September 15, 2020

Doing Better Work, With Max Yoder

By Wes Winham

Max Yoder is the founder and CEO of Lessonly, a team learning and training software company that raised a $8M Series B in late 2017. Max’s team is dedicated to helping people “Do Better Work,” which is where he got the title of his new book, Do Better Work: Finding Clarity, Camaraderie, and Progress in Work and Life.

In this episode, we talk about:

  1. Sharing work before you’re ready
  2. The importance of vulnerability to leadership
  3. Nonviolent Communication

Max’s book is available here.

You can subscribe to Max’s weekly note here.

Listen to the Full Episode Here



One of the concepts from your book that resonated with me is about “sharing before you’re ready.” So in the software world it’s “put a prototype out there, put it in front of a user to get a review or pull request early.” I think that’s becoming really common practice – how to share before you’re ready. How does that interact with the work that we do as knowledge workers?

We just all have such a limited perspective… and it’s not that we can’t come to good ideas in the vacuum of our minds, it’s that we can only see so much in the vacuum of our minds and if we very quickly – you know, 30 to 60 Minutes into whatever the initiative or the project we’re working on – we get in front of some folks who ultimately depend on that initiative being a success and we say, “What am I missing? What’s working, and what isn’t working? What should I add?” [By doing that] we can start to see new angles – and whether those angles are good ones or not isn’t the point, it’s that we should at least see if there’s good ones out there that we’re missing. Sometimes there will be, and sometimes there won’t be. It also just builds a tremendous amount of trust between teammates – that, “I value your opinion, go out there and ask for it” [ethos].

I could really use your help to figure out what I’m missing because I want to nail this and it’s really important to me that you tell me what I’m missing, or what I should be adding. It’s going to help me.

— Max Yoder

But I think knowledge workers need to do this because there’s not a single answer. This isn’t mathematics where there’s just one result. There could be a whole bunch of different ways to deliver a final product, and when we go out and share before we’re ready I think we get much more closer to delivering a good final product than if we tried to stay in the vacuum of our minds and do it all by ourselves.

What do I do with the feeling that I’m going to show something that’s gonna be bad? That I haven’t spent very much time on it? How do I deal with that?

If you’re a designer who’s designing a product, the same way that you’d want to keep something in a tool that makes things look low fidelity and kind of “sketched out” so that you don’t make somebody anxious about saying, “This is bad, and I can tell you’ve been working on it a long time but I don’t want to tell you that it’s bad because I can tell you’ve been working on it for a long time” – [instead] coming to somebody and saying, “Hey I’ve been doing this for 30 minutes, I know I’m missing some things. This is me sharing before I’m ready.”

Setting that tone and that precedent, that invites the feedback and says, “You’re doing me a favor right now – if you give me your two cents, you’re not blowing up a project I’ve been working on for three months.”

So I think it’s just all about [setting expectations]; walking up to somebody and saying, “I could really use your help to figure out what I’m missing because I want to nail this and it’s really important to me that you tell me what I’m missing, or what I should be adding. It’s going to help me.” And just setting that precedent with folks.

A part of transitioning to a manager is maybe producing fewer artifacts sometimes – I’m not shipping code anymore, you know? How do I share those more intangible decisions I’m making as a manager before I’m ready?

I tend to try things in small little groups that I’m thinking about doing in big groups.

So if I bring somebody in, I might preview an idea with them and say, “How does that hit you?” Just the same way I do it if I was on a project. It might take a lot longer for it to come out and be in front of the rest of the team, but I think it’s just trying it in small pockets. It’s the same iteration.

And you’re right, we don’t have these deliverables. The more we manage, the more we have these “daily” deliverables. I really struggle with that – I don’t know about you, Wes – but that was hard for me to get off that dopamine train of being able to check five boxes a day and say, “Oh I’ve done a good job because I checked those five boxes.”

And I say “dopamine train” because I think we get this positive feeling – it’s either serotonin or dopamine or whatever it is – that [feeling] of completing something. And I still have to work really hard at not going back in and trying to find these really quick wins that don’t ultimately add up to the job I need to be doing.

