#99 Kris Cordle: Releasing the Ego

Transcript from https://podmenti.com/t/3ac14a7248bc93b7

You know, if you're curious about something, explore it. Especially in a lot of ways, if it's unrelated to what you're doing, it'll free your mind up in so many ways. You'll find parallels.
And relieve your brain from the same problem that you've just been trying to nail on.
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Today I'm talking with Chris Cordle, most recently the Chief of Staff at Slack.
Chris has spent the past twelve years working directly with some of the best CEOs during her time at Yahoo, Twitter, and Slack.
She joined Slack and Twitter when they were small and helped them scale into public companies. Now she works at Devenue Collaborations, a firm dedicated to helping rapid growth CEOs scale.
We're gonna talk all about
her upbringing in a religious cult, and how that shaped her world, automatic rules for success, lessons about decision making and scaling, why it's hard for founders to scale in particular, the common patterns to success, and so much more. You'll walk away from this episode with a new perspective on leadership and practical tools that you can implement today with your team.
It's time to listen and learn.
You grew up in an extremely religious environment, like a very closed system, you might even call it a cult.
How has that influenced how you see the world?
Well, to start off, let me explain what that was like and uh
cult are very big these days. Lots of T V shows about them. So, you know, my thunder is stolen a little bit here, but it was
sort of similar to what you might see in a Hasidic Jewish community or conservative Mormon
group essentially it was this group of a couple hundred people.
We had no interaction with the outside world except, you know, grocery store and of course knocking on doors to invite others to join.
Um, no secular m movies or music, long skirts, no booze, no touching the opposite sex until marriage, of course.
In fact, in my college, I went to a college that was
run by this group.
As a woman, the only uh majors you could choose were to be a teacher.
a church secretary or a major called Christian Womanhood, which essentially we called the MRS degree.
um to, you know, get married.
be be the wife of someone who was working in the ministry and I decided to study to teach teach English.
And I tried to take the Greek class that we had at the college and I was told that I wasn't allowed to take that class'cause that wasn't
You know, the level of knowledge that was necessary for a woman.
So very different from the world that I am in today.
But a lot of the things distilled
in me at a young age have been really helpful into getting where I am and also help me in my role.
Things like humility, which, you know, and
terms today I may might maybe talk about like death of ego.
Compassion, empathy is kind of another parallel to that.
Servant leadership, really caring for people, seeing them.
And then of course building a sense of community towards a greater good.
And uh I had this goal early on of wanting to
And actually, the most ambitious thing that I could be was to work alongside a leader to support someone in the background. And I thought a lot about.
what that would require. So
Lots of observation and kind of guiding behind the scenes and you know small advice here and there. And it's funny a lot of ways
You know, it's it's parallel to my work now.
But on the flip side of that and breaking out
At the age of twenty six, through a certain set of circumstances, I separated from that community.
And in breaking away, I kind of had to leave everything that I ever knew both
you know, emotionally, intellectually
And my core belief systems were just
You know, I had to start from ground zero again.
And in that experience of separating from everything that I've ever known, I I did this one eighty and
I to question my purpose in life, you know, I my purpose before was
saving souls from eternal darkness and hell and everything else after that seems kind of, you know, insignificant.
But
You know, figuring out my own way and
you know, ha that process of having to do that.
It's kind of felt like everything after is so easy.
You know? So in the work that I do, I work with these highly intelligent individuals who are leading these large organizations.
organizations that are really affecting the world, how the world communicates.
But you know, being able to speak truth to power in that situation.
And realizing that that transition out of
religion into a personal discovery of science and
uh learning about evolution. It's taught me about
Our ability to change and grow and adapt to new environments, and that to me is just
So exciting, even just as a concept.
And then to be able to apply it in my work.
has been um
Really rewarding.
I want to get into a deep dive on some of that and how you apply it and what you've learned in your role, but before we get there, I've been thinking a lot lately about automatic rules for success at a personal level.
what are the rules that we can make for ourselves that put us on the path for success?
For each person these are different. I'm curious to hear
What your automatic rules for
um success are
Yeah, um I'd have to s say the first one that applies to work in personal is delegation, and that may seem pretty
simple, but as a person who was taught I'm here to provide for others, to serve others, the fact of having someone else do something for you was a really difficult concept.
But in working with the people that I've worked with and in my own personal life, I've realized that you should only be doing the things that you can do.
