Surviving and Thriving Post-PIP with Cari Olson

Jordan talks with Cari Olson from Workato about the PIP he put her on and how it has equipped her to provide valuable advice to any SDR that's on one.
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Show notes

In January of 2018, Cari Olson was put on a PIP.

Jordan Greaser, RevOps Therapist and now founder and CEO of Greaser Consulting, was the one who put her there.

How does Cari feel about it now?

Thankful. Because being placed on a PIP changed the course of her career forever.

Now Senior Manager of Sales Development at Workato, Cari sometimes has to place others on a PIP. Having experienced both ends of the PIP, she has advice to share for SDRs who need to overcome what many consider to be the “kiss of death”.

Jordan  00:00

Hi everyone, this is Jordan, the owner and CEO of Greaser Consulting. On today’s episode, we’ve got Cari coming. Listen, checkered history with Cari: I was actually the manager that put Cari on a PIP back in the day. Now, it’s not too often that somebody that was put on a PIP set comes back to you later and says “this was one of the best things that could have happened to me.” Oof, usually those conversations go a lot more sideways; they’re a little bit more difficult to navigate and yeah, yikes. But to give credit to Cari… all the credit in the world, really. Not only did she overcome that PIP, like she dominated in the company she was at after that. She is now managing multiple teams. At her current, her current company, just does fantastic work across the board, highly-productive, widely-loved, all those kinds of things. But there was just some things early on. It wasn’t like attitude or anything like that. There was just some things early on, that we needed to get right with Cari, and it just took longer than working with others. So we’re gonna have a fun conversation today we’re going to talk about like, from a manager’s perspective, what’s it like to put somebody on a PIP? Everybody talks about the person on the PIP, but what about the other side? For the person who’s on the PIP? Like, is this just? Is this not just? Like, shoot, how do you recover from it? Point is, this one’s interesting. So I’d encourage you, as always, lean in, have some fun, Cari’s fantastic; get ahold of her after, after you listen in today. She’ll help you any way she can. Let’s do it. 

Intro Jingle

Say you want some clarity in sales and marketing and SEP? Well, we have just the remedy: Our podcast, RevOps Therapy. Yeah.

Jordan  01:57

Hello, everyone. We’ve got Cari with us today. Cari, introduce yourself.

Cari  02:03

Hello all. My name is Cari Olson. I’m a senior manager of sales development at Workato. And I currently live about an hour and a half out of Seattle with my boyfriend and my two dogs.

Jordan  02:15

Cari, happy to have you on. Listen, this is gonna be an interesting conversation today. I didn’t know when I reached out to you if you’d be like, “yes, let’s have this conversation” or you’d be like, “listen, dude. When you rolled out of Outreach, I didn’t ever want to talk to you again.” So the reason I say that is we’re talking about surviving and thriving post-PIP. I was the manager who had the heart-to-heart conversation with Cari back in the day to say, “Cari, do you know what a personal improvement plan is?” Right. So anyway, thanks for coming on, Cari. I wasn’t quite sure what kind of reaction I was gonna get.

Cari  03:01

Of course, no, you’ve definitely… It was January of 2018. No, yes, January 2018. And, yes, we definitely had a great conversation that I would say turned out great in the long run. So… 

Jordan  03:14

Well, so let’s, let’s walk through this because most folks, and this is really to your credit, Cari, above anything else. Most folks hear the word PIP, and maybe you did this, and I’m not even saying this is wrong. The first thing they do is they start looking for a new job. The second thing they don’t do is double down and really try to make it work. Now I’m not saying that’s everybody; somebody’s going to ping me and say “Oh, when I was on a PIP, but I really went strong.” Some folks in SaaS now don’t even think PIP is the appropriate thing to do. Like what are we in the 1990s? You know, all this kind of stuff. So like walk me through, you got put on a PIP because obviously, you came out the other side, very different. What was going through your mind? What did you do? And I’ll get to the and why were you different?

