#CSH Episode 2:

⏱️ Timestamps:

00:00:00 - Intro

00:01:19 - Did we answer Peggy's question?

00:02:47 - Today’s question: managing customer risk as an IC

00:04:47 - Setting expectations with leadership based on data

00:06:53 - Avoiding emotional reactions and staying objective

00:10:14 - How leadership can approach ICs when discussing risk

00:13:55 - Keeping track of customer actions and progress

00:15:36 - Importance of leadership providing context when asking questions

00:17:17 - Balancing leadership pressure and customer outcomes

00:20:55 - Proactively setting vs. managing expectations

00:25:31 - Set expectations, don’t just manage them

📺 Lifetime Value: Your Destination for GTM content

https://www.lifetimevaluemedia.com

💁‍♀️💁‍♂️ Connect with the hosts:

Kristi Faltorusso's LinkedIn: https://www.linkedin.com/in/kristiserrano/

Kristi's website: https://www.kristifaltorusso.com/

Stijn "Stino" Smet's LinkedIn: https://www.linkedin.com/in/stijn-smet-%F0%9F%90%B3-330435a9/

Key topics: managing expectations, customers at risk

[Kristi] (0:00 - 0:15)

Oh, they're not engaging because they're busy. It's their busy time of year. They're so busy.

We're all so busy. If it mattered, they would engage. Like, let's stop.

We make excuses for bad behavior all the time. All the time. All the time.

[Stino] (0:15 - 0:15)

Yeah.

[Voiceover] (0:17 - 0:50)

Good morning, good afternoon, and good evening to all you customer success professionals. We are back with another episode of the CS Hotline, where we're answering your burning questions about the customer success profession. Hosted by the effervescent Kristi Faltorusso and one of one personality, Stino Smet. Give them your best shot and they'll give it to you straight while having a good time along the way. Now, here's the show.

[Kristi] (1:07 - 1:11)

Stino, we are back for another episode of the CS Hotline. How are you doing today?

[Stino] (1:13 - 1:18)

I'm doing good. I'm excited. It's our second one.

All right, this is awesome.

[Kristi] (1:19 - 1:57)

Oh, my God. I'm still uncertain if we answered Peggy's question, so we're going to need some validation there. But regardless, if you didn't listen to our first episode, go back.

We talked about how do you build executive relationships when somebody transitions out of the partnership. So we tackled it from a few different angles. Hopefully, Peggy will get the answer that she needs somewhere in the 30-minute conversation that we had.

I'm confident that even if we didn't answer her exact question, she's going to find some value in there anyway. So if you didn't catch our first episode, please go back, give it a listen. Tons of insight around relationship building, how to leverage your leadership.

So please go check it out. Stino, we have another question for today. Are you ready?

[Stino] (1:57 - 2:00)

We have even two. I've dropped two into the chat.

[Kristi] (2:00 - 2:06)

I know, but I don't know if we're going to get to both in the time that we have today. So we're going to see. We're going to do our best.

[Stino] (2:06 - 2:07)

I know, I know, I know.

[Kristi] (2:07 - 2:46)

But you and I are chatty. And so I'm not confident that we are going to fit multiple questions in an episode. But we're going to try.

We're going to try. So everybody, welcome back. My name is Kristi Falcer Russo.

I am here with my co-host, Stino, at CS Hotline. And so we are thrilled and excited to be back for another episode where we are tackling community questions. So customer success community, whether you've got questions on customer success, revenue, SaaS, anything related, Stino and I are here to dive in and give you some insights from two pretty different perspectives, different experiences.

And so we are hoping that between the two of us, we are going to give you something that you can go do something with.

[Stino] (2:47 - 2:56)

Yeah, I hope so. Like, I truly hope so. Imagine that people are listening in and be like, this is bullshit.

[Stino] (2:57 - 3:00)

Well, I mean, I think they'll call us out on it because I appreciate that about the community also.

[Stino] (3:03 - 3:16)

If you can guess where Kristi is from, and it ends with a Y, New York City, that is the vibe that we're going for. Tell it to a stranger served on a cold platter, please. Give us the tea.

Give us everything.

