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In modern work, no one operates alone. Tasks are too complex, knowledge is too specialized and fragmented. We need to work together – to collaborate – to drive the outcomes we want to achieve. Slack’s James Sherrett explores how small tactical changes can affect the collaboration culture of teams and how that culture drives the business results of our organization. If you are a digital leader wanting to influence cultural change in your organization, this is the podcast for you.
Every organization is in the business of two things: the products/services it brings to market and the culture that it builds internally. Everyone talks about and prioritizes using the former, but in fact, your culture is what allows you to successfully bring that thing to market in the first place.
Slack CEO sees the way we work together as a competitive advantage.
‘The only thing that likes change is a wet baby.’ As humans, we tell ourselves the lie that the world is static and unchanging, but the reality is that the world is changing all the time. We have to acknowledge this reality and become comfortable with it.
Organizations need to root themselves in the things that can help their probability of success in times of change and adapt those things from abstract theory to tactical, daily practice.
Use the ‘yet trick’ to help you become more comfortable when outside of your comfort zone, to create a growth mindset. Add the word ‘yet’ to the phrase ‘I don't know to do XYZ...YET’ because you will work out how to solve it.
You need to show people that the inherent habits that you have learned, as part of an evolutionary process within the organization, have worked. Imitation is a natural way that humans learn.
In defining success, we often make an assumption that there is an ‘end-state,’ which is often untrue. Build the muscle to know whether you are making the right decisions for what you are optimizing for, and look back and be honest with yourself about whether you achieved in.
People optimize for the metrics they are given, which can lead to over-indexing for that specific metric. We should use metrics to analyze performance, but not as the end-state.
Having intellectual trust in your teammates is incredibly important. A psychologically safe place is the most productive. How can you create a regular cadence where we can be intellectually honest with each other to stay on the right track.
We have to talk about the things that could go wrong. The scariest monster is the one you have never seen. It’s always worse in your imagination, but when you turn on the light you can come up with tactics to address it.
Sam: In modern work, no one operates alone. Tasks are too complex and knowledge is too specialized and fragmented. We need to work together, to collaborate, to drive the outcomes we want to achieve.
Welcome to Pragmatism in Practice, a podcast from Thoughtworks where we share stories of practical approaches to becoming a modern digital business.
I'm your host Sam Massey, and I'm here at ParadigmShift with James Sherrett, Senior Technology Strategist at Slack, exploring the ways in which small tactical changes can affect the collaboration culture of teams and organizations. Welcome James and thanks for joining us.
James Sherrett: My pleasure.
Sam: You've just been talking on the stage at ParadigmShift about nurturing a collaborative culture and you mentioned essentially there's two things a business builds: it has a product or a service, the thing they sell and the culture with inside the company itself. Just elaborate on that a bit more for us.
James Sherrett: Sure. Thanks for asking. The idea originally I think came from one of our senior engineers internally at Slack, his name is Nolan Caudill. He was one of our early employees and he had a great perspective that he shared in an essay that's actually still available online that every the organization is in kind of the business of two things.
The first thing is the thing that it brings to market. So the product it sells, the service it sells, whatever it is. And the second thing is the culture that it builds internally. And that the focus of the organization is almost entirely on that first thing. All the metrics are instrumented around it. Everybody talks about it in the meetings. All of our priorities are driven by that. We think of it as the thing that actually determines the survival, the success, the positioning of the firm.
His argument was that in fact the culture determines your ability to bring that thing to market in the first place and then determines your ability to successfully find customers, serve customers, iterate on the product and so on.
And that there needed to be an equitable attention to each facet of what you're bringing, and what you're creating essentially. And it was really, I think for me, a foundational moment in Slack's formation. And I think it's been consistently reinforced over the last six years that we've been in business as important to us for our success.
Our CEO says, I want the way that we work together to be a competitive advantage. And I think that that's a really enlightened and interesting way of thinking about things because the way that organizations work together ends up being in many ways, their competitive advantage or disadvantage.
Sam: Interesting. So it was the company was built on that ethos from the ground up.
James Sherrett: Yeah, I think we were probably about 30 people at the time. So, we'd already done kind of a preview release of the product. We're getting some good traction and had hired some people who had worked together before and then some new people who hadn't worked together before and was just kind of finding its identity at that stage, I would say.
So it was really kind of, I think, foundational to how we think about how we work together.