Cari  03:58

Okay, um, so yeah, I just remember I started Outreach, October 2017. I’d made a transition from full cycle selling in the boutique recruiting and accounting or recruiting and staffing space in accounting and finance so completely like out of my wheelhouse, and just completely changing emotion and had never missed, like, my targets in my life and I find myself like I’m super competitive and harder on myself than anyone else. So when I miss my ramp quota, which back in the day the AGOGE program was definitely not there. It was kind of a sink-or-swim. Here’s your two-week ramping and off you go. I was already like, “Oh great. Why did I make this change?” And then November didn’t go my way. December didn’t go my way. And then you and I were having a conversation in January. I was like, “Dude, I kind of already know, was expecting this,” but like also just having it there and kind of having like someone call you on it was like alright, but with that, I am a very transparent person, very upfront. Like, I don’t sugarcoat things. And I kind of don’t expect that in return. So I think getting put on the PIP while my pride was hurt, and I was definitely embarrassed that it was finally like called out, but I mean everything in sales is called out like, especially there back in the day like we had the little ticker up on the window back in the pit where like, you’d book your meetings; you’d book your SALs, and there was Cari being like, she’s got these meetings, but nothing’s converting and it was sad, sad, sad, sad, day back in the dark…

Jordan  05:26

I loved that ticker, by the way,

Cari  05:29

I learned to love it once I got to like, you know, get my ticks on it. But when you weren’t performing, it wasn’t a good ticker. But at the same time, loved the openness of it, and also then drove you to do better. So I think getting put on the PIP was honestly the best thing that happened in my tech sales, tech career, unpopular opinion, I’m sure. Because I think it also then shaped me into the SDR I became at Outreach, all the opportunities I had there, and then being able to kind of transition into management and now shaping me into the manager that I am today.

Jordan  06:03

So what made the PIP the difference? Because usually, PIP is not synonymous… Here, here’s the, here’s the unfortunate truth. Okay? The manager comes in and sits down and says, “Listen, this is a PIP. This is to get you back on track. It’s not like we’re trying to manage you out here. We’re actually trying to give you things that get you in the right direction. Yada, yada, yada.” And I’m not saying that’s not true. Okay. It is true; it legitimately is. That being said, the percentage of folks who get put on a PIP that then overcome it is really small; it’s even smaller if you got put on one and then you don’t get back on a PIP and just a couple of months like usually the behavior change doesn’t stick or the way you’re operating doesn’t stick. And so what I’m trying to understand here is, in your case, don’t hit me, you weren’t performing well on the job. You had the hard conversation, which I did say to you, I do remember this saying like, “Cari, you got all the right stuff. Like we just got to find a way to get there.” Which obviously was true. But what was different for you? Or how did you think about it? What was the process of being on a PIP that actually made a difference?

Cari  07:18

I think and it’s something I still say today, because I have one who’s literally like me; he got a PIP, didn’t go back on, and we actually just promoted him off. But I think it was I leaned in, and I also kept that open communication. I think I use that as the tool to just be like, “Okay, you are going to tell me this, and I’m going to brain dump everything of where I’m being frustrated, where I’m struggling, where I see it working for other people, but it’s not necessarily working for me.” And I think that’s kind of where the difference was, was, I was like, “Alright, you’re gonna put me on this PIP. I’m gonna tell you everything that I think is wrong with what you guys are kind of coaching us to…” now in a respectful and like, way of like, “Hey, I’m hitting these KPIs, but it’s not working for me,” because we were very much a KPI-focused shop back then; it didn’t necessarily matter who, what; it was very, like, just hit these numbers, and it should work. And I think I challenged you on that with, “Hey, I am hitting the KPI numbers, but my results just aren’t there.” And I think that’s where then we were able to get creative in figuring out what wasn’t working. And I think we did a lot of talk tracks and realized that my pitch needed to be a lot different than it had been in my previous role where talking to sales and marketing leaders was a lot different than talking to accounting and finance people. And then me being a little more aggressive on the phone with the sales and marketing leaders and it was just like, little changes, but I think where it started was opening up to you like where I was struggling and then at that point, I think you gave me Fletch as a mentor and then Farnsworth kind of came in and helped too and just like really working with them and realizing that one size doesn’t necessarily fit all like yes, we all have the same goal but how I’m gonna get there versus how Fletch got there, Farnsworth got there, even Nav got there was gonna be completely different. And I think that’s where the differentiation lies was that I think that was kind of the first time, at least in my opinion, that I was able to get to quota by not necessarily following the same methodology that had been working.

