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3 Ways To Start Sales Dinner Conversations in English with ChatGPT

Kevin Naglich
Sales Engineer English Coach

You're a Spanish-speaking Sales Engineer. 

Your Account Executive just scheduled a dinner meeting with a prospect.

The problem? It's in English. 😬

The conversation feels forced whenever you have casual meetings in English.

It's hard for you to keep the conversation going.

When you finally think of something interesting to say, the conversation has already moved to a new topic.

The dinner ends, and you failed to make a good impression.

You don't need to suffer like this.

Here are 3 powerful ways to combine ChatGPT with classic conversation strategies to impress in your next dinner conversation.

Strategy 1: Pretend you're a podcast host and ask open-ended questions

Here's a terrible conversation starter: "Are you having good weather?" 😴 

The only way to answer this is with yes or no. 

Then the conversation dies. 

Yes/no questions force you to think of new topics constantly. It's stressful, and you don't learn much about your prospect.

Imagine if your favorite podcast host only asked their guests yes/no questions. It would be very boring!

Instead, they ask a lot of open-ended questions.

You might be thinking: I don't know the questions to ask.

No problem.

With a little ChatGPT magic, you'll have a ton of ideas.

Maybe you sell software and have a casual dinner with a large financial prospect. You need some good ideas for an engaging (interesante) chat.

I'm a native Spanish-speaking Sales Engineer at a software company. I have a dinner meeting in English with a prospect at a large financial institution. Give me 10 open-ended casual questions to ask to have an engaging conversation.  How did you first become interested in finance? What do you enjoy most about your job in finance? How has the financial industry changed in recent years? What are some challenges you face in your job? What do you see as the biggest opportunities in finance right now? What are your favorite hobbies or interests outside of work? Do you have any travel plans coming up? What are you reading or watching currently? Do you have any recommendations for good restaurants or entertainment in the area? What was the last adventure you went on?

Or perhaps you have a formal dinner meeting with a defense contractor. Ask ChatGPT for a few ideas.

I'm a native Spanish-speaking Sales Engineer at a cybersecurity company. I have a dinner meeting in English with a prospect at a defense contractor. Give me 10 open-ended formal questions to ask for an engaging conversation.  Can you tell me more about your company's current cybersecurity initiatives and challenges? How does your organization prioritize the protection of sensitive data? What are your primary concerns when it comes to cybersecurity threats? How do you envision our solution fitting into your company's overall cybersecurity strategy? Can you share any examples of successful cybersecurity implementations within your organization? How do you measure the effectiveness of your cybersecurity measures? What role do employees play in your organization's cybersecurity efforts? How do you envision our solution addressing any potential gaps in your current cybersecurity measures? How do you stay up-to-date on the latest cybersecurity threats and best practices? Can you share any specific pain points or challenges your organization has experienced in regards to cybersecurity?

Your prospect can't answer an open-ended question with yes or no. 

When your prospect answers an open-ended question, you'll learn more about them and can continue to ask follow-up questions.

For example, they may be excited about adding smart lights to their home. You don't need to be an expert on smart lights. Just be curious:

  • What types of smart bulbs are you considering?
  • What features are you most excited about?
  • What else have you automated in your home?

Pretend you're a podcast host, ask open-ended questions, and all your pressure will disappear. ✅

Strategy 2: Share vulnerabilities to make yourself likable

Nobody likes people who think they're perfect. 

Sharing something that makes you uncomfortable or that you're not good at makes you more human and relatable. 😊 

Your prospects will start to see you as a trusted advisor. They'll stop thinking of you as a corporate robot.

The more they trust you, the better your chance of winning the deal.

Plus, if they have the same vulnerability, you just found another great conversation topic.

A vulnerability can be anything:

  • Something at work that makes you nervous
  • A sport you're bad at
  • Your English
  • One of your biggest fears
  • Making small talk

Combine vulnerabilities, open-ended questions, and ChatGPT for a powerful way to start conversations with prospects. 

This is where ChatGPT can help.

Tell ChatGPT you need a few two-sentence conversation starters

  • The first sentence should share your vulnerability.
  • The second should be an open-ended question.

Maybe you are very nervous when speaking in public.

Give me 10 two-sentence conversation starters for sales prospects. The first sentence should be a statement about my fear of public speaking. The second should be an open-ended question. I'm really nervous about public speaking - have you ever experienced similar nerves before a presentation? I get really anxious when it comes to speaking in front of a group - how do you usually prepare for public speaking engagements? Public speaking is definitely not my strong suit - what tips do you have for calming nerves before a big presentation? I'm always worried about making mistakes when I'm speaking in front of people - how do you handle any unexpected challenges during a presentation? I get so nervous before I have to give a presentation - do you have any techniques for calming your nerves? Public speaking is something I'm still working on - how do you stay confident and composed when presenting to a group? I struggle with confidence when it comes to speaking in front of others - do you have any strategies for building self-assurance? I tend to get really nervous before I have to present - how do you focus and stay calm under pressure? Public speaking is definitely not one of my strengths - what do you do to stay engaged and on track during a presentation? I get really anxious before I have to speak in front of a group - how do you handle difficult questions or challenges during a presentation?

