Nathan Barry Had One Shot at Kit.com. Here's His Framework for Getting It Right.
Kit founder Nathan Barry on walking his leadership team back into a rename they'd rolled back once before, the question that surfaces what nobody is saying, and the decision framework Kit uses for every call that matters.
Welcome to Episode 4 of Beyond the Meeting — Contio’s podcast about what happens after the room clears, where what gets said turns into what gets done.
Most founders will tell you what they decided. Nathan Barry walks you through how, including the part where he admitted he was scared.
Nathan started ConvertKit in Boise on January 1, 2013. Today it’s Kit, the email platform behind newsletters from a lot of the people you actually like reading. It does about $50 million a year in revenue with 114 team members across 86 cities. Getting from the first name to the second one took two tries, and the second try is the episode.
One shot
ConvertKit had tried a new name once before. In 2018 it went poorly enough that they rolled the whole thing back.
Then, in November 2023, kit.com came available. Three letters, a standard English word, impossible to misspell. Nathan compares it to house hunting. When you’re looking for a home, there are a few neighborhoods you’d be happy in. When you’re buying a domain like that, there’s only one. By late December they’d negotiated a price. It wasn’t bet-the-company money, but it was real money, and it’s under NDA. His line for it: if you don’t know domain names, you’d be shocked how much they paid. If you do, you’d be shocked how little.
So the question in front of his exec team wasn’t whether a rename was a good idea in a vacuum. It was whether they were going to make this particular mistake again.
The stake nobody names
Every big decision has hard costs and soft costs. Nathan’s point is that it almost always has a third kind, and nobody says it out loud. Sometimes it’s a revenue goal: a rename might be a great decision five years from now and do nothing for this year’s number. Usually, he says, it’s ego.
So he asks the room a version of one question: what do you feel you need to say, but you’re a little nervous to bring up? Then he lets it sit.
In this meeting, the person with the unnamed stake was him. He told his leadership team he really wanted to do this, and that if he was honest, he was afraid he’d fail at it again and go from the entrepreneur who made a mistake to the entrepreneur who can’t learn.
Aaron’s read, in his outro: the CEO went first. Nobody in your company is going to name the unspoken thing until you do.
Picture the worst case first
The other tool in that room was a pre-mortem. Instead of letting one camp argue it would work and another argue it would be a disaster, Kit splits the time. Half an hour fully inside the version where everything went perfectly, no devil’s advocates allowed. Then a stretch fully inside the version where it’s a year from now and it failed.
During the worst-case half, his CRO asked the useful question: what’s the worst thing that could happen? Say they buy the domain and never rebrand. Is it only worth something to Kit? It wasn’t. A three-letter .com would resell for more than they were paying. That took the purchase off the table as a risk, and let the team argue about the part that was actually risky.
Structure beats debate
For the decisions that follow, Kit runs a decision-making framework it borrowed from Brian Armstrong, the CEO of Coinbase. They just call it a DMF. Nathan’s claim is that the setup does most of the work: one decision maker, ideally the person closest to the problem; six input providers or fewer; a clearly stated decision; a timeline; and how long you’re committing to it. Get those clear and you’re 70 or 80 percent of the way to a good decision before anyone has argued about anything.
Then comes a blind vote, so nobody knows where anyone else landed. Then everyone speaks in order from least senior to most senior, so the room doesn’t anchor on the boss. Then a second vote. The decision maker still isn’t bound by it. The system organizes the input, and a human makes the call.
They put it to the test in summer 2024 on the logo. A UK agency had narrowed it to a few concepts, and everyone looked to Nathan to pick. He had a favorite. Seven of the ten people who cared most preferred a different one. That’s exactly the kind of decision that usually ends with everyone deferring to the founder. Kit ran the framework instead.
What we cover
- Pick a corner. Label the four corners of the room strongly agree, agree, disagree, strongly disagree. Put a statement on the board and have everyone go stand somewhere. No middle. You see where the room is in ten seconds, and you can call on a corner instead of going around the table. (They do it in FigJam on Zoom.)