[Kristi] (3:16 - 3:22)

We are not here for fluffy conversations. We're going to get down to it. So Stino, are you ready for our second question?

[Stino] (3:23 - 3:24)

I am. I am.

[Kristi] (3:25 - 4:47)

OK, all right. So listen, and this is one that comes up a lot. And I know that so many individual contributors struggle with this.

So this is a great one, I think, for our conversation today. And I'm going to have to go back and remember what it was like to be an IC. But then I also want to offer some perspective as a leader, too.

So our question today is, as an individual contributor, so we'll say CSM, account manager, whatever your role is in the business, renewal, onboarding manager, because we all have to do this. As an IC, how do you manage expectations with your internal senior leadership about customer risk? Now, this comes up all the time.

In fact, I ironically did a LinkedIn post today talking a little bit about something tangentially related here. And so I'm excited to dive in. So Stino, let's start to tackle this, right?

Obviously, you've been an IC. I've been an IC. And we know how difficult it can be when you're trying to manage expectations up, right?

Because your executive leadership team, your investors, everybody has certain expectations and certain demands. And there are certain outcomes as a business we are required to deliver on. But we also know that the reality of delivering on that is not always easy.

And so as an IC, how do you think about managing up expectations when we're talking specifically about customers that are at risk?

[Stino] (4:47 - 5:12)

Let me tell you this. Where I fell short a lot of times in the beginning of my career is setting in your gut feeling or your assumptions as a weapon. Like, get rid of that.

Like, get rid of everything to manage expectations. Don't start from a place like, yeah, but I think, or I have a feeling. Oh my God.

[Stino] (5:12 - 5:16)

I think and I feel are literally the two worst things you can say when you're dealing with any executive.

[Stino] (5:17 - 6:53)

You're set up to fail. What I've learned along the years, and especially now I'm still trying to the best of my capabilities to go in to the leadership meetings as well, is back it up with data. That is the best way.

And also the second thing that I want to already give to you is, it's not your fault. Don't take it all on you. Those two things I would say are the two major things that really helped me getting out of my comfort zone, but also trying to start to manage the expectations on a healthy way.

If a customer is at risk, it doesn't mean that you suck as a CSM. If a customer is at risk, you need to investigate on why that is. And that investigation starts often from very solid data.

Like even if you're hating on data, which I was for the first five years, I couldn't figure reporting out for the life of me. But like you need to, if you want to evolve yourself as a better CSM, every decision needs to be made. And also the expectations should be managed from data, from solid data.

Whatever you do afterwards, from gut feeling on, based on data, you do you. Like I do it as well. Once I have my data, I do some gut feeling decisions on that.

Also with managing expectations. But like everything starts from a good set of data. And that is something that I never thought to say ever in my career, right?

So data is like my main thing.

[Kristi] (6:53 - 10:12)

I couldn't agree more. I mean, listen, here's the reality of it, right? You first have to put yourself in this place of like, just bringing facts to the conversations.

I think so often CSMs want to defend themselves, defend the situation. We are so defensive. Why are we so defensive?

I don't know. So we're on the defense all the time. And I feel like when you enter into these conversations with any executive, when that is your stance, it's really hard to have a productive conversation.

And so what I'm going to tell you to do is just like check your ego, remove any level of personal accountability to this and bring facts, right? Bring the facts of the situations. Now, one thing that I see great customer success professionals do is they ask really hard questions with their customers.

And this is not something that is done easily, right? You have to practice this. You have to know what are the questions to ask.

And so what I would say here is when you are managing up, you need to come and have thought of all of the different scenarios. I always say like, let's envision what is the outcome I'm trying to work towards with every customer. And then where are we today?

And then what are the viable paths? Because if I start to think that way, I'm going to start to think about, well, OK, well, how do we get to this? And then if we go there, then what happens there?

What do I need to know? And then who's involved? You just have to come prepared with all of the information that you need to make a really strong, informed decision.

If you're coming and you're telling your leadership team, yeah, this customer is going to churn and you are not presenting not only the data, right? But you've had really thoughtful, strategic conversations around how we're navigating this. You went and asked the customer, well, why aren't using the product?

