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Today, I'm talking with Chris Cordell, most recently the chief of staff at Slack.
Chris has spent the past 12 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 Devenu Collaborations, a firm dedicated to helping rapid growth CEO scale.
We're going to 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, just start off, let me explain what that was like and culture very big these days, lots of TV 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.
No secular 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 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 to, you know, get married, be the wife of someone who was working in the ministry.
And I decided to study to teach English and I tried to take the Greek class that we had in the college and I was told that I wasn't allowed to take that class because 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 helped me in my role.
Things like humility, which, you know, in terms today, I 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 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 parallel to my work now.
But on the flip side of that and breaking out at the age of 26 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 did this 180 and had to question my purpose in life.
You know, 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, that process of having to do that has 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 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 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.
And I'm curious to hear what your automatic rules for success are.
Yeah, I'd have to say the first one that applies to work in personal is delegation.
And that may seem pretty simple, but as a person who is 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 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 figure out why my roof is leaking.
Or it's a very simple and obvious answer, but there are a lot of parallels in life.
Another thing is constant learning.
And 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 this phase, in this constant phase of like, everything is new.
Like, what do I not know?
Like, what else is 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, you know.
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 have got a friend that's a neuroscientist, a particle physicist, someone that's doing CRISPR research, like just being able to sit down with those people and ask them questions.
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 to turn it all off, turn the electronics off, but also turn off the constant need or desire to optimize.
And I think people like you possibly, or people like me, think like, how can I be faster at this?
You know, even in little ways.
I'm going from this one 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 we become more effective at delegating?
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.
A lot of times you think 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 on anxiety and that 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 all the things that only you can do 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 to let go.
I want to double click a little bit too on turning it off.
How do we learn to turn it off?
How do we turn off that part of our brain and not only walk away from electronics, but walk away from the constant 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 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 up to reading like, you know, listening to like 50 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 fortunate to live in an area where I can go on a walk and not have cell 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 cell 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, 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 cell phone 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, 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 us, 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, uh, successful companies I'm thinking specifically kind of patterns of success patterns of failure.
Right. Well, I'm, I'm going to kind of 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 models.
The first one you talk about necessity versus sufficiency.
You can probably describe this better than I can, but it's like, what's necessary for success, you know, working hard, having financing what's sufficient.
You know, that's kind of the, like, I would say it more like a genizé coi 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 rings 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 higher, 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 to hire 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 feels like sink or swim.
If you let that person go and 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 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 rear of your mirror a little bit, see who's coming behind you, but maintaining a solid focus on, you know, your core goals and your customers.
I truly believe that focusing on this is something that's been true at pretty much every place that 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.
I started at around 140, 150 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 set, you know, that you have at this size, you know, 140, 150 people, you know, they're usually a really special group of people that you've put together.
Maybe you've worked with them before.
Maybe they're just really the best at what they do.
And they have a difficult time with that scale.
You know, there's stages of change.
And I like to think of it as reject, tolerate, accept.
You have an engineering culture and you bring in salespeople 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 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 in 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 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 50 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 50 to over a thousand?
Yes and no. It depends on the leadership and the company.
At Slack, we would use this comparison of when you go from one stage to another.
So let's say, you know, 50 to 150, 150 to 300, three to five.
We would refer to it as 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 break and a break in just in terms of let's sit for a moment, let everybody kind of get
to know each other 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 where 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 people into the leadership that, you know, there's still an 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 of the challenges are different depending on what the product is.
I would say the biggest thing really is the people.
And you know, culture is so 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 finding that balance and also bringing, bringing the people along mentally.
You mentioned hiring and firing is being 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 addressed earlier what's happened.
And yeah, I think a lot of times the people that I've worked for and with, and the reason I worked for and with them is they are kind people, you know?
And I think it, especially as a first time CEO, which is people I might be working with in the future and similar to folks I worked for in the past as 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 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, ah, you know, 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, you know, small things can be solved, but overall you've got to develop that 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, you know, Silicon Valley is talk about a cold, you know, the cold 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, and 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 and this other group of people that they are trying to please.
So they've got this guy who was like, oh, 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 or 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 going to bring on people that are, you know, you, you hire people that are of the same quality, hopefully even better than you are.
They're going to, they have a lot of, a 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 that other thing that someone talked about recently and that's called no trans firing.
If someone's not fit for a role, a lot of times what they do is just put them in another role, you know, let's just, let's just move them other to this.
Somebody else's problem.
But I love that term, no trans firing.
And so just do the hard, hard thing and sort of let them go in the most human 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, few runs for you to 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 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 seeing it on your phone and then slowly after a while you just come to like, Oh yeah, there's that thing again.
I'm going to tolerate it.
And after a while you're like, Oh, actually I kind of 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.
You know, 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 in 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 picture, 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, the first salesman that comes in?
Or is this? No. Yes.
Yes. I can see just all these faces in my head of engineers that I've worked with that, 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 for the classic engineer who's wearing his Ibrums, you know, his utilla kilt, his tech t -shirt, you know, he was up late coding and he comes in 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 still love being able to sit down with a group of engineers and just kinda 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.
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 in.
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?
So there's a lot of these dynamics.
And one thing that I did at Twitter was we actually had all the salespeople, this is 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 the engineers, of course, wanted margaritas and tacos.
So they had to go and spend time with the salespeople and ask them about their roles.
