How to Have Great Conversations: Your Guide to Small Talk and Sales

Geoff Whiting

 small talk for great conversations at networking event

How to Have Great Conversations: Your Guide to Small Talk and Sales

The most valuable people in our lives were no longer strangers thanks to great, impactful conversations. This reality is true whether you’re thinking of a spouse, partner, best friend, or client. The ability to connect and share, while creating a relationship and trust, was the pivotal point in every interaction.

Who doesn’t want that to happen again? Who wouldn’t like to be able to talk to strangers about almost anything and have them warm up to you?

The key to getting strangers to become comfortable with you is the same as a lesson on how to have great conversations. It’s all in the approach, the way you speak, and how you behave in the interaction itself. Unfortunately, we’re not all blessed with intuitively understanding how to do this.

So, if you’re like me and even the thought of small talk causes the blood pressure to rise, here’s a comprehensive guide on small talk, sales talk, and conversational greatness to give you a helping hand.

Guide to Small Talk

The first conversation style to touch on is small talk. This is the informal, light conversation that we all use when we don’t know someone or will have a brief interaction. It’s useful to start networking or break the ice at social events, as well as chatting with people in line for coffee, sharing a ride, or when there’s an awesome dog you want to meet, but you need to talk to their human first.

men have a conversation in a hotel lobby
Every interaction is a chance to practice how to have a great conversation

Your best bet with small talk is to ask questions and let the other person talk about themselves (this is great for almost all other conversations too). Give someone a chance to express something they like or are interested in, and there’s also a chance they’ll steer the conversation somewhere.

Open-ended questions are a top way to get the other person to open up and share. But, asking a question that gets the other person rolling is only a single part of small talk. You’ll also want to listen attentively and actively. That means paying attention (no phones!) and asking additional questions for clarity or to get further details.

It’s an easy strategy for getting to know someone, and it’ll lead to more in-depth questions that you may find easier to answer. Keep topics related to the event, and you’ll be better prepared to ask more questions and get someone talking, plus their related questions will be easier to answer.

  • If you’re at a mutual friend’s party, start by asking how they know each other. This can lead to simple follow-ups related to that, such as the work the person does, what major they had if the two met in school, or more about the hobbies and activities that brought them together.
  • For networking and work events, you can start with a basic question about their profession or products. Follow-ups are just an expansion on that, such as asking what skills they need in the job, what their favorite part of the work or product is, or about anything you find unusual or unexpected.

HubSpot has a killer guide for small talk conversation starters that also includes tips on how to end a conversation or transition to more in-depth topics.

5 Tips on How to Have Great Conversations

Thinking about small talk and sales conversations for this piece got me looking at the common threads for enjoyable interactions. So, I took notes on the conversations I’ve had over the past week when they were work-related, at the coffee shop across the street, using ride-share apps, and at the park (I’m the shy human for an awesome dog).

 people laugh while eating and talking
Start by thinking about a conversation you’ve enjoyed lately

There were a few exciting hallmarks of high-quality conversations that I found the most useful and engaging, no matter where they occurred. I paired these notes with expert opinions to build this list of how to have great conversations regardless of setting or what else is happening. 

  1. Truly listen and engage. Lots of us worry about what to say next. But, when that occupies our mind, we’re not participating in a conversation. We’re just saying things that may or may not be related and don’t engage the others — more like lines in a script than human interaction. Think back on the small talk tips and ask open-ended questions and relevant follow-ups. Natural breaks in the conversation will occur so that you can share and respond too.
  2. Don’t lie. If someone is paying attention and actively listening, you can easily get caught up in a lie that makes them want to end a conversation. This is especially dangerous in any work-related conversations because it can cost you a sale or terminate an existing relationship.
  3. Be honest. A little different than not lying, being honest is about expressing yourself clearly and being straightforward. It helps the other person trust you and what you’re saying, plus makes it easier for you to set boundaries. This isn’t about being rude, just confident in yourself. If the conversation steers into uncomfortable territory, look for a topic to transition to so that it doesn’t end right away.
  4. Treat everyone like a friend. If you’re nervous about talking to someone, try to picture your friend or coworker who is most like them. It can help relax you and ease any tension, plus it might give you a direction to take the conversation. “You remind me of my friend X, do you also like hobby/sport/etc.?
  5. Use your face. Building on the friend note, you want to make the “best friend face,” according to researchers. It’s a “quarter smile” that where you’re smiling with your mouth closed. Take a moment to relax your face and smile now, and you should feel a slight tug at your eyes. If you smile with your eyes too, it’ll read more genuine and can trick your brain into having a good time even if the event or prospect of a conversation makes you nervous. While doing this, be sure to make eye contact too.

There’s plenty more you can do to have a great conversation and enjoy networking events, but those five are solid fundamentals that you can practice regardless of time, topic, or location.

