sometimes when I go too fast into that, like I want to deliver value bucket, I miss out on some foundational things that eventually you can learn, but it’s some stuff where if you go into a customer call, and you don’t really know the product, right? Like it can be uncomfortable, and you quickly, I think get found out in the sense of okay, maybe this person really doesn’t know what they’re talking about. And so to build that trust, I have found in the roles in the teams I’ve built that start with the basics. Start with the what, and the who, and the why. Even if it takes a little bit longer to really ramp to full end seat up and running role. It’s worth it.

What CSMs might miss

Irina Cismas 13:53
Hearing you speaking, I just envision a title – Even Rome was not built in one day. So I think the 30-60- 90 days, or allocating at least three months to know all the nitty gritty details will basically pay off medium and long term, we often rush into proving to our bosses, to our colleagues, that we were the right person and we usually neglect I would say this part.

Actually besides this, I want to remain on the Learning Path. But I want to ask you besides what we discussed. Do you think that there’s one thing or maybe more things that even experienced CSMs might sometimes miss or not give enough attention to. Similar with what we just discussed that we often rush into “let’s prove that we were a good hire” and we don’t allocate enough time to settle in. Besides that, any other misconceptions or things that we miss?

Con Cirillo 15:09
There, as you get settled into a role, and you’re a CSM, and you’ve been around for a couple years now, you get the story and you get, you get the who. And one thing I have sometimes seen as particularly in a scale up or a fast moving company where there’s a lot more of a product being built, you might have started. And when you started, right, the footprint of the product was x, or the market you were in was was pretty defined. And as strategically those things shift and evolve, which is good, right? That’s a healthy sign. Some CSMs go, yeah, yeah, I already did, like I could the upfront work, I, you know, first couple months, I spend time going slow to go fast.

And I feel there is this like constant growth mindset that really serve CSMs? Well, and it can be easy to kind of fall into that trap of like, okay, I know what I know, I don’t really need to learn anything new right? Now I need to just execute on what I’m already doing. So I’d say being more curious and being just always looking around at what new features are coming out and how is sales talking about this product, and just being more of an anthropologist within your company, I do think for a great CSM.

That’s the differentiator, right? There’s a lot of CSMs within your company or in other companies who can go through the motions and do the basic stuff well, but the people who are really curious to find how the dots connect and constantly push themselves, to find other parts of the business to talk to or to find other ways to learn from their peers. Those are the people that I generally think do much better in the long term. And it’s a tough muscle to build, it certainly is not in anyone’s job description, and it’s hard to start building that muscle and build that mindset. But if you can cultivate it as a CSM, I think you’ll be in a much better place. And that’s more on an internal side.

One other thing for CSM on an external side is like what else is going on in the space, your product does not exist in a vacuum, your solution is not the only one. You look at the Martech map, right? There’s 11,000 more tech tools this year alone. So you’re not the main character of your customer story and for some CSMs and honestly founders and anyone else that’s tough to hear. And so what I would say is figure out how you as a company exist in the landscape relative to everything else? What are your competitors doing? How can you look a little bit externally to follow what they’re up to. And see, are they talking about things differently? Are they starting to do some stuff different that might be relevant to the conversations you have with your customers, or not even competitors, but just other tools in the landscape that you know your customers might be using.

Let’s say you sell a marketing performance attribution reporting tool, that’s great. Okay, if something happens to the CRM tool that your customers using, even if you’re not selling a CRM, or competing in that space, if something happens to that tool that might have a second order impact on you. And so for CSM is being able to look internally to be curious, but bringing that same curiosity externally as well and saying what else is kind of happening in this space and finding ways to share that internally and share that with customers.

That’s the stuff again, that shows you care and goes the extra mile, especially in a world where SaaS products in particular are pre commoditized, there’s a SaaS tool for anything, and there’s a bunch of SaaS tools for everything. So the customer success software itself, yes, you have cool bells and whistles and features. But that can’t be the thing that really differentiates you long term. There’s the old expression of “we don’t remember what people say we remember how they made us feel”. And so I think that’s true from a CSM side. If you can differentiate yourself on that white glove, really VIP experience. That’s the kind of thing that again, you might have to push yourself to get to as a CSM. And if you do that, the score works itself out.