I think that’s a really common struggle, especially for developers, where the dopamine hit is even faster when you’re doing unit tests and a test goes from red to green. You can get that multiple times an hour. Versus a manager – it’s just slower. It’s really hard.

It’s like retraining your brain, right? And it takes a long time.

Charity Majors was going to be on the podcast, and she talks about this taking two years. You are changing your brain whenever you become a manager. You need to sign up for two years because you really are rewiring your reward structure. And if you sign up for less, you’re just gonna be halfway and you’re going to get most of the pain without a lot of rewiring and gain which… sounds like my career. The first two years were the roughest.

And it’s so helpful, though, to to have that context.

I don’t know if you’ve read any of Amazon’s shareholder letters, [but] Jeff Bezos talks about a friend who wanted to master the perfect handstand. And they set their own benchmark for when they should be able to get it done, and they thought they’d be able to get it done in some number of weeks.

And, of course, they weren’t able do the perfect hands in that number of weeks. So they went out and hired a handstand coach and the handstand coach was like, “It’s going to take you six months to nail this – of daily progress.”

And that person had just kind of set themselves up to think a certain number of weeks – and they had nothing to base that on, they just said, “Well I should be able to do this in a certain period of time.” So it’s super helpful for you to share that, and I’m really excited to hear that podcast because I think we all need to know how long it takes so that we’re not making fake goals for ourselves that just aren’t achievable, and are gonna cause us to be disappointed.



Speaking of maybe being disappointed and disappointing people – one of the big themes in your book is vulnerability. Can you talk to us about why vulnerability is important as a leader?

I think… when we’re vulnerable, we model the behavior that we need to see from our teammates.

So a leader that isn’t vulnerable would be somebody who puts on airs that they have all the answers, they know the way, and they dominate life.

So they’re generally not wrong. Even if they’re wrong all the time, they would posture as though they know exactly what they’re doing. Well, every time a manager does that, they need to understand they’re modeling the behavior that their teammates are then going to emulate. So everybody that reports to that manager is now going to posture as though they also have the answer, and dominate life, and know the way.

When a person in a management position makes it safe to acknowledge reality, they’re gonna get more of the full story from their direct reports.

— Max Yoder

And that’s incredibly dangerous, because what you’ll do is start distorting reality. You as the manager won’t get the full picture of reality, because your teammates will start hiding it from you. Because inevitably something will go wrong, and for somebody who is posturing, it’s gonna be difficult for them to raise their hand and say “I made a mistake” because the manager themselves has not made it safe to say that, because they never raise their hand and say, “I’ve also made mistakes and you’re gonna make mistakes and it’s okay because we’re not perfect.”

… [Vulnerability is] knowing that you have gaps in your armor, that you’re not capable of doing everything; that you’re going to need help, that you’re going to be scared.

So when a person in a management position makes it safe to acknowledge reality, they’re gonna get more of the full story from their direct reports. But if they make it unsafe to acknowledge reality, don’t be surprised when you find out about something way later than you should have, and it’s too late to do anything about it because your team kept it from you.

If I’m telling my team I don’t know things are they gonna lose respect for me? I’m the leader, aren’t I supposed to have the answers?

You just gotta kind of rewire their expectations in that case, because that’s just a false premise. And I write about it in chapter 2 of the book… I talk about how there is this myth that leaders know the answer, and I learned that over seven years at Lessonly – as I became a manager and as people around me became managers – the nervousness of not knowing what to do, but then realizing, oh my gosh nobody knows what to do. We’re paving new territory here – it’s not that I never know what to do, it’s that a lot of the time it’s new territory.

So the myth of “leaders know the answer” needs to be shifted to the reality that leaders learn the answer. And I think if you’re nervous about teammates walking out the door because you’re exposing the fact that you’re a real human – first and foremost I think they’re going to respond differently; I think they’re going to respond and say, “Well that’s pretty cool because that kind of jukes my expectations in a positive way.”

And then I also think that you can let them know that they need to understand that leaders learn the answer, and that’s what you expect of yourself and that’s why you expect of them; you expect them to ask questions if they’re unsure, you expect them to talk about it if they need help, and ultimately that’s going to make it safe for them to do so.