And yes, this might cost a little bit of money, but I've realized
And I've seen in other people, whether it's people that I've worked with or the people that I've worked for.
that if you can free up your mind space, free up your time to
be doing the things that only you can do, you'll be a lot more successful in the things you're trying to do versus
me trying to, you know, figure out why my leak my roof is leaking, or you know, it's a very simple and obvious
Um, answer but answer, but there are a lot of parallels in life.
Um another thing is constant learning.
Uh and I I've had the fortunate experience of having
to
learn about the world at a later stage in life and I feel
so grateful for that because I'm in in this phase in this constant phase of like everything is new. Like what do I what do I not know? Like what else is then like I've learned the more you know about something, the less you know about it. And that to me is so exciting because the answer just used to be
Because God
Yeah. Um
So
And that could be
You know, constant learning could be the people you surround yourself with and I feel
Lucky in Silicon Valley, there's so many interesting individuals, and sometimes it's unfortunate it's a little homogenous in terms of what people do, but
You know, I've got a friend that's a neuroscientist, a particle physicist, uh, someone that's doing CRISPR research.
Like just being able to sit down with those people and ask them questions and and people want to have a conversation and you have something to bring to other people as well. And that exchange is just
really beautiful and a part of what makes us human and what's
made us be able to adapt and grow as humans.
So delegating, constant learning, and then this last one.
you know, has been developed over time is just turn it all off. Turn turn the turn the electronics off, but also turn off the constant
a need or desire to optimize. And I think people like you possibly or people like me who think like how can how can I be faster at this? You know, even like little ways. I'm going from this room to this room like what's the most efficient way that I can go and what can I bring with me? And you know, and that's just it's a cognitive overload.
And I feel just being able to turn off the electronics, your brain, and just really, you know, it's a form of meditation.
Anyway, so those are some of the things
Delegating, learning, turning it off that I utilize.
Well, let's double click a little bit on delegating. What are the ways that we delegate more effectively? What have you learned about delegation?
How do how do we become more effective at delegating?
It's it's really a mental hurdle, honestly, for people.
There is
the perception of
Like
I don't want to make someone else do this. Well, a lot of times people need the opportunities or they need the growth experience.
Um, a lot of times you think it it could be expensive or
I think the real fear that a lot of us have that we don't want to admit is based in anxiety and that's no one can do it as good as I can.
And
Let's just go with that and say
Perhaps no one can do it as good as you. It's unlikely. But if that's the case
Is that like I said before
Are you doing only things that you that only you can do?
And and making sure that the things that only you think you can do are actually those things. You know, there are a lot of talented people out there and you have to give up and release that anxiety.
Of
This may not be perfect.
You know, this may not be the way that I would do it, but I've got a
Let go.
I wanna double click a little bit too on turning it off. How do we learn to turn it off? How how do we turn off that part of our brain and
um not only walk away from electronics, but walk away from the constant
how hypervigilance and I need to listen to an audio book and need to read a book when I'm in line at the grocery store.
And just constant sort of self improvement with no time to digest that material. It's always sort of like what's next.
Yeah, I mean
This is one of my my key things because I struggle with it so much, honestly.
when you're talking about listening to audio books
I'm there. I just looked at my audible stats.
And I'm I'm up to reading like, you know, listening to like fifty hours a week right now. Like okay, maybe that's a sign for me.
But um, you know how to turn it off. I think you just have to go cold.
Turkey.
I'm I'm fortunate to live in an area where I can go on a walk and not have self service.
I can choose to walk one way or another way.
Um, so making that choice to walk to the right where I won't have self service because
You know the temptation is huge, and there's always something that seems really important.
But taking that step back.
It's it's so relaxing. It's just this like
Cognitive massage, you know, it's what we need.
Uh but I think
Really you just have to set up
Habits and mechanisms.
to be able to, you know, the same thing as like don't go to the kitchen if you're on a diet.
You know?
Like don't take your cellphone with you. It'll be okay.
You know?
It's interesting how those little small changes in our environment make a massive impact in terms of what's the d our default behavior becomes in the path of least resistance.
Yeah.
You've taken the proverbial sort of like rocket ship twice now, once at Twitter, joining as a small team in Slack, uh, and you scale both of them.
through the IPO.
Can you walk us through that journey a little bit and the important things to look out for in terms of
um successful companies.
I'm thinking specifically kind of patterns of success, patterns of failure.
Right. Well I'm I'm gonna kinda answer you a little bit with some of your own
Your own thinking here.
And that's in your book that I was just reading, a mental model is the first one.
You talk about necessity versus versus sufficiency. You can probably describe this better than I can, but it's like what's necessary for success, you know?
Yeah, working hard, having financing, what's sufficient.
