- Hey, everyone!
I'm doing something today
that not many people do on YouTube,
and I'm filming a video with my boss.
This is Nathan, he's the CEO of ConvertKit,
which is the company that I work for
as a marketing designer,
but you're also an online creator yourself.
- Yeah.
- Do you wanna tell the people about your things?
- Yeah, all my things.
So, I run ConvertKit,
which is what I do with nearly all of my time.
I also run a blog at Nathanbarry.com.
I play around on YouTube just a little bit.
Trying to do slightly more.
I've written a couple books on self-publishing.
My backgrounds in software design,
so that's kinda where I started.
Lots of random stuff on the internet.
(upbeat music)
I tweeted out saying I wanna film a video with Nathan
while we're on our team retreat right now
in Oceanside, California,
and most people say that what they really wanted to hear
you talk about is leadership
'cause you lead a company of what, 38 people now?
- 38 people.
- And this company started as a side project for you.
Did you set out with the intention of leading a big team>
I guess it's a small, relative to most--
- Yeah, it's hard to say.
You've worked at bigger companies than I have.
Did I expect it to get this big?
No, my goal was to have it much smaller.
Like, my hope actually was for ConvertKit
to get to about 25 or 30,000 a month in revenue,
and if it got to that point, I knew it could support me
and then, you know, maybe one other full-time person
and the contractors.
- Right.
- And that was the goal when I set out,
which was actually just over six years ago.
So you've accidentally ended up running a team of 38 people?
- Yeah.
Yeah, and it took a long time to get going.
- Yeah.
- But it's certainly succeeded better than ever.
- Yeah, so what's that been like,
going from like never really intending on leading a team,
like that wasn't the goal, to lead a big company,
but what's it been like to be leading those people?
- Yeah, it's been a lot of learning as I go.
There's more times than I would have hoped for
where I have to go back to the team
and ask for grace and understanding.
And people going like, really,
that's how you chose to lead this company, through that?
And you're like, yeah, I'm learning.
- But I mean, I can say as an employee at the company
that we really like that about you.
- Right.
- That you don't come in pretending to know everything.
You know.
- Yeah, and I mean, I think that's huge, right?
- Yeah.
- The people who get in trouble the most,
who like get too far out of their skews,
where they're pretending.
They're like oh yeah, I could totally do this,
I know exactly what I'm doing, trust me.
And then they end messing up in some way,
and then the next time they're like yeah, trust me,
and it's like, I don't know that I do.
- Yeah.
- But if instead you're saying these are the values
of who I am as a person.
These are the values of who we are as a company
and where we're trying to go,
and we're gonna do our best,
but we're going to make mistakes along the way.
Then everyone expects that,
and there's just a lot more grace
and I hope that more people see themselves
in my leadership style of like,
sometimes they may think, okay, I could do better,
but for the most part they see, okay,
there's someone doing their best, making some mistakes,
and we're learning from that.
I like to think there isn't any arrogance
in my leadership style.
Maybe it comes through in some cases.
- Only when you're like, I don't know,
playing a game or something like that.
- That's competitiveness, which is different than arrogance.
- Well.
(laughter)
So how did you learn,
like even about having a leadership style,
obviously when you're just working on a project by yourself,
you don't really have a leadership style
because you're not leading any person.
So how did you develop your leadership style
and figure out what kind of boss you wanted to be?
- Yeah, so I'd actually disagree a little bit.
- Okay.
- Not having a leadership style
when you're working on something by yourself.
We have a core principle at ConvertKit
of work in public.
And I actually think that that is a leadership style.
You may not be leading anyone, but as you work in public,
so as you finish the project,
and you share on Twitter something about the process,
you record a video about
any tutorials from it, what you learned,
then you're teaching and you're leading other people.
- Yeah, that's fair.
- That's my background, right?
- Right.
- And so then when it comes to more people in there,
then I naturally have that style of like,
this is what I'm working on, this is where I'm going,
this is what I just learned.
And so then that happens within the team.
And that makes me super natural and like,
of course everybody does that,
but the most common thing
is that people make a decision behind closed doors.
They never explain why they made that decision,
why they thought that way, how they got to that point,
and if a team member says "Hey, quick question, why..."
It's like, "Are you questioning me?
"Are you questioning my leadership style?"
- You talking to me?
- So much the opposite.