And other 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 into 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 commute, there's this communication barrier
that you have to overcome and it takes a certain personality type of, 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 man, those 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, the thing goes to the engineer 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 in Slack that you would like to share with other people.
I, I come from a set of beliefs that especially in the startup world, and this is actually proven in a lot of things.
Like you've just got to, you've got to make the decisions you've got to, like the market changes so quickly, of course have all the information that you have.
And at Slack, we adopted a form of the Amazon memo, thinking through something, having someone think through something in advance, write 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, 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 going to get into that group of executives and someone's just going to 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 got a, like we talked about earlier, just like let go, like 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 rearview mirror too much.
You know, I think there is, there is this, um, someone was telling me recently about, um, this seal teams, they do this action review.
It's after action review AAR.
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 going to happen step by step, you know, you could put that filter on an acquisition on, you know, a higher on an employee change and looking.
And if I feel like there's something very similar in your book that talks about this, what you thought was going to happen.
Did that happen? And not who, who fucked up who did something wrong.
Um, not working where you're going to put the blame, but I think that continue continued iteration of how your specific team makes decisions is really important.
But I firmly believe like you've got to 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 are the best leaders tend to have in common?
So in this particular case, I'm talking about founders.
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's efficiency. You don't know 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 entrepreneurs or opportunists who just love the game of business and just a quick sort of in terms of problem solvers, I believe that's kind of what Stewart, 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 out like, wow, that was so smooth.
Like they really got to 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 20 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 his authentic self and people love that and that's what you should be.
But he would say, Oh, I roll over, I 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 the, kind of the three different buckets that I see people in and then it takes 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 adaptability, but that's what I believe is the number one key for leaders.
It's what has made humans successful over the evolution of time, which is a new understanding for me.
And so therefore it's just really, it's in big headlights for me because my personal adoption from, you know, a world steeped in religion towards belief and 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 aren't 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 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 and you have to 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 uncomfortable situations.
Actually know they're put into this other level, like the conferences they're going to the dinners are 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 and also curiosity.
You know, if you're curious about something, explore it, especially in a lot of ways of 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.
When I think about my own personal journey, like coming 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 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 got to 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 Moss's right now.
Like, I don't know anything about Moss's 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 like, hey, did you know?
Like, no, 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 and giving yourself that that break.
Freeing your mind up is really helpful.
So that's, you know, stick out things greater than you.
And also really important is not believing your own narrative or your own story when you found a company, hire a 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, it 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 reporters or on stage and been reading about yourself in terms of like even hiring people, if you put your self worth into that, then you're going to be sorely disappointed.
And there's this blog post by Aaron Zemos, who's the former head of PR at Square.
And it's called What's Your Hour in Silicon Valley time?
It's it's so great and it's so true.
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 disrupter, your 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 going to make money.
You can't do it right.
Your privacy issues are horrible.
You're the evil empire.
Like you're going to go away soon.
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 new vision and it's this cyclical thing because, you know, stories are interesting and change is interesting.
And so you have to realize that that's going to happen.
It's inevitable. And you have to tell your employees that it's going to happen and just be focused on the right things.
And so, yeah, being grounded 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 too good for me now or they have important friends now.
But, you know, those are the people that you want to hold onto those people that have known where you came from, known who you are, who are going to treat you disrespectfully and, you know, in a friendly kind of way.
And I asked those people to call you out and 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 that, that sense of being willing to learn and to grow, if 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.
What was that impact and how was that even recognized by the organization was a quick or slow one?
I mean, I'm not going to talk about specifics really, but I have a lot of friends who are in this line of work in tech.
Um, I know a lot of other chiefs of staffs of companies that, you know, you would know, and you know, you get together and you talk about the things.
And it's pretty much the same things.
And they're all kind of applicable to our daily lives.
There's this, the sense of leadership that, you know, your, 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 in 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 solid.
And if I'm not here to see every change that happens, then you know, these things aren't going to 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 want to 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 match top, if you will, seeing what's coming in the different, in the distance, market awareness, competitors, potential acquisitions, setting a strategy, constantly asking yourself, you know, what is taking us too
long to learn? What should we 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 set out for them.
You get invited to things and you are the only person in your company that can take that seat at that table 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.
Well, actually, no, you should, you should be working.
You should create, you know, time for deep work.
And one of the best help, help say that I've seen is 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 mount to top, 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 the position that's yours that you haven't done before, or you haven't necessarily seen sat next to someone who's
done it. So it feels so unnatural, doesn't feel right, but it is what it's right.
You know, you having a sense of what's going on across the organization, hiring night people, letting them do their job, not having them run everything through you, but getting them to work together.
That's kind of just like 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 this opportunity 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 their livelihood in a sense.
And obviously they could get a job somewhere else, but that, that pressure is, is really huge.
You were the chief of staff most recently at Slack.
What does that role consist of?
And what is the hardest skill to transfer to somebody else that takes the mantle after you?
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, you know, 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 base
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 read something the other week and it said the most, the most thinkless decision you can make is the one that prevents something bad from happening and that epitomizes the chief of staff role because you're out there not just solving problems, but finding problems.
Ideally, you are keeping so much from coming up to for the leader.
You're, you're taking things off of their plate, you know, and there's different types of chief of staffs.
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 of nothing, jack of all trades there.
I forgot the expression.
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 going to 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'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 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 will 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, 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 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. Hey, one more thing before we say goodbye.
The Knowledge Project is produced by the team at Frontump Street.
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