You know, that's kind of the like
I would say it more like Je ne sais quoi of success, right? It's it's not something you can define in advance. In fact, you can't go back and necessarily point to exactly what the
Right things were, butterfly flaps its ring wings, and you have this product that takes off.
Um, but there are some key things, um
The people, of course.
hiring the right people and firing in the right people, honestly. There's that, you know, montage, hire slow, fire fast. And startups you're moving so quickly.
that you don't have time. You've got customers knocking at your door. You need ahead of sales, you need one now.
So you've got you got high the right
Hire the right people and then
When you see that there's not a fit, you don't have
time, you don't have capacity. It's it's feels like sinker swim if you let that person go. And it it feels like it's better to have
you know, someone who's maybe not completely what they should be, but
All of the
the the mistakes will set you back. You know, six months of the of a person in the wrong position will set you back.
two years because you're building these foundational blocks.
I think one challenge people have and one thing that's important is
Obviously looking ahead.
And then you also, you know, need to look in the rearview mirror a little bit, see who's coming behind you.
But maintaining a solid focus on
You know, your coracles.
And your customers.
I truly believe that focusing and this is something that's been true it
pretty much every place I've been at, focusing on the customer.
will really not lead you astray.
And it's it's really interesting journey of both Slack and Twitter started it.
around a hundred and forty, hundred and fifty employees scaled to, you know, a couple of thousand.
Got to see them be a public company and see
that transition. It's just it's fascinating and
The employee said
you know, that you have it at this size, you know, a hundred and forty, hundred and fifty people.
you know, they're usually a really special group of people that you've put together. Maybe you've worked with them before.
Um, maybe they're just really the best at what they do, and they have a difficult time with that scale.
You know, there's
states of change, and I like to think of it as reject, tolerate, accept.
you have an engineering culture and you bring in salespeople and
And the engineers are you know, this is not who we are. We're not
people who like sports ball and get excited about things, you know, but you ha as a leader, you have to
explain the value. And I know it probably sounds really obvious, but these are these are real things when your environment changes so rapidly.
And there's also there's a lot of talk about the Legos, letting go of your Legos. You know, initially
No job is too small. Every job is your job.
But then as the company grows, there's someone to do that job.
And you think, Well, I've been here since day one, I know how the company would really do, and this person is new.
What do they know?
But to be sustainable and to grow, you have to focus on your thing.
Not worry about the other thing. Stay in your lane.
Focus on your role. And that can be really difficult to make that transition. Maybe a good parallel would be
raising a child and then setting them out into the world. But you have to do that in in your role.
And also realizing that just because you're the right person for your job today.
doesn't necessarily mean you're the right person for your job tomorrow.
Is there a
particular place in growth where companies tend to experience hiccups when you're scaling from 150 to thousands of people, is it
'Cause one fifty is sort of that threshold for a human network. And then what happens after that as you go through these? Are there patterns between growth from one fifty to
Over a thousand.
Yes and no. It depends on the leadership and the company. Uh
At Slack we would use this comparison of um, you know, when you go from one stage to another. So let's say, you know.
fifty to one fifty, one fifty to three hundred, three to five.
We would refer to it as
Yeah.
A snake eating a horse, I think, or a snake eating a goat, I believe. And you've taken this big thing on and you just have to sit for a bit.
And you gotta let that digest.
Because
You've got
recruiters who have just been hired and they need to
go and recruit, but first they have to actually figure out what you are and what you're about.
And giving yourself a a break.
A breaking just in terms of let's sit for a moment.
Let everybody kind of get to know each other.
At um at both Twitter and Slack, there were tools that were put into place, internal tools, where there was kind of like a game like mechanism.
Or you could see a picture of
Two employees, and you have to like guess, you know, this name is the name of which employee. And uh those little things like that that.
Obviously aren't sustainable in the long run, but
can give faith
from the the people into the leadership that you know there's still an a attempt
to try to keep like what you had at the beginning.
Um I mean, I'm not being completely succinct here, but that that's because like every
Every startup is a snowflake. All the challenges are different depending on what the product is.
I would say the the biggest thing really is the people.
And
you know, culture is so um important. And sometimes there's this balance you have to play of how much do you focus on the culture and how much you focus on the business. Like what which one is the priority? And there's not really a priority. It's this fine
Balance.
But that's kind of really the key thing, I think, is is finding that balance.
And also bringing bringing the people along mentally.
You mentioned hiring and firing is being uh very important and sort of firing quickly.
Talk to me a little bit about that. What have you learned about hiring and firing and in cases where you've left people in their position too long when you know all along it should have been
uh addressed earlier, what's happened and
Yeah, I think a lot of times
people that I've worked for and with and the reason I work for and and with them is they are kind people.