Sam: For those companies that aren't yet necessarily in the foundation state of thinking like that, there's probably a few barriers or obstacles that they're going to have to jump over or through. What would you say are those barriers and how do we break them down?
James Sherrett: My wife has a great phrase, which is: the only thing that likes change is a wet baby. And so I think that as humans, we have this lie that we tell ourselves consistently that our kind of lizard brain reinforces for us that the world is fairly static and unchanging.
And the reality is that the world is changing all the time. Lots of us are in new jobs from last year, two years ago or three years ago. We commute new ways to work. There's all kinds of new things that are changing in our lives all the time, but it's really challenging for us to assume that change is the constant because we want to kind of have so much of that consistency fade into the background.
So I think acknowledging in the first place that change happens all the time. And that our responsibility is people who know that and people who can drive that change and influence it is understanding the best probabilities to make it successful.
And that ... We talk a little bit in the presentation about innovation and change in times of innovation as being a stochastic process based on probabilities. And that's kind of a fancy way of saying there are things that you can do to improve your odds and things that you can do to hurt your odds.
And it's quite clear from research what those things are. And so organizations I think need to root themselves in understanding what can boost their probabilities of success in times of change, and what are the things that can hurt their probabilities of success in times of change. And then adapt those to from the abstract to their specific situation. And what are the things that they do on a daily basis.
So, in a way it's like how do you operate at a really abstract high level way? And then how do you drive that down to a really tactical daily practice kind of way? And in between you're kind of lost.
Sam: How can we, how can organizations cultivate this growth mindset that you're kind of talking about?
James Sherrett: Yeah. Growth mindset is really, I think, a compelling idea and an idea that's gained a lot of traction because it's so aligned with influencing change and maximizing the probabilities of success in times of change.
So growth mindset for folks who may not be super familiar with it is a phrase coined by a psychologist, her name is Carol Dweck. She's written some great books about it. I definitely recommend checking those out. And essentially the foundational idea is a bias towards errors of commission and not errors of omission.
So what it essentially says is that we can sit on the sidelines and let things happen, or we can be an active participant, even if that means that we fail, that we uncover things that are, you know, not comfortable, that that is where growth is.
I love being active and physically fit. And one of the things that I constantly kind of try and remind myself of is your comfort zone is your comfort zone for a reason. That's where you're comfortable. But all progress exists outside of your comfort zone where you're uncomfortable.
So you have to be a bit uncomfortable in order to be progressing. And there's a great psychological trick that I've found about a growth mindset, because I think a lot of the discussion around it is pretty abstract about errors of commission versus errors of omission and things like that. Okay, well how do I put that into practice? Right?
So I think for a lot of people the 'yet trick' is a really good one, which is there are times in your career, and in your life when you didn't know how to do something. All of us have faced that. I don't know how to get the budget for this project. I don't know to hire the team. I don't know how to communicate this hard thing.
At each stage you succeeded or you got through those problems and you faced the same kinds of problems today. So adding 'yet' to the phrase: I don't know how to hire the team yet. I don't know how to get the budget yet. I don't know how to communicate these things yet tricks your brain into realizing that at the past you faced problems like that as well and you've gotten through them and you've faced those kinds of problems today and you probably avoid them or only do them off in the corner of your desk or anything like that.
But addressing them is like I don't know how to do this thing yet, but I'm going to engage in it and try and communicate to my team around me in how to do that as well and acknowledged that we are in a process that is not A plus B equals C, but is A plus B equals a 70% chance of C, let's maximize our probabilities to get to that 75% chance of C and here are the things we can do to do that, is the best approach.
It's hard to do. It's the kind of thing that you constantly have to be reminding yourself of because our inherent human biases I think are towards the static outlook, the minimizing risk. And the larger the organization gets, the more it tends to be optimized towards repeatable, scalable, predictable processes.
But the world is changing all the time around it. And so you have to be able to acknowledge that what are you optimizing for at this stage? Is it a repeatable, scalable process or is it actually discovering new markets? Is it finding new ways of addressing customers? Is it solving a problem, is it inherent or that you're losing to competition or anything like that?
Sam: Well, I'm really interested in is this, the working culture of the organization itself. And it's fine if you've been in the organization for however long you've been in there, six, seven, three years, whatever. But if I'm new to the organization and I've just joined, are you looking for the talents of people who have this attitude already, or can we as individuals adopt that working culture quite quickly? And if so, what's happening when people join the company? So you can say, hey look, you may have done this a different way before. We're going to show you a new way.