Or what is it about the partnership that isn't working for you? Like you have to go and have the tough conversations to bring those insights to bear, to use that as part of how you're going to go drive your strategy to get out of this situation that we're in. And then you can manage up to your leadership team and say, look, here's all the information.

Here's everything I know about where we are today. And you're either going to provide, I always suggest, provide a recommendation, even if your recommendation sucks, provide it. Here is where I think we should go based on what I know about the situation.

Now, your leadership team has an opportunity to lean in here. And this is the other thing. If you've got great leadership, and I know not everyone does, I know that great leadership is a blessing.

We need to lean into that, right? And so you should be able to create a safe space where you're saying, here's everything I know about this situation. I've asked all the hard questions and I've used all the data that I have access to.

Here's what I know. Here's what I recommend. How do you suggest we move forward?

Does this feel like a good strategy and a path forward? And that leader should lead into it. They should either be like, that's great.

Okay, yes, that's what I want you. And expect you to go execute on it in our next meeting. I expect that we have done XYZ.

Or that recommendation is thoughtful, but not great. And here's what I would advise you to go do. Or here's the other information we don't have today that we should go get.

And then they should be coaching you on what are the other questions? What are the different insights that we need to lean into? Who else do we need to talk to?

They should be advising because no CSM should feel like they've got to figure it out by themselves. And I feel like that deserted island mentality is what prevents them from being the best kind of strategist with their leaders.

[Stino] (10:14 - 10:38)

Yeah, but also coming back to that emotional and offensive mechanism that we have as a CSM, it also comes a lot of times from how the question is asked, right? Like, I hate it with every fiber in my body when one of my founders is coming to me and is like, what the fuck is happening?

[Stino] (10:38 - 10:43)

And I'm like, okay, yes, I think as a leader, what the fuck is happening?

[Kristi] (10:44 - 11:21)

You're right, you're right. If we are attacked, you're right, you're right. If we are put on the defense, it's hard not to be defensive.

And it is also hard to feel empowered to diffuse that situation, especially if you're an IC, you're a CSM and your CEO is coming at you and asking you something very directly. It's hard not to want to justify all of the things that you have done or the entire situation and come up, I hate to say excuses, but they might feel like excuses. They might not be.

But to give all of those details because it feels like that's what you're supposed to do given the situation and the way the conversation is being handled.

[Stino] (11:22 - 13:54)

Yeah, 100%. But what really helps or helped me especially is whenever you have your set of customers and you already know that they're going into risk, like keep everything in your track record. Everyone normally has this amazing CSP tool that they can use or still Excel, but like keep track of everything that you're doing because you just always start from the point of view that they will get questions asked one day about this customer.

So if you keep a clean track record about everything that you've done, the risks and how, like you said, the conversation that you had with the client, the moment someone comes to you and you're like, Reid, this is my recommendation, then come back to me because in like managing the expectations always happens on the spot. In all the jobs that I've done, not once did I had a week to prepare. The question that was like, OK, what are we going to do with these sets of customers that are at risk?

Because it comes from the executive leadership or it comes from conversations that you were not maybe part of. And then one of the execs is coming to you and is like, can you tell me a little bit more about that? But they expect an answer on the spot and that's when you get offensive.

Also, from a leadership point of view, if you have a question, like also there, ask your CSM, ask your team to give them room to prepare because often, and I'm guilty of that as well, like I go into our CSP, I pick up a client and I have all these questions and I read the notes but I have all these questions that come forward from the notes and the stuff that my team has been doing and I ask them straight away. This is not healthy leadership. Like you need to give your team also the room, the time, I'm not saying a month of time, but give them the day to really formulate a well-formulated answer back to you, stated on facts, stated on what they can provide you.

Don't be that manager, okay, like you need to know everything about this customer. Don't forget that your team is managing 50, 100 accounts. They can't know everything about your accounts, like not literally.

So also from a leadership point of view, manage the expectations back, like your team is trying their hardest to mitigate the churn. Cut them some slack, please.

[Kristi] (13:55 - 15:34)

All right, I'm gonna give some other leaders some other piece of advice here. I know this is about ICs, but I'm gonna offer some leadership advice. Give your team the context of why.

