
I drove to Napa last weekend for an event with clients (I know, rough life). I started thinking about the event, what information I would like to get from the host/customer about the current market, projects I wanted to sell, questions about the projects we have sold that were in process, information about my competition, and a lot of other things. I also started to think I wanted to be respectful of the event. It was an event with spouses; it was supposed to be an escape from work and a fun activity. At the same time, I still wanted to get information while enjoying the weekend and deepening my relationship with this customer.
How do you entertain the sincere sales way? I think there is a lot to take away from this, and it is one of the most important things to learn as a salesperson. I have never had anyone sit down and teach me how to entertain and the dos and don’ts rules.
Hopefully, I can pass on some lessons to help others entertain and deepen the strengths of their relationships. I want to say entertaining is necessary and the best way to step outside work and develop a great rapport with a customer. I love this clip from Mad Men to illustrate how to handle entertaining clients from an account.
There is a lot to consider when entertaining, whether it is a lunch, dinner, or happy hour. The location is critical; the type of customer and your current relationship with that customer are critical to deciding the setting. If it is a new customer, lunch is probably more appropriate to get to know them better in a situation where you are not expected to entertain on a significant level, and no drinking is expected. If you have seen the customer, dinner or drinks may be more appropriate, especially if it is someone you do business with frequently. The location is essential; you know your expense limits based on your customer–how much this customer has purchased or their capacity to buy? As a salesperson, you should take control of where you go. Pick places that fall within your budget so it is something that you can keep under control. When ordering, always let the customer go first; they should set the tone, especially when drinking. You should follow suit if they don’t order something to drink. If you know the client is drinking, you could lead the way, especially with wine; you could set the direction of the evening by picking a wine that is in your budget. What to order may depend on the return on investment in the event.
How do we entertain and get the information we need to succeed? The event’s start should be small talk and good humor chit-chat. At some point, there does need to be a discussion of business? You shouldn’t be ashamed or made to feel bad that you bring up business. After all, it is why you are there. If we are sincere, the business is paying for the event, and business has to be brought up. I typically bring it up after ordering before the food arrives. Lead the conversation with targeted questions that you are looking for but ask an open question to allow the customer to talk. Have targeted questions played out in your head but most importantly, be listening. Everyone wants to talk about themselves; allow that to happen. If you find yourself leading the conversation, you are losing.
One crucial step if drinking is knowing your limits. If you can’t stop, don’t drink; salespersons don’t need to partake. In fact, some of the best salespeople I know don’t drink. It is a good social not drinking time that defines you as a salesperson.

When the event is done, make sure you do an internal inventory to determine if you achieved everything you wanted. There must be some next steps or action items as you leave. Plan to see each other again. Then the work begins; you must complete the action items so that the next time you see the customer, you can check off that you listened and that the event was worthwhile. Also, always send a thank-you note. Send an email or if you text with the customer, send the text. Even if you have paid for the event, the thank you thanks them for their company and conversation. The thank you goes a long way. There is nothing more effective the sincere sales method than a thank you.
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