Writing About Contact

The Six People Who Don't Know They're on My Team

An answering machine gives you one answer. This thing was designed to be incapable of that.

A note before we start: the client in this story is a composite. Details, industry, and specifics have been changed, because the pattern is what matters, and the pattern is everywhere.

“I have to get this thing back on the rails,” I muttered (not for the first time). And so our adventure begins: with me stepping in as an escalation point on a strained account. Their project has taken way longer than originally planned, and understandably, they aren't thrilled about it. There were reasons for the delays. There always are. But none of them matter when someone is unhappy and you are responsible for the relationship.

My first reaction in these scenarios is to pull out the big guns. I had a pre-built tool sitting in my dev sandbox from an old proof of concept, loaded with more bells and whistles than any reasonable person would ask for. I showed it to them and told them I could tweak it for their environment and elevate their user experience, and I'd only charge for the port time (like 30 minutes with Claudio, my AI coding partner). If you didn't catch the sleight of hand there, my move was to hand over something over-engineered and expensive-looking for nearly free, and buy back some goodwill with the difference.

It worked. Sort of. The bad news was that things weren't as plug-and-play as I'd hoped. Feedback came in. Then more feedback. Then feedback on the feedback. Every round was reasonable on its own. But all together they were becoming a whole second project that nobody had scoped, nobody had priced, and nobody but me could carry forward.

As a consultant, I'd know what to do here. Keep setting good expectations, keep delivering, slowly re-win the trust. But I'm not a consultant on this project. I'm not even on this project at all. I lead consultants. Which means my actual job was to figure out what to do before I set a bad precedent and sink the budget by giving away too much free consulting work in the name of repairing the relationship. Because we all know what happens when you give a mouse a cookie.

So I assembled the squad. The A-team. MY team.

I briefed them on everything I could remember (I even showed them all the email communication), and then asked the question that had been rattling around my head for too long:

How can I get this project back on track without giving away too much free or discounted work and keep repairing the shaky relationship we have with the client?

Rodney took it all in and said: “Back on track? I want to stop on that phrase before anyone gives you advice, because I don't think you've defined the track, and you can't land a trick you haven't picked.” (He still skateboards, so he's always finding ways to slip that into conversations.) “I think you mean: give the unstructured stream a structure and let the relationship heal by watching the structure work. That reframe matters because it tells you where the effort goes. You don't fix this with a gesture. You fix it with a visible, boring, repeating pattern.”

Anthony tacked on to that with: “There's a thing I remember from working in restaurants and it's the difference between hospitality and servility. Hospitality is: you run a great room, you charge full price, and the regulars feel taken care of because the place has standards. Servility is comping desserts for the table that complains, and every server alive will tell you what that produces: the table that complains every time, and tells their friends which restaurant folds.”

John agreed. “The discipline is simple. Stop giving away free work. What do you give instead? Certainty. Dates you hit. A proposal that shows up when you said it would. If you want to be generous, be generous with clarity. That costs you nothing and it's the only currency the client is actually short on.” John has always been a disciplined guy. I think it goes back to his days as a professional wrestler. And right about now you should be hearing “The Time Is Now” because we're talkin' 'bout 17-time World Champion JOHN CENA, babyyyyyy!

What's wrong with asking the machine?

So obviously I don't actually know John Cena (as cool as that would be), but I do have access to Claude and YouTube. As I started getting more heavily involved in using AI to build things I became more interested in what other people were doing and building with AI. I came across a few videos that showcased this concept of creating a personal board of directors. The idea is you choose a handful of public figures that you would want advice from and you build a custom skill in Claude that convenes the advisory personas to work through hard decisions with you.

You see, the thing with asking AI an important question is that it's actually pretty hard to tell if the AI is being objective. If you ask it “hey is this a good idea?” it's likely that you get confirmation that you had a good idea. Maybe that feels good in the moment: a confident, well-structured answer in the same shape as what you were looking for when you asked the question. But that confidence is actually the failure mode. The danger isn't wrong answers. The danger is the plausible answers that you don't push back on because they show up looking like a conclusion.

The danger isn't wrong answers. The danger is the plausible answers that you don't push back on because they show up looking like a conclusion.

What I actually needed was a structure that makes one-dimensional advice impossible. A well-constructed board of directors offers that. The friction caused by the different perspectives is the whole thing.

For those of you keeping score at home, three chairs haven't said anything yet (which is just my way of foreshadowing some “friction” for now because you haven't met the others yet).

What's the design rule?

I took the same approach I take when assembling furniture from IKEA: I briefly skimmed the instructions, got the gist of it, and started building what made sense to me.

Most of the examples I saw included selections like Mark Cuban, Elon Musk, Steve Jobs, or Warren Buffett. I'm sure they're great choices if you're trying to achieve massive amounts of wealth or success, but I am setting my sights lower and much more intentionally. I don't want advice from some random strangers who would put wealth or success over everything. I want advice from the people I look up to and who are willing to hold me accountable to a higher standard. I want the board to represent the aspirational real-life examples of my values so that whatever outcomes it produces reflect a version of me. That's the only way I feel comfortable using AI (or anything) to help me steer my thinking.