Here are some ideas for sharing the fact that you're a terrible cook.

Give me 5 two-sentence conversation starters for sales prospects. The first sentence should be a statement about how I'm terrible at cooking. The second should be an open-ended question.  "I'm really terrible at cooking. Do you have any recipes or cooking tips you could share with me?" "I can't seem to get the hang of cooking. What are your go-to meals when you don't have much time or cooking skills?" "I'm the worst cook in the world. What's your favorite thing to cook for a quick and easy meal?" "I don't think I've ever successfully cooked a meal. Do you have any favorite cooking hacks or shortcuts you use in the kitchen?" "I've never been able to cook anything without burning it. Do you have any tips for avoiding common cooking mistakes?"

And, maybe you hate golf. Try these.

Give me 5 two-sentence conversation starters for sales prospects. The first sentence should be a statement about how I hate golf. The second should be an open-ended question.  I absolutely hate golf. What about you, do you enjoy playing or watching it? Golf is definitely not my cup of tea. How do you typically spend your free time? I could never understand the appeal of golf. What hobbies or activities do you find the most enjoyable? I think golf is such a boring and tedious sport. What do you think makes a sport worth playing or watching? I would rather do almost anything else than play golf. Do you have any hobbies or activities that you feel the same way about?

Strategy 3: Use a shared experience to build friendships

We call this technique "triangulation."

You + Them + A Shared Experience. 

These are the three points of your triangle. 🔺 

Remember how easy it was for you to make friends as a kid in school or a young adult in college?

A big reason is that every day was a shared experience for you.

  • You had the same teachers.
  • You had the same annoying homework.
  • You worried about the same grades.
  • You played the same sports.

It's easy to relate to people and build relationships when you share an experience. 

It's harder as an adult. But there are still plenty of shared experiences you can discuss.

  • Do you hate getting SPAM emails? They get them too.
  • Did you both sit through a boring meeting? They probably hated it too.
  • Have you ever had a bad boss? So did they.
  • Do you have crazy-busy days with tons of meetings? So do they.
  • Was COVID hard for you? It was hard for them too.

Here's how you can turn these into conversation starters:

  • Today's been a crazy day of endless meetings. How are you feeling? 
  • I used to go to the gym three times a week before COVID. It's been hard for me to get the habit back. How about you?
  • What'd you think of that last meeting? I thought it was very insightful. 
  • There's nothing more annoying than vendors sending you 1000 emails. Do you get them too?

Not sure how to think of ideas like this? Time to ask ChatGPT.

I told it I needed 10 "playful" questions (definitely try experimenting with tones) to ask cybersecurity employees about shared experiences. Here's what ChatGPT said:

I'm a Sales Engineer at a dinner meeting with a prospect. Give me 10 playful questions I can ask about common annoying experiences most cybersecurity employees have.   Sure! Here are some playful open-ended questions you could ask about common annoying experiences that most cybersecurity employees might have:  "What's the most frustrating thing about constantly having to stay on top of new threats and vulnerabilities?" "Do you ever feel like you're playing a never-ending game of 'whack-a-mole' with cyber attacks?" "What's the worst thing about having to deal with difficult or noncompliant users?" "Do you ever feel like you're constantly being pulled in different directions by different priorities and requests?" "What's the most annoying thing about having to do repetitive tasks, like updating security protocols or systems?" "Do you ever feel like you're fighting a losing battle against the bad guys?" "What's the most frustrating thing about trying to explain cybersecurity concepts to people who don't understand them?" "Do you ever feel like you're working in a thankless job, where people only notice you when something goes wrong?" "What's the worst thing about having to work with outdated or inadequate security tools?" "Do you ever feel like you're constantly having to justify the importance and value of cybersecurity to upper management?"

With open-ended questionsshared vulnerabilities, shared experiences, and ChatGPT, you'll be able to start much more natural casual conversations with prospects in English.

How are you supposed to remember all these ChatGPT suggestions?

Getting ideas is just the first step.

To use these in a real conversation, you need deliberate practice.

I'll teach you how.

Every week, I email 5 English tips for Latin American Sales Engineers.

These tips include practice strategies, mini-lessons, and useful apps to help you stop worrying about your English in the sales process.

Use the form below to subscribe to the free Sales Engineer English Newsletter today. 👇

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