So I doubt people will run. I think they’ll probably be appreciative because you’ll be, again, acknowledging reality. The reality, Wes, as you and I both know, is that we’ve got a lot to do, too. We have a lot of learning to do and everybody else is the same way.

I thought everyone thought I always knew the answer – so I just pretend they don’t know I’m imperfect, Max. That’s my whole plan!

[Laughs] The thing is people really do believe that! Whether they mock it in reality or not, if they say, “Well that’s obvious.” Just watch their behavior… sometimes the behavior reflects that they think they should know the answer. So I think we all need to be models for this, and we all need to keep saying it out loud even if people intuitively get it. We all need to keep giving more and more examples.

Could you share a story of a time you’ve been vulnerable when it was hard to do so?

One of the first things I do with teammates – every month we have our new hires get together and I just share the background of Lessonly. And the main idea of that engagement is for me to say, “I’m assuming you want to know why Lessonly exists, I’m assuming you want to know what we’re after and what we’re aiming for.”

And so I just spend that time answering questions… oftentimes people ask, “Why did you start the business?” And I give them a background on the fear that motivated the business getting started.

I mean, I was motivated by the irrational fear that I needed to be some sort of superhero for my family. My family didn’t need me to be a superhero – but I made up a story in my head that I needed to save my family from any kind of catastrophic issues that might hit them, that I didn’t know if they were prepared for or not.

It’s not a great call to start a business in order to do that… but I was a young man who didn’t know any better. And by telling the story of struggles that I felt as a member of my family, and fear that I had, immediately afterwards I tend to get one or two people from that group of new hires who come and they say, “I have something going on in my family that I would love to talk to you about some time.”

They open up to me! And to me that’s not difficult because I’ve been doing it for a long time. It comes naturally to me now to be vulnerable, and I see the positivity that comes from it. And I see the beauty of it; I see how it liberates people. I think there was a time when I would have been a lot more uncomfortable sharing that story, but now I’ve seen how helpful it can be.

I think it’s easy to imagine what that conversation should be like [with regards to why you started the business] – about how you saw the future, and as a result you are continually crushing it.

Not the case [laughs], not the case.

And it does not create an environment where we’re comfortable saying “I’m not crushing it right now” or “I think I might not be crushing it next month unless I get some help.”

I share stories about my wife, too, that are more modern, right? Like this isn’t just, “Oh I had struggles when we started Lessonly.”

It’s, “Here’s things I’m not doing as well at home and… can you relate to that?” It’s all really relatable. That’s the humanity in all of us. But it’s just about doing it in a genuine way. If it’s not a genuine demonstration of vulnerability, don’t do it because it will come off as disingenuous. And if you’re not comfortable being vulnerable, start by doing it in a place with people you really trust. You might not be comfortable doing it at work… if you’re more comfortable doing it with your significant other or a family member, start there, and you’ll start to see the benefits, and they’ll start to snowball.

I like that. Start in a safer place, see the benefits, get the feedback and try to get bigger and bigger.

How is emotion like a pipe?

So one of my favorite parts of the book is in the first chapter I talk about being vulnerable, and I quote Dr. Joe Bolte Taylor, a neuroanatomist who made waves by having a stroke and then coming back from that stroke as somebody who knows a lot about the brain. So she had to rebuild her brain as a neuroanatomist, and then she did a TED talk on it and it blew up and she went on Oprah and her book became this bestseller.

I’m just lucky enough that she happens to be my mother-in-law’s best friend, so I got to spend some time with her and I got to invite her to “Yellowship” (which is our annual user conference at Lessonly), and she… talked about building a better brain; basically reminding us how much power we have over our emotions and our brain. And she talked about how she views emotions and our [emotional processing] like a pipe.

She [told us to] imagine a pipe where emotions either flow through like water if you’re processing them, or they get built up and stuck if you don’t process them. Over time, if you don’t process your emotions the pipe can only handle so much of that water getting built up in it, so it’ll either burst or you’ll feel such an unease that you’ll try to tamp it back down with maybe drugs or alcohol or any other addictive behavior… if you don’t process your emotions, they don’t go away, they build up in the pipe. And we all struggle with this – where one day we just kind of have a breakdown or in one day we have an outburst and we’re like where did that come from? Well it came from the fact that we didn’t process our emotions.

