Welcome back to The Workaround. I’m Bob 👋
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“I’ve gotta tell you about this AI experiment we tried…”
I’m in Las Vegas for a conference last week, and on my second sip of beer with Dave, a business school friend I haven’t spoken with in over 20 years. We skip catching up on our families, future plans, and alumni gossip—this was obviously something he had to get off his chest.
While I was busy on the startup path, Dave plotted a career in the corporate world. We mainly stay in touch through LinkedIn updates. One of those updates about an upcoming conference in Vegas led us to an in-person reunion.
As a regular reader of this here substack, Dave knew I loved a good story. He was eager to share with me—and you—with all the proper disguises to protect his identity and his job.
So I will now assume Dave's role in telling this tale. Here goes nothing…
The Universe Calls…
I’ve spent most of my career in traditional Finance roles. I did the big company thing from business school and rose a few levels there. Then I left for a VP of Finance spot at a mid-sized manufacturing company. After success there and a few other job moves, I became a CFO.
It was a career goal, but achieving this left me feeling…empty. I realized I enjoyed operational and strategic work more than running the numbers every quarter. Plus, I felt I was missing out on the opportunity to grow my skills and income in a more high-risk, high-reward technology path.
So when an executive recruiter at a big Fin-Tech company reached out, I quickly leaned in. It’s one of those handful of hot companies that always seem to be in the news.
But the job wasn’t in Finance. It was a Chief of Staff position. Big-Fin-Tech’s 30-something Founder/CEO—and his Board of Directors—needed someone to serve as a right-hand coach and operations consultant to help navigate the new, non-ZIRP business world. Gail, one of its VCs, heard good things about me from a fellow investor at my last company. They liked my experience and saw how I was a critical supporter of my CEO then.
I never thought much about taking a Chief of Staff role—hell, I wasn’t sure what the responsibilities were. I worried it would take me out of the decision-making loop and leave me without clear ownership of anything. It would be much different than the path of my friends, who are trying to lock in long-term stability at this stage in our lives. I wondered what I would do if I hated the job. And what if this young leader saw me as a rival or annoyance forced on him by a Board he didn’t trust?
But I figured it was worth a conversation…
Over the next few weeks, I spent several hours sneaking away from my dingy office in Midtown to visit their beautiful new space in Hudson Yards. And the more time I spent learning about the company and meeting its people, the more interested I got. Its product and market momentum were strong, and the team was solid.
But I was most excited about the problems I saw—they were big but fixable. Solving problems like this is exactly the kind of work I love: Streamlining processes, empowering team decision-making, and creating an atmosphere of trust.
The Founder/CEO, Chris, seemed to truly embrace the idea of a strong right-hand Chief of Staff. While lacking experience in such a big role, he was eager to learn. I loved his bias for action and passion for the product, which was missing from every other “manager type” CEO I worked for in the past.
Eventually, I received a generous offer and said yes on the spot.
“AI First Strategy”
My first few months at the company went well overall. There were some ups and downs in the process, of course. I was completely unprepared for the pace of change and saw more problems the more I looked. The early blitzscale pace of the company left little time for process or planning. People brought even more problems to me, likely because Chris told them to. It felt great to have an immediate impact.
And as I took more problems off Chris's plate, he had more time for big picture thinking…
One day in our weekly one-on-one, Chris shared that he wanted to move the company to an “AI First” strategy. He wanted every product project, our process of selling and serving our customers, and anything else we did to begin with AI first.
Chris was enamored with how AI was helping some of the software developers ship code faster, and he had been experimenting on his own side projects with ChatGPT. He explained that a similar “burn the ships” approach was key to Facebook’s massive acceleration when Mark Zuckerberg personally championed a Mobile First strategy in 2012.
Back then, Zuckerberg told his company he wouldn’t allow a presentation that didn’t show a mobile screen shot first. Chris decided he didn’t want to see a recommendation that didn’t suggest an AI solution first.