Jordan  09:17

Yeah, I think there’s a lot to unpack there. Okay, so first off, what you just talked about was a masterclass of, of how to talk to a manager who sort of has a way right, but then challenging it but not in a sort of disrespectful “Well, I can’t hit because you blah, blah, blah. But listen, like I like I’ve done what you’ve asked, and it’s not working. And so can you work with me on maybe some other areas too?” Okay. I think that, like, that’s an entire conversation in itself of quite frankly, how do you manage up right? How do you manage up in a stressful situation? The second thing that you brought out there that is incredibly important; you mentioned I brought Fletch in to help, said, “hey mentor this, this budding SDR over here.” Farnsworth swooped in. The second thing is community. Right? One of the things right out of the gate, you said you got put on a PIP, maybe it hit your pride. But usually, when your pride gets hit, the first thing you do is go inward. You don’t want to talk about… you don’t want to bring people in. But what I’m hearing you say, is you got put on this PIP and you’re like, “Okay, let’s talk about it. And I need a community around me here that like, I’m going to admit, I’m not hitting the number. How can you help me here?” Right? I mean, isn’t that part of the key?

Cari  10:35

Yeah, no, definitely. And I think, I think that’s why like sales, I think is also so great is, I mean, it’s obvious, when you’re not hitting your number, no matter how big your team is, like, whether it’s in a remote environment, or even back in the day in the office, like, people know; we all have dashboards, but I think instead of going inward, and just kind of hiding from it, and being like, “hey, what’s working, what’s working for you?” I’m going to take a little bit from there. “What’s working for you?” I’m gonna take a little bit from there and kind of molding it into your own workflow, your own pitch, your own process, is really where you can get those fledgling SDRs like I was, or kind of even those middle of the packs to that next level. And I think there’s something great and kind of that healthy, like checking on both sides of you having those conversations with you as my manager to me as the rep and then also me being like, “Hey, I am doing this, but it’s not working. So like, what else can we do? Because I want to be here, just as much as you want me here. But I am doing what we’re asking.” Yes, I agree. I wasn’t doing my job. I wasn’t getting to what I needed to, but I think we, I think we, we found something that worked.

Jordan  11:36

If you had felt, when you got put on that PIP that folks weren’t actually for you, like would that have made it, would have made a difference? Would you, you’ve been the personality that’s like, “I’m gonna prove you wrong”? Or was that actually an important piece of the puzzle?

Cari  11:50

Um, I think there’s always part of me, that’s going to be like, “I’m gonna prove you wrong.” I think it’s just, I think it’s just me in general of, “Oh, you don’t think I can do this? Watch.” But I do think having that like, extra, like, even managers that weren’t necessarily mine, like, helping me along the way, or like I remember specifically, on like, towards the end of that January, it was close whether I was gonna hit. Because we finally started finding something that worked. And I just remember, we were in the pit. And there were like three days left of the month. And that day, like, every single person had hit quota. And I still had a couple out there. And I just remember, this is back when we were still at the original office. And I walked out that back door, and just started doing laps around Fremont, basically. And Nathan Broome was calling me and was like, where are you? And I was like, “trying not to cry because I’m a stress crier.” Like, you know, I’m a stress crier. Everybody that I’ve ever worked with knows I’m a stress crier. Don’t cry when I’m sad. Don’t cry when I’m happy. If I’m pissed or if I’m stressed, that’s when she cries.

Jordan  12:53

Here we go. 

Cari  12:54

Here we go. And so all of a sudden, Broome’s like, where are you? Where did you go? Because I did, I did run at that point. I was like, I just, I can’t do this. I’m gonna get fired. Like, da da da da da. So he’s just like, come back, let’s talk. So we ended up going to Tableau and kind of just decompressing there. But I think the community was definitely something that kept me in it. On top of just I’m gonna prove everyone wrong, because there’s that point where it’s like, I’m gonna prove everyone wrong, but you’re still not getting there. You’re like, “okay, am I?” But having that community and having those extra people there really, really did help. 