- The devil doesn’t need an advocate. Nathan’s favorite Seth Godin line, from a friend who interned for him: the devil is great at advocating for himself. What do you think?
- Make their best argument. When two sides are entrenched, Nathan has each argue the other’s position. If you can make my case as well as I can, disagree and commit actually means something.
- Giving up the big reveal. Nathan wanted a Steve Jobs moment. They announced the new name in June and cut over in October instead. Less flashy and more prudent, and he says it was the right call.
- “You are the large language model.” For an eleven-month rollout touching every surface of the company, Nathan put one person in charge: Charlie, Kit’s creative director, nine years on the team. Her job was to answer anyone’s question about the rename. Aaron’s take: if you don’t have a Charlie to compound your workspace intelligence, AI can help.
- Let the wine breathe. Aaron on the decisions he’d most like back. Almost all of them were made under time pressure.
In his words
Anytime you’re making a decision, list out all of the costs. Audit all of the downsides. And then a question I like to ask is some version of: what do you feel you need to say, but you’re a little nervous to bring up? Or, what’s not being said that needs to be said? And we’ll just let that question sit in the room for a little bit.
It turns out that if you put structure to a decision, you end up with much higher quality decisions.
Try this in your next meeting
Before anyone leaves the room, ask what’s not being said that needs to be said. Then wait. Don’t fill the silence.
One more thing
ConvertKit exists because of a surprise in a spreadsheet. In 2012 Nathan was a designer who self-published a book on designing iOS apps, mostly to win more clients. He launched it to 798 people on his email list and made $12,000 on the first day. What shocked him wasn’t the money. It was that email sold more copies than every other channel combined.
He took the discovery to his friend Ron, a Boise internet marketer who’d been at it since 2002. Ron’s response: we’ve all known this for a long time. You want a gold star?
Nathan never took another design client. He went looking for an email tool with those best practices built in, couldn’t find one, and built it. Two years in, it was doing $2,000 a month. Thirteen years in, it’s Kit.
About Nathan Barry
Nathan Barry is the founder and CEO of Kit, formerly ConvertKit, the email marketing platform for creators. He started the company in Boise, Idaho in 2013, after a career in web and app design and a self-published book that taught him what email could do. He writes a weekly newsletter at nathanbarry.com and hosts The Nathan Barry Show.
About Beyond the Meeting
Beyond the Meeting is Contio’s podcast about how leaders actually lead, build, and get real work done. Hosted by Contio CEO Aaron Klein, who spent twelve and a half years building Riskalyze — now Nitrogen — for financial advisors before founding Contio. New episodes every three weeks.
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Transcript
Read the full episode transcript
Cold open
Nathan Barry: What’s not being said that needs to be said? And we’ll just let that question sit in the room for a little bit. Maybe everybody journals on it for a little bit, or that sort of thing. And often some good stuff will come up. In my case, it was me saying, “I really want to do this, but if I’m totally honest, I’m worried that I’ll fail at it again.” And then it goes from entrepreneur that made a mistake to entrepreneur that can’t learn, right?
Intro
Aaron Klein: Welcome to Beyond the Meeting, the show about what happens after the room clears, where what gets said turns into what gets done.
I’m Aaron Klein. I spent twelve and a half years running a fintech company called Riskalyze. These days, I build AI to amplify the impact of human relationships at a company called Contio.
Our guest today is Nathan Barry. If you subscribe to a newsletter from somebody you actually like to read, there’s a decent chance it reaches you through Nathan’s company. It’s called Kit; you might have known it as ConvertKit. More than $50 million a year, 102 people across 70 cities, run out of Boise, Idaho, which happens to be my hometown, too.
Here’s what I wanted from him. Two years ago, Nathan renamed his company. Now, that’s not the interesting part. The interesting part is he’d already tried it once, back in 2018, and it went so badly they rolled it all the way back. So when the domain name that he’d wanted for a decade finally came available, he had to walk his leadership team into the exact thing that they had already watched fail.
I wanted to be in that room. So I asked him to take me there.