Whereas if you come into it as a blogger, as a podcaster,
you know, as a YouTuber, then you're just like...
I document, I explain, and I lead in that way.
It's completely different and it's very very effective.
- What about when it comes to more specifically,
leading people, though?
And dealing with maybe the hardest stuff that...
I mean, you don't have to deal with firing anyone
when you're working by yourself.
Was there like, I don't know, a mentor that you had
or how'd you go about that?
- I didn't have a specific mentor for those kind of things,
but a lot of people brought
specific aspects to it over time.
- Yeah.
- There's a few different books that were really good.
I really liked Derek Siver's "Anything You Want".
- Mhm.
It's the best book for like, chart your own path,
think outside of the box.
It's really short, takes an hour to read.
- Link in the description!
- Yeah, there ya go!
I would say "REWORK" by the guys over at Basecamp.
That was really good.
And then, I guess two more like management-specific books
would be "Predictable Success".
- Mhm.
- Which, I mean, these are all books that we've done as--
- Yeah!
- The book club.
- We've all read them as a company.
- (giggles) Yeah.
But that one was really good for just understanding.
This is the arc that you're gonna go through as a business.
And, so like, everything is crazy right now,
things were good, they'll never be good again,
and then, like there's always examples
of people who are experiencing things just like you,
and you're like, okay.
I'm not alone, I'm not crazy, et cetera.
The last book is "Radical Candor"
It's actually the most recent book
that we did in our book club
And that's all about delivering direct feedback.
But the best people management thing that I've ever learned,
and it just comes down to like a simple phrase.
But to set the scenario,
this is basically if someone comes to me,
let's say you come to me.
- Yup!
- Who should we pick on in the company?
Like, in a nice way.
Like Derek, maybe?
- Or Barret.
- Barret, okay!
Yeah, so Barret's our COO.
He's wonderful, but we're gonna pick on him for a second.
- He won't mind!
- Yeah, he won't mind at all.
If you come to me and say,
"I have this serious problem with Barret.
"He hasn't been performing,
"we're supposed to do this project together
"I had to do all of the work."
I might say, okay, first, thank you for bringing that up.
Thank you for sharing that with me.
I'm gonna think about it.
I'll figure out how to solve that,
like, you don't need to worry about it.
You can do your work.
I'm gonna solve that and let you know how to do that.
And that's something that I used to do all the time.
- Yeah, it seems like the most normal thing to do.
- Yeah, and then, you know, as the leader,
it's my job to then go and tell him.
I go talk to Barret and be like, so here's the deal,
I've been hearing about your performance, you know,
we go through that whole conversation.
And then I can report back to you.
But what most likely happens is I do that,
and before I get a chance to talk to Barret,
someone else in the company comes to me
with another problem.
Before you know it, I've taken on not just these tasks,
but like the emotional burden that comes with each one,
and that's where as a leader you just get drained
so so quickly.
And so instead what I learned is
when you come to me and you outline the whole problem,
I still thank you for bringing that up
because it does show that you care,
'cause the much easier thing is to like
subtly resent Barret--
- Yeah!
Maybe gossip about him--
- Yeah, exactly.
And then I say, wow, thank you for bringing that up to me.
I assume you're telling me that for one of two reasons.
Either one, you needed to talk through it
to get more clarity before you went and talked to Barret,
or two, you're worried how that conversation might go,
and you'd like someone to be there
to help facilitate it.
So the question is, when are ya gonna talk to Barret
and do you need me to be there?
- Right, completely different.
- It's completely different, 'cause then,
well, a couple things.
One, from my perspective,
I am going to walk out of that conversation,
and I don't have anything on my to-do list
other than possibly facilitate a meeting,
but like nine times outta 10 that I've used that,
someone's like, "I'll talk to him right away,
"and no, I don't need ya there."
Like, I can just have that conversation.
The second thing is that
you don't carry any emotional burden from it.
Right, so I put that hopefully in a supportive way,
but I put that back on you
and my goal is to empower you
to have that conversation directly.
And the final thing that I think is the most important
is that there's now no opportunity
for you or anyone else in the company
to talk about someone behind their back.
- Yeah.
- 'Cause you know that,
hey, it's important to figure out your thoughts
and bring clarity to it
and say is this a real thing that I'm upset about,
or should I just brush it off?
- Yup.