So she is a big fan of processing emotions, and she’s not alone in that – that’s a very good thing for all of our psyches.

And I don’t think we ever really learn how to do it. I don’t know about you, Wes, but I think our parents’ generation didn’t learn how to do it. They weren’t taught how to do it; social or emotional learning wasn’t a thing. Our grandparents [were in the] same boat – so that nobody learned how to do it.

I think we were undereducated about social and emotional learning, and I’d like to see that change.

One of my co-founders, if we’re in a meeting and it’s a hard meeting, and we’re disagreeing about something… he’ll say, “I really didn’t sleep very well last night, so I think I might be having trouble with this” or “I’m feeling kind of defensive right now, give me a moment.” He creates visibility and legibility into his emotions. And I’m trying really hard to copy that, because it just seems magical. Do you work with people that do that sort of thing? Is that helping process or am I talking about something else?

Ultimately that is a really good way of helping people understand where you’re at so that they don’t read into [your behavior] in a way that you don’t need them to. When somebody says, “Hey I didn’t sleep very well so I might come off as a little agitated” it doesn’t give them an excuse to be a jerk, right? But it does help you understand that if they’re being quiet it’s maybe not you. And if they don’t say that out loud you might read into it and say, “Did I frustrate this person?”

You know we can all create these really wild narratives in our head about why something’s happening, so I really respect your co-founder for doing that, and for using that not as a weapon but as a way to just show people reality…

That is an element of acknowledging emotions, but I think processing emotions – and, again, a psychologist is the best person to weigh in on this – is kind of… going back and thinking through an emotion and saying, “How did I feel when it happened? What good came out of it? What really frustrated me about it? What really upset me about it?” You can talk through that. I wouldn’t do it in the middle of a group meeting, and I know you’re not suggesting as much.

But, you can go on a walk [alone]… or just go out and walk with your significant other or your friend or your family member or go talk to a counselor or a therapist and just have somebody help you see new angles. Because when I think about process it’s expanding your limited vantage point to see more of what’s happening.

We tell ourselves a lot of stories, and those stories are generally uninformed and sometimes they go very negative and other people can help us see that maybe we’re telling ourselves stories that are needlessly negative or are not true reflections of reality.

I feel like my biggest job is to change my mind about things I used to believe really strongly – I believe things strongly and then change my mind. So your comment about processing emotions feels like that’s often what I’m doing. How do you change your mind?

In a general sense of just like when I learn a new fact?

So there are things about Lessonly that you used to believe strongly, that I guarantee are wrong – like fundamental beliefs about how you’re going to market, how you’re gonna build a product, etc. How do you come around to the new reality?

I think I’m blessed with a lack of conviction, where I just want to do the best thing for the team. So the main thing I need to do is surround myself with people who see things differently than me, and if I have an opinion on something to state it – but, you know, not hold it too strongly.

I want us all to be builders of this business, so it’s not my job to say exactly what we need to do, it’s my job maybe to post the questions that otherwise wouldn’t be posed, and then to be a participant in the discussion. The beautiful thing about Lessonly is I don’t know what to do, and it really helps me when other people come up with good ideas, and when they come with good ideas it’s just a tremendous benefit for me. So I just I think I’m fortunate not to walk into things and feel like I have something to prove with with my intellect – I don’t have anything to prove with my intellect.

I’m blessed that people appreciate me as a teammate whether I contribute that day or not. And I think that’s just something [that’s the result of] a little bit of self compassion and time giving me the ability to put my ego aside and say, “My ego’s the thing that’s going to sink this ship – if anything’s gonna sink this ship it’s my ego.”

So how do I let that just be set aside, and how do I set an example that I want everybody else to set? It doesn’t matter if I’m right or wrong, it matters if we make a good call. And I believe that.