Jordan  13:26

So something you may not know, is, you know, Broome actually came up to me and said, “hey, you know, what’s going on with Cari?” You know, whatever else. For those listening, Broome was another manager. Okay? And so he, I mean, he just said to me, “he’s like, man, is there any way I could help?” And the conversation we had was, listen, like, you’re not gonna step on my toes at all. I think Cari is fantastic. She’s getting there. Right? But like, I think, I think she needs extra voices. And so you’re not stepping on my toes at all, to go and have that conversation. Because every once in a while, it’s like a weird thing, right? Like managers can get a little territorial. Like, well, that person is on my team. Let me do it. But I think that culture needs to be broken just in general, right? Like, yeah, we’re on the same team big and whether, whether it was my phone call that made the difference, or Nathan Broome’s or this person or that whatever else, like, what does it matter? You know what I mean? Like, like, let’s figure out a way because this is, this is a person who’s really trying, right, like, this is a person in general. So let’s find out a way. And so I’m glad to hear that, and it really, this is the goodness of his own soul here. You know him reaching out to you, having that conversation was, was a big deal. So listen, you, you actually did you started to hit the number. You started to not just hit the number; you started to become one of the mainstays in the organization. Despite that, and seeing that success, having that… there was an old book, I think called The Scarlet Letter. I can’t even remember what happens, right? But a woman’s got the letter on it, and she’s got all these things… having been put on a PIP, like do you, like, think about that sometimes and you’re like I don’t want to go back there or do people know? Or it just doesn’t even matter?

Cari  15:13

I’m super open that I was I’ve been on a PIP. I think even today like one of the things like I tell my, my teams, when we do get to like leading up to those conversations is, “hey, this is where I was at; this is why I think they can be a very powerful tool. They don’t have to be a kiss of death; they don’t have to be a one-and-done and you’re out. It’s, it’s a mutual kind of, hey, this is just bringing us to the table. We’re gonna call it the elephant in the room. It’s not, it’s not working. But if we both want to work on this together, let’s figure it out.” And I think where it has been successful is kind of just kind of breaking that wall of communication. Like it’s awkward. Sure. But let’s figure out what’s not working; you are, on paper, doing what we’re asked for. If, on paper, you’re not necessarily meeting kind of those metrics, that’s fine. Let’s start doing that and seeing where we can go. That I definitely, I feel like I… this is going to my high school teachers listening, I really doubt they are. It was one that I liked Spark Noted, said I read, definitely didn’t. But I think she like wears the A in pride like afterwards or whatever. I definitely would say I wear the P for the PIP in pride afterwards. I never went back on one. But I definitely don’t shy away from the fact ever that I was on one and that it definitely kind of helped shape and change the course I would say of my tech sales career.

Jordan  16:29

So even in terms of the way you manage folks, right? You lived that experience. So you know all the stress and things that occurs. Do you think differently now, as a result of going through that process? Is there like a unique way that you approach your reps? Even before PIP? Right? Like if something’s going on that you’re already thinking about measuring and, and adopting? Or? Listen, “this is experience you had you found a way to overcome” and that’s just it is what it is?

Cari  16:58

Um, I think it’s a little bit of both? Like I think, obviously, I definitely manage each person or approach each person very differently. I think there’s some that they can just kind of take it like, “hey, it’s not working. Let’s figure this out.” And there’s some you kinda have to coddle a little bit, a little bit more. But I think, yeah, it’s a little bit of both, like, hey what, what do you see? What do you kind of feel is working or not working? Like as we’re approaching kind of those few months of not, not tracking, not pacing, and trying to get a gauge to at that point of like, if we have this PIP conversation? Are they going to lean in? Or are they going to kind of be the “Okay, I’m leaning out, like, I’m gonna start looking for a job and kind of start gauging from there.” Because I think just even the communication with your rep, even when they are performing or they’re not, or they’re not is important of just like how, how do you feel your guys’ relationship is to start with, like, from a communication standpoint. Um, and then I think when it does come to those tough conversations already having kind of that framework in mind, of this is how our conversations have gone in the past, you can definitely frame and build your PIP to, to that and to their strengths so that they can excel. And maybe it’s not as aggressive the first month and maybe you do an extended one. But I think it’s all about kind of figuring out the person and really figuring out where their strengths are, and then building in those wins in the PIP. So then that way, they can still feel like they’re thriving, or at least, like successfully achieving things as we’re fixing the bigger picture.