Nathan is one of the most deliberate operators I’ve come across, and he gave us the whole playbook. Stick around to the end. I’ll be back with my three takeaways.
The iPad, an iOS book, and 798 subscribers
Aaron Klein: Well, Nathan, thank you so much for joining me today. We’re super excited to have you on Beyond the Meeting.
Nathan Barry: I’m honored.
Aaron Klein: Kit is a legendary company, and it’s kind of crazy that it’s based right here in my hometown, your hometown of Boise, Idaho. Tell us a little bit about that founding moment and where you came up with this idea.
Nathan Barry: Yeah, so quick backstory. I got into web design and then software design in high school and then into college, and that was my world. Everything that I cared about was in that space. I definitely got obsessed with it. I worked for a few companies around the Boise area, did a bunch of freelancing, and then I was working for a company out in Eagle called Unity Media Group when the iPad came out in 2010.
I worked as a UI designer, and I was given the task of working on a new iPad app for the day the iPad released. It was really fun, because we didn’t have the actual devices. We’re like, wait, how big is it? Let’s make a cardboard version, software emulation on the Mac, trying to figure out what this is. It was a cool experience to get to do the design side. We flew to Portland the day the iPad was released, because that was the closest Apple store at the time, and bought our iPads. But that really immersed me in the world of iOS development specifically. And then I spent a bunch of my nights and weekends after that learning to code in Objective-C and building apps.
After moving on from that company, I freelanced for about a year. And I was thinking, okay, what will help me get more clients? How do I build credibility in this space? I was starting to follow people who were self-publishing books around more technical topics. And I thought, “Oh, if I write the book about how to design iOS apps, then people are going to be more likely to hire me.” Do you want to hire the random designer, or the guy who wrote the book on it? If that’s me, I’m going to get more clients.
So I thought, okay, I’m going to write this book, and I want to make some money from it. If I can make $10,000 over the lifetime of the book, maybe three, four years, that’d be incredible. But really it was about clients. And I just dove down this world of online marketing. How do you build an audience? How do you get people on a Mailchimp email list, these basic things?
I ended up launching the book in September 2012, self-published. Launched to 798 people on my Mailchimp list. Ended up making $12,000 in the first day, $19,000 in the first week, and over time the book went on to sell a couple hundred thousand dollars’ worth. I never took on another design client, because I was fully immersed in this creator world of building an audience and earning a living that way.
Email outsold everything
Nathan Barry: And somewhere in there, a couple things shocked me. The first was that you can make a lot of money selling digital products online. If you teach a skill that makes money to people who have money, there’s a pretty great alignment there. The next thing was that email sold more copies than every other channel combined. And this was 2012. Instagram was really hot, up and coming then, and it just really surprised me.
Now, the interesting thing about Boise is there’s an OG internet marketer group here. If you think about ClickBank and Bodybuilding.com, both being founded here, ClickFunnels, there are a lot of people here who, under the radar, have known internet marketing forever. So I was talking to my friend Ron, and he’s one of these people who’s been at it since like 2002. And I was like, “You would not believe this. Email is selling more than everything. It’s incredible.” And he’s like, “Yeah, man. We’ve all known this for a long time.” It was like I had discovered this huge breakthrough, and he was like, “Uh-huh. You want a gold star?”
So I was just obsessed with email, and with learning all these best practices and implementing them. And I immediately got frustrated with Mailchimp. I was learning all these best practices, hacking around Mailchimp, and I was like, you know what? Someone should make an email marketing product for bloggers and content creators like me, but that has the best practices built in by default. And so that is how the company started, January 1st, 2013.
Aaron Klein: So just celebrating, what, thirteen years?
Nathan Barry: Thirteen years. Yeah, it’s exciting. There was a long journey in all of that, but that’s the origin story.
Two years in, $2,000 a month
Aaron Klein: And now, just the incredible scale that you’ve built. Kit has such an incredible name around the world, really.
Nathan Barry: Yeah. So it went from my little self-funded “let’s just build this up,” and it was not an immediate success. I think two years in, we were at $2,000 a month in revenue. But today we do about $50 million a year in revenue, have 100 team members globally, and serve 60,000 paying customers and about 500,000 free users. So it’s fun to be able to homegrow that business from Boise.
