Monthly Commentary

May 2026

In both sales and client service, most new managers and supervisors are promoted as a result of progressing from individual contributor roles. Ideally, the senior managers making these decisions are experienced enough to recognize that it’s often more effective to place new leaders in charge of a different team within the same business unit, so they aren’t managing their former colleagues.

This approach works well for a couple of reasons. Their coworkers likely respect them, otherwise they wouldn’t be considered for promotion in the first place. It’s also common for the individual being promoted to have mentored many of the team members, demonstrating the leadership skills needed for the role. However, especially in sales, the assertive, and sometimes aggressive, traits that make someone a top performer can also create friction within a team. Starting with a “clean slate,” without previously exposed flaws, often makes for a smoother transition.

In a not-always-perfect world, new managers are sometimes hired from outside the organization or division. This can be intentional—an effort to bring fresh ideas into the business unit—or simply the result of not having enough qualified internal candidates. The latter was the case in my last corporate leadership role, when I was transferred from a legacy department into a relatively new sales organization within the same company.

Although the product itself wasn’t new, the company had decided to move up-market, creating a sales organization focused on larger, higher-revenue business clients. In this case, all of the sales representatives hired into the division were experienced, and most had already enjoyed a high level of success. The training classes held monthly at corporate headquarters felt more like advanced coursework than the basic skills typically taught to first-time sales reps. However, most of these reps came from highly transactional sales environments, with little to no experience in strategic selling.

Senior managers are often invited to corporate headquarters to serve as guest trainers during these sessions. Many see this as a good opportunity to sharpen their skills—at making excuses for why they can’t attend. The travel can be exhausting, and a week at the home office with no flights or hotel rooms is not only welcomed, but probably deserved.

Since I was new to the division, I did just the opposite and volunteered to guest train as often as I could. This wasn’t altruistic. I saw it as an opportunity to identify the characteristics that led to success in this new initiative, while also giving myself a crash course in the product.

As mentioned, these were highly successful transactional reps, while my background was more rooted in enterprise-level, strategic sales. I knew I could offer some value, as these professionals would need to develop new word tracks and scripts—and adjust to a much longer sales cycle with far fewer prospects to convert into clients.

The differences were immediately obvious. On the first day, the discussion began with the group brainstorming what had made them successful in the past. Early on, I had to delicately challenge one common tactic: offering prospective clients a “free estimate.” In most cases, a CFO authorizing a $50,000 purchase isn’t expecting to pay for a proposal, but they are expecting something thoughtful, thorough, and credible. The language matters.

As the session continued, the conversation shifted to cold-calling techniques, and one eager participant asked the group who had the best scripts to “trick” prospects into agreeing to a meeting. Their classmates were more than willing to share. One rep described a tactic he used when calling existing clients to upsell additional products. He would leave a voicemail designed to create urgency: “I see something strange in your account that I need to speak with you about.” “Guaranteed callback,” he said confidently.

So what did he say when the client returned the call, often with some level of concern? “What I saw is that you haven’t signed up for this new product yet.”

I asked them to stop using that approach immediately. Keep in mind, most of these participants only saw me as a manager. They didn’t know I had already spent decades in sales, so when I suggested a different approach, it was met with a healthy dose of skepticism. They asked how I would handle it instead.

I told them my approach would be much simpler: “Hi, this is Bob. Are you happy with the service we currently provide? If I had an additional solution that could benefit you, would you be open to hearing about it?” Laughter followed as they dismissed it almost instantly. “That will never work,” someone said.

Funny, I thought. It’s worked pretty well for over 25 years.

They were looking for shortcuts—ways to get more clients with less effort—instead of investing the time to identify the ones who genuinely needed what they were offering. That instinct isn’t unique to sales. It shows up in leadership, in client service, and in just about any role where results matter. The temptation to find a faster, easier path is always there, and sometimes it even works—at least in the short term. But over time, people tend to recognize the difference between being guided and being maneuvered. One builds confidence, the other creates doubt.

The longer path of asking direct questions, being transparent about your intent, and giving the other person the space to decide doesn’t always produce immediate results. It can feel slower, even inefficient. But it tends to lead to better conversations, stronger relationships, and outcomes that last longer than a single transaction. In the end, it may be less about finding a better way to “get” the meeting and more about doing it in a way that actually holds up once you’re there.

April 2026

When I lived up north, I knew families that set up special savings accounts designed specifically to fund an Orlando vacation. They would make small weekly deposits for years so their kids could eventually experience a magical week, surrounded by a princess, some dwarfs, a big mouse or two, and a cast of oversized animal characters.

I was always fascinated by their discipline, and even more impressed that they were willing to make a series of small sacrifices that would ultimately result in the experience of a lifetime for their family.

Disney World, Universal Studios, Sea World, and countless smaller attractions and water parks make Central Florida the self-proclaimed theme park capital of the world. When I was given the opportunity to transfer to Orlando in the late nineties, I wasted no time accepting the position, assuming there would be an endless supply of entertainment options waiting for me in my free time.

In the 29 years I’ve lived here, I’ve been to the Magic Kingdom twice.

But that’s okay. I realized early on, living in the northern suburbs of the Orlando metropolitan area, that this was a real city too. There would be plenty to do and experience without venturing into the crowded tourist corridor south of downtown. Still… twice?