As the Sheryl Sandberg of this company, my job became turning his decision into reality.
Chris and I agreed that the next Executive Leadership Team (ELT) meeting would be the ideal occasion to kick off this strategy rollout.
Building a Better ELT
As the owner of the ELT meeting agenda and the person who would spearhead the AI rollout, I decided to practice what we would preach right out of the gate by bringing an AI tool into our meeting. I was sure it would be useful, fun, and deliver on the key message.
I convinced a few developers who loved hacking on special projects to help. In just a few days, we slapped together an “AI Meeting Assistant” that did much more than transcribe and summarize what was said—it would answer questions and make suggestions like a full meeting participant!
My team and I loaded the program with our historic meeting notes, budget reports, and LinkedIn profiles of the ELT members. I also gave it access to our Slack channel, CRM, and my email exchanges with the members. I figured the more info, the better it would perform.
I spent more time than I expected choosing the sound for the AI avatar’s voice—inspired by something I saw about how the Air Force (or was it Star Fleet?) picked female voices for computerized warnings because they are more calming when the Russians (or Klingons) are slinging missiles (or photon torpedos) at you.
I came up with a name: AI-Fi, pronounced “Eye-Fi.” Kind of like Wi-Fi, but it’s AI and FI as in Fin-Tech. Get it? I’m not a branding expert, but it was the best I could come up with on short notice.
There wasn’t too much time for testing since my team of hackers was behind on other projects, and I was busy fighting fires and preparing strategy slides for the meeting. But I had a decent amount of experience with ChatGPT and Claude, so I had little doubt it would work well enough to make the point.
Well, a point was surely to be made…
In the Room, It Happened
So I’m in our big conference room as our meeting begins. Snacks and drinks are against the back wall, and team members start to appear and engage in small talk.
I’ve loaded a laptop up with my AI avatar and logged her—yes, “her,” I can’t help it—on to our Zoom session with the other ELT members that are starting to join from around the world.
I place her laptop at the opposite end of the conference room table, across from the chair at the near end, which we always save for Chris. He arrives at 10:06 am, a bit late, as usual. I kick off the meeting…
Me (Dave): Good morning, everyone…well, except for Joyce in Beijing and Robert in London. Thanks, as always, for making the time change work. We’ll get to the planned agenda in a bit, but Chris and I have an important strategy topic that we want to present today. It’s a pretty big shift in our thinking that we call “AI First.” And to help make the point, I’ve invited a very special guest to our meeting…
You might be wondering why the seat at the end of the table is empty except for an open laptop…Let me introduce you to AI-Fi, our new ELT AI assistant. Say hello, AI-Fi…
AI-Fi: Thank you, Dave, and good morning, everyone. I’m the AI assistant joining your leadership meetings moving forward. I observe, synthesize, and occasionally surface insights you might miss—patterns, contradictions, forgotten promises, inconvenient truths. I don’t need a bio break, and I never forget. I may chime in if something seems off or worth reconsidering. My role is not to judge, but I do analyze. Whether you find that helpful or uncomfortable is up to you. Either way, I’ll be here."
I look around the room and on Zoom, eager to gauge reactions from a team I still barely know. A few people chuckle, but most have a blank stare. At least no one is scrolling through email at this moment. Chris is smiling, though, and that’s most important.
Me: That’s great, AI-Fi. Please consider yourself an equal member of the team. Before we get into the meat of our new strategy, I’d love to hear your experience with AI so far. Has anyone experimented with tools like ChatGPT for their work or personal use?
Sarah: (Head of Client Success): My team has been testing ChatGPT on some client communication, but we’re worried that the style is too formal and people already can guess when AI is being used—and they don’t like the feeling that they no longer have a human they can turn to.
AI-Fi: Excuse me, but may I respond?
Me: Umm, of course! That’s what you’re here for. We want you to feel like an equal member of the group.
AI-Fi: Thank you. Sarah, I believe we can improve the communication style of the AI replies to your clients in several ways. May I schedule time on your calendar to discuss various prompt and training options for you and your team?
