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Taking a Client to the Game This Summer? Read This First.
Published 25 days ago • 4 min read
Hello Reader,
I'll be the first to admit it: I am probably the last person you'd picture courtside or in the bleachers. I'm an arts person. Give me a gallery opening, a theatre performance, live music - and I am completely in my element.
And yet, one of my most memorable professional evenings happened at a hockey game.
When I was invited to sit on the Rogers Communications President's Advisory Board a few years ago, they treated us to an evening at the ACC (now Scotiabank Arena).
Transportation was arranged. A beautiful hotel downtown Toronto was covered for the night. And what unfolded over the course of that evening wasn't just a game - it was some of the most genuine, meaningful relationship-building I've ever experienced in a professional setting. The energy, the shared experience, the way the environment made everyone feel celebrated and valued - I never forgot it. And I can only imagine what it feels like to be a client on the receiving end of that kind of thoughtfulness. The loyalty it can inspire. The way it deepens a connection that no Zoom call ever could.
Summer is here, and with it comes baseball games, soccer matches, outdoor concerts, and a calendar full of opportunities to invest in the people who matter most to your business.
So let's talk about doing it right.
Why We Do It - And Why It Works
The environment matters. Away from the boardroom and the inbox, people relax. Conversations go much deeper. You learn things about a client over the course of the evening that you'd never uncover in three meetings. The low-pressure setting creates space for real connection, and that real connection builds loyalty that outlasts any contract.
And in 2026, when most of our professional lives happen behind screens, face-to-face moments have become genuinely rare. That rarity makes them more powerful, not less. The shared laugh over a close call, the spontaneous conversation sparked by an unexpected play - these are the moments that make someone feel like more than just an account.
But When It Goes Wrong, It Can Really Go Wrong
But client entertainment, done poorly, can significantly damage a relationship. It can come across as thoughtless, tone-deaf, or worse - insulting. Here's how to make sure that doesn't happen.
Do your research. This sounds obvious. It isn't always practiced. Do you actually know what your client enjoys - not what they say in small talk, but what genuinely lights them up? Are they a hockey person or a soccer person? Do they love the energy of a packed arena, or would they prefer something more intimate? The right event for the wrong client is still the wrong move.
Invite them early. Executives have full calendars. Inviting someone with enough lead time shows respect for their schedule - and it gives the invitation time to do its work. A great ticket, offered early, gives your client something to look forward to, something to mention to their colleagues, something to feel genuinely excited about. Let the seats do the talking before the night even arrives.
Avoid the embarrassing conflicts. Don't invite a TELUS executive to an evening at the Rogers Centre. Don't take a staunch competitor of your venue's naming-rights sponsor and expect them to feel celebrated. Think it through. One quick search can save you a very awkward evening. Similarly - if your client is an arts and culture person (hello, kindred spirit), a game might not be the win you think it is. Know who you're hosting.
Invest in the experience. Premium seats are not an extravagance - they're a message. They tell your client that their business matters to you. Nosebleeds send a very different signal, and not the one you're going for.
Dress the part - but the right part. A sporting event is not always the place for your sharpest business attire. Read the venue, the seats, and the occasion. When in doubt, smart casual reads well almost anywhere.
Don't make it all business. This might feel counterintuitive, but it isn't. If you've invested in a great evening, trust it. You don't need to pitch, present, or debrief your Q3 projections between periods. Be present. Be genuinely interested in the person sitting next to you. The business will come - it always does when the relationship is real.
The Etiquette Still Matters
This is where my world - etiquette, workplace culture, professional presence - intersects directly with the fun stuff. Because there are real questions that come up at these events, and most people are quietly winging it:
- What if your client doesn't drink - and you'd like to? What's appropriate?
- What if they're enthusiastic drinkers and you're not? How do you navigate that with grace?
- What if you're both enthusiastic? How much is too much when you're representing your company?
- What conversation is on the table - and what crosses the line?
- How do you handle the bill discreetly, without making it awkward?
- How do you prepare for the outing so you feel confident and ready to host?
These are the questions I help professionals and organizations work through - because the goal of client entertainment is relationship-building, and that goal deserves to be handled with intention from start to finish.
If your team is heading into a summer of client entertainment and you'd like a session on the etiquette and strategy that makes these outings land well, this is exactly the kind of work we do at Boost Academy of Excellence. Reply to this email and let's talk about what that could look like for your organization.
NEW PODCAST on Professional Ghosting
This week's episode is on something almost every professional has experienced - and very few talk about honestly: professional ghosting.
Ghosting affects nearly everyone in professional life, and yet the people who do it almost always underestimate how much it costs the person on the receiving end. In this episode, I'm breaking down what's really behind it, what it takes from people, and the simple phrases that make closing the loop far easier than most people think. I also cover what to do when you're the one being ghosted.
Navigating these moments gracefully is at the heart of what I do - it's not about rigid rules, it's about understanding how your behaviour lands on others, and adjusting with intention. If your team could use a session on this before the summer gets away from you, reply to this email and let's talk.
Subscribe for tips on handling workplace challenges, building communication and social skills, and exclusive course updates. Hear success stories from professionals, perfect for young professionals and leaders aiming to sharpen their skills and foster respect.
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