739- First-Time Leader Mistakes: Asking for Help, One-on-Ones, and Firing People, with Kate O'Neil - podcast episode cover

739- First-Time Leader Mistakes: Asking for Help, One-on-Ones, and Firing People, with Kate O'Neil

May 03, 202413 min
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Episode description

Collin Mitchell interviews Kate O'Neil, CEO of Teeming, about her experience transitioning from sales to marketing and the importance of alignment between finance, sales, and marketing. They also discuss the challenges faced by first-time leaders and the common mistakes they make, such as not asking for help and neglecting one-on-one meetings with their team. The episode also touches on the topic of firing employees and the impact it can have on their future job prospects.

Follow the Host:
Collin Mitchell (Partner, Leadium)


Our Episode Guest:
Kate O'Neil (CEO, Teaming)

Sponsored By:
Leadium | The leader in outbound sales appointment setting

*If you'd like to be a guest on the show or have any questions, email us at [email protected] - Just tell us why you're reaching out and we'll contact you as soon as we can!

Transcript

All right. Welcome back to another episode of Sales Transformation brought to you by Ledium. I'm your host, Collin Mitchell. And today we've got Kate O'Neill on the show. She's the CEO over at Teeming. Kate, welcome to I'm good. We had you on recently. We dig a little bit more into your story, talked a little bit about your transition from sales to marketing, and even got into how finance, sales, and marketing really all need to be on the same page and have alignment. So today

we're going to talk about something a little bit different, something I know you're super passionate about. But before we jump in, can you give us Sure. Kate O'Neill, CEO of Teeming and co-founder as well. My background is in, I started in sales and then moved into marketing. I was a B2B marketer for about 10 years, a little more than that. And it was my experience as a VP of marketing of a venture-backed startup. where I became a manager of managers for the first time, I

had a team of 22. Instead of a team of five, I got manager training for the first time. There were so many new management challenges that I faced there. That is what sort of inspired us to start teaming. So I Really excited to chat about leadership and management. Hopefully, all of the mistakes I made can Yeah, I think every first time leader makes a lot of mistakes. I know I did. But learning how to manage people on the job is a recipe for

disaster at the expense. I mean, it's like at the expense of your team. So just kind of curious, like, what are some typical first time leader mistakes that a lot of folks make that we could maybe help them avoid if they're newer leaders or thinking about Yeah, good question. I'll share mine first. This was like, I became a manager at like 25 and I didn't, I had no idea what I was doing. The way I became a manager was the

company I was working for was going to go through a layoff. And they said to me, your jobs being eliminated, but we want you to stay and we want you to move to this other completely different department and we want you to lead a team. Okay, And I remember trying to ask if I have a choice in this matter. And I was implied back that I would not have a job if this was not the job that I would be willing to take. So I think that happens to a lot of managers. And

it's in a time of turmoil. And it's hard. And so you feel like you can't ask for help. And you also feel like you got to know exactly what to do all the time. Because there's chaos happening. And you were put in this position to do the job that you're supposed to know how to do. So that like, number one mistake I made that I think also a lot of other leaders make is not asking for help. And not, you know, and not having the expectation that you

should have all the answers. The leader who put you in that position knows that you don't have the experience and it they should be reaching out to you proactively to help provide that support. But if you're not getting it, Don't. Yeah. Yeah. Air quotes. But that's the thing is like, you got to ask. That's number one. Number two, I remember this so clearly. Oh my gosh. I went from leading product marketing to leading demand generation, which is really what my background was in at that time. And

I had a channel marketing manager reporting to me. And, you know, it was a time of turmoil, we just had a layoff, she doesn't know me really, like, we're in the same company, but she doesn't know who I am. So I remember I'd been in the job for like a month. And she finally turns to me, we're at the same office, we sit next to each other. And she goes, Do you think we can have a one on one sometimes? Like, Oh, yes. Oh, my gosh, I cherish my one on one time with my manager. And I just, forgot

that I needed to do that immediately with my team. And thankfully, she asked for help and said, we got to do this thing. And I so that would be like learning number two, I guess, or mistake number two is set, you got to have those one on ones, you got to have that time. it's how people know what they should be doing, know what's important to the business or to the, you know, to the team, to give you feedback, to learn something new, right? It's such important time. So that would be mistake and