Why are you asking that question, right? If I'm a leader and I wanna know what's going on in an account, I'm not just gonna say, hey, why is this customer at risk? I'm gonna say, hey, I'm going through a book of business.

I noticed X, Y, and Z. I went and looked at this stuff, or I'm preparing for a board meeting, or I'm starting a customer outreach program and I wanna engage these customers before I do and I noticed these things. Give them some context so that they know that it's coming from a good, healthy place.

And it's not about them and it's not about their performance, but it's about something that you are trying to do as a leader for the business and you need this context and here's why that's gonna be helpful and here's exactly what you need. I think the other thing that leaders do poorly is they give these general statements of like, well, what's going on with this? Well, what do you wanna know?

What do you wanna know? Like be specific and say, hey, looks like this customer hasn't been engaged or this customer isn't doing X, Y, and Z or they're onboarding, right? Like they've missed three sessions or they're falling behind or I saw X, Y, Z.

Give them the context so that you know exactly, like tell them what you're asking. Don't give these broad open-ended questions where it's like they wanna then provide you a novel response of everything that's happened in the past six months since you asked about this account previously. Like ask a specific question or go a little bit deeper, give them the context why, but help guide it so that the CSM doesn't feel attacked.

[Stino] (15:36 - 15:45)

Oh, and then it's always when you write up that novel, they dare to ask you or dare to say to you, this is not what I've asked. Then I'm like...

[Stino] (15:45 - 15:52)

Well, you didn't ask anything. You didn't ask anything. You said, what's going on here?

This is the 30 page report on what's going on here.

[Stino] (15:53 - 16:02)

I would like take that report, shove it where the sun don't shine and like do it yourself. Like that is the worst. But from an IC perspective, I would say like preparation is key.

[Stino] (16:02 - 16:02)

Yep.

[Stino] (16:03 - 17:17)

As in prepared, as in if you keep your track record, it would be normally super easy to give you like the latest rundown. Like this is last point that we had of meeting that we had. This is what we've discussed.

This is what we're going to do. And then indeed, like you said in the beginning of this episode, like ask for recommendations. Like this is my plan of attack.

If you have any recommendations, please do. If not, I'm going to go ahead. That's the easiest way.

But I do have the feeling that this question is also like we can only do so much. It also comes from top down, right? The top needs to be also receptive to this feedback to do better, to actually do better with their team when they're asking these questions.

It's not about we, and then I'm talking about me as an IC. It's not about me like catering to every brain fart that my executive leadership team has. It's basically them managing my expectations on what they need from me.

Like I easily can switch this question around. Like how can we as a leadership be more mindful on managing expectation on what we need from our team? Like that is the better question.

That is the question that we should ask.

[Kristi] (17:17 - 19:30)

I think they're both valid questions as a leader and a former IC. I think they're both valid. But I think it's also just like, here's the challenge that I know that I see in this situation.

The CSM knows that there is nothing left that they can do to preserve this partnership, right? Like this customer is, there's no turning it around. Here's all the things that I've done.

I think some of it comes from like, how do you set the expectations, right? Because your executive team, your investors, they have, you have targets. You have certain numbers you have to hit.

But how do you back in to that number when you know certain things don't have a path, right? How do you set an expectation to say, I know that 95 is our target, but it doesn't seem like there is a path forward beyond 85. You know what I mean?

So how do you also set the expectation that like we have exhausted all the efforts and here's an alternative to how I think that we can creatively get closer to that target, but it's not gonna be through this pathway. And so I think that there's also like this top-down pressure that just exists in business because businesses have to perform. Let's just call it what it is.

I get that there's a lot of feelings and there's a lot of opinions and there's a lot of, we are doing this because we are trying to drive an outcome for our business and that it usually is tied to revenue. And if CSMs aren't doing their part to hold these accounts accountable and do the things that need to get done, we're not gonna hit those numbers. There is bigger pressure.

And I think that's from the executive side what is driving sometimes their shitty behavior because that's what it becomes, right? Like we behave badly because we are also under pressure of driving our business. And so your CSMs, it's this compounded effect of like your CSMs are under all this pressure from trying to do all the stuff that they have to do with all of their customers.