How does it happen actually operationally on the ground when people come into Slack?
James Sherrett: Yeah, that's a good question. So I'll be really tactical about how we do it specifically, which is for everybody who joined Slack, they actually, before even their first day, they join a Slack workspace with a cohort and they actually start collaborating together and solving some of the simple questions, introducing themselves.
And then there's sort of a Slack leader that joins that workspace as well and manages that cohort. And that cohort is together for the first, I think three months of their journey at Slack. So, they start getting to know each other a little bit and communicating and working on some things. They're given a couple of almost digital scavenger hunts.
Then on their first day they have context for each other and everybody spends two weeks in San Francisco in onboarding. The first week tends to be standardized for the company. And then the second week is more role-specific.
Then from there they retain that cohort and they can answer each other's questions and things like that. And we try and create like a little mini community almost. So for us, that is where we've got to. That's been through many evolutions. And I'm sure this is not, as we said earlier, change is constant.
This is not the end state, but this is the state that we're in today. And what we're really trying to drive is from a pure business point of view, time to full productivity as well as the ability to provide people a context of a culture that we want them to emulate.
So what I mean by that, that's a pretty fancy way of saying it. It's like you want to give people the habits that are the ones that you've learned in almost this evolutionary process inside the organization have stuck and worked and then they inherit in their way.
And if you've ever been inside a really strong culture, you realize there's all kinds of ticks of language and things like that, right? People do these things and you're kind of like when you're new to it, you encounter it and it's almost like an anthropologist encountering a culture that they're unfamiliar with.
But then you get into it and you hardly even recognize it anymore and you find yourself doing those things and so on.
So, humans are great imitation machines and all of us learn best through imitation. If anybody's got children, they certainly realize that very quickly. When I was learning to write many years ago, they said one of the things that's the best thing to do is actually just imitate the writers that you aspire to be like and just work on that and you'll find your voice actually by imitating.
And that seemed really counterintuitive to me, but I think it's the way that we learn as humans is by imitation. I think we talked more about how the one plus one equals three, like the team really part of it, right? I think it's really interesting.
In some contexts some individual performers are very strong. In other contexts, they're actually not that strong. And you can see this in the world of sports. You can see this in the world of business, you can see this all over where people are sort of lauded as superstars, but actually they're the product of a team.
I think that what we're realizing more and more all the time in our work life is that the things you can do to foster the productivity, the engagement, the full fulfillment of the team are actually the things to focus on as an organization because individuals come and go and individuals are actually mostly influenced by the team that they're in.
Just think of, I'm sure you've got situations where you've been in where you've been on the team and you realize this team is just performing so well. I love working with them. I can trust them. We have each other's back. When I say to somebody, you know, could you do that thing? They've already done it or something, right? That is the state, the flow state as an organization that you want to be in.
Contrast that with when you've been in a team and you're kind of in that I don't even know if they're going to do things or they fail to do things. They're not upholding that trust that you have. They're unreliable. The work product that they generate is subpar. It needs a lot of revisions and how much emotional and psychological baggage that creates for every single person on the team. Right?
There's just a huge difference there. And the more you can bias towards that first situation where you've got strong alignment, strong trust, the higher performing the whole organization's going to be as a result.
Sam: I couldn't agree more and I've definitely been in those situations where you are in a flow state with the team and then the opposite and you sometimes cannot pinpoint the why and that's the hardest part of the change sometimes with that, you know that that nurturing of the team itself and creating the right culture within inside it, it's something that then obviously ripples through with other teams.
Then like you say, I think the best example you said was imitating or creating the behavior because we are all very good at copying. I know that because I've got a two year old and she does tend to copy everything that we do.
You talked about the probability of success and how do we recognize the characteristics or how do we know when we are being successful?
James Sherrett: That's a good question. And of course it sort of in a way presupposes almost like end states or like cycles to projects and that exists. But I think in many ways it kind of is a framing device our brains use to create some kind of compartmentalization, right?
Whereas most of the time we do this thing where we look backwards at a situation, at a project and we say, well how did that project go and how were we doing with it, and stuff like that. And we look at the result.
But if you think about just what a lie that is in many ways, because when we're in the project and doing the work, we don't know what the result is. We have no clue. And so we're making decisions with imperfect information all the time. And so we always have to, I think, as much as possible create a decision journal or some way of keeping track of decision making.
