The Dance of Meetings

A Second Annual reflection on +300 individual chats

Welcome to the latest entry in The Workaround. You’re in good company with thousands of fellow entrepreneurs and innovators!

I’m Bob, your host. My mission here is to share personal, behind-the-scenes stories of the ups and downs of my career leading tech startups and corporate innovation.

I write to make you think, smile, and discover a shortcut to success or a trap to avoid.

Here we go…

You can find me at The Coffee Emporium in downtown Cincinnati for one of our in-person meetings. I’m the tall guy with brown hair who sits without a laptop and usually wears something blue.

We all know there are 365 days or 525,600 minutes in a year…But how should we best measure a year in our work+life?

For me, it’s the number of people I met with.

These key moments of presence, our melding of minds—whether in person or on Zoom, with old friends or new—increasingly feel like the most important parts of my day.

Last year, I began tracking meetings on a simple spreadsheet and shared the results in my end-of-2023 post. As another year ends, I’ve crunched the numbers again. But, as tends to happen, my gut feeling when looking back is much more meaningful than the data.

How I Met

I am most interested in how many people I had “meaningful interactions” with around business topics. “Meaningful” means we’ve gotten to know each other—moving past slide decks and small talk, and usually in no more than groups of two or three people. I exclude regular team meetings, 1-on-1s, and client check-ins. I counted get-togethers with friends if one or more of us had a juicy work topic to discuss. Finally, when I say “number of meetings,” I mean how many people I met. For example, meeting with the same person twice in a year is counted as two meetings.

Here’s this year’s totals:

• 307 Total Meetings—This is a big decline from the 421 people I met in 2023. Still, it’s easy to explain: Last year, I got two businesses off the ground, which involved many discovery conversations and personal pitching. As my role evolves at Fleet, I’m less directly involved in launching our businesses. However, I still met an average of 1.2 people per working day.

• Spring’s the Thing—March, April, and May continue to be peak months of my meetings. It fits with a natural seasonality of business—and life. We start the year with fresh hopes, dreams, and plans. And we’re saving our vacation time for summer and the holidays.

• 69% Virtual—I jumped on Zoom, Teams, or Meet most of the time. However, this was down from 76% virtual in 2023. I made a real effort to get together in person more often this year, practicing what I wrote about this May. I especially look forward to recurring conferences and community events, where I can get three-dimensional with several people over a few compressed days.

• 51% New Relationships—This was the biggest surprise, especially because it increased from 42% in 2023. Looking back, many of my new relationships came from people who found me through LinkedIn or Substack. I added 1,500 subscribers this year, which brought in more new clicks on my Office Hours calendar link. Several old friends reconnected with me by reading my writing here and thoughtfully introduced me to people in their networks.

Reviewing my tracking sheet and revisiting my calendar took about an hour. If you’d like to try it, here’s a link to a Google Sheet that you can use.

My Takeaway: Enjoy the Dance

A few months ago, I finished my third meeting of the day and reflected on their differences.

The first was a bit clumsy as we failed to find a connection. I think my meeting partner was nervous. In the second, I got pushed to buy something I was not in the market for. That meeting ended early.

But the third meeting was like a work of art. We both quickly got into sync and traded insights and ideas, and we were truly disappointed when our calendars forced us to finally break it off.

They all felt like a dance.

Now, dancing might bring unwelcome memories to many readers. I still get sweaty thinking back to middle school dances and the awkwardness of asking one of the flowers on the wall to join me under the slow dance spotlight.

I got more comfortable dancing once I had a girlfriend and then a wife. Stephanie and I got into Swing Dancing in New York City in the late ‘90s. I loosened up, learned a few moves, and gained confidence. I’m no Lord of the Dance Floor, but I can hold my own and sync with a range of partners—whether at a wedding or honkey tonk.

This dance analogy kept coming to mind in meetings…

You never know how it will go until you get on the floor together.

It’s best approached with a smile and positive intent.

Facial expressions mirror, breathing syncs, and smiles beget smiles.

We dance to old music and meet to an agenda or topic—but each dance or conversation is an original creation.

Things don’t go well if you’re too scripted or pushy. A dance is balanced.

The less thinking, analysis, and self-doubt, the better it will feel.

Someone has to lead the dance or conversation. That’s just part of the game.

A great dance or meeting involves Love—not necessarily in a romantic way, but in Love for a fellow human. Love as the opposite of Fear. We let our guard down and make ourselves vulnerable for a few moments, allowing us to connect as the social creatures we are.