How to Have Impactful Customer Conversations

When we think of how to sell in the modern-day, we’re often thinking of how to have great conversations with potential customers. It’s all about the interaction and putting someone else at ease while answering questions, solving problems, or otherwise being useful.

 businessman looks at phone call
Customers will screen calls, so create rapport early

The modern sales cycle, especially for you SaaS companies, is all about providing support and education on both sides of a sales pitch or product demo. Knowing that, there are a few things you can do to ensure your customer conversations are more impactful.

First, you want to have a great conversation. That means treating this potential customer like a friend, not foe, and asking questions about their needs. Listen and respond specifically about their problems before any attempt at a sale. Your mission is to learn and understand what they need in the same way you’d want to know more about a friend’s problem.

Because this is a customer, our second note is to think before you speak. Not only do you need to say things that won’t be offensive or unsettling, you also want to be aware of how you’re speaking. Avoid raising your voice or using a condescending tone. Empathize with problems and share in the excitement. Tone can say a lot even if the words don’t change — like how saying “I’m sorry” in a dramatic way comes off as insincere.

Tone is extremely important to our third point: match the conversation with the mechanism. More and more sales journeys are starting on chat or text, then moving to email, and finally a phone call or a video demo. Being impactful in the right way requires you to understand the differences that these create. Jokes or sarcasm may not come off well in texts and emails — sarcasm at work might be a bad idea in general — but could work on the phone once you have built some trust. Very direct answers might come off as being rude in a demo, but they’re usually what people want when asking questions in a chat.

Match the tone and length of interaction to the medium. If you need more space to talk, it’s a smart way to pivot to a better customer service channel. When someone emails about a quote but you need a lot more information to be accurate, for example, use your follow-up note to set up a time to talk and explain that a good quote requires a discussion that’s usually faster and more helpful to the client when it’s on the phone.

woman smiles and raises her eyebrow
Aim for an eyebrow moment

Finally, find the “eyebrow moment” in your conversation. Vanessa Van Edwards, the lead investigator for Science of People, notes that people raise their eyebrows when they see or hear something interesting — and this appears consistent across most cultures. So, while you’re talking, look and see if something gets an eyebrow raise and come back that. It might be a mention of a sports team or hobby, or it could be tackling a problem like a specific kind of waste or efficiency loss, which will clue you in on where to focus on building your connection.

If you’re on the phone, the eyebrow moment should also have clues in their tone of voice and excitement level — or even directly expressed interest — so you’ll need to be paying careful attention to catch it.

How to Improve Your Sales Conversations

Now for the meat that led many of you here: how to improve your sales conversations. 

woman takes a business call at a cafe
Remember that your customers and conversations can be anywhere

You’ve done the small talk to learn about a customer, helped them out along the sales journey so far on different mediums, and been helpful with past great conversation. Now you want to land this big, beautiful fish.

Here’s the best advice I could find from experts who generate millions of dollars in sales each month. (Admittedly, one of them successfully sold me their book during our conversation, so these are the tips I’ll be following too.)

  1. Kill synergy and other corporate speak. You want people to understand exactly what you’re saying and promising, or else they’ll come back after the sale upset by results and you lose a long-term customer. Industry jargon can also be a pain unless everyone knows what you’re talking about. You can determine that by waiting for the customer to use acronyms first.
  2. Narrow your pitch to their pain. The sales conversation happens late in the funnel, so you should already know something about what the customer needs or wants. Talk about that and focus almost exclusively on it until the customer asks questions. 
  3. They set the topic, you set the tone. That means you can focus on your company’s best attribute or advantage and keep it front and center during the conversation. Combine this with #2 and you’ve got a well-structured conversation plan.
  4. Ask one question about their business that’s not squarely related to your pitch. You want to create trust and show interest in their business as a whole. An unexpected question helps it feel less like a sales pitch too.
  5. End on a question about them. This is for your long-term planning. It helps you gauge the success of your efforts. Don’t be bland with something like “Are you interested?” Close with a specific question about their business that highlights the benefit you provide.

You’re not just selling. You’re painting a picture of a new reality that alleviates their pain. 

Boost Conversations with Memorable Visuals

You’re in a great position to sell today because people are visiting your site and listening to your marketing and communications a lot more than in the past. And, on many new mediums. That means plenty of ways to deliver interesting items that you can tailor to each individual because visuals are strong sales enablement tools.

Around 90% of the information processed by the brain is visual (and we remember about 80% of what we see), and these mediums can deliver visuals in a variety of ways. From infographics and photos to GIF creators and short videos, storage is no longer an issue and devices are powerful enough to render all of these properly.

business agreement after a great conversation
Visuals help sales get to “yes” 

Show visuals early on and boost trust while also ensuring that you stay top of mind. It’s a fantastic way to market, even if you’re just having a conversation or saying things.

CloudApp is designed to make the creation of your visuals simple and effective. The tools are powerful, it integrates with many channels you’re already using, and you can take one image or video and annotate it in no time at all with the name or other info of a top prospect. You can even use it to make your forms perform better.

Build a stronger funnel and have better sales conversations and start for free with this trial from CloudApp.

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