You know, and I think it especially as a first time
CO which people I'm gonna be working with in the future and
similar to folks up for in the past is you care about people. You see this person, you see that they're trying
you see, you know, you know their family situation, you know that this is a huge opportunity for them, you know, both in their career and also, you know, in in their industry.
when you when you see that they aren't the person you you don't want to believe it.
You know.
Like, oh, they can they can get there. It's almost kind of like being a relationship you shouldn't be in anymore. Like, uh, you know, th they'll they'll figure it out or I can help them, or we can just get them a coach.
And a lot of times the the
You know, small things can be solved, but overall
You've gotta develop that.
Under understanding that it's it's best for them in the long run.
And there's ways to treat people kindly.
Of course.
In terms of the hiring aspect, it's really interesting, you know, startups rely a lot on their investor base.
to introduce them to people. And you know, Silicon Valley is talk about a cult, you know, the cult of Silicon Valley and the community. It's all about
Who, you know, all the jobs I've gotten have been through someone that I knew.
And there can be this danger though, in that you have this investor and you know that they're just interested in your success, right? That's
Success for you, success for them.
However
They also have this other network in this other group of people.
that they are trying to please. So they've got
this guy who'll let go of this job and they're like ooh I can quickly put him in this
in this puzzle piece of your company. And like, Oh, this guy's great. Yeah, hire, hire him. You know, he's he's amazing. But you know, you have to realize that they are kind of they're playing both sides in a way in terms of their network.
Is there a point where
You think people reach the ceiling of their capability. Like you said, hiring often comes from word of mouth.
But are you hiring for the next
growth phase, are you hiring for the existing job? How do you think about that?
It took the words out of my mouth. That's exactly it.
I think you should hire for
Where you want to be.
You know, and all you need to do in that case is work on your narrative and on your story and how do you convince that guy.
who's in some ways too big for this job to come work for you.
You know, you convince them to come on, they're going to
Want that to succeed.
And they're gonna bring on people that are
Yeah, you
you hire people that are of the same quality, you're hopeful hopefully even better than you are, they're going to they have a lot of
Lot of at stake there, a lot of risk. So they want to bring on the best people that they know.
And it's this trickle down effect of who you hire.
But I wanted to mention a other thing that someone talked about recently and that's called no transfiring. If someone's not fit for a role, a lot of times what they do is just put'em in another role.
You know, let's just let's just move the mother to the somebody else's problem.
Exactly. Um, but I I love that term, no transfering.
And so just do the hard hard thing and sort of let them go in the most humane way possible.
Yeah, and it can be difficult. It's a skill, unfortunately, that you have to work on developing
In the end, it's better for everyone.
And it takes a few

feel that and
And see that.
One of the other things you said was reject, tolerate, accept these phases. Walk me through that a little bit more.
Yeah, I think it's it can be applied towards a lot of things. Let's let's take a
a new brand unveil.

Any company I've ever worked for.
You have this this new mark that you've hired the best people to put together and you release it to the world and everyone hates it.
You know, you hate it. You hate singing on your phone.
And then slowly after a while you just come to like, Oh yeah, there's that thing again, I'm gonna tolerate it.
And after a while you're like, Oh, actually I kinda like this. You know, it's way better than the other one. And you know, be that for a brand, be that for a change in a company, be that for a structural
alteration inside of an organization.
Not that you should just barrel through things be like, Oh, eventually they'll accept it.
Yeah, I'm talking about things that have been well thought through.
You there are things you can do along those different stages.
you know, by explaining why you came to a decision. I think that's really important, especially
and leadership.
listening to people, people need to feel heard.
Um, and a lot of times you can actually
Get some good counsel by listening to your people.
And you know, eventually people there are
Other things to focus on
And that acceptance has a lot to do with that.
And if you are focused on, you know, the right things.
Then this change that's not really significant to the broader pitcher.
You'll acclimate it acclimate to it over time.
Is that also I think you mentioned earlier about culture too, like going from an engineering culture to a sales culture and how that, you know, it's a originally it's probably a group of founding engineers and then they reject, I'm assuming.
A sales culture or the first salesman that comes in, or is this
No?
Yes, yes. I can see just all these f faces in my head of engineers that I've worked with that are, you know
They are
Certain archetype for for better or for worse, and it's not always true, but they definitely think a certain way.
You know, let's just say it's the classic engineer who's wearing his
Irams, you know, his utility.
If
Tech T shirt.