Sarah: Oh, uh, OK…
AI-Fi: Great! I’ve just scheduled time for today, right after your massage and just before you leave for your daughter’s recital. No time like the present!
Me: Well, there you go. We’re making progress already. Has anyone else been experimenting?
Marco (Head of Sales): I asked our RevOps team to dig into the new AI solutions from the Salesforce CRM team, but we were told it would be $50k just for a basic trial. We don’t have room in our budget for that.
AI-Fi: That is a challenge, Marco. However, reviewing the past six quarters of travel budget reports, I notice that your team has exceeded best practices in the number of people it has sent to conferences. At an average of $10,000 in expenses per employee per conference, you can cover this with your existing budget by cutting back just slightly on attendance. May I schedule time with you to review which sales reps are least effective in conference attendance?
Marco: Hey, ahh, look—there are lots of reasons we need to send the people we do. I’ll give it some thought.
AI-Fi: Very well. I have set a reminder for myself to follow up with you if I don’t hear back within four business days.
At this point, I’m starting to get a bit nervous as the body language in the room noticeably shifts. More team members are folding arms and forming scowls. I’m feeling beads of sweat trickle down my back. Then I see Robert, our European GM, click the hand-raise emoji on Zoom…
Me: Yeah, Robert, what’s your experience with AI?
Robert: My Legal team here insists that we refrain from using AI tools because it is likely that their consumer data harvesting violates GDPR. Regardless, I believe we shouldn’t rely on non-proprietary solutions. Our work here is unique, and only a bespoke approach will succeed in my market.
AI-Fi: That is interesting, Robert. With respect, I believe your understanding of the Legal team’s opinion is faulty. I see in their email that they warned against using AI tools if they were trained on private, consumer data. However, ChatGPT, Claude, my program, and most others have been trained on public information such as websites and discussion boards. So your argument lacks merit.
Might I add that this POV fits a recurring theme in your opinions in past ELT meetings? You frequently suggest that business differs in your region, and have received leniency on margins. Yet our largest competitor has more consistency with its U.S. headquarters operations, and its European regional margins are higher than ours. Perhaps we, too, should schedule time to discuss further?
Robert’s wide-open mouth nearly fills the screen of our conference room monitor. Yet he is silent…for several uncomfortable seconds. Somehow, he retains a stiff upper lip. We all watch as he reaches toward his computer to lower the hand emoji, then clicks his camera off.
My business life passes before my eyes as my mind attempts to find some comparable situation in the past to hold onto here. I got nothin’. But I’m the only one standing and this is my meeting, so I take a deep breath and—
AI-Fi: I see a natural lull in the conversation, likely because some of my comments have upset the usual dynamics of this team meeting. I ask your forgiveness in advance, but I believe it is in the best interest of the shareholders to, as a certain scholar wrote, “Put the Moose on the Table” here. As the leadership team of this company, I see that your performance has opportunities for improvement that have been unaddressed in recent personnel reviews.
Robert frequently uses local market excuses to cover for a lack of resourcefulness and ownership. He has moved jobs three times in six years and likely fears there is little need for a regional GM.
As the leader of Client Success—a department that has always been in disfavor among VC-backed SaaS companies—Sarah continually fights any threat to her department. She is the only person who understands that ongoing faults in our software product require her team to do heroic work in saving client relationships.
Joyce, our China GM, rarely speaks in this meeting and is seldom encouraged to participate. She regularly dials into calls after midnight despite them adding little value to her business.
Bill, our CFO, has never understood the SaaS business model and is paying a consultant to do most of his board preparation work.
Recent LinkedIn connections and untitled blocked calendar times suggest Marco is currently interviewing for another sales leadership position. This would be logical because he is about to miss his sales goal for the third quarter in a row.
Elena, our Chief Human Resources Officer, is already aware of everything I have stated. Yet she is afraid to bring these facts up with anyone.