So what are the rules of engagement? How can I get the most out of this tool that I am building for myself? Here is what I started with:

I also want a flag to be thrown on the play if all of the seats agree. That just turns this whole thing into an echo chamber and that falls into the same trap as “asking the machine” with more reading. To prevent that from happening, I built a steelman into the skill.

A strawman is the weakest version of an opposing position that you argue against, usually in bad-faith arguments. The strawman is easy to beat on purpose and sounds convincing, but it's a distraction from finding the real answer. “So you're saying we should just give clients unlimited free work?” No, nobody said that, but it's easier to beat than what they actually said.

A steelman is the flip side of that. It's the strongest possible version of an opposing position. Ideally, even stronger than the real-life version. Made of steel instead of straw. If the idea survives contact with that, you've actually earned your conclusion. If it doesn't, you just found out something important before reality found it out for you.

Who holds the six chairs?

So you've already met John Cena and I'm sure it's easy to think that his champion pedigree and loud, entertaining persona are what earned him a spot on the team. But I was never really a fan of John Cena, the wrestler. That's not why he's here. I'm a fan of John Cena, the man, because of his compassion and discipline. His work with Make-A-Wish and his interactions with his fans are awe-inspiring to me. I love that he comes from a world full of showmanship and violent, surface-level entertainment (and some would say at least a moderate amount of toxic masculinity) and still comes across as one of the most humble, caring, mindful, and genuine people in entertainment.

I also talked about Rodney and how he still skates, and I'm sure most readers still need a little more of a hint because Rodney Mullen is not quite as well-known as John Cena. But if you have ever seen a modern skateboarder do a trick, you can likely trace it back to Rodney. It isn't his accomplishments or even his impact on the sport of skateboarding in general, but it is his dedication to his craft that lands Rodney on my team. At 60 years old, it's absolutely inspiring to me to see that he still skates for hours at a time, even after double hip replacement surgeries. It would be easy to rest looking back on everything he's accomplished, but he keeps going. Because it wasn't ever about accomplishing things. It was about the craft. In the final scene of Tony Hawk: Until the Wheels Fall Off, when he says “there's something inside of me propelling, that I'm not going to give up until the wheels fall off. That's what I'm made of” I totally get it. I aspire to be that dedicated to my craft.

And the former chef you met earlier? Anthony? That was Anthony Bourdain. And beyond being a fan of food and culture, I knew that the board needed a healthy dose of unflinching honesty. What I love about Bourdain's brand of honesty is that it isn't some squeaky-clean ideal. It's unfiltered and self-aware. Raw and lived-in. That's what I need if I want to keep this whole thing grounded in reality. The other aspect that made it easy to choose Bourdain for this seat is his voice. I always loved hearing him wax poetic about his experiences. I'm hoping that the ugly truth is easier to stomach when it sounds nice.

The next seat on the board I was looking to fill was the attunement seat. Attunement is the discipline of noticing what the person in front of you is actually feeling, and it is an invaluable skill for a consultant to have. My best projects have always been the ones where I have a tight partnership with my key stakeholders and that partnership is quickest to bloom when you can align with the wants, needs, and feelings of your partners. When I think about this concept there's one voice that jumps out in my head from when I was just a kid, and he's telling me he wants to be my neighbor. Fred Rogers spent a whole career proving that attunement is a skill and not just a personality trait. I truly admire how he answered every letter a child ever sent him, but that didn't make him a pushover: he also sat in front of a hostile Senate subcommittee in 1969 and won the room in six minutes, not by arguing harder but by paying closer attention than anyone else in it. That's his job on the board. When I bring a question, Fred ignores the mechanics everyone else is debating and asks about the person on the other end of my decision. What are they afraid of? What have they already been through? What will my carefully worded email feel like to read? He's the chair that remembers the other side of the table is a person, especially when I'd rather they be a line item.

The next seat gets filled because I went to therapy in my early 30s to help deal with my anxiety. And that's the kind of vulnerability I learned from Brené Brown. Brené is a researcher before she's anything else and she's got more than two decades of experience analyzing the patterns that cause people to armor up, avoid hard conversations, and tell themselves flattering stories about both. Her seat exists because my situations always feel unique to me, and thankfully I am self-aware enough to know that they never are (although I can forget sometimes). She's the straight-faced flight attendant I turn to whenever I'm going through a one-of-a-kind crisis who calmly informs me that any turbulence I experience has a name, a literature, and a predictable ending. Being told you're a data point is humbling. It's also the fastest way out, because a named pattern comes with a documented exit.