You know, he was up late.
coding and he comes in at at noon and that's totally fine. You know, they're they're getting their job done. They're they're brilliant.
And the focus of
those other conversation is so different. I loved and I s still love being able to sit down with a group of engineers and just kind of like
eavesdrop at Twitter I used to
Fave tweets of
Engineers that I really respected, that I didn't understand. I didn't understand the tweet, but I faved it.
That's what we used to call call it. Um, I liked the tweet because I wanted them to think that I got it.
And so that the next time they had a conversation with a group of people and I walked up, they wouldn't think that that was abnormal and they would, you know, continue talking the same way. And I learned a lot, like that learned a lot in that way. They're really special creatures. And then you get these
salespeople and they, you know, typically not to put everyone in a box, but a lot of times they are
really healthy, they're into sports, they're super outgoing, and they want to give you a hug, you know, they want to like ask you about your week. And I'm more of an introvert and I'm just like, you don't actually care about my weekend. So could you just not ask me about it? And
Please don't hug me, especially the way that I grew up. I'm like, you want to, you want me to take my chest and push it up against yours. Like I just met you, you know? Um, so there's a lot of these dynamics. And one thing that I did at Twitter.
was um we actually had all the salespeople, this was when the sales organization was newer, we had the salespeople in a different building. And so we organized a like margaritas and tacos, but like in the middle of the sales building. So
All of engineers, of course, wanted margaritas and tacos. So they had to go and spend time with the salespeople and ask them about their roles. Another thing that we did at Slack is sending engineers on sales calls.
And once people understand the value, like I don't want to go and
Two
a you know, a huge client meeting that's in necessarily in a industry necessarily I don't know much about and just
just really convince these people and show them the value and the value is there, but the commun there's this communication barrier that you have to overcome. And it takes a certain personality type once you realize that like wow, these people are so great. I can never do that work. I don't know how they do it.
And this mutual appreciation can develop.
And the same hand though sales salespeople can go to the engineers
And once there's, you know, a sense of community and talk about my customers really struggling with this versus filling out a form that then goes to the engine and like, oh, what is this person talking about? But to be able to really explain it and to develop those relationships really helps the company.
Are there things that you've learned about making better decisions from working at these companies, uh
Twitter specifically. You worked at Yahoo before, but Twitter specifically and Slack that you would like to share with other people.
I
I come from a a set of beliefs that
Especially in the startup world.
And this is actually proven in a lot of
things. Like you've just gotta you've gotta make the decisions. You've gotta like
The market changes so quickly.
Of course have all the information that you have.
And at Sakwe adopted a form of the
Amazon memo.
Thinking through something, having someone
Think through something in advance.
Right about it.
um, be able to spend time with a group reading against it. And the format that I always like to follow is here's the situation, here are
Three different solutions. Here are the pros, here are the cons. Here is my recommendation.
And then also communicating like I don't care which one you choose. In fact, we could brainstorm something else completely different.
And the real key there in that thing is the person who's
you know, or the group of people that are writing that memo or coming up with these propositions understand the full context. So they don't understand the full context of the situation, then they're gonna get into that group of executives.
And
Someone's just gonna brush them off, like, well, they don't they don't really get what we're trying to do here. You know, so I think that's the the huge key.
I think you have to make sure that you have as much information as you can in a moment and
At some point you've gotta, like we talked about earlier, just like let go. Like we we have enough.
And you know, a lot of these decisions are reversible. If any decision is reversible, then keep going with it.
That's really key. And then also
Try not to look in the rear view mirror too much, you know? I think there is
there is this um someone's telling me recently about um this seal teams they do this
action review. It's after action review AR. They talk through what was expected to happen.
What actually occurred.
What went well and why
What can be approved and how?
Writing down, you know, what you thought was gonna happen step by step, you know, you can put that filter on an acquis, on, you know, a hire on an employee change, and looking and I I feel like there's something very similar in your book that talks about this.
what you thought was gonna happen, did that happen, and not
Who
Who fucked up? Who did something wrong. Um, not where gonna where are you gonna put the blame. But I think
The continue
Continued iteration of how
Your specific team makes decisions.
is really important.
But I firmly b believe like

You've you've gotta move and if you don't move then there will be forces that move you.
Whether you like it or not. Yeah, totally.
Um one of the reasons that growth is hard is because it's really hard to scale the CEO
What is leadership to you and what do the best leaders tend to have in common? So in this
So a lot of times
And what's so interesting about, you know, the work that I do and want to do in the future is these are people who have never run a large organization before.
thinking a lot about your distinction between necessity and sufficiency. That sufficiency, you don't know w what the magic sauce is, but something happened. You launched something, it's taking off.