Aaron Klein: That’s awesome. You’re running an organization with a pretty decent level of scale, but also good efficiency: a hundred employees at that kind of revenue scale. I like that $500,000 in ARR per team member. That is a great place to be. I’ve served on a few boards with entrepreneurs where the number was probably a tenth of that, and I was like, oh no, you can do a lot better. We might need to fix this. And in a world of AI, you can push it even more.
A CEO’s week: 80% CEO, 20% creator
Aaron Klein: But that’s still a lot to juggle, AI or no AI. AI does give you more efficiency, but it’s almost like you’ve got more threads running at the same time. So take us into a typical week for you. What kinds of meetings and what kinds of decisions are you having to make week to week?
Nathan Barry: Inside of Kit, I try to delegate as many things to the individual leaders as possible, but I’m not very good at that. So I probably have my hands in way more things than I ought to.
Now, I kind of have dual roles. Something that I realized from the world of being a content creator is that attention is this incredibly powerful thing, and creators are amazing at getting it. If you point that attention toward businesses that have incredible fundamentals, like SaaS, especially SaaS with good expansion revenue, then that’s worth so much. So the last three or four years, I’ve gotten back into the content creation world.
I split my time: probably 80% of my time is on what you’d expect from a typical CEO. I find sales, marketing, and product are the things that I’m best at. And then the other 20% is on content creation. I have a podcast, I write a weekly newsletter, I’m growing a social following, because I’ve realized that I can grow Kit’s brand, and that works. But if I grow my personal brand, I can reach new audiences and direct them back to Kit.
So a typical week is usually product and strategy meetings on each of the core initiatives that we’re driving forward. We’ve got four of those. An executive meeting. Usually three to five customer calls throughout the week, whether it’s something new that we’re trying to get feedback on or a deal that I’m trying to close. Teach a workshop or a webinar somewhere in there, and then usually record a couple podcasts. I’m also trying to finish a book, so there’s probably 15, 20 hours a week of writing in there. But that might be Sunday morning.
Aaron Klein: I was going to say, that’s the last 15 or 20% of 120% of your week.
Nathan Barry: Yeah, exactly. That was Sunday morning from 5:30 to 8, before my family woke up.
The meeting where everything changed
Aaron Klein: That’s awesome. So take us into the meeting where everything changed.
Nathan Barry: So maybe a little bit of context: Kit was not always called Kit. We had a different name. When I founded the company, it was called ConvertKit. I was looking for a .com that wouldn’t be misspelled, and it was available for $9 on GoDaddy. Not $9,000 or $900,000. And so we ran as ConvertKit for a long time.
One shot at kit.com
Nathan Barry: So the decision was really that we had this opportunity to buy kit.com. If you think about it, we were talking before about real estate.
Aaron Klein: Three-letter domain names.
Nathan Barry: Three-letter domain names. It cannot be misspelled. It’s a standard English word. Highly brandable. We’d been in this search for a new name for a long time, at this intersection of: can you get the domain name, can you get the trademarks, can you get the social handles? And we were starting to realize, wait, this might actually happen.
But the hard thing is, if you and I are looking for a dream house, there’s probably a few neighborhoods that we’re okay with. There are a few different options. When you’re buying a domain name like that, there’s only one. And so when this came available, we’re like, this is the only shot that we have.
So it was in that meeting with our exec team. We’d gotten to the point where we had the price negotiated, and we realized, okay, this is a huge amount of money. But not as much as you’d think.
Aaron Klein: Not bet-the-company money.
Nathan Barry: Not bet-the-company money, but ouch. A fraction of our annual revenue, but also not a fraction of the annual profit.
I’m transparent about everything. Unfortunately, I can’t say the price of the domain name. The sellers’ NDA was very strict on that. So what I always say is: if you don’t know domain names, you’d be shocked at how much we paid. And if you do know domain names, you’d be shocked at how little we paid.