Now, there are things that if you came to me and said, “Hey, Wes here, I think we should change and go this direction.” If I’ve got good intel [and] good experience that suggests you’re incorrect, I’m not going to say, “Wes, let’s do that.” I’m going to say, “Wes, what do you base that on?” And I’m gonna listen, but my experience has taught me a lot about what trading software should and should not do. And if you’re telling me something that it should do that I’ve seen is just contrary to the evidence, I’m not just going to go with the flow, if that makes sense.

I think so. I think my struggle is that second thing you said – I know about trading software, I have evidence. I feel like I’m maybe too good sometimes of convincing myself of that when I know it’s not true.

One of my co-founders [and I] were talking about [whether] everybody in the company need to be a missionary or is there room for some mercenaries in some roles? And I I was immediately defensive because I was like well, what about contractors? What about people who are just doing small jobs part time… and he’s totally right. There’s benefits to being a missionary in all of those jobs, and I had just taken some shortcuts.

And it took me just processing and thinking, “Why did I react so strongly to that conversation?”

Yeah that’s fair. If somebody came to me and kind of poked right on one of my wounds I would react that way; if they poked some strongly held conviction. But the ultimate thing is: we are smarter when we’re together. If you’ve ever read anything by Jonathan Haidt, he talks about how individually we’re not that smart, but in a group we can be way smarter. The way that we actually get less smart in a group is if we’re surrounded by people who all have the same opinion as we do. So if… we’re all from the same background with the same beliefs we’re probably not going to be better as a group, we’re probably actually going to be more silo’d and insular than… we would be alone.

But if we can get a group together with different backgrounds and different perspectives, we can all hear one another out. I’m all for going a different direction, I just want to know what we’re trying to accomplish in that direction. How will we know if it’s not working, and how will we know if it is working? Then we can give it a shot. We can probably constrain it down to a period of time where it doesn’t have to risk the business in order to do it right.

So those questions were: how do we know it is working and how do we know it isn’t working?

Yeah… how do we know if it’s working or it isn’t working – kind of the same thing. It’s like what bar are we measuring, and how can we constrain this to a certain timeline that we can figure that out in a short period of time without giving it too little time?

And that’s not easy but we can all come together and say we all agree that this is enough time and this is a good measure. And if it doesn’t work, it doesn’t work. And you know, some things will work and they’ll just be random. That’s why this business is so hard; we won’t even have enough data to know if something worked or not.

I don’t have the answer to that. I don’t feel that’s my specialty, but together with a group of folks around me we can all help one another see the best route.



What is nonviolent communication?

Nonviolent communication is a communication method developed by Marshall Rosenberg, a doctor who is all about helping us communicate in more compassionate and empathic ways. It’s basically communication that tries to minimize hurt and harm – so the idea is that violent communication can be something that causes hurt and harm, while nonviolent communication is something that tries to avoid causing hurt and harm.

And Rosenberg argues that a lot of violent communication is actually not very clear communication; there’s not a lot of clarity to it. An example of violent communication would be a judgment – i.e. “Wes, you’re not good enough for this team.” It isn’t very clear. I’m not really telling you what I base that on, but if I say, “Hey Wes, four different times this week you have been behind schedule on deadlines that you committed to hitting. I’m frustrated. I value consistency. What’s going on?” Well now I’m being much clearer…

I like it. Do you mind diving into that example with me? So let’s say you’re my engineering manager. I’m a new around the team, I’ve got a story I’m working on – and every day in stand up I’ve said it’s gonna be done today, and it hasn’t been completed, and now you want to talk to me about it. How would we use nonviolent communication to structure that conversation?

Yeah. It’s trying to separate how you feel about a situation from what actually occurred. So I can be frustrated that you’ve been delayed – let’s say you’ve done it the last three days, where you said you’re gonna get something done and you didn’t do it. Well, my observation – which is just concrete fact – would be to say, “Hey Wes for the past three days you’ve said that you were gonna finish something and you have not done so – to your own admission. I’m frustrated that happened.”

So the thing that happened is three times you’ve missed a deadline. My feeling about it is frustration, and then I’m going to tell you what I need because we’re teammates and I’m going to say that I value consistency and communication. And I’m going to tell you I value those things because I don’t feel consistency or good communication here; you’re communicating things that aren’t happening and you’re consistently missing deadlines – which is an inconsistent contribution [to the business].