Now what's next? You have to transition from creating a product to building a business.
And
I see that there's a lot of different characteristics of those
individuals there's like the dreamers, the world builders, like the Elon Musk
And then there's the problem solvers.
And then there's the entrepreneurs or opportunists who just love the game of business and
Just a quick uh story in terms of problem solvers, I I believe that's kind of what Stuart, the CEO of Slack, is
We would travel together all across the world.
We'd go through
An airport security in a foreign country, and I would get up like wow, that was so smooth. Like they really gotta figure it out here. And he'd come out shaking his head like oh that could have been so much better if and he'd just rail off twenty things and I'm like
Oh, like yeah, I guess you're right, but it was fine. You know, and there's just certain people that think that way. And
you know, we would he would speak at a conference, do a Q and A, and
They would ask him, Oh, what gets you out of bed in the morning? And as a chief of staff, I would be like, Oh no, don't say the thing you always say. But it was good that he said it because it was uh his authentic self and people love that and that's what you should be. But he would say, I roll over
Grab my phone and I scroll through Slack, I scroll through Twitter, and I find something that just frustrates me so much that I have to get out of bed and fix it. To me, that sounds like a lot of anxiety, but you know, some people are motivated in that way. And it was interesting I was listening to a podcast this past weekend of Jerry Seinfeld, and it's very similar to
comedians, you know.
They the more like frustrated they are at the world, the more they can articulate why they're frustrated and therefore have a solution against it.
You know, people who think, Oh, everything is great, you know, it's hard to get those people and like, Well, how can we make this better?
So
Just starting off as a kind of a
three different buckets that I I see people in and then it takes a
A lot of luck.
And then it takes a lot of adapting to get to that next stage.
We've we've talked a little bit about ad adaptability, but that's what I believe is the number one key.
For leaders, it's
What has made human successful over the evolution of time.
Uh which is a new understanding for me. And so therefore it's just really it's
and big headlights for me.
'Cause my personal adaptation from you know a world steeped in religion towards a belief in science and science is like wow, like we have the capacity to change ourselves. Like that's within us.
And for a business, the skills that
you know, brought you to create the product that you have created.
are going to take you to building the business that you're going to build. And you know, your product is your baby. You're there to like shepherd it and take it every every step along the way. And then once you build a business, you've got to kind of let go of that.
I could talk more about
that for a long time. That's a that's a key thing that found founders really struggle with. But you've got to change quickly. There's really not time for it. You know a lot of people talk about every time you're promoted, you're put into a job you're unqualified for. And I feel like with startup founders, that's just happening every three to four months.
You have to con
completely change your perspective.
And when I think about being adaptable, I think about, you know, release of the ego.
And you know, that's something we can talk more about, of course, but Yeah, let's double click on that.
Let's double click on releasing the ego. How do we learn to do that? What does that look like? How do we recognize what's holding us back?
I think if you surround yourself with the right people
you will get that feedback, but you have to
Ask for it.
And you have to want it and people know the difference. People know when you're just asking to ask, and they know when you really want to know. And you have to ask repeatedly, especially if it's for
The first time.
But I believe one of the keys is
you know, staying grounded and
Ways to stay grounded or
You know, seeking out the things that are greater than you.
putting yourself in uncomfortable situations. And you think, well, as a CEO, they're in charge. They're always in uncomfortable situations. Actually, no.
they're put into this other level. Like the conferences they're going to, the dinners they're being invited to, the
you know, conversations that they're having with investors, it's it's the hot seat in a lot of ways.
So seeking out things greater than you could be, you know, your in your peer group.
Um I also
Curiosity.
If you're curious about something, explore it. Especially in a lot of ways if it's unrelated to what you're doing, it'll free your mind up in so many ways. You'll find parallels.
and relieve your brain from the same problem that you've just been trying to nail on.
Wanna think about my own personal journey like coming
you know, into the world is kind of how I describe it and having to like figure out how does one even order a drink at a bar? Like who is Michael Jackson and what is this song? And I went to Paris for a year after Twitter and did a French immersing immersion course. And that like gave me that same like buzz, you know, like
I don't know what I'm doing here. And it just like
You have this like heightened like state of alertness because you're like, I just I've gotta figure this out. And it's almost kind of this adrenaline thing. And I feel you can replicate that about anything that you're curious about. You know, I'm reading a book on mosses right now. Like I don't know anything about mosses. Like
What can I figure out? And I
A lot of people that I've worked with and the people that I've
you know, known that have been really successful are like that. They'll come into work and be like, Hey, did you know? And like
No, I I didn't know that completely random fact. Can we get back to this? But actually what that does, you know, there's patterns everywhere in the world.