Jordan  18:28

How long do you run a PIP? Just in general? And do you? Like do you ever just get to a place where you just kind of call it, like PIP’s not even over but you’re like, yeah…

Cari  18:43

So yeah. I’d say each PIP is kind of different. I think it all depends upon what got us to this situation, and what the track record was before, and what the coaching and the feedback on both sides has been up until that point; there have been some that have definitely been kind of we’re going month by month. And then there are some that we have definitely decided to part ways early. Um, and then there are some that we’ve done multiple months and just kind of extension because they are doing what we’re asking and leaning into the coaching. They’re, they’re kind of that carry back and they have, “Hey, I am doing or asking here, but we’re not still getting there. What else do we see? What else can we be working on?” And that’s all I ask as a manager is being open and communicating with me in a respectful way. I’ll communicate with you in a respectful way. And if it’s not working, and we still can’t figure it out, like there’s a point where that’s on me and like my team leads and the management team to figure out what’s not working here if they’re truly committed to wanting to do the work and trying and just failing versus “I got put on PIP; I’m not going to do anything or I’m gonna barely call it in and then we’re at the end of the month or we’re at the midway month midway part and there’s no path.”

Jordan  19:56

Do you, do you get nervous whenever you have to go have the PIP conversation?

Cari  20:03

Yeah. I do. That’s something that I hope never changes. PIP conversations, even to this day, always still make me nervous. I feel like I’m kind of like sick to my stomach the night before. And just want to make sure that whichever, whoever I’m talking to understands, like, this is not the kiss of death. This is not a one-and-done. This is not, I think, do or die. This is, “hey, let’s have an uncomfortable conversation and figure this out together.” And we’ll grow from it. But yeah, no, I definitely still, I still get, get nervous.

Jordan  20:41

What percentage of conversations do you have that you walk out of, you’re like, “well, that actually went really well”?

Cari  20:49

I’d say about 75% of the initial PIP conversation, I would say we walk out going like, “okay, that went, that went well. But we, we’ve identified kind of where SDR wants help and is struggling; we’ve kind of level set where we’re coming from.” There are still a few that definitely go a little haywire and keep you on your toes.

Jordan  21:11

You mentioned, I’m going to take us back just a second. You mentioned when a rep is saying, “Hey, listen, you did everything we asked. And so let’s, let’s get into lab here”. I think that’s an important thing. And I don’t know, just speaking transparently, I can’t, I can’t remember if it was a conversation with you if it was before that, or after that, or whatever. But there was something that happened during that Outreach tenure when I was a manager there. When sure there was definitely a recognition of “Well, listen, not everybody’s gonna get there the same way.” Now you still have to have some baseline numbers. So what are those baseline numbers? And then how do you allow creativity, whatever else in between? That being said, it was always a different conversation, when somebody was not doing the minimums, whatever those minimums are, just doing their own thing and they’re not, they’re not even close, right? Versus somebody. This was like, in your shoes, who you’re doing all the right things. And I used to tell people “listen, like, if you’re not doing the minimums, and you’re not hitting the number, like, don’t come talk to me.” Yeah, this is gonna sound hard. But listen, if you’re doing the minimums, you’re not hitting the number. That’s this is like, this is my job. Like, this is my problem. It’s not your problem, because you’ve done everything I asked. And we’re not getting across the line. And so like the frame was even different in those scenarios. Now, folks listening might not like that, like, well, it’s your job to inspire and bring people along and all kinds of stuff. And I think well yes, listen. SDR job’s hard like your mind’s either in it or it’s not. And there’s different times that you need to bring people back in for sure. But like, you kind of know if someone’s been checked out for a couple of months, right? Like, I don’t think they’re, you know, you’re not hitting the minimums, your mind is gone. You’re upset, you’re not hitting the number, and we’re having this conversation Well, okay, there’s some things you need to adjust. But on the flip side, 100% there’s things that I need to learn or do different or coach differently. And this is now my problem, not yours. 