- And that that's okay,
but then it immediately has to go to that person,
and so you have direct healthy confrontation.
- Mm, I think that's a really important part of our culture
in the way that you lead the company
because that's an issue I've had
in every single other company I've worked at
has been like talking behind people's backs.
Like, someone leaves the room and it's like,
"Ugh, you know what she said to me in the last meeting?"
- Yup.
- And that just makes for a really toxic environment
for everyone to work in, which is not fun.
And yeah, I never really thought about it before,
how ConvertKit got to be this way
where we don't really have that, and that's how!
- It's exactly that one rule.
I mean there's so many others,
like there's the personal care
and things that we work on so much,
but you just never let it get to that point.
- You talk about the emotional burden
of like taking on people's problems.
What have been some of the hardest parts
for you about leading?
- Firing people is always really hard.
- Mhm.
- We've had experiences from letting people go
who knew that that was coming.
- Right.
- But then even some of the harder ones.
So I guess in that case,
you're talking through it over time,
and you're trying to decide
how much do I invest in this person,
how many chances do you give that kinda thing,
versus protecting the rest of the team
and honoring the rest of the team
who's working incredibly hard.
- Yeah.
- But then I've been surprised, even if you let someone go
and they had no idea it was coming,
you're like, okay, but, huh.
And that's when you realize that what is obvious to you
may not be obvious to them.
- [Charli] Right.
- And so there's even a level of communication.
Like, do they know they're doing a bad job?
And you're like yeah, of course.
And you think about it and you're like,
no, I think there's a scenario
where they could think that that is acceptable work.
So you realize that the amount of effort
that has to go into that communication.
It's just substantial.
- Yeah, especially because if where they worked previously
had a very different tolerance and things like that.
They maybe wouldn't know.
What's your favorite part about being a leader?
Let's spin it more positive.
- Yeah.
Trying to pick a favorite.
These retreats are really special.
Being able to sit with everybody.
I mean, I don't know if it comes off
as somewhat selfish or....
I guess it's proud, right?
Looking over the group of people.
I walked into dinner the other night.
Every table was totally packed with everyone sitting down,
eating dinner, having great conversations,
and there was that feeling of like,
oh, this is the thing that I started.
Yeah, you brought all those people there.
Yeah, and it's an incredibly talented group of people.
- Yeah.
- The other thing,
every six months we hand out profit-sharing checks.
- Mhm!
That's one of my favorite parts.
- Yeah, it's really great.
And it's something that I rarely get through without crying.
- Same, yeah.
- I think I actually pulled it off this--
- Well done, yeah!
- I don't think I cried this year!
Of just being able to share that celebration together,
and we worked super super hard
over the previous six months,
and we, one, we actually earned money as a company,
which is hard to do.
- Yeah.
- And then to be able to share that success with everyone.
And to think about what...
You know, in some cases, it's a lot of money.
Like this time, the average was $9,000 per person.
- Yeah.
- For six months.
And so that's--
- And that happens twice a year for us, so yeah.
- Yeah, so those are my favorite moments,
of like, we worked really really hard to achieve this goal,
and here's the reward for it,
and being able to share that with everybody.
- Yeah, that's fair.
What would you recommend to people who, I don't know,
are wanting to get better at leadership,
or maybe have found themselves in a situation like you
where okay, this thing is growing,
I need a team now, I need to learn like...
You don't know what you don't know,
so what were some of the hardest lessons
and things that you found most difficult to learn.
- Yeah, well I think to learn more,
the first thing I would do is ask for feedback.
- [Charli] Yup!
- We do this thing called unsolicited feedback,
where basically, you open up,
and it's basically, I'm gonna sit here and be quiet
and you give me all the feedback.
All categories are open.
Because the example we gave earlier,
that's you coming to me about a problem with someone else..
- Right.
- So how do I create the environment
where can come to me about a problem that you have with me.
- [Charlie] Yeah.
- And the biggest thing that I've learned,
and I really struggle with this, is actually listening.
The biggest problem with you coming to me with a problem
is that I'm immediately , this is just my personality,
I'm immediately going to like explain it away.
- Yeah.
- If you knew what I was working on,
you just don't understand, you know, all of those things.
And then I'm gonna feel like, oh, okay,
now Charli understands, and she realizes
that that was not my fault, it was--
- So I don't need to worry about that feedback anymore.