Eventually, our time is up, and our meeting ends before the magic is lost.

And looking back, the best meetings—like dances—created a kind of original artwork that we may look back on and treasure.

“When you meet with people, at work or wherever it may be, give them your fullest attention. The field of awareness that arises between you becomes the primary purpose for the interaction. It does not mean you neglect whatever needs to be done on a practical level. In fact, the doing unfolds not only more easily, but more powerfully when the dimension of Being is acknowledged and so becomes primary.”—Eckhardt Tolle, A New Earth

The Art of the Meeting Dance

I’ve been working to be a better partner in my meetings.

I don’t “sell” anything anymore. While I’m happy to discuss how my companies could help solve clients’ problems, I’ve stopped pushing people to sign on the dotted line.

I bring fewer expectations into meetings. In square dancing, you have seconds between seeing your partner for the first time and swinging them around the room. That helps minimize any prejudices and awkwardness. Now I go into meetings with no prep—except a mentality of, “Let’s see where this goes!”

I let others lead more often. By “leading less,” I mean “listening more.” A good dance or meeting partner pays attention to the other person and senses where they want to go.

And I bring more of the spirit of play. You’ll see me smiling and laughing more than I used to. As I get older, I gain more appreciation for the value of human connection. I guess I’m “the old guy in the club now” and get energized whenever people want to take my hand. The real purpose of this game of life is to have fun together.

So, put on your meeting shoes and prepare for more meaningful moments in the year ahead. If your dance card isn’t full, I’d be honored if you scheduled time on my calendar. I have no idea what we’ll talk about—and I don’t care!—but I’m confident we’ll have a good time.

“What I really enjoy is not you; it’s something that’s greater than both you and me. It is something that I discovered, a kind of symphony, a kind of orchestra that plays one melody in your presence, but when you depart, the orchestra doesn’t stop. When I meet someone else, it plays another melody, which is also very delightful. And when I’m alone, it continues to play. There’s a great repertoire and it never ceases to play.—Anthony de Mello

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How we might work together…

• Are you interested in launching your own consulting or service business or need help taking your current services business to the next level? Fleet is our holding company for services, and we’re actively looking to build business partnerships with winning leaders. Let’s talk!

• Need guidance with revenue alignment or revenue growth management? We built Revelin to serve organizations through fractional and project-based execution. We specialize in GTM alignment, CRM optimization, territory design, annual planning, M&A integration, and building your RevOps function to support growth. Schedule your revenue assessment.

• My team and I lead Hearty, a boutique recruiting service that helps tech-forward companies hire proven talent. Our senior team of operators sources and screens, saving you time and money. When you need help, let’s chat.

• Do you need help with a software project? Perhaps a product MVP, a project that requires outside help, or a fractional CTO for key strategic decisions? Our team at Shipwright Studio has worked together to build multiple successful startups. We love helping leaders turn their dreams into reality, and our clients trust us for software built to last.

• Are you looking for Influencer Marketing and Content Creation? By popular demand, the team from our previous company is back with A2 Influence. We’re ramping up now and would love to share more.

• Feel free to schedule a time during my Office Hours to discuss questions, feedback, networking, or any other topic. You can also reach me on LinkedIn or by email.

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BONUS: Cool Content of the Week

A little something I found meaningful. You might agree…

My Favorite Stories of the Year

One of the fun things about following a bunch of killer writers on Substack is borrowing their tactics. Joe Hovde was the first one I saw list his favorite writing of the year. Now it’s my turn…

I picked the following based on what I enjoyed writing and what readers complimented most.

Don't Follow Mentors, Seek Signposts—My story about an amazing college professor, which afterward led to a connection with his daughter here on Substack.

The Five Worst Pieces of Startup Advice I Received—A must-read if you’re in the startup game or thinking about jumping in.

The Four Keys to a High-Performing Organization—This is my model for building and growing companies where people accomplish greatness together and love the journey.

Mind on your Money, Time, and Freedom—Great read if you’re looking for some New Year’s Resolutions.

The Reference Check Where I Lied—A real-world ethical dilemma…What would you do in my shoes?

Threatening to Quit for What You Believe In—If you haven’t done this, you’re missing a big square on the BINGO card of work+life. Read this one when you need a sip of courage in a corporate situation.

Thank you for finding and/or sticking with my writing in 2024. There is nothing I enjoy more than crafting and sharing these stories and suggestions. Every week, I get notes from people who say a certain post was just what they needed to hear at that moment. Your moment is probably coming…

Bob