Um and giving yourself that that break
Freeing your mind up.
is really helpful. So that's yeah, seek out things greater than you. And also really important is not believing your own narrative or your own story when you found a company.
Higher PR firm.
They sit down with you and like, all right, like let's make an origin story. Where were you when you thought of this? Was there a napkin? Did you go to a garage? Whose garage was it? You know, and they weave this beautiful story that, you know, gives you buzz, makes you interesting.
memorable, but a lot of times what percentage of it is completely accurate and how great you are, or how you thought of this great idea. A lot of it is usually chance and one person said this and one person said this, and it kind of all came together and you can't remember exactly how it happened.
But if you put your self worth into
that narrative that you've been repeating over and over again to, you know, reporters or on stage and been reading about yourself, um, in terms of like even hiring people, if you put your self worth into that.
Then you're gonna be sorely disappointed. And um, there's this blog post by Aaron Zamos, who's the former
uh head of PR at square
And uh it's called What's Your Hour in Silicon Valley Time.
It's it's so great and it's so true. Um, he has this clock and he talks about he goes, he walks you through how you're this up and comer.
Then you're an industry disruptor, your hot hottest company, then you've like rapid growth, and then you're you know the biggest thing ever, and then your product kind of sucks.
You're never gonna make money, you can't do it right, your privacy issues are horrible, you're the evil empire, like
You're you're gonna go away soon, the competitors are coming for you, but then there's this like rebirth story and the comeback and then you know, the CEO who has a do new vision. And it's this this cyclical thing because, you know, stories are interesting and change is interesting.
And so you you have to realize that that's going to happen. It's
inevitable and you have to tell your employees that it's gonna happen.
And just be focused on the right things.
Um
So yeah, being grounded is is huge.
That's really interesting because we all tell ourselves these stories about ourselves and then we see the world through those stories.
And then, you know, unintentionally we probably insulate ourselves to people who might poke holes in those stories.
Are there patterns that you've seen that we can prevent that or?
catch ourselves when we're starting to walk down that path.
Yeah, I think maintaining
relationships that you've had for a long time.
You know, it's it's difficult, especially when your life changes.
you know, a lot of people could think, Oh, well, that person's too they're they're too good for me now, or they have
Important friends now. But
you know, those are the people that you want to hold on to, those people that have known where you came from, known who you are.
who are going to treat you disrespectfully and you know in in a friendly kind of way.
And
Ask those people to call you out, invite them to come. Will you come hear me speak at this thing?
You know, and like, what did you think about that? Tell me for real.
Open up yourself to that.
kind of feedback and
It's
It just really goes back to the that sense of being willing to learn and to grow.
I I think is just really key.
What are some of the biggest mistakes without getting into names maybe, uh, that you've seen leaders make inside these organizations? And what was that impact and how is that even recognized by the organization? Was it quick or slow and
I mean, I'm not gonna talk about specifics really, but I have
A lot of friends who are in this
Line of work in tech.
Yeah.
Um
I know a lot of other chiefs of staffs of
Companies that you don't you would know.
And you know, you get together and you talk about the things and it's
pretty much a lot of the same things. And they're all kind of applicable to our daily lives.
There's this
This sense of leadership that
You know, you're
have this higher perspective, right? Not that you're better than someone, but you are the only person that can sit in this seat who can have all of this information.
And if you're spending your time
And down in the weeds.
You know, because you know you can make it better.
There's this
error in the UX and I'm the only person that saw it. And if I'm not here to see every change that happens, then you know
These things aren't gonna be fixed. And you know what?
Maybe that's true. Likely you should hire someone that's good and
Perhaps they won't catch everything, but it's almost like some people wanna wait around for that one thing that's wrong, so they can prove, ah, see, look, you need me here.
On the other hand, there's this other role for you.
you know, sitting on this kind of mountaintop, if you will, seeing what's coming in the different in the in the distance, uh, market awareness, competitors, potential acquisitions, setting a strategy.
constantly asking yourself, you know, what is taking us too long to learn?
what should we build be building faster? What should I be looking out for that my people can't see because they're they're down in the weeds getting the work done that I've you know set out for them.
you you get invited to things and you are the only person in your company that can take that seat at that table.
And and not taking advantage of that and it feels
it doesn't feel natural. It feels wrong. You should be I think this is the case with anyone who learns, you know, delegation also. Like if it feels, oh, I have all this time to think.