I used to have a hard time saying “no” in work situations. I guess I was always afraid it would come across as uncooperative or problematic and I want to be a part of the solution, not the problem. Boundaries don't have to be cold, though. A boundary can be held with complete warmth and zero apology. Setting appropriate boundaries and expectations and then following that up with warm enforcement is what separates a good consultant from a great one. I heard the story of how Elvis wanted to record Dolly Parton's “I Will Always Love You” and how as a young songwriter, she believed in herself enough to turn down what must have felt like a once-in-a-lifetime opportunity. The catch was that Elvis's manager wanted half the publishing. Dolly cried all night and said no anyway. She kept the song, and the song took care of her for the rest of her life. That's enforcement. She's also proof that generosity and boundaries aren't opposites. Her Imagination Library has given away over a hundred million books, on purpose, with a budget, as a program. When the board needs someone to tell me a no is still a no, however nicely I've dressed up the yes, it goes through her.

Where did the friction happen?

With everyone in the room, I got what I asked for. Just not the way I expected.

Things were shaping up nicely, built mostly out of Rodney's boring repeating pattern and Anthony's full-price hospitality. We had a plan to stop the unstructured feedback loop, put the history and the path forward in writing, and move delivery back to the consulting team where it belonged. Heads were nodding. And then John, being John, wanted to make the handoff feel like a gift.

“Send it with a sweetener. One more round of tweaks, on the house, as a thank-you for their patience. You close the free-work chapter and you close it with class.”

Dolly didn't even let the dust of that crusty suggestion settle before jumping in.

“Honey, no. One more free round is not a bow on the box. It is the box. That is the exact behavior we are retiring, and you don't retire a behavior by doing it one more time.” Then she said the thing I have been thinking about ever since: “If you want to be generous, be generous somewhere the generosity can be seen. Put every free hour you have already given on the next summary at full rate and bill it at zero. Generosity nobody can see isn't generosity. It's leakage with a nice story.”

Generosity nobody can see isn't generosity. It's leakage with a nice story.

Fred agreed, but from a completely different direction. “Think about what the sweetener feels like to receive. After all these months, another free gesture doesn't say we value you. It says we still feel guilty. It reopens the very question you are trying to close. What they need isn't another present. It's to watch you keep your word at a normal, boring, professional rhythm.”

And then Brené, quietly, with the one nobody asked for: “The sweetener isn't for the client. It's for you. It's how you avoid sitting in the discomfort of holding a boundary. You have been paying to skip that feeling for months. That's what the free work was.”

Ouch.

But as much as it stung to be called out by Brené Brown herself (the shame!), there still wasn't enough friction between the board and me. They were fighting with John, but no one was fighting with me. The board had basically aligned on my read of the situation and the general next steps I needed to put in motion. So the skill did the thing I built it to do, but in a way I didn't expect. It threw the flag and called for the steelman, but the steelman wasn't someone on the board. The strongest case against my whole plan, argued at full strength, actually ended up coming from the client's side of the table. To my client, I represent a vendor whose project ran long and is now introducing paperwork and a managed-services structure to try to patch things up. That boils down to the least flattering read of the situation: the people who broke the relationship finding a way to charge for the repair. If my response to the situation couldn't survive being received that way, then I wasn't ready to respond.

That reading changed my response. I had to acknowledge the history plainly, show the goodwill ledger at zero, and put the priced path forward in the client's hands as a choice instead of a bill. Not because the board told me what to say. Because the friction showed me who I was actually speaking to.

What did I learn?

As I sit in my office and write about all of this under a giant neon sign that says “Don't Over Think Shit,” I chuckle at the irony that someone who needs that reminder just built a tool to inject six new intentionally conflicting voices in his head. The sign (a super thoughtful gift from my incredible wife) is a replica of the one that hangs in The Cave, a YouTube series that documents how one of my favorite music producers, Kenny Beats, collaborates with his friends and fellow artists. But the reminder is too real for me as someone who struggles with anxiety. My anxiety's most sinister shape is a spiral. I've gotten good at free falling and looping endlessly through my most negative thoughts. But the loop is only endless because there is only one voice shouting these thoughts at me, unchallenged. The board is six voices that are designed to challenge each other and resolve.

The most useful answer came from the chair I didn't want to hear from. Brené called me out and I could write it off as “just the advice of an AI,” or I could reflect on a real observation about how I work and follow a less comfortable path. One that leads to growth. And that growth doesn't feel cheap or unearned. The machine didn't just hand me an answer to my problem that I accepted without question. The AI surfaced patterns and perspectives I hadn't thought of, but the decisions stayed mine. A single-answer tool structurally cannot produce that experience.

The most useful answer came from the chair I didn't want to hear from.

The honestly pretty anti-climactic ending to the story is that we got that thing back on the rails. I was able to meet with the client, set the warm boundaries, and transition the project back to the consulting team. The structure is what made it transferable. Unscoped favors can't be delegated. Scoped work can. The client even purchased a new block of hours to continue the high-value customization work we started and our partnership is stronger than ever.

It turns out the sign and the board were never really at war with each other. The sign tells me when to stop thinking and the board is what helps make stopping possible. A spiral has no last word. It goes on for forever if unopposed. A board meeting concludes. The six people on my team still have no idea they're on it, but they've already helped me achieve better outcomes. If you decide to build a board of your own, I'd genuinely love to hear who gets a chair.

FAILURES INCLUDED

Subscribe

New build stories, by email. Occasional, honest, easy to leave.