But in this meeting, we’re talking through: are we going to pull the trigger? And for context, we’d renamed the company once before, in 2018. It went poorly, and we’d rolled it back. So it’s not just, can you make this decision in a vacuum? It’s, oh, you’re going to make this particular mistake again.
I had all these things that I wanted to do with the company and the brand, and I felt like ConvertKit held us back from that. But I also felt like I’d used up kind of the one shot.
Naming the stake nobody says
Nathan Barry: If you think about a big decision, it’s always good to align on what’s at stake. There are often the things like the financial risk: okay, we’re going to be spending this amount of money in hard costs, and then here’s a soft cost, like the time and all of that. But then there are usually some unnamed things at stake, too.
Often there’s ego. In my case: oh, you’re going to try again at the thing you failed at in the past. There are sunk costs. Maybe people have particular revenue goals. Your CRO, in our case, is like, hey, we’re trying to hit this revenue goal this year, and this is going to be, maybe in five years, a great decision, but brands do not help you in the next quarter. So it was really helpful for us to go through and name all of the hidden costs, the things that weren’t stated in the conversation.
And I would say, anytime you’re making a decision, go do that. List out all of the costs. Audit all of the downsides. And then a question I like to ask is some version of: what do you feel like you need to say, but you’re a little nervous to bring up? Or, what’s not being said that needs to be said? And we’ll just let that question sit in the room for a little bit. Maybe everybody journals on it for a little bit, or that sort of thing. And often some good stuff will come up. In my case, it was me saying, “I really want to do this, but if I’m totally honest, I’m worried that I’ll fail at it again.” And then it goes from entrepreneur that made a mistake to entrepreneur that can’t learn, right?
Aaron Klein: Totally. How many people were on your leadership team then?
Nathan Barry: It was five at the time.
Aaron Klein: And was it pretty unanimous that you should do it, or was it a little bit charged? People weren’t sure?
Nathan Barry: I would say 70, 80%. Not that it was split between each individual. I think each person themselves was 60/40, 80/20, somewhere.
Netflix, Qwikster, and the -10 to +10 vote
Aaron Klein: It’s interesting that you describe it that way, because one of the greatest boneheaded business decisions of all time, that most people will rank up there, is Netflix deciding to split out and make the DVD business Qwikster. And I heard Reed Hastings once say that what he didn’t realize when he went into the decision was that basically everybody felt very strongly that it was a bad idea. He was the only person who thought it was a good idea, but they’re all sitting there like, well, Reed’s really smart and he’s gotten a lot of decisions right.
So one of the things he said he learned from that was to ask people, on big, high-stakes decisions, to rank their feeling on it from -10 to +10, each of them individually. They’d each write it down separately, and then he’d put them all up on the screen. What you would have gotten were a bunch of plus sevens and plus eights. Everybody was pretty confident, and that’s actually really good, and hey, proof is in the pudding, it worked. But as he put it, he would have ended up with a bunch of negative eights and negative nines, and he would have been a plus seven or a plus eight, and that would have at least slowed him down. He says in hindsight he thinks it would have slowed him down and gotten him to see the downsides. But that’s too far into the weeds. We can come back.
Nathan Barry: Do people still view that as a bad decision?
Aaron Klein: I think so, because as it turned out, doing it all under Netflix turned out to be a great plan: keeping people engaged and just doing that transition of the business. The DVD business is gone, and it all worked out very nicely, and everybody transitioned. You didn’t need to make a bet-the-company-level decision, and make people angry about having to pay for two services.
Nathan Barry: Oh, that’s interesting.
Pick a corner
Nathan Barry: So what you’re touching on there is frameworks around decision-making, which I think are so helpful. There are a couple that I use that we can weave into this conversation.
One, just really simply, for team alignment: I like to put a statement up on the board, and I will label the four corners of the room strongly agree, agree, disagree, and strongly disagree. Then I put a statement up there, like, we should rebrand the company, or whatever. Now, I didn’t use this technique back then, but I use it pretty often. And then you just go and stand in the corner of the room that represents your perspective. Someone’s like, “Well, I’m kind of between agree and disagree.” We’re like, “Pick a side. Go to the corner. We already gave you four choices.”
