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