Well, that's not what I should be doing. I should be working. Um actually no, you should you should be working. You should
Create.
you know, time for deep work.
And one of the best help
help saree that I've seen is um
Even holding having someone hold you accountable for deep work, someone to just sit there.
You know, all of us can can stray and and when you're the leader, it's just it's so so difficult.
But
you know, getting up to the mountaintop. I guess that's kind of like the big thing that I have to say is
Is letting letting go.
and letting your people do their work and
Taking
Taking a position that's yours that
you haven't done before, you haven't necessarily seen sat next to someone who's done it. So it feels so unnatural. It doesn't feel right.
But it it is what it's right, you know, you having a sense of what's going on across the organization.
hiring the right people, letting them do their job.
not having them run everything through you, but getting them to work together.
It's kind of just like a s a smattering of things, but in general I think of it as just like
Being on that mountain and it's
You know, it may seem to other people like it's it's fun, but it's a lot of responsibility.
you know, you you think about the people who are depending on you to make the right decisions.
so that they can take advantage of those opportunities so their kids can go to college.
You know, you have this
Burden, if you will.
of all these, you know, thousands of people who are counting on you to
have the right perspectives to make the right decisions for for their livelihood in a sense. And obviously they w could get a job somewhere else, but that that pressure is is really huge.
You were the chief of staff most recently at Slack. W what does that role consist of?
And what is the hardest skill to transfer to somebody else that
Takes the mantle after ye.
Yeah, it's
It's a great role. It's it's very interesting. I'm a musician and I'm
play some instruments and I'm a singer.
And the way that I think about it is
You know, there's this person, the leader.
And they're kind of they're singing the melody.
You know, and they're they're marching forward, they're doing their thing and then
Yeah, my favorite thing to do in singing is harmonies.
And you're kind of
You don't
stand out as something different. You know, you're still one voice if you're doing it well.
And you're kind of just dancing in and out of the melody.
And just you know
you know, filling in like
the bass filling in like this like higher harmony part that's like following along. That's you know visually how I imagine it.
And in reality I I read something the other week and it said uh the most the most thankless decision you can make is the one that prevents something bad from happening.
And that it put kind of epitomizes the chief of staff role. Cause you're out there not just solving problems, but finding problems.
Ideally
You are keeping so much f from coming.
Uh.
To
For the for the leader, you're you're taking things off of their plate, you know, and there's different types of chief of staff. It depends on the person that you're working with in particular.
Um, there's people who, you know, are very much about like
The exact I'm here to manage your goals. I'm here to prioritize, delegate.
and complete, you know, work on behalf of you. There's operators.
There's people that, you know, implement, they drive business priorities. There's people who are proxies where they act on behalf and any chief of staff really will act on behalf of
their executive to make, you know, decisions and I think of it as you are almost a master
A master. Master of nothing, Jack of all trades, though.
There you go. Yeah.
Yeah.
That's the one. Um, and what you're doing is just, you know, I would sit in a lot of meetings that I wasn't really participating in, but you're just absorbing information. You understand what different departments are working on, um, you understand what different people's motivations are. So that when you know someone comes and they need something, you can say,
you know, this is not gonna be a priority. Let me just save you the time.
Or
I can fix this for you in 10 minutes. Give me a second. Let me go talk to someone. Bam, it's done. And there are all these things across the organization and it it's so fulfilling personally.
Um it's really difficult to say
Here are the things that I did this quarter because it's it's a lot of it's really personal.
You know, and there's there's different types of chief of staffs, but me, I think of myself like in the background.
Making it so that when my boss comes to work, he only has to focus on the things that he needs to focus on for us to be successful.
What would be the hardest
um skill to transfer to the next person taking on that role, do you think?
Yeah, I
And I actually, you know, if someone is in my role now and I got to spend a lot of time with him
And I think the
It depends on the individual.
Um I
I see myself as having a high EQ.
For the people that I've worked for, I can hear them breathe and I know
What's going on?
You know, just being able to really take in a room
Understand the dynamics, know what's happening.
that's a skill that's developed over time and not everyone really has that skill.
And I think that there are different people needed for different circumstances.
But being able to really understand people because at the end of the day, that's the job.
Of
Any job that you're working at in an organization, you know, there's computers and there's the things that we put in that we need out from them. At the end of the day, you know.
People is the work and the way that our technology has developed that becomes more and more true every day.
I think that's a great place to end this interview, Chris. I really want to thank you for your time.
Thank you, Shane.
Mm.
Yeah.
Hey, one more thing before we say goodbye.
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