Mistakes are just lessons in disguise

Irina Cismas 19:09
I want to ask you, what do you feel about mistakes? Because usually everyone is afraid of mistakes, and we don’t take the good sides out of it. In my case, the best lessons I’ve learned were from mistakes. So I’m not afraid of actually mistakes or failure in some cases. What’s your point on this? What’s your experience with mistakes in general? Mistakes with clients in CS or generally in business?

Con Cirillo 19:40
Yeah, you learn or you missed the lesson. That’s the way I put it in and I didn’t say you win or you miss the lesson, right? You learn or you missed the lesson. I try to find something in everything I do. The highs and lows, the times things went great the times I bought something there’s always a lesson.

So I would say as a CS leader, or as a young CS, any leader within a company, creating that space where it’s okay to make mistakes, it’s okay to screw something up, right? If you don’t mess something up, you’re frankly not trying enough. Growth teams will talk about experiments. And a good growth team only succeeds with their experiments 30% of the time, so 70% of the time, it didn’t go the way they thought it would. That doesn’t mean that experiment teams are bad or growth teams are bad, it means you’re trying stuff and learning.

So from a CS that applies just as much, it’s okay. And it’s good to try new things. And so long as you have a feedback loop with yourself for that, for that learning mindset, and you have good coaching and good mentors, and leaders, and there’s a great culture around. We’re all doing our best, we’re all doing our best and that’s the best we can do, and we’re going to make mistakes, and we’re going to learn and move forward.

Creating that type of atmosphere will move a business faster. You might go two steps forward and take one step back. But on the flip side, if it’s a culture where people are scared, and it’s rigid, and if I make one mistake, like that’s it, you’re not going to take two steps forward, you might only take one step forward. So there’s certainly this, how do you build a culture where over the long term, you do better, things move faster, and you learn a lot quicker. Having that mindset in that framework of it’s all right, that things will go wrong. It’s not. If things go wrong, it’s when they go wrong.

And when we make mistakes, so I certainly welcome and cherish when people are willing to try something. And it’s something that inherently is outside their comfort zone. And sometimes it doesn’t go the way we had hoped. Though, the framework, I also try to give as let’s not make the same mistake twice, right. So like, I have messed up in uncountable amount of things over my career, I try not to make those same mistakes twice, I try to take the lesson from everything that went well, it didn’t go well. And bring that forward. And if you try to improve little bits at a time and one lesson at a time getting that compounds and so trying to create an atmosphere in which other CSMs and people in your company feel that same psychological safety and sense of trust. Those are the teams that win.

Keeping up with trends and tech

Irina Cismas 22:23
Very good advice. Very, very good. I’m comparing this with the CSM job with the job of the parents who are basically raising the kids and trying to basically help them develop accepting that they are making mistakes, let them make mistakes, because this is how they are actually developing and growing. Learning how to think. The CS world , actually the world in which we are believing is constantly changing and developing and it’s a fast moving thing around the around us. How do we how do we make sure that we stay up to date? With everything that comes up with the trends with the tools with with everything? How do we make sure that we aren’t losing trends? What’s your recommendations for CSM that are actually entering the landscape and maybe also for the leaders themselves?

Con Cirillo 23:36
Learning to separate the signal from the noise is a very helpful skill. And it is only a skill I feel you can develop and own and refine after you go through it a bunch, right. So I remember early in my career, I would hear about a new competitor or new technology and you just run 100 miles an hour, you drop what you’re doing, and you fire drill and go right towards whatever that new shiny thing is.

And oftentimes, there’s something to be learned there. And there’s like, Okay, that’s a cool technology, right? But eventually, like trends or trends and fads or fads. And so eventually if you spend way too much time on the shiny new thing, you can lose competencies, or like lose some of the proficiency you have in the core stuff that made you really good in the first place.

Now, every time in every trend that you’re a part of and every cycle you go through where that’s the hot new thing. It gets easier to hone and refine your own core as to what really matters and what’s like, Oh, that’s cool, but that’s not really going to impact us for a couple years or okay, like I don’t think this technology, you know, NFT’s probably don’t make any sense for me to spend a lot of time on and that is a that’s a gut sense that just takes time to refine. So it’s certainly I think that being curious, being an anthropologist just being on the lookout for what is coming next. What are people talking about both within your company, within your team, even just within your industry, right?