And then I’m going to ask you, “What’s going on?” And I’ll let you explain, and I can make a request to you that says, “If you’re going to tell me that you’re gonna be done today, be done today. And if you’re not going to [be done today], please let me know before the next day that it didn’t happen. And that’s my request.”

So it’s observations, and then it’s feelings, and then it’s needs and requests. Observation is it happened three times. Feeling is I’m frustrated. My needs are consistency and communication. My request is a specific time and place and person doing a specific thing that you can either agree to or not agree to. I’m not allowed to coerce you into that – I’m not allowed to intimidate you into that. You have to want to do it if it’s going to be a genuine request.

And then you can also tell me how you feel or what you’ve observed and what you feel and what you need and we can come to some good common ground in an empathetic and compassionate way.

So the fourth step was getting agreement, and not being coerced into the agreement which I think is an important point. Why are agreements important?

Yeah. So Rosenberg would call them requests, and but I would say it’s just it’s the same thing; agreement and requests are very similar. We’re negotiating a shared course of action –  agreements are super important because we tend to walk around with these unspoken expectations in our heads about what should happen and how people should behave.

And I don’t know about you, but I don’t want to be held to unspoken expectations that I never agreed to. What I’d prefer is you coming to me and saying, “Hey Max, here’s something that’s been on my mind or something I could use your help with” or “here’s something that I need you to do” – laying that out for me and then allowing me to come in and say, “Well here’s what I actually can do.”

And it could be the whole thing or it could be part of the thing or it could be kind of some deviation or modulation of whatever you need – and you and I coming to a shared course of action that says, “Here’s my part in our agreement. Here’s your part of the agreement. Here’s when we’re going to come and deliver our parts of the agreement down the line.”

It’s just clarity. That’s helpful because it shows a tremendous amount of respect for you and me. When we’re respecting people, we don’t hold them to unspoken expectations – we make things clear. And then if they don’t live up to the clarity that they’ve agreed to live up to, we can have a conversation about being frustrated or disappointed. But only then, otherwise it’s our responsibility to get on the same page, and talk about what that same page looks like, and then we move forward.

And what’s cool about that is, if we achieve the goal, we can celebrate together because we are both on the same page about what the goal was. And if we don’t achieve that goal, we’re clear about where the ball was dropped or what happened that [prevented us from achieving] the goal. And I argue in Chapter 7… that no matter who drops the agreement, it’s your responsibility to own it. And I think a lot of times even if we do get agreements the easiest thing to do is… let’s say you and I have an agreement and I just say, “Well Wes didn’t hold up his end of the agreement” and then I kind of throw the whole thing out. That’s not teamwork. That’s not how I would want somebody to behave if I dropped my end of the agreement, so that’s not how I’m going to behave if you drop your end of the agreement.

I’d love to hear about some agreements that you used whenever you’re interacting with engineering team and the product team. Have you found any particular styles of agreements to help you work better?

It’s a trial and error thing, you know? Each agreement has a certain level of clarity that is required. If this is a longer term, multi-step agreement, it’s super important that we lay out those steps and we document them. If it’s a quick agreement of, “I’ll call that person so you don’t have to” it’s probably not as important that we write that out.

But the main thing that I’d recommend in an agreement that needs to last and stand the test of time is that I, [as a team member] write what I heard so [my teammate] can verify that I got it right – and I can verify that I got it right. And now we have an artifact, because your mind, and my mind, and everybody else’s mind distorts reality over time. And I’m not saying it does this on purpose or for any malicious intent but we shorten memories, we change memories – we know this to be a fact… it might sound really rigid but it’s really thoughtful, because it ensures that you and I both remain aligned as our brains warp and change things.

In our example where I was saying I’d get something done in stand up, and then the next day it wasn’t done…  a common agreement I might hear is that you agreed to “keep me updated.” What’s missing from an agreement like, “keep me updated”?