In addition to the theme parks, the space industry is big business in our area, and the Kennedy Space Center offers a unique blend of entertainment and education. The visitor complex is just over an hour from my home, and as of December of last year, I had walked those grounds exactly zero times as a resident. My only visit prior to that was in 1979, when I sat through a presentation describing the goal of launching a spaceship like a rocket and landing it like a plane. My father and I were convinced the engineers had a few screws loose.

Driving past the Space Complex? Probably a hundred times, without exaggeration.

Coming back from a late-December cruise, my wife and I decided to make a quick ten-minute detour and finally check out the exhibits. About an hour into our self-guided tour, we came across an IMAX theater with a sign that read, “Next Show at 11:00 a.m.” The timing was perfect. We figured we’d get out of the sun for a bit and watch a cool movie, maybe even sit in one of those seats that shake and make you feel like you’re actually in the rocket.

The theater was packed with both adults and children, all waiting with anticipation for the lights to dim and the show to begin. Apparently, none of us read the fine print. Instead of a movie, they were using the theater for a lecture. A woman with a microphone and a diminutive gentleman—fit, but clearly in his seventies or eighties—took the stage. Once it became apparent there would be no 3D thrills, some people quietly made their way to the exits.

We had middle seats, so leaving would have been both a distraction and a bit rude. We decided to stay and give it a chance. I’m certainly glad we did, as it turned out to be one of the highlights of the entire trip.

Sherwood “Woody” Spring, the man dressed in the astronaut suit, spent over 165 hours in space, including serving as a mission specialist in December of 1985. His shuttle assignment came just one mission before the Challenger disaster the following month. For the next hour, Woody shared story after story, some inspiring, some harrowing, about his time as a Navy test pilot and his journey to becoming an astronaut.

After the talk, I quickly looked him up to learn more about his life, then took advantage of the “meet and greet” autograph session next door.

There was no line. Just my wife, Woody, and me.

Although I could sense his disappointment with the turnout, I used the opportunity to ask more questions than I probably would have been allowed otherwise, and I walked away even more impressed.

It struck me afterward how easy it is to separate “entertainment” from “education,” as if they belong in completely different categories. Sometimes the most memorable experiences are the ones that quietly deliver both at the same time. We walked into that theater expecting a show, and instead found a story, a lesson, and a moment we’ll talk about far longer than any simulated rocket ride.

The truth is, opportunities like that are all around us. They don’t always come with flashing lights or long lines. Often, they’re sitting right there in plain sight—waiting for us to slow down, pay attention, and realize that the best experiences aren’t just entertaining… they’re meaningful too.

March 2026

“Sign here, press hard, pink copy is yours.”

That was always the joke we used when discussing the “best” way to close a deal with a prospective client, the joke being that we skipped the hard part: identifying needs and presenting solutions.

My first sales job required no legal agreements. It was a service business, and our founder didn’t believe in term contracts. Instead, he believed we needed to earn the client’s business every day. If we fell short of expectations, we deserved to be fired. As the business evolved and products began incorporating the electronic movement of money, there became a need to outline responsibilities more formally. Even then, with minimal notice, the client was free to leave whenever they chose.

While it was much easier to get a verbal “yes” and a handshake, we knew we needed to adjust our approach (hence the pink copy joke) with the introduction of client service agreements. We learned quickly that sliding a contract across the table and staring awkwardly while a prospect read a legal document was not only uncomfortable, it also put the deal at risk, often killing any chance of a one-call close.

One evening, I took the contract home, read it in full, and wrote out word tracks to summarize each section. My new approach was simple: hold the document in my left hand, point to each paragraph with a pen in my right, and walk the client through it in plain English. With a memorized script, I could put them at ease while reinforcing a key point, we had no long-term commitment requirement if we failed to deliver. I used that approach for years and trained others to do the same.

Then something changed, and you can probably blame Apple.

With the introduction of the iTunes Store, buying a $1.29 song required agreeing to the “Apple Media Services Terms and Conditions”, a document totaling 8,459 words. For context, that’s roughly a quarter of a typical paperback book. To spend just over a dollar, you’re expected to read something approaching book length.

A cynical person might say that was intentional, make it so long that no one reads it. If it were only a few hundred words, someone might actually notice details like the limit on how many playlists a file can be used in. (No, I didn’t know that either.)

Which got me thinking about all the things we sign, physically or electronically, every single day.

Just this week, I had two morning appointments outside of work: a doctor’s visit and a trip to the car dealer for service. At the doctor’s office, I was handed six electronic documents to read and sign. At the dealership, a routine oil change and tire rotation somehow resulted in three copies of the same document, five pages each, with multiple initials and signatures required.

I should have had a clue when I noticed four paper shredding bins positioned near the service advisor’s desk.

I read none of it.

And the honest question is, did I really have a choice? If I disagreed, would they have held my keys hostage?

In my first book, I wrote a chapter called Belts and Suspenders, comparing excessive caution to unnecessary risk. If a car dealer can’t change oil and rotate tires without protecting itself with 15 pages of legal language, the issue probably isn’t the customer, it’s the process. Adding suspenders when you’re already wearing a belt rarely solves the real problem.

Somewhere along the way, contracts stopped being about clarity and started becoming about protection. The irony is that the more we add, the less anyone actually understands. And when that happens, the signature becomes less about agreement and more about necessity. We sign not because we’ve reviewed the terms, but because we don’t have much of a choice.