Aaron Klein: You don’t get infinite choices.
Nathan Barry: You don’t get to be in the middle. And something with our management team: on Zoom, they’re pretty hesitant. They’ll be pretty quiet. You’ll bring something up, and people will be quiet and not really say anything, or people will fall into a devil’s advocate kind of thing.
There’s a line from Seth Godin, who’s this amazing marketer and author. A friend of mine did an internship for him, and this is a story from that. Someone’s like, “Well, devil’s advocate,” and Seth goes, “No. The devil’s great at advocating for himself. He doesn’t need any more advocates. What do you think?”
So what I love about this system is you can immediately see. Should we split out Qwikster from Netflix and run it as a separate business? Everybody’s at strongly disagree. And you can have a conversation from there. You immediately get this without having to go around and ask every single person. And then when someone’s standing there, it’s, okay, you chose strongly agree or strongly disagree. Why? “Well, yeah, I am standing in this corner of the room. Here’s why.” And you can kind of popcorn back and forth, and it gives you permission to call on different groups.
Aaron Klein: I like that. I haven’t thought about corners before.
Nathan Barry: And you can do it virtually. We’ll do it with FigJam, where we’ll have people in a shared meeting just go put themselves in a spot.
Aaron Klein: I like it, because I think a lot of time in meetings is wasted going around, “What do you think?”, all the way around, and it’s unclear what the point is.
From decision to rollout
Aaron Klein: One of the other things I’m curious about: you make this decision, and then there are a million details that go into it, and they ripple down and impact every single person in your organization. First of all, how long did it take from making the decision to actually executing the rebrand?
Nathan Barry: It wasn’t overnight. It was probably November 2023 that we realized the domain was available. By late December, we had a price negotiated, and by early January, we pulled the trigger on it and actually had the contract. February is when we told the broader team. We had a team retreat, and we’re like, “All right, we’re telling them.” We knew that was going to get some great reactions. “Did we already do this? Do you never learn?” And then we announced it in June.
There were sub-decisions within that. I wanted to have this big reveal moment. I thought kit.com was a pretty sexy domain name, and so I wanted the whole brand all at once. But then we realized we shouldn’t rush into it. So we actually made the decision to delay, and to announce in June that we’re going to rebrand, here’s the new name, domain name, all of that, and we’ll actually cut over to it in October. The plan was September; it ended up getting delayed to October.
And I didn’t like that at first, because it wasn’t the flashy Steve Jobs moment. But it was the prudent, responsible thing to do. Hey, this is a big deal. Let’s make sure we get it right.
One person in charge
Aaron Klein: But for all those months, you’ve got all these people scurrying around trying to implement a whole bunch of different things. I’ve been through a rebrand before. It affects basically every surface in the company. It’s a big deal, and it reveals everything: oh yeah, I forgot we had that product, or, I haven’t thought about that button in a long time. So talk to me about how you worked to keep all of those details and context straight across 100 people, over the course of those many months, while all that work had to get executed.
Nathan Barry: The first thing was making one person in charge of the whole thing. Charlie, who’s our creative director, has been on the team for nine years now, and we just said, you are in charge. You are the large language model that can answer questions from everybody in the organization on what to do with this.
Aaron Klein: Exactly.
Nathan Barry: So there was clarity on that. We had someone else who ran the project management of it all, so that wasn’t the same person.
The pre-mortem
Nathan Barry: And maybe rewinding, an important thing going back to that first meeting where we’re trying to decide what to do. I want to share another framework that’s helpful for us. Dave, our CRO, asked a good question: what’s the worst thing that could happen?
A tool we really like is a pre-mortem. People often say, here’s why it’s going to work amazingly, and then someone else says, here’s why it’s going to be terrible, and we just argue about this thing. It’s not very effective. So what we do is we say, hey, for the next half hour, we’re going to fully step into the dream scenario. This worked perfectly. We’re just going to brainstorm that. And someone’s like, “Well, devil’s advocate,” and, nope, that’s not the phase that we’re in. And then, to make everyone comfortable with that, you say: and after that, we’re going to spend a period of time fully diving into, it’s a year from now, it failed. Here’s everything that went wrong.