Because without that transparency, there's no way to get better at it. And there's no way to actually be accountable for the decisions at the time with the information you had. I don't mean it to sound like a defensive kind of thing where it's like you're covering your ass and stuff like that, but just using it as a self-reflective mechanism to actually drive that growth mindset without that kind of documentation. We all have these amazing abilities to frame narratives looking backwards, right?
So your question was more so around how do you know you're succeeding? I think that you build that muscle, even using that phrase, you build that muscle as a metaphorical phrase, right? But you build that muscle to be able to know whether you're making the right decisions for what you're optimizing for and you try as well as you can to then look back and be honest with yourself and do it in a team way so that it's not just an individual.
And individuals can be biased by all kinds of things and only have a single perspective. And I think in many ways that's a really abstract way to say heterogeneous teams outperform homogeneous teams because they have more perspectives, they have brought a repertoire to draw on and they can actually bring more experiences to bear on any current situation. That's one of the things that we consistently see.
So I think that that's a really powerful way to think about it. How do you, back to your original question, how do you know whether you're succeeding? I think it's breaking things down as small as you can and directionally, and I think focusing on getting movement instead of just outcome.
What I mean by that is if you're making progress on a project and it's progress towards a goal that's far more important than not making progress or worrying about where you're going too much. And that in times of uncertainty, you need to be able to progress in ways that feel like they're getting somewhere as an organization, as a team or as an organization versus just, you know, optimizing for a metric.
Because optimizing for a metric will almost always lead to over-indexing on just that specific metric. And there are great examples of stories like this. When they found the dead sea scrolls in the Middle East, they offered a reward for people finding them and so people would find them and then tear them up into smaller pieces to collect multiple rewards for the same scroll, right?
So people optimize for the metrics all the time. So I think we want to use metrics to analyze performance, but we don't want to use them as the end state. Nobody wins the basketball game by looking at the scoreboard, right? So you've got to play the game, play the game, play the game and understand what are the things that make us play the game successfully.
Sam: Yeah, I think it's so true. I was thinking so much of how you decide if something's gone well or not or is retrospectively is on a measurement of success and say, oh, it's a number. It's we know we've done well because this is the return.
In the moment you can't measure it. And in the moment you can't measure the team dynamic. You can only say that's frustrating or that's not going well. I like the idea of a decision journal to be able to actually be able to say, okay, we've made that decision then and then there was a change and it felt good or it felt ... or it didn't feel good.
But it's such a hard thing to measure the team dynamic and the culture as you're going through that. You can measure the success obviously after the fact. And that's typically how most teams and businesses operate. You know, even year on year you're looking at your revenue or your, you know, your profit margin.
It's not based on anything else, but it's being able to measure that team dynamic and how things are going within the team at the time. I think that's the real challenge for most people I think day-to-day.
James Sherrett: Definitely. Definitely. I mean, I think you've had it in your career. I've had it in my career where you're like you're in the moment and you're like, things feel like they're going great. I think, right? Like it's always a level of uncertainty.
And so I think having the intellectual trust in your teammates is incredibly important. There's all kinds of great research that a psychologically safe place is the most productive. I think that's one of the driving factors.
And then the other part of it is just like how do you make it into a cadence where you're being intellectually honest with each other, right? So, is that a weekly cadence, a daily cadence. Make it small because that's as humans, what we optimize for and what we're focused on, and how we structure our worlds. So, make it small so that we're always on the right track.
And I think the other thing too is we have a phrase internally at Slack, which is hug the elephant. So like there's an elephant in the room all the time. How do you embrace it? Right? We could fail at this, we could fail at that, we could fail at this. There's all kinds of things that could go wrong. Let's talk about those. Those are the best way to actually talk about them, right?
The scariest monster is the one you've never seen. When you finally open the closet door and turn on the light, you're like, oh, it's got these strengths and these weaknesses and okay, well now I'm building tactics to address it, right? But before that, it's just as scary as your imagination can make it.
Sam: Great advice. You've made me feel so much safer and so much happier to just sort of, you know, go and embrace that elephant in the closet.
James Sherrett: If only it was so easy.
Sam: Thank you so much James.
James Sherrett: My pleasure.
Sam: Thank you for listening. If you enjoyed this episode, help spread the word by giving us a rating on iTunes, Spotify, or wherever you listen to your podcasts.