Cari  23:14

Yeah. No, I definitely agree. I think that’s, there’s plenty, plenty ways I want to go at this. Definitely like, I think how like, even I managed today is, “hey, you’re hitting your number. I’m never really gonna dig. I might come back and be like, ‘hey, what’s working just so then that way we can use your good juicy little tidbits to take to other places are help scale that.’ But if you’re not doing the bare minimum, and you’re not hitting your number, and I think you even used to say this, then you’re inviting me into kind of start really digging and figuring out what’s going on. If you are doing the bare minimum and you’re not doing that, then yes, it’s 100% on us. But if you’re not doing the bare minimum, and you’re not hitting your number, then like we need to have that conversation, is this job for you?” And it’s okay, we can… like, the SDR job is not for everybody. I know on paper it sounds all good. It’s in tech. It’s sexy. You get to make calls; you get to make theoretically money.

Jordan  24:06

I don’t think anybody says Cari, you get to make calls.

Cari  24:11

True, I liked the call part. I’m weird. But I think the point. Like, I think everybody looks at this like okay, this is my intro to getting to an AE or getting wherever I want to go. And I think the people that get it and want to stick with it can ride the roller coaster. I think the people that get into it because the allure of where it can take them but don’t necessarily understand the grittiness or like how high the highs are and then how low the lows are. That’s kind of where the disconnect is. And I think that’s where those initial conversations when you’re heading down kind of that path is like “Hey, aren’t you happy here, like are… is this still what you want to do? This is kind of what I’m seeing.” How do we get to at least here because that’s then where I have a baseline of is it a talk-track issue? Is it a targeting issue? Is it a just simple workflow issue of we’re just doing a little bit of everything everywhere versus like dedicating time, and I think, for the PIPs that I’ve had that have been successful, I think even including, like when you put me on one, it was minor tweaks if we’re doing the right thing. They’re definitely committed, they’re doing what’s asked, but it’s minor tweaks of workflow and making sure we’re blocking out times correctly or tweaking some small things in the talk track. That is not a big fix. Like, okay, well, we’re just not even doing the table stakes of the job at this point. I think that’s where the difference lies. 

Jordan  25:28

How long did it take, even for the folks that you’ve worked with? Maybe your own story, whatever, you make it through the other side? How long does it really take, though, for you to get the confidence back that like, this isn’t just a fluke?

Cari  25:39

I think like for me, I didn’t start believing that it was going to be consistent, I think, until the summer, because I mean, I hit January, I think that full like, end of year, first quarter was still like, okay, but like, let’s really see how we can do it. And then I think… so I went to January, but then February, March, April, I think that May, June, July was like, “Okay, maybe we really are onto something.” I think that’s when I was tapped to go help build enterprise with Nav and Broome and whatnot. And that’s when I was like, “Oh, maybe I really am back. Like maybe I really have figured this out, because now I’m being tapped to go do this.” And I think what that looks like for even people on my team that we’ve had successful ones for is when it’s like, “okay, I no longer have to be like super cognizant of what they’ve got coming and like kind of doing my own due diligence and checking everything, so I can forecast and whatnot off them or help like, kind of be like, ‘Hey, here’s a little thing, you might want to go back and check or here’s one that you might want to respond to that I think they get the confidence back.’” And you can just you can see it. And I think it’s also then, as a manager, kind of relinquishing the reins instead of like, okay, we did figure it out. Let’s give them a month, see how it goes? And then that’s kind of your, your make or break of are we gonna have the same conversation again? Or are they, are they off?

Jordan  27:04

This is… we don’t have a ton of time here. But I am curious. Like, obviously that PIP scenario was a like a pretty significant, almost like gate for you that you pass through and like you’re different on the other side. Is there, has there been anything since in terms of like really career defining, this is something that happened and I made it through the other side that, that you’d want to share?