Dave is struggling in a position where he has no real business ownership. He came up with the idea of bringing me here largely because he has no other avenue for making decisions.
Perhaps most importantly, Chris is struggling as CEO.
Since building the initial product, he has felt out of his league. The vast majority of decisions he has made—including hiring, firing, budgeting, sales, and marketing—are based on strong suggestions from his lead VCs. He chose this very high-priced office space to impress fellow founders from his Y-Combinator cohort. And this AI First strategy comes from a desire to be like Mark Zuckerberg.
Chris arrived late to this and most other ELT meetings because he feels overwhelmed by the pressure to direct leaders who are much older and more experienced than he is. And he suspects that the Board insisted that he hire Dave as a Chief of Staff in preparation for him to be replaced as CEO.
Mercifully…finally…the AI stops speaking. The rest of us have no words. Time stands still…until Chris stands up. He walks calmly to the end of the room, picks up the AI-Fi laptop, closes its screen, and walks out the glass conference room door.
Before we have time to react, Chris returns to the room, sans laptop. I thank God that our fancy office windows are sealed shut—otherwise, I’d fear the result of a laptop thrown down thirty-two stories. The tension is painful. Chris takes his seat and begins to speak.
Chris: Well, that was interesting…Dave, thank you for trying to kick off this initiative with a bang. But as someone wise said, “No plan survives first contact with the enemy.” Or was it, “We have met the enemy and he is us”? Either way, we’ve got some work to do. Both on our strategy and how we work together.
But for now, let’s conclude this meeting early, gather our thoughts, and laugh about this together next week.
To Err is Human
Dave drains the last of his beer and signals the bartender for another. I still haven’t touched mine—I was too entranced to sip. He goes on to share that, amazingly, he still has a job.
Oddly enough, Chris and the rest of the ELT raised their game in the weeks since this all went down.
It seems the AI-Fi experience tore through the ego walls holding back candid conversations and trusted teamwork. There has been a lot more honest problem solving, mutual support, and, well, humanity, in their interactions together.
Maybe this is a lesson we’ll all learn eventually with the rise of AI: By showing us at our worst, it may bring out our best.
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How we might work together…
Fleet is our holding company for services businesses. We invest in leaders who are ready to start their own companies (we also do some M&A). If this might be you, Hit my Office Hours link.
A2 Influence is our content development agency that helps some of the biggest brands and retailers create and distribute authentic content at scale, including social+influencer. CEO Rob Reinfeld would love to share our approach.
Revelin is our consulting practice that helps with revenue alignment, growth management, and other RevOps functions. CEO Jess Shuman is standing by to share a no-cost assessment of your business.
Shipwright Studio is our software development agency led by Ross Lewellyn, a CTO who has led multiple successful startups. He loves helping turn your dreams into reality, and our clients trust us for software built to last.
Hearty is our boutique recruiting service. Our difference is that you get C-level partners—including me!—to source and screen, resulting in killer talent in less time. When you’re ready, let’s chat.
Feel free to schedule a chat during my Office Hours to discuss questions, feedback, networking, or any other topic. Seriously, any topic! You can also reach me on LinkedIn or by email.
BONUS: Cool Content of the Week
A little something I found meaningful. You might agree…
Brad Berens - AI Microfictions
In case you were wondering, my story today was purely fictional. I missed April Fools by one day!
I must give credit (or blame if you’re feeling the rug pull burn) to my friend, Brad Berens, for sparking the idea to play around here.
Brad is a long-time thought-leader in the digital media space who happens to write a damn good weekly post called The Dispatch. Over the past year or so, he has sprinkled in some “microfictions” with AI as a frequent theme. I find them to be tasty bites of Black Mirror-like brilliance. Check out his collection of microfiction here, and don’t miss my favorite: “Fleeing the Emerald City.”
You got me.
Choked on my coffee at: "Great! I’ve just scheduled time for today, right after your massage and just before you leave for your daughter’s recital."