That is all very good thing to just be curious about what’s going on. And again, there’s internal ways to try to learn more. And then there’s external stuff. So both are important. Trying try not to drown yourself as a CSM in all that new stuff to your point, there is so much happening. If you look on Product Hunt on any given day, right? There’s dozens of new tools that could do X and solve for y. And that’s all well and good learning to really tighten your blinders on like, okay, there’s a lot of cool stuff out there that’s worth a little bit of my time. What are the few things that are really worth a lot of my time and leaning on other people to help validate some of those things?

Yes, some you might think generative AI right now, that’s the hot tool. I personally think that’s a really long term sustainable trend versus more of like a trendy flashy thing that’s going to fade away. But that doesn’t mean that I unilaterally am going to drop what I’m doing and just go work on that right, I’m probably going to be talking to other departments and other customers and really try to like figure out what my perspective on that is more long term. And I think CSM, that’s not all up to you to decide what’s the trend that you should drop everything and run towards.

It’s good to keep your ears open, it’s good to listen. And through the conversations and through the osmosis of what you’re doing in your job, you eventually will start to pattern match and find those trends. And it’s okay especially early in, in your role or in your career. You may not have that intuition that sense yet. And that’s all right, that’s where you should be, but to be self aware of it and to say, Okay, this trend, Wow, that really made me excited. Just knowing that you’re gonna go through those motions and knowing that stuff’s going to evolve and new releases from your competitors are going to scare you like knowing that’s what to expect, means that every time it happens, it feels less scary, because you have more of a framework to fall back on. And more of that intuition that you build. So it’s one of those stay the course remain curious. And things work out.

Biggest challenges as a CSM

Irina Cismas 27:13
Staying on the topic of challenges. What do you think is one of the biggest challenges that CSMs do face on their day to day jobs in the current ecosystem that they are acting?

Con Cirillo 27:31

One of the hardest things for CSMs is trying to give every customer special love, right? Every customer is different. They don’t have one size fits all problems, they are in different geographies and different industries and like everything is different, right?

The one thing they might have in common is that they’re paying you for a tool or a solution. As a CSM knowing like “Okay, how do I prioritize who to reach out to? How do I come up with what to say?”. That prioritization can be tough, especially as CSMs are getting generally asked to do more of the ratio of customers to CSM. I feel like that is increasing. And there’s definitely automation and stuff that’s helping augment and make that a little bit easier for CSMs. And in general, they’re being asked to do more.

Knowing how to prioritize and knowing how to not get overwhelmed of “Okay, I have all these customers, and a bunch of them might be on fire, and I don’t know who to talk to first”.

That’s a challenge. And that’s a challenge, I think, in general, and especially for CSMs, where the problems you need to solve might be wildly different, right? So it’s context switching. And it’s learning different skills on the fly, which is a struggle for any human. And especially for a CSM, who’s inheriting a bunch of relationships that aren’t met new, they’ve been around and have expectations. So that’s a definitely a big challenge. I think that prioritization, what I would say is a way to start working through that is finding what are the signals? So are there certain, let’s say flags within our usage a customer’s usage of your tool, right? If they’re doing X, good, and if they’re not doing X? Okay, those are the people that we really want to think about talking to see if we can help them get more value.

So trying to find what are some of the quantitative ways to sort and stack stuff a little bit, and then still having that latitude to interpret and say: “Yeah, I got five customers who maybe aren’t using this feature this month. But when I really drill into it, I think this one is the most important”. It’s like jazz, right? It’s structured enough that there’s foundations and infrastructure there. Yet there’s still creative art to it that gives you live to try stuff out and really put your own special human spin on it.

Balancing expectations as a CSM

Irina 29:54
You mentioned jazz, I have a metaphor with dance. I feel like when working with clients, it’s a balancing act between expectations and reality. And do you have any recommendation on how to keep that fine balance in between?

Con Cirillo 30:14
Transparency and communication. I have yet to find something that works as well as being honest and being open, and just talking. Which is so funny, we live in this world where, you know, it’s all of these new shiny technologies, and we’re going to the moon, and we built AI like that all that’s awesome, all that stuff is awesome.

I’ve yet to find anything that helps me as much in my career as talking to people and being open and being empathetic. So it’s really the thing that separate good CSM from great CSMs doesn’t cost any money. And it’s way simpler than I think we make it out to be. Being honest with customers, hey, this is what’s in the roadmap, this is what I know, I’m still working through this thing, you know, here’s the steps I’ve taken to escalate it.