What does it mean to keep you updated? That is an ambiguous term… My definition is going to be different than yours, more than likely. So we should be clear about what “keeping me updated” means. If it’s an hourly check in – that might sound onerous but that might be one example of what you mean by keep me updated – we’d have to come to a conclusion on that, and we can do that by communicating.

I think that… what’s that quote – the illusion that communication occurred is the biggest problem?

[Laughs] You’re right, man. You’re right. I mean think about it like this:

If I say that Connor and Megan and Brian are working on something and they’re gonna let you know when it’s done, well as soon as I say “they’re” you don’t know if I’m talking about Connor, Megan or Brian – who’s gonna let you know if it’s done? Are they all gonna do it? Pronouns can make it tough, so when I’m writing out sentences what I try to do – and this is me just trying to be as clear as I possibly can be, as often as I can be – is just saying “Megan is gonna let you know when it’s done” or “Connor is gonna let you know when it’s done” instead of saying they because even that little bit of ambiguity can hurt a conversation.

I’m not arguing everybody needs to do that, because I don’t want people to quit on clarity before they even start. I want you to try 1% at a time to be clearer, and not try to take on this whole big amount of things that need to change in your behavior… Let’s just start by being 1% clearer… and we can do that in small ways like getting more agreements, like sharing before [we’re] ready, like asking clarifying questions.

The book is about clarity and camaraderie, but I don’t want anybody to kind of summarily shut down and say, “Well I’m never gonna be able to get there by trying to take it all on at once.”

What is “anti-fragility” and how does that relate to difficult conversations on a team?

Anti-fragility is this idea that something is gained from stress and disorder and chaos. Nassim Taleb is the gentleman who coined the term and he coined the term because he realized we don’t really have a word for things that [we] gain from stress and disorder and chaos.

But many things do – our muscles or some of our systems gain from stress, disorder and chaos. Our teams gain from stress, disorder and chaos. They do so by learning. You don’t learn a lot in a situation where everything goes according to plan. But you can learn a ton when certain functions break down.

What you can learn in that is, well, why did they break down? How can we avoid it next time? You can build strength by having things not go the way you want, and then learning from that situation. When I talk about anti-fragility in the book I talk about it as anti-fragile relationships, so I think we tend to look at our relationships as really fragile and that’s one of the reasons why we don’t talk about conflict when we feel it, because we worry it’s going to damage the relationship. The reality is, we will damage the relationship if we argue our way through it and we judge our way through it and we villainize people.

There’s a lot of ways you could ruin relationships in the midst of conflict and a lot of it has to do with violently communicating. But if we choose to nonviolently communicate through our conflict, we can actually understand one another better; we can grow and learn with one another and when we do that, we strengthen our relationship over time so we use the chaos – we use this stress and we turn it into something that is positive.

Nassim Taleb argues that chronic stress is not what we’re after here. We’re trying to make sure there’s acute stress and we learn from that acute stress…

An example would be… let’s say I’m going to go out and bench press today. If I repeatedly lift that weight and never give my body time to take a break and rebuild the muscle that I broke down, I’m going to put chronic stress in the muscle. I’m overusing it to the point that it actually starts to atrophy and almost sicken… [as compared to] acute stress, [in which] I would lift and then I’d rest – and that rest period allows the stress that I put on my muscles to grow back and become stronger. That acute stress was momentary – chronic stress is long term and continuous.

I want to tie that chronic versus acute back to that first conversation – the developer not updating their manager on their progress. What would be a chronic version of that, and what’s an acute version?

Yeah! So the acute version ends – you figure out how to communicate better if you’re the developer about where you’re at, and you set better expectations. And whatever our communication is along the way, the checking in starts to happen. So the behavior changes based on the stressful three days where the way that you were communicating was about what was going to happen and what didn’t happen – that changes for the better.

Chronic stress is when I’m frustrated with you as a developer and I don’t talk to you about it. I allow it to continue, or I do talk to you about it and it continues anyway. That would create chronic stress. So it’s ongoing – it’s over time. Whereas the more acute stress would happen over a smaller amount of time. And we benefit from having had it happen in the first place, because now we understand one another better.

My guest today has been Max Yoder. Max thank you for being on Scaling Software Teams.

It was my pleasure. Thank you, Wes.