Understanding, Upgrades, & Uncertainty

Dear Leaders, Entrepreneurs, Dreamers, and Creators of Great Things: I write these Love Letters each month with the hope of bringing you a little encouragement, some marketing help, and a few minutes of joy. Whether we are already friends or have yet to meet, I hope you’ll enjoy my stories from the road and some awesomely random takeaways, tools, tips, and updates.

Understanding

Years ago, it was part of my role to prep speakers for corporate events.

Specifically, it was my role to prep American speakers who were coming into Canada to speak to Canadian audiences. And, as a dual citizen who has lived and worked on both sides of the border, I understood the small details that would often turn an audience off or keep a speaker from getting their point across.

One particular speaker repeatedly resisted the request for a prep call. Over and over, he would tell me that he’s fine, he’d spoken in Canada before, and he didn’t need my guidance or my advice – even though a prep call was a condition of his contract.

When the day came for him to take the stage, he opened with a joke that included both of the topics that I typically tell speakers to avoid at all costs. The joke fell flat, the audience was visibly annoyed, and it only went downhill from there. He had the worst feedback and ratings of any speaker at the conference.

It’s been over a decade since that event, and I still think about it often – usually when I am in prep calls with my own clients.

What I’ve come to realize is that his failure wasn’t just about a bad joke or a missed prep call—it was about arrogance over empathy. He assumed that just because something worked before, it would work again. But when we lead people—whether from a stage, a boardroom, or a storefront—we are not entitled to their trust, their attention, or their loyalty. We earn it by being willing to listen, to adapt, and to understand that what works in one context can fall flat in another.

The lesson is simple: expertise never excuses you from preparation. The minute you think you’re above learning, adjusting, or taking feedback, you’ve already started losing your impact. True leadership means showing up curious, not just confident. And when someone offers insight to help you connect more deeply with those you serve—take the call.

Upgrades

I remember the very first time I flew in an airplane. I was 15 years old- and headed for a year of studying in Europe. I knew nothing about air travel, and I found myself in a window seat, next to a man who was not even a little impressed by my excitement. As a first time flyer, everything was exciting, even the little trays that the meals came on. I will never forget that first flight, when everything was so new and interesting.

These days, I am considered a “frequent flyer,” averaging 90+ legs a year legs a year. I am one of those people who parks in the same place at the airport, knows how to get through customs and security quickly, and has the packing thing down to a science. I know how to sweet-talk the flight attendants into extra Biscoffs and which seats not to book on almost any model of Boeing aircraft. And I know exactly how long it takes to run in heels from Terminal 1, Concourse H to Terminal 3, Concourse C at Chicago O’Hare. (Hint, it takes about 2 minutes longer than you need, and no, they will not hold the door.)

But, it took about 4 years of this kind of travel before I started receiving the holy grail of travel rewards – the complimentary upgrade. Finally, I was one of those people. You know, the ones you walk past on the way to the back. You avert your eyes and pretend you don’t even care that you are not one of them. You don’t need those comfy blankets or cozy seats. You don’t even care that they are being offered champagne and juice in front of your very eyes, as you struggle to fold yourself like human origami into a seat built for someone without legs. But the truth is, you are seething with envy the entire time.

This upgrade thing has happened often enough that I have a really good understanding of what it’s like. (It’s heaven. Straight up.) Recently, on a particularly long, early morning flight, I was upgraded to a lie-flat pod. The angels sang, the sun poured down, and everything was new and exciting and fun again, just like that flight when I was 15. And for six hours, I totally loved air travel again. (Yes, I’ll have the salmon, how kind of you to ask. Champagne? Why not?!) And as I sat there, in my little bubble of personal space, I looked out the window and considered a few things.

Imagine if I felt like this all the time? Imagine if my life was full of customer experiences that made me feel like I was in first class? Would it change me? Would I be happier? Would I start to take them for granted? Now, it should be noted that I was not upgraded on the return flight, so it’s safe to say my normal person status is still firmly intact. But I still think back on that flight and I wonder if I’ll ever really feel the same about economy travel again.

The question is, do your customers feel like they have been upgraded? Do they use your services as a benchmark? Every time someone works with you, do they feel as if they are sipping champagne under a comfy blanket? Do they feel as if they are personally attended to and cared about, rather than lumped in with all the others on the same journey? These are questions that could be asked about any industry, really. And it’s not that hard to make people feel special these days. In a world full of self-checkouts and SlyDial, it just takes that little bit of extra personal attention. And y’all, once you get a taste of that kind of service experience, you’ll pay more for it. And that is the truth.

This is where I share the good stuff.

… the latest websites, books, & tools that are inspiring me, the people who are making me smile, and the stuff I have been writing on sticky notes.

“People will choose unhappiness over uncertainty.” – Tim Ferriss

“Marketing rule of thumb: If everyone else is doing it, don’t do it.” – Alex Hormozi

“Learning and innovation go hand in hand. The arrogance of success is to think that what you did yesterday will be sufficient for tomorrow.” – William Pollard

“Life is shorter than you think. Love is important. But passion is most important of all. The things that will mean the most, in the end, are the ones that made your toes curl and set your hair on fire. Get looking for those as soon as you can.” – Grams

Thanks for reading, friends! If you want to get these in your inbox every month, be sure to get on the mailing list. And if you are looking for a speaker who will motivate your organization to get up, get moving, and face change head-on, I would love to chat.