- Yeah, and then you're gonna walk away and be like,
all right, that was not worth it.
- You didn't listen.
- I wasn't heard, my opinion wasn't valued.
And so that's really difficult
because you're not gonna get the feedback
because you ask for it.
- Mhm.
- You're going to ask for it,
and someone's going to test it in a small way.
"Okay, you say that, but my last boss though...
"All right, lemme give you feedback on this."
- Mhm.
- And you probably won't even realize
that you're getting the feedback.
Most of the time I don't,
and you brush it off in some way, and then
"Okay, you are like every other leader
"that I've experienced."
And so trying to be very very conscious of that.
- Yeah, and that's something that I've had to work on a lot,
and there's other leaders in the company
who have coached me on that and pointed out,
or pulled me aside later and said hey, actually,
you thought this interaction went that way,
but did you notice the body language as they walked away?
- Right, yeah.
I think it's great that you can admit that there's still
a lot of things like that you need to learn.
- Oh yeah.
Another one is, this I find really entertaining.
Other people don't,
but because I've been working on it so much
and I still have so far to go,
is just like dropping in and asking a question.
"Hey, what's your trial number for this month?"
You know, you're like wait,
he hasn't asked about that for whatever.
You know, where's this project at.
Zero context, just drop it in slack,
just one sentence, and on the other end,
there's somebody freaking out,
and they're going like, "Okay, what's going on?"
There's 38 people in the company,
and for whatever reason, the CEO has gone laser focus--
- On this.
- With zero context on this one thing.
And really, I was having a conversation and I was like oh,
planning this thing,
it'd be really nice to know this piece of information.
- Right.
- And so I create an entirely different reaction
than I need to.
- I have an example of when this happened to me.
- Yeah!
- Oh, I'd been at ConvertKit for a few months,
and you just dropped in our direct messages,
you're like "Hey, can we set up a time to talk?"
And I was like "Oh my god, what have I done?"
'Cause at my last company, if the manager or the CEO
asked you to like have a chat,
like wasn't scheduled in advance like a regular thing,
it was bad!
- Right.
- Like, you're probably gonna be fired,
or like, you know, be told your performing
isn't up to standard.
So we got on the call, and you're just like,
"Sometimes has gone and..."
We just chatted, it was great!
And so now I know that when Nathan drops in on us to talk,
he just means to talk.
- Right.
- Yeah! (laughs)
- And that's taking like the solution to all of that
is me taking the extra three seconds to say
hey, I'd love to have one on one to just catch up.
- Right.
- And you're like, that would be great.
- Yeah.
- Now, you may not believe me, that I mean just catch up,
but then after the first--
- It means that I don't have the fear. (laughs)
- You don't have the fear.
And so when asking for certain data or anything else,
I can just give the context as to why I want it.
- Yeah.
- And then everyone understands more.
I rearranged desks so I don't have the sticky
on my monitor anymore.
- (laughs) But you used to have one that reminded you?
- Yeah, it just said add context.
- [Charli] Yeah, like it.
We should make you a print for your wall or something.
- What, you're saying I still need to work on it that much?
- Well, a little bit. (laughs)
- It's a work in progress.
- Thank you for sharing all that though.
I think that's awesome.
Hopefully you enjoyed watching it.
Nathan and I are also filming a video together
other on his YouTube channel.
Do you wanna tell people what it's gonna be about?
- Yeah so, I'm working on a book called "Create Everyday",
and it's about how to grow an audience,
earn a living as a creator,
really all the things that we help people do at ConvertKit,
and so over on my channel, we're gonna do a video
on teaching and storytelling
and how to intertwine those two things
to really attract an audience that really cares about you
and really wants to follow all of your work.
- Cool, so head on over and watch that.
I'll leave a link to it in the description.
It'll be on a card and things as well.
Thumbs up if you enjoyed it,
and thanks for being here, Nathan.
- Yeah, thanks for having me.
- All right, I'll see you all next time.
Bye!
(beeping)
- Does it bother you that that tripod's crooked?
- Nope, 'cause it's just a microphone.
Is it bothering you? (laughs)
- (laughs) Just a little bit!
- We're not gonna have wonky sound.
- One-key sound?
- Wonky.
- Oh, wonky!
I heard one-key sound!
Like, this is the sound--
- Accent problems, yeah. (laughs)
(upbeat music)