You've got executives who are trying to hold themselves and their organizations accountable for hitting certain targets. And then you take the pressure from both of those sides and you kind of put it together. And now you have this conversation that feels combative.

It feels like it's at odds. But the reality is you both have to come together as partners driving to the same outcome but also recognize what is the best we can do and then how do we do it together?

[Stino] (19:31 - 20:55)

Yeah. And I think that is a super valid point because it's a common saying that everyone within the company does customer success, right? It's not a one man's job.

It's like an entire company's job. So in that sense, I truly if we could be very mindful of each other I think under the pressure that we're on whether you are in leadership or an IC or both then you should be definitely just be very mindful and take the emotional and that is so weird coming from me because I'm the most emotional person on this planet but take the emotional sense out of the equation especially when it comes to managing expectations because Kristi beautifully said it.

It's like your leadership is under pressure to get the business going. As a CSM, as an IC, you're under pressure because you want to hit the targets that are set for each customer. It's just the pressure.

I know it makes you emotional but at the end of the day, like you said this is how we exhausted every resource that we have in the book. Let's come together to think about other resources. It's not a blaming game.

Don't go into a managing expectations game doing the blaming game. It's not his, hers, whoever's fault. We've done X, Y, and Z.

Let's try A, B, C. That's it.

[Kristi] (20:55 - 22:22)

Listen, for most leaders they want to know that you're doing something. So show them what you are doing. I think that the conversation becomes a little toxic if you feel like the teams aren't doing what they should be doing.

And there could be a multitude of reasons of why things aren't happening. And in which case, this is why I always tell my team I don't like surprises. Don't surprise me.

I don't even care if it's a good surprise. I don't want it. I want to know, I hate surprises.

Give me my gifts early. That is my preference. Don't wrap it.

I want to see where it's from. Okay, enough about me. But we don't like surprises.

We want to know what's going on in the business. And we want to know the minute something is trending poorly. I think that's something also that causes some challenges in the business is all of a sudden this customer is at risk.

All of a sudden this customer is churning. How the hell did you not read the writing on the wall? If you have not had a conversation with this customer in six months and they're not returning your emails and then you're like, I can't believe they're churning.

What the hell? What have you been doing for six months? Can we not ignore the obvious things?

I think as leaders, that's what we expect is that let's not be ignorant. Let's pay attention to everything that's happening. If something doesn't look right in the data, if something doesn't look right from the behavior standpoint, lean into it.

Get ahead of it. The surprises I think are what really kill people. And that is hard to manage.

[Stino] (22:23 - 22:37)

Yeah, I think, yeah. That is so true. That is true.

But that takes me way back to my early I see days where I was like, okay, if I don't say anything, no one would ever know about it.

[Kristi] (22:39 - 22:43)

And I see- Because you know that's bad. Bad, you know, bad.

[Stino] (22:45 - 22:46)

Don't do that.

[Kristi] (22:46 - 23:03)

No, it's because everyone wants to assume best intentions. Oh, they're not engaging because they're busy. It's their busy time of year.

They're so busy. We're all so busy. If it mattered, they would engage.

Let's stop. We make excuses for bad behavior all the time. All the time.

All the time.

[Stino] (23:04 - 23:18)

Yeah, and I was going to say in my very early days, I was like, I will do it tomorrow. I will do it tomorrow. And then for six months, there wasn't a tomorrow.

And then when it happens, they're turning or they're not returning back your emails. And then someone is asking you like, what the fuck happened?

[Stino] (23:19 - 23:21)

Well, then it's hard not to be defensive because guess what?

[Kristi] (23:21 - 24:14)

You just crapped the bed. You didn't do your job. And that's also the thing.

If you're doing your job to the best of your ability and if you can't do something, you're communicating that early and often with your leadership team, you're having that dialogue proactively. And again, it just goes back to people don't like surprises. If something is going bad and you've done everything you can and we have been talking about it for months and the outcome still is not a positive one, I can swallow that.

What I am uncomfortable with as a leader is you tell me for months and months that this is OK, things are going great, everything looks wonderful, they love us, and then they churn. Well, clearly, that wasn't the case. So either you weren't asking the right questions, somebody is blowing smoke up your behind, and or something happened.