So when we did that, one of the things that came up was: okay, let’s say we buy the domain and then decide not to rebrand. Our CRO was like, “Is the domain only worth something to us?” And I was like, “Oh, no. If we tried to sell this in a year on the open market, we could definitely get more than we’re paying for it.” And he’s like, “Then why are we still having this conversation?”
It was like buying a house that was heavily undervalued. As a three-letter .com, just to a domain investor, it’s worth way more than we paid. So he’s like, okay, so at least for the purchase of the domain, that’s a pretty de-risked decision. And then we got into the other things.
Aaron Klein: It’s interesting what happens when you break decisions down into components. That’s such an important thing.
The DMF: Coinbase’s decision framework
Nathan Barry: And then another framework that we use a lot, we call it a DMF. It’s just a decision-making framework. It comes from Brian Armstrong, the CEO of Coinbase. He has an article on Medium breaking it down. And I think too many people try to make decisions without structure around them.
So if you fast-forward to summer of 2024, we’ve announced that we’re going to become Kit. We’ve done a lot of the branding work, but we are still stuck on a logo. We’d hired this agency out of the UK, who’s amazing, and they did all this great design work for us, and they had a few logo concepts. It comes down to it, and we’re really stuck on which one to go with. Everybody looked to me to say, all right, ultimately it’s your company, so which one are we going to do?
I had one logo that I wanted to go with. Say there are ten stakeholders who actually really cared, across design and marketing. I’d say seven of them were strongly for the other logo, and two were like, they’re both pretty good. It was not super clear. So we went and followed Coinbase’s decision-making framework.
Basically, the way it starts is you appoint one decision maker, ideally someone who’s the closest to the problem and isn’t fully invested in one camp. Then you decide who the input providers are. It’s not the hundred people in the company. It’s, who are the key people? Like the ten people we were talking about. We really try to get down to six input providers or fewer. And if someone’s like, well, I don’t have a say, it’s, great, tell your coworker who virtually sits next to you, and they’ll represent your perspective.
So we define that. We clearly define the decision that needs to be made, the timeline that we’ll make the decision on, and how long we’re committing to it for. And then we have this kind of open period, for maybe a few days or a week, where anyone can weigh in and comment on the Notion doc: here’s what I think. And then you roll into the actual decision.
So first, just the very act of getting really clear on what we’re deciding, how long we’re committing to it for, and who the decision maker is gets you 70, 80% of the way toward a good decision. We’ve done this for product decisions, like, what should the product behavior be when someone gets to the end of their email sequence? We’d debated this for months. Should it be a setting? Should we build opinionated software that doesn’t have it as a setting? And usually, when we dive into something like that, we get to a really clearly stated problem and four possible solutions, and people get really clear. In this case, with our logo decision, it’s: we’re going to go with logo A, logo B, or we’re going to go design some new options and go back to the drawing board.
Blind vote, least senior first
Nathan Barry: And then, kind of to the Reed Hastings example, the very first thing that we do when we come to the meeting, after we agree on the constraints, is we do a blind vote. You’re allowed one vote for every option that there is. In this decision there were three possible options, so everyone has three votes to allocate however they like. We do it all in a Google Sheet template. You reveal the votes, and you can immediately see: oh, turns out we already agree. We just didn’t know it. Or you can see how it’s split. Some people are equally split between all of them.
We ran through that whole process, and then the next thing is everybody shares their perspective in order, and you go from least senior to most senior. That way people don’t anchor their perspective. Then often your VP of whatever, who went almost at the end, is like, “Oh, and what Charlie or this other person said, I agree with that, too.” They’re just plus-oneing instead of monologuing and being the most important person in the room.
Then you discuss, and go all the way around. You get a chance for open discussion, and then you vote again. And the decision maker does not have to go with the vote, but they use all of that input, what everybody said and everything they learned, to say, either in the meeting, “Here’s my decision,” or, “I need 24 hours to collect all of this.”