learning number two. And number three, I would say, or at least for me, as a new manager, this was a little later on, but I we went through another layoff. And someone on my team was laid off. And I didn't know until the day before that it was going to happen. And the my boss and her boss did it. And I will always regret not having at least asked to be in the room when this happened. She didn't know them very well, you know? And as hard as it is,

your direct manager should be the person that fires you. right? It's the person you have the relationship is the person who's responsible for you in the organization. So sometimes people can't control that. I think today it's like I got an email that I got fired. Great. But but you're gonna remember that, like, I know she remembers that conversation. And Wow. I mean, I think the first thing that you kind of mentioned. is

asking for help, right? And I think that that one can be tough for people, especially if you're like first time leader, you might feel like, geez, I'm supposed to have all the answers or like, I don't want them to think I'm not qualified for this job. Um, but nobody expects you to have all the answers. You got to ask for help. It's super

important. Um, and the second point you made there with the one on ones, like super important, you know, I think that that's, Especially if you're kind of taking over a team and it isn't a team that you've built, establishing those relationships, building that trust and rapport with people, earning their respect. Those are all things that are really important and one-on-ones are going to be kind of the key to that.

Third point there is firing people is the worst thing to do, especially when it's in a situation where it's like they're actually doing a good job and it's just an unfortunate circumstance. That's really hard. And especially when you build relationships with these people and like, you know, that they have a family or whatever the case is. It's one of those things that just never gets easier. Unless

you have like no soul or something. I don't know. But it actually shocks me because this is one that like big companies, you know, still don't follow. People are basically firing people that they have no idea anything about them. And there's even been a lot of noise lately about people getting fired for performance issues and they have no data to even back that there is performance issues. The only person that really knows is

That's so right. I'm assuming you're referring to the tick tock that went viral. Uh, Well, you should talk about it. It's a, she brings up the point. Um, if, I don't know if you want to give the, I can give the backstory or you give the backstory. Um, yeah, go for it. Uh, yeah. So it was cloud flare, um, company company called cloud flare and they, hired a sales rep in, I believe, August or September. I can't remember the exact day, but basically she had like three months ramp,

right? Which is built, my understanding. During holiday time. Yeah. Ramp is also built into your comp plan, right? So you're you kind of know I've got this amount of time to learn the products and learn the market and learn all this stuff. And I'm sure I'm sure this I'm speaking to the choir with this audience. But so yeah, so she had September, October, November, and then two weeks of holiday in December. And also like, you know, especially in this environment, who is buying on

December 24? Like, no, it's like, most likely not, especially from a new rep. Like, I think that's the thing. Yeah, you know, it's just not going to happen. And so she got fired, what, like January 15? Not even January, early January. And, um, And she recorded herself, like she kind of knew it was coming because her whole call. Yeah. And she uploaded it to TikTok. And, you know, it's one, I think it's representative of a new generation of workers and like

what, like employers need to think about. Number one. Number two, she brings up such good point, which was show me how I'm not performing. If you talk to my actual manager who should be in this meeting firing me, you would see, yeah, you would see that I, I've gotten nothing but positive marks from my one-on-ones and from my manager. So show me the receipts,

you know, and I think that's a fair question. Um, especially Like if it's not performance, then just be straightforward about that, which is, could be, Hey, finance, sales and marketing weren't all on the same page, and we That's right. And it has like a really important

impact on when she goes to find her next job, right? Because, you know, Cloudflare, I'm sure will do a reference for her to say when you do like a reference, well, when you do like an employment check, they'll say, legally, yes, she worked here or no, she didn't. But when a future employer, they're allowed to ask like, hey, what was why did? Why are you no longer with your previous company? I don't like it's hard because she's not really going to be able to say she was laid

off, even though she was laid off, right? She, you know, if you want to be honest about it, especially now that it lives on the internet, I guess she has to say I was fired for performance. Um, And if it didn't live on the internet, like that's really hard, you know? Um, yeah. So I think it's, even if you were firing for performance, um, but you're doing it with lots of other people, call it a layoff, you Right. Yeah. I mean, I think, Companies are more concerned with saving face of the

attention around layoffs, right? And, but what's worse, what's worse is what's out there now, right? We're a company who lets people go because we miss, you know, for whatever reason, nobody really knows, but they're performing well. We let people go that are performing well and don't give them adequate time to

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