4 secrets to conquering your fear and winning any conversation

Updated to Business on January 3, 2023.

Wouldn’t it be awesome if you could go up to anyone and strike up a conversation? Maybe it’s your next sales meeting, networking events, summer parties, or even meeting a new neighbour. Actually, it’s not that hard, if you know a few tricks.

Sure, you might feel uncomfortable, but with a few skills and a dash of practice, you will have a recipe you can use over and over.

We are all the same

When I was a guide, I always thought it strange how my clients changed from DAY 1, when we first met at the airport, or trail head, or side of the river, to DAY 10 when we say our good byes. These strangers, who all looked very different from me, had become close friends. Did they ever change!

The reality is that we are all the same. It’s our ego that wants us to be different. 

It took many years for me to learn I can easily accelerate that magic transition from day 1 to day 10, by taking the first step. The same thing applies at work, at home, at a conference, or at your kid’s hockey practice.

Here’s how to win in any conversation.

#1 Drop the outcome

Fear is a natural outcome of high expectations. If you want to win the sale, make a new friend, win the argument, or sound really really smart, you are going to fear failing. If you drop expectations, fear drops as well. 

Of course, we want more sales, but sales can come with unexpected costs (I’ve had my share of contracts that have become nightmares). Making new friends is great, but there’s like six billion to pick from, so I doubt missing one will matter. Winning an argument is nice, but not at the cost of making the other person feel bad. And sounding smart is for spelling bees, not for connecting with other people.

When you mentally drop the expectations, you drop the thought of failure. The Adrenalin drains away, muscles relax, blood returns to your brain, thinking becomes clearer, and you can enjoy the conversation.

The ninja trick I use is this question: “What’s the worst that could happen?”

I’ve never had an answer worth worrying about (try it).

#2 Lean in

Our brain can process words at about four times the speed of the other person’s mouth. That can be a problem. 

There they are, gums flapping, describing their morning, or mishap at the grocery store, or issue with their child and your synapses are firing uncontrollably. “I can fix that”, you think, “They sure talk a lot”, you muse, followed by, “He reminds me of my Dad”, and “I wonder if I should pick up salmon for dinner?”

Not good.

Your eyes glaze over, your face goes blank, you have left the room.

Listening is work, and the better you get at it the better the results. I don’t care if you are deep into a sales call, arguing with your partner, or talking about the weather with a grocery store clerk. The formula is predictable: better listening, equals better results. Every time.

Here’s the ninja trick to better listening: let your face know you’re interested. 

We’ve all been taught that some 93% of communication is non-verbal. Whether that number is correct, or not, is debatable. But, what we do know, is that in a conversation people look at your face. Raise your eyebrows, smile, lean in, throw in a few “Ah ha!”, “Oh really”, and “Wow, that must have hurt” and they’ll be eating from your hand. 

The line from the bible still holds true “Seek first to understand, then to be understood”

If you want to spoil a conversation quickly, make it all about you.

#3 Make it about them

It sounds something like this:

“So, I’m thinking of taking the family to Portland this spring for a fun get a way.”

“Oh, I love Portland, when you go you MUST spend a day at Powell’s. It’s unbelievably huge. When we were there, we lost Tim in the American history section. It was the funniest thing. I was checking out some classic post-war novelists – I’m a huge Hemingway fan.”

“Uh, we thought maybe June.”

“Well, then you MUST head over to Sea Side, though Astoria. We all hiked to the top of the Astoria Column. What a view of the river! When you get there, buy one of the balsa planes they sell, and launch it from the top. We all did this twice! Definitely have someone take picture of that.”

“Or maybe we’ll just stay home.”

People want to feel that their thoughts, questions, struggles, and ideas are valued. You can help them.

The ninja trick here is to “double click” by asking the other person to tell you more about what they just said. It’s like searching Google for a local massage therapist. First you enter what you are looking for – there are thousands of results. So you double click on something of promise to learn more (hat tip to my friend Matt MacEachern for the “double click” technique.) The search gets narrowed; you get closer to your goal.

Two things happen when you double click 1) you keep the other person talking so you get to think (remember the speed difference between brain and mouth, above?) and 2) you direct where the conversation goes.

Cool, right?

It can sound like this:

“So, I’m thinking of taking the family to Portland this spring for a fun get a way.”

“Nice. I love Portland. What are thinking about doing there?”

“Uh, we thought maybe check out shops and then head to the coast. I don’t want to blow through Portland – there’s so much to take in there.”

“Sounds great. Have you heard of Powell’s Book Store?”

“Yeah, I heard it was huge. In fact, that’s a great idea. I can hang out there with the kids while Sherry does some shopping – could be a real win/win.”

“What about the coast, what are the kids favourite activities around the ocean?”

This simple technique is a win/win every time. You steer the conversation where you think it should go (imagine how well this would work in a sales call), you learn more, and the other person feels valued. Try it today.

#4 Know when to fold’em

Like the old Kenny Rogers song the Gambler, there’s a time to “Know when to fold ’em. Know when to walk away.” and break off the conversation, or change the subject. 

Talking more about the weather is nice, but it won’t get you closer to a sale. Same thing at parties, sales calls, in office chat, or meetings. At some point it’s time to fold ’em and move on.

You aren’t being rude (you could be doing the other person a favour), just practical. It can sound like this.

“Thanks for sharing that and I’m getting ready for a meeting, so I’ll catch up with you later.”

or, “Great to see you and I hope we bump into each other again soon.”

or, “I can see we have to talk more about and I’ll make a note to follow up.”

The operative word is “and”. Try replacing “and” with “but” in those sentences and notice how everything changes (for the worse).

If you need to correct someone, or disagree with their opinion, or change the topic, use “and”. What you need to say will always sound positive, even if you are announcing your departure from the conversation. You might think this is sneaky, even a trick, AND it works!

There you go. Four ways to conquer your fear and win in any conversation. Super simple – totally effective. Try them a few times and I think you’ll be surprised how quickly they work.