Because there’s so much asymmetry of what’s happening between the company and the customer, right? As a company, you know, that Dev is looking into that bug and that this feature is on the way or like all that stuff, you also generally know how your customers are using the tool. But if you put yourself in your customers shoes, like they know you, they don’t know your development team, they don’t know that your CEO is really excited about this new thing.

And so there’s a lot of asymmetry. And the best way to break down those barriers is just to be as transparent as you can and communicate as best you can and not assume that your customer is going to know any of this internal stuff, because there’s no way that they can, again, you’re not the main character of their story, and that’s totally fine. So don’t assume that your customer is going to have read every blog post and knows all of the industry trends as deeply as you do. If you can be the messenger to help communicate that stuff and translate it and break it down and say, here’s what it means for you. Here’s what I can do for you. Being open like that. And talking like that adds a lot of value, and frankly builds a lot of trust, which for a CSM is probably the most important thing you can do. And it doesn’t cost any money to do that.

Not on the same page with the customer

Irina Cismas 32:21
One with all the communication in the world and trust that you are trying to build, there are situations in which the CSM and the client are like water and oil. That’s simply the way it is. How do you overcome those situations? What do you do when basically everything it’s not working?

Con Cirillo 32:47
There’s an exercise I like to do, it works well, when you’re in person with a colleague or with a customer or just someone that you find you’re just not on the same page with and rather than sit across from them at a table. I like to sit side by side with them. And to look at a whiteboard or imaginary point on the wall and say it’s us versus the problem.

Oftentimes, it feels very adversarial and very confrontational of, okay, and it’s a zero sum game. And it’s easy to fall into those those traps in that mindset. And almost that if your customer like you’re trying to compete with your CSM, or you’re trying to like get something out of them. And I understand why that mindset exists. I don’t think that’s the way it has to be. And so really trying to orient in our relationship, “hey, it’s us versus this problem, right? You want to solve for x, I want to help you solve for x, let’s find some common ground and find things that we have in common”.

And I think generally, if you start there and can really spend whatever time it takes to build that core, and that shared understanding and shared respect, the other problems may not get solved, but it certainly will be easier to navigate them when there’s at least a share. Okay, I might be annoyed, this features taken a while to come. But I really trust that this person’s doing everything they can. I find again that goes back to the communication piece.

And just trying to calibrate and listen openly, does go a long way. And to frame it as it’s not me versus you. It’s us versus as a problem. I found that an effective way to kind of reboot and reset relationships where maybe it hasn’t gotten off to the start we had hoped or maybe it’s not trending the way we had hoped. You can’t do that every single time something goes wrong.

But I do think that’s a card that CSMs can have up their sleeve of like, look, let’s reboot, let’s rethink about this from a fresh perspective. And, you know, let’s start over. I think there is there’s a power in a in saying that and just saying, Hey, I think we should start over. I think we should rewind a little bit. I find generally people particularly in a business context where the incentives should align are open to that and sometimes we just need someone to say it to get us out of this very rich. Due to countless business shell and remember where people and I find, especially in a CSM role that works more often than not.

The CS team

Recruiting the right people

Irina Cismas 35:09
We started the discussion about the collaboration and about teams, we’ve been talking about the way we interact, I want to zoom in into building Customer Success teams. And I want to ask you, when you are building your team, when you are recruiting, what are the most important things, the most important traits you are looking that are non negotiables? If it’s not this most probably it’s not the hire. What are your things?

Con Cirillo 35:43
The things I look for are things that are really hard to communicate on paper. And that’s tricky in a world where this certification and that software tool, it’s great, but like, anybody can learn any tool in my mind. And so it’s the intangibles. It’s a growth mindset, right? Is this somebody who likes to learn things? Is this somebody who is curious about stuff being coachable and saying, hey, I recognize I am a mere mortal human doing my best and there are going to be things I need to work on. Trying to look for people who, again, are just curious. Those are the types of intangibles that really go a long way people with an ownership mindset and a mentality of their a CSM.