So we use it for everything from should we rebrand the company, to what is the logo, to how should the product behave: all the things that are important. It turns out that if you put structure to a decision, you end up with much higher quality decisions.
Let the decision breathe
Aaron Klein: That’s pretty cool. And the other thing I think is so powerful about what you just described is where you said you put it in Notion and it lives there for a little bit of time. It’s a little bit like letting wine breathe. Great decisions are that way. They oftentimes need a little bit of time to breathe. When I look back at my career, some of the decisions I’d love to get back were ones that were made under massive time pressure. If you can let that wine breathe a little bit and get the benefit of really, really good input from smart people, things are always a little bit better.
Argue the other side
Nathan Barry: And just forcing people to actually take a stand. Pick a side, articulate it, and walk into that.
The other thing that I like to do in decisions, if I don’t have a stake in it and people are stuck, is I’ll get everyone to argue the opposite side. If they’re entrenched, I’m like, okay, what’s the best argument that you have for this person’s perspective? Because then what happens is everybody ends up feeling heard. If you and I cannot agree on a decision and we’re 50/50 partners in a business, but we can each articulate all the best points, if I can make your argument for what you’re advocating for as well or better than you can, then you’re going to feel pretty good about it. It’s the true definition of disagree and commit.
Where to find Nathan
Aaron Klein: That’s awesome. Well, this has been a blast of a conversation. Talk a little bit about where people can find you. Do you, by any chance, write an email newsletter or anything like that?
Nathan Barry: Yes. If you just search Nathan Barry, pretty much anywhere on the internet. Probably my favorite thing is my podcast, just called The Nathan Barry Show. It’s all about business. NathanBarry.com is my weekly newsletter; that links to everything. And then kit.com, where you can check out the little software product that we build to help creators and businesses build an audience.
Aaron Klein: With that beautiful three-letter domain name. What a story. Thanks so much for joining us.
Nathan Barry: Thanks for having me.
Aaron’s three takeaways
Aaron Klein: Hope you liked that one. Here’s what struck me about Nathan. He shows his work. Most founders will tell you what they decided. He walked us through exactly how, including the part where he was scared.
So, three takeaways from that conversation.
First, clarity does far more work than anybody gives it credit for. Nathan’s claim is that just getting clear on three things (what exactly are we deciding, how long are we committing to it, and who actually makes the call) gets you 70 or 80% of the way to a good decision. Seventy or eighty percent, before anyone has argued about anything. I’ve sat in rooms where six smart people talked for 90 minutes and couldn’t make a call. If your meetings feel exhausting and inconclusive, it usually isn’t the people. Get the clarity first.
Second, and this is where the framework comes in. Nathan uses a decision-making framework he picked up from Brian Armstrong at Coinbase; they just call it a DMF. One decision maker, ideally the person closest to the problem. Six input providers or fewer. A blind vote before anyone talks. Then everyone speaks from least senior to most senior, so nobody just anchors on the boss. And then you vote again. And the decision maker still doesn’t have to follow the vote. It’s not a democracy. That last part matters, because the system organizes the input. The human still makes the call. That’s five moves. You could run all of them tomorrow.
Third, every big decision has a stake nobody has named, and it’s usually rooted in ego. Nathan’s version of this: he sat in front of his own leadership team and told them he was afraid he was going to fail at the rename again, and that he’d go from being the entrepreneur who made a mistake to the entrepreneur who can’t learn. So the CEO went first. And that’s the whole trick. Nobody in your company is going to name the unspoken thing until you do.
One more, and it’s the part I keep thinking about. When they finally executed the rebrand across a hundred people in eleven months, Nathan put one person in charge: Charlie, nine years on the team. I think about how companies use Contio, and I say, wow, I’ve spent a long time building software to do a fraction of what Charlie did in those eleven months. But if you don’t have a Charlie to compound your workspace intelligence, I’ll bet you AI can help.
Nathan is at kit.com, and you can find him just about anywhere by searching his name.
The second half of the work starts now. I’ll see you next time.
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