Your Playbook for Entertaining Clients

By: Craig Caron , Chief Operating Officer

Since the start of 2024, one thing has become clear: relationships matter.

As a hospitality veteran, this sentiment has always been near and dear to my heart. However, in a tight economy, the importance of maintaining strong alliances with those you do business with is more crucial than ever. To ensure that the partnerships you’ve worked so hard to initiate last the test of time, it’s key to invest in face-to-face time with your clients. But I know that’s easier said than done! That’s why I’ve jotted down some of the goalposts I follow when it’s time to take customers out on the town.

Keep it By the Book

First, the unfun part: following the rules. I know, I know, we all want to get started planning exceptional experiences ASAP. However, many companies have rules regarding accepting gifts or favors from vendors. Often, there’s a limit on how much you can spend without them needing to contribute or decline. Trust me, there’s nothing more awkward than needing to quibble over the bill — especially with a client. In order to not put a bad taste in anyone’s mouth, it’s best to ask about any restrictions. If you don’t want to spoil the treat for your customer, try to contact someone in finance at their company, as they’ll most likely know the details.

Planning with a Purpose

Now that you have some guidelines to work within, it’s time to roll up your sleeves and get started.

At 360DG, we talk about ‘finding your why’ when planning corporate events. Uncovering the core of what you want your audience to take away is essential. When putting together an experience to share with a customer, or potential customer, you need to understand your purpose in bringing everyone together.

Are you looking to kick off a new quarter together? Celebrate a shared win? Are you considering bringing them in early so they can experience the destination's offerings before the program begins? Often, it helps to remove the ‘buyer and seller’ mentality from the relationship and just think of your customers as, you guessed it, people. As hospitality heroes, we know people!

Get Help from the Inside

Picture this: You think you are hitting a home run planning a five-star steakhouse dinner for your client…only to discover that they’re vegan. Yeah, a plate of asparagus probably doesn’t have the excitement factor you were looking for.

You know where I’m going with this: do your research! Administrative assistants are some of the most helpful resources for uncovering executives' likes and dislikes — they’re a treasure trove of information.

If you don’t have someone like that to tap, go to your client’s LinkedIn profile and peruse your common connections. If you have mutual contacts, reach out and see if they know more about your client’s hobbies, preferences, or interests. You can also discover quite a bit about them from their feed and any membership organizations they’re a part of. A health nut who never misses running in the annual corporate-sponsored marathon might prefer a daytime hike or kayaking excursion to a lavish meal. With the right intel, you could also plan to treat them on their cheat day!

Pass on the Passé

We now live in an era where formerly luxury experiences or VIP privileges are available to all. In a world where a TSA PreCheck membership and options for more legroom make even an economy trip feel first-class, it’s time to throw out our old assumptions about what will make people feel special.

Many times, it’s not as much about what you do as how it’s done. For example, if I have a client group that I know enjoys a gourmet experience, I certainly won’t throw it out for something more unique. Instead, I like to fully preorder a dinner from start to finish with wine pairings. This takes the ordering process and waiter interruptions out of the mix and creates a seamless flow to the evening. Now, to plan for this you definitely need to get quite the understanding of your guest’s likes and dislikes. But, when you do it right, they will really feel catered to. If you want to roll out the red carpet, check out 360DG Partner Shelly Archer ’s article on giving VIPs the star treatment!

Don’t Forget the Follow-Up

Now, remember when I said maintaining strong alliances is key? Well, it’s not enough to just wow your guests; you need to be thoughtful in your follow-up as well to really make a lasting impression. While you don’t necessarily want to take notes during your time together, try to listen for tidbits about their family or interests and use this to guide you. It can be as simple as sending an email with a link to that gluten-free recipe you told them about, all the way to having a box of their favorite chocolates waiting for them when they arrive home. When in doubt, think about something that would make you smile and go from there. 

Next time you’re looking to wine and dine your client, come back to this playbook! No matter what your goals are, I hope you feel empowered to build an amazing experience for your clients. If you need help, send me a message.