And they should have the same perspective and the same investment or interest in the company as the founders, like people who have those types of intangible skills and that that mindset, to me, those are the people that I like to hire, and I see do well, because you can teach someone how to click the buttons, you can teach someone how to say it in a certain way, but you can’t teach people to care. And so finding people who are learned alls and they really like to try new things, and are comfortable being on this journey of growth and self discovery and want to succeed.

It’s those things or if you have those come work for me. And if you don’t have those, I think inherently you’ll hit a ceiling. And that’s not to say people can’t do their job well and punch in and punch out. I’m not advocating for, you know, a grind mentality. It’s unsustainable. But if that internal passion is not there, I think you can only go so far, I like to find the people who have that hunger and just want to be good and want to go on a great journey, because we’ll go there together.

Irina Cismas 37:42
Now, I have to ask you, how do you test this in an interview or in a discussion, because that’s the difficult part. I was asking genuinely, as a hiring manager? How do you test this out?

Con Cirillo 37:59
Yeah, I asked a lot of questions. And I try to elicit stories from people because the storytelling, I think it’s easy to phone in like, “Oh, I’m prepared for the one line answer of you know, what’s, what’s your biggest weakness?” Right? Like, it’s too easy, I think, as a candidate to anticipate some of those questions and come up with like, the really captured one line response, there’s a place for that.

I try to spend more time understanding, okay, tell me about a time when x or like, how do you think about blah? Or what was the last new thing you learned? Right? Tell me about the last time you changed your mind on something and why I tried to ask these questions that are really hard to capture with bullet points on a resume or in a LinkedIn profile. And I tried to just ask open ended questions that give me insight into the person’s mind. The thing is, they’re not trick questions and not loaded questions. I don’t necessarily like there’s not one specific answer. That’s like the right answer. But it’s more of the way in which they approach answering that question there. If you see the gears turning in their head, or you see them get excited about what they’re talking about, or even just feeling comfortable.

Think that body language in that, I don’t know, you can feel that sense when you have a good conversation. And it’s on the hiring manager to know ahead of time. Okay, what are the things I’d like to hear and the types of approaches I might want to hear? Because that way, when you go into that conversation with a candidate, it can be more open ended and just more have more flow to it. There’s certainly tangible technical things you might want to test them on or understand, hey, have you worked in X industry and like, totally valid.

I do try to know what my really really tactical, tangible, quantifiable things are. Make sure those competencies are there, and I spend most of the time just trying to understand who this person is, especially if you’re trying to hire for someone that you hope can grow and be around for a long time and be on the journey. To be with you for a big chapter of their career, you got to know that the long term mindset is there solving things short term. And can you do this job today? That’s important. Can you do what this job could be over the next couple of years? To me, those are the more important perspectives to understand.

Working together as a team

Irina Cismas 40:20
One more thing in regards to the team, because you mentioned about how to recruit. I am recently watching Formula One Drive to survive. And I noticed the importance of keeping the team united and basically create that cohesion and have that tone of balancing and everything. How do you make sure that your team is driving towards the same objective, and not working one against each other, which I saw it a lot in for Formula 1 games?

Con Cirillo 41:00
You know, I have yet to get into f1, as much as they should. And so I think that’s next on my list. And maybe we can talk more about all the good racing stuff there. What I generally will do in this I actually, I’d say is a newer appreciation for me is the storytelling component.

The stories we tell internally and the way as leaders, we articulate and surmise and distill what’s happening, our pulse on the company, or the industry, or whatever the challenge of the month might be. The ability to tell one story that a team can get behind and rally behind as humans inherently we like storytelling, and we do really well, we are really receptive as creatures, to stories being told, and it’s easy for us to let stuff kind of like, seep into our brains, and then we internalize stories really well.

So I try to find the right times to tell those stories. Okay, if there’s a big release coming out, what’s the narrative, right? What’s the hero’s journey as to why this thing is happening and leave it open ended enough that again, people can interpret it and bring it into their own work and understand for themselves how it is going to impact them? Overall, though, finding the storytelling, that’s one thing leaders across industries and across disciplines, right, don’t do enough, is telling that story. There’s a lot of, okay, I wrote a Google Doc. And like, that’s, that’s great. That’s one artifact. But that’s not compelling. That’s not emotional, that doesn’t get people to believe and trust and all of those deeply rooted things that inherently you need as a leader to really get anywhere.