Cari  27:32

Not from like a PIP standpoint, I think just, I have used kind of that like mindset that I have like, it’s tough now. But just, just wait once you figure it out, and it’ll, it’ll switch. And I think like that even kind of happened, like earlier this year, when I did take on a second team and I was doing a great job of being a hands-on manager to the one team that I did have, and then all of a sudden had another team that was under my wheelhouse and responsibility and kind of needing to bridge that gap of how do you come in and kind of be like, “hey, what’s working, isn’t working? Let’s figure out a way to kind of course-correct all together and get everybody on the same boat rowing in the same direction,” while kind of politely poking holes in the process before, of just keeping that mindset of that open communication and sharing, like, “Hey, we’re all in this together. My goal for you guys is to hit your numbers to blow it out of the water so we can get you on that next step.” And I think just kind of remembering, like, how I felt in that like, initial part of like that embarrassment, and that gut check of like, oh, it really isn’t working. And just kind of leading always with that in a sense.

Jordan  28:44

So this may seem like an absolutely ridiculous question. Because we know the folks that are, you know, individual contributors, there’s a lot of stress. And there’s, there’s a lot going on, I think, though, we forget about, or at least we have less compassion toward managers who are going through things too. So you’ve lived on both sides of this. Is it worse to be the person hearing you’re getting put on a PIP? Or is it worse to be the person telling somebody they’re going on a PIP?

Cari  29:14

I honestly, I think now have been, had been, been on both sides. I think it’s harder for the manager because as a manager, you want nothing but your team like nothing more than for your team to succeed and be crushing it and doing all the good things. And I think when you realize you’ve got those SDRs that despite maybe their effort or are putting forth their best, best effort and aren’t getting there, there’s kind of that like, “oh, no, what am I not doing to help them but yet here we are” type of thing. And I think I think now it’s I definitely see it being harder on the manager for twofold because you have to admit you possibly didn’t do the best job hiring or hiring and like onboarding and training them or even continually developing them or giving them the coaching that they needed until we got that, we got to this point. So I think there’s kind of a whole nother level from the manager side of, you kind of have to have that we’ve got to have this conversation, depending on your organization, it’s you got to talk to your manager and possibly HR, like, “Hey, here’s where we’re at, here’s what we’ve tried so far, this is why we’re having this conversation.” And then you have to deliver it to the person and hopefully that person doesn’t take this as a shock. I mean, theoretically, you’ve had multiple conversations before of downtrending or not great performance. But I still think it sucks. Like, you have to be like, “Hey, we’re going to have this conversation, there’s going to be this document, and we’re going to figure it out together.” And that’s kind of when you get the people that either are, yep, sure. Or you do get the people that lean in and are like, oh, and I’m going to prove you wrong, and they get that fire back.

Jordan  30:43

I think that’s a great call out though. Nobody should be surprised if that’s what’s coming. Right? Like, if, and this is actually on you as the manager, if you as the manager have done your job, you sort of set the expectation. If they’re outside of the expectation by a certain date, which you’ve communicated, then you know, we’re going to have this conversation. So anyway, my point in saying all that is, yeah, I just, I just had this thought as I was listening to you, that we always think about the person that, like, the, got the bad news, but how does it work for the person who’s delivering the bad news? Right, like, that’s not, that’s not fun, either. But hey, Cari, we’re right at time. I appreciate you coming on and sort of talking through this whole PIP process. Like I said, I wasn’t sure when I reached out to you if you’re gonna be like, “Hey, dude, like you’re the one who did it to me. So get lost.” If you’re like, “Yeah, let’s, let’s chat through it.” But I’ve always appreciated your positive attitude and just the way that you’ve tackled things. And yeah, I’m not sure how many people are going to want to reach out to talk about PIPs. If somebody, if somebody wants to get ahold of you, and they’re like, “I don’t know how to do it,” whatever. How should they get a hold of you?

Cari  31:58

Um, they can find me on LinkedIn. Cari Olson, I think, my handle is literally slash CariO or something like that. And then, if not, they can always email me. My email is

Jordan  32:12

Cari, thanks for coming on board. Appreciate it. 

Cari  32:15

Thanks for having me.

Jordan  32:17

Stay out of trouble.

Cari  32:18


32:20Hot dog. That was a great episode. Thanks for listening. If you want to learn more about Greaser Consulting or any information you heard on today’s episode, visit us online at Be sure to click the Follow button and the bell icon to be notified on the latest here at RevOps Therapy. Thanks and see you real soon.

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