Like you tell me what happened. Help me help you because I'm baffled. Nobody likes this.

And that's why people behave poorly.

[Stino] (24:17 - 25:30)

Oh, I just lost like two pounds of laughing. But that is a very good statement because if you're doing everything already proactively, and I know it's very hard because no one wants to be that vulnerable saying like this doesn't work, like this is a process that you need to evolve yourself in. This doesn't happen overnight where you're like, tomorrow I'm going to be super proactive.

It's like you're vulnerable, like saying that you failed at something, which is 100% agree, but just try to do so. Because if you're doing what Kristi says and being proactively, basically the conversation, managing expectations to your senior leadership isn't happening. If you are proactively already reaching out and say like, okay, this client isn't doing too good or this client is doing...

Also celebrate the wins. And like when I say it, like the sun is shining on my face, but like also celebrate the wins. Like God says it's the great advice, you know.

But also celebrate the wins. Everyone is aware of everything that is happening within your book of business. And then the conversation of what the fuck is happening here doesn't take place.

Then you go way beyond managing the expectations because you're proactively not managing the expectations.

[Kristi] (25:31 - 25:39)

You have actually set the expectations. You're not managing them, you've set them. And that's different.

Set the expectation, don't manage to it.

[Stino] (25:40 - 25:53)

There you go. Stay in the lead, be in a driver's seat. You are the CSM of that account.

You set the expectations for that account and you communicate those expectations. You're not managing them internally.

[Kristi] (25:55 - 26:24)

I think that's it. I think that's where we end. Cause I don't know that we...

Like, I don't know that there's a better place. Don't manage the expectations, set the expectations. Boom, there you go.

That's how you be proactive. That's how you remove yourself from these crappy conversations. That's when you remove yourself from being on the defense.

Everyone knows what's going on. We are now all accountable for this, making it a success, work with me. I'll do my job.

Help me do my job, right? Cause you're my leader. You need to help me and we'll get where we gotta go.

But if you're managing to it, it means you haven't set them.

[Stino] (26:26 - 26:30)

Boom. If I had a mic, I would drop it. Well, I have a mic, but I can't drop it.

[Stino] (26:30 - 26:31)

Don't drop it.

[Stino] (26:32 - 26:57)

This shit was expensive. I hope this question came from Andre Terrell. So Andre, if you are listening in, I hope our fiery passion for setting the expectation came across.

If you have any questions regarding something that we've told, submit another question, go to our LinkedIn, the inbox, and we're more than happy to elaborate on anything that we've said in this podcast.

[Kristi] (26:58 - 27:55)

So, you know, and like going back to exactly what I said at the start of this episode, we are only getting to one question per 30 minute episode. It's just not like, it's impossible because we could probably do an hour on every question. If I allowed myself, we'd get down some rabbit holes, but hopefully there is something here that was insightful for somebody.

I think it took us 30 minutes to get to that end statement. If you're doing your job and you're setting expectations, I think it makes managing the expectations up a lot easier. You're not having to do that.

So hopefully we've given you some advice on how you can create better relationships with your leadership team by setting expectations early and being proactive about it and leaning into the fact that your leadership team, they're there to work with you, right? So embrace that. And if they're not helping you and they're not doing their job, well, call them out on that too.

Don't quit yet. It's really hard to find another job. Or you could just start a podcast.

[Stino] (27:58 - 28:14)

You can just start a podcast with one of your idols. Like this is the dream come true, basically also everyone. Like eight years ago, I saw this little goddess popping up on my LinkedIn page for the first time and fast forward eight years later, I've seen her in the flesh and now I'm doing a podcast with her.

[Kristi] (28:16 - 28:18)

I literally live to make all your dreams come true.

[Stino] (28:20 - 28:21)

I could die now.

[Stino] (28:22 - 28:41)

Okay, no, I think I'm practically dead. Anyway, thank you so much everyone for listening in. We can't wait to catch you for another episode of the Customer Success Hotline.

Call us, email us, submit your questions and we can't wait to dive in into some more questions. Into the next episode. Hear you soon.