So I would say I’ve started to find more of an appreciation for that storytelling and say, okay, yes, there’s a lot of stuff going on. And if you have one on one conversations with your team, or other people in the business, you get part of the story. But that comes at the risk of that game of telephone where everyone’s heard different things.

And there may not be a shared truth and a shared perspective of like, how are we doing? What do we got to focus on this month. And so that’s I feel your role as a leader is to give clarity for that stuff, and to storyteller and find a way to articulate it’s us versus this problem. Again, that seems to work pretty well. And if you can create, what’s the enemy, maybe the enemy is the competitor you’re trying to beat out on deals with the enemy is the economy is a little tough right now. And you got to help customers through it. Just finding what that story is, and learning how to tell it in an authentic way that will do more to build cohesion and unity within your teams than any pizza party or any, you know, any token gesture, I feel it’s the giving people purpose that that pays off that really does.

Wrapping up

Irina 43:49
I want to remain on that tone, and wrap up our conversation with your favorite quote, book, or even a mentor in the CS world that guided you. What would that be? It doesn’t need to be all, it can be one of them. So quote, book or CS leader that inspired you.

Con Cirillo 44:14
A quote that I take with me a lot. And at the start of the pandemic and start a COVID I said it pretty ironically, I would say “every day is a gift”. And I would say it is kind of like a throwaway thing and just, you know, this sucks.

We’re all in it together every day is a gift and I’d say it pretty ironically. And lo and behold I said it long enough I started actually believe it. And so I find this philosophy to be true in my professional life. My personal life, like every day is a gift, every day is a chance to learn something, and to get better in some way.

Particularly in a CS environment where you always need to be learning and there’s always things that are going to go right and go wrong. And frankly, a lot of it’s not really within your control. You’re kind of at the mercy of the winds. And as a CSM, who’s sitting between all that stuff, it’s easy for your ship to be kind of blown around in the sea. So what I tried to do is come back and say, okay, every day is a gift.

Let me focus on what I can control. And let me learn to separate things that are external that are happening to me, and then how do I respond to those things. And trying to keep that mindset has really helped me in all facets of my life, because a lot of stuffs not something you can change necessarily, but you can always change how you respond to it.

And to me, it always comes back to this everyday is a gift, be grateful that there’s another opportunity to learn something and to get better in some way. And maybe that way is through adversity and a challenge. But if you get through it, you’re going to be better off for it. So that’s a mindset that started off ironically, and I’m started saying it sarcastically and for better and worse, that has really seeped into my brain. And I gotta say, it changed my life. So never thought I’d be one of those rosy one liar, optimist people. But here we are, and I think I’m better for it.

Irina Cismas 46:09
That’s awesome. And your quote actually reminded me of something that I’ve learned. A few years back, I was in Miami at a conference, we were sitting at the hotel, we’re waiting for the taxi to go and install the booth and everything. And we were talking with the one of the people working at the hotel. And he was saying the following thing every day “above the ground is a great day”, though, and it’s stick to me, and we repeated it. And now your quote reminded me of that. And in that note, I want to say thank you for taking the time to discuss with me. It was indeed a pleasure and definitely will stay in touch. I’m grateful that I met you and we had this conversation. Thank you!

Con Cirillo 47:00
Thank you very much! Until next time.


Want to hear from a certain CS leader? Let us know and we will try to have them on our next episode!

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.

You might also enjoy:

Webinars and Podcasts

Quiet Quitting: Why do 86% of CSMs want to quit their jobs? | Webinar

Quiet quitting is not just another buzzword. In our most recent survey, we focused on quiet quitting in …

Webinars and Podcasts

Mastering CS – Candid Leader Insights – Ep 15 – Keishla Ceaser-Jones

In our new episode of the Mastering CS – Candid Leader Insights podcast, Irina Cismas, Custify’s Head of …

Webinars and Podcasts

Mastering CS – Candid Leader Insights – Ep 5 – Will Stevenson

In our new episode of the Mastering CS – Candid Leader Insights podcast, Irina Cismas, our Head of …


Notice: This website or its third-party tools use cookies, which are necessary to its functioning and required to achieve the purposes illustrated in the privacy policy. If you want to know more or withdraw your consent to all or some of the cookies, please refer to the privacy policy. By closing this banner, scrolling this page, clicking a link or continuing to browse otherwise, you agree to the use of cookies.