My day job is to have conversations with hard to reach people. Most of the time I only get 15 minutes to make a first impression.
Recently, I connected with a decision-maker that the two people who did my job before me were unable to reach for two years.
The first thing I was told, when it became obvious this individual was someone we had to work with was, “we’ve tried already — he refuses to talk to us because we failed him already.” It was supposed to be a lost cause.
I tried to email him. Nothing. I tried to call him. Nothing. I tried to reach him via LinkedIn. Nothing. I tried to get an introduction to him via mutual connections. Nothing. I tried to get an introduction again and was told “sorry he won’t talk to you.”
Then I tried to get an introduction again from the same person. This time I said “can you coach me through how to reach him and what personally matters to him?”
I said “I know you have nothing to gain from helping me but as you can see I’m an underdog, and I don’t give up. The odds are stacked against me. It would be a huge help if you could give me your advice, or point me in the right direction at least.”
That heartfelt, genuine ask got his attention. He made the introduction. He even ended up booking the meeting for me. And he gave me a personal recommendation even though we had never worked together before. Why did all of this happen?
See, people love a fighter and an underdog. People love it when you ask for their help and are sincere about it. People can’t help, helping someone who needs help.
I’m not brilliant. I’m introverted at best. I become shy easily. I often suffer from imposter syndrome. Yet, I’ve found a few things that change how a conversation flows and take small talk to new heights.
You can use these things to reach more people and build strong relationships with people you believed previously were unreachable.
Have your first impression be relatability, not highlight reels
Bragging kills the potential for a good conversation.
A first conversation with a new person isn’t a valid reason to flash your achievements in front of them in the hope they’ll like you for all your successes. People don’t care about your success; they care about whether you’re listening to them. They care if you’re what they deem to be a ‘good human’ worth talking with.
A conversation feels effortless when the person you’re talking to is relatable. Relatability is the goal of a conversation.
If you walk away from a conversation with the other person feeling like you’re relatable, you’ll get a follow-up conversation.
A follow-up conversation is where the magic happens
It’s rare you’ll change your life in the first conversation.
Big breaks are nonsense. Conversations help you achieve your goals when they are held over multiple time slots.
The conversation that won me a big business opportunity from the opening story of this article was four conversations deep. It was a regular, short, scheduled conversation that built the relationship.
One-hit conversations aren’t going to help you.
Everything good about a conversation is in the follow-up. The quality of your relationships is directly related to how much follow-up you do.
Is now a good time?
A big mistake I made in the beginning was calling people for the first time and going straight into the conversation. I learned via an Instagram video posted by conversation expert, Sabri Suby, that you have to start with finding out if you’re reached someone at an acceptable time.
An inconvenient call someone isn’t ready for won’t take you far.
Surprisingly, if you ask whether it’s the right time, even if it isn’t, the very fact you asked will often make the other person allow you to continue.
Ask a personal question
Work and life are extremely personal.
You become more likeable when you are personal. I’ve started a lot of conversations recently with “how are you dealing with the covid situation?” It’s a topic that can get most people talking a lot. That’s why it makes for a good conversation starter.
Once someone is talking, they forget they don’t know you or why you reached out to them in the first place.
The goal isn’t to one-up their response either. If anything, when they ask you your answer to the same question, you want to underplay your answer. Let the light shine on them. Let them have their moment.
My approach to answering a personal question is to add in a small amount of vulnerability. If it feels a little risky to say, then I say it.
Playing it too safe with vulnerability in a conversation just doesn’t cut it. It feels difficult to mention my near-miss with cancer, or my work colleague that caught the plague, or the business I walked away from, or my unconventional thoughts on finance. But every time I do, the conversation goes up a level.
A touch of vulnerability strengthens a conversation and shows a person who you are.
Prepare for the conversation
There are two ways to prepare for a conversation:
- Roleplay the conversation.
- Write down a few dot points as a guide.
Option one is tempting. Don’t do it because conversations are supposed to be unpredictable. You end up sounding like a robot when you roleplay a conversation. Robots kill rapport.
I use the second technique and write down a back-of-the-envelope series of dot points using the Notes App on my iPhone. I rank the dot points into two categories: must-haves, and nice-to-haves.
This means I never have to worry about running out of things to say. While I don’t say a lot of what is in my preparation notes in the actual conversation, it helps me curate ideas in my head to talk about beforehand.
Writing is the act of curating ideas in your head.
Curation is a superpower when it comes to thinking about what you want to say and building a genuine relationship.
A person can tell when you’re unprepared. A lack of preparation shows a lack of care. Caring is how you have someone feel like they like you without completely understanding why.
Research the person on LinkedIn and Instagram
LinkedIn tells you how someone appears professionally. Instagram (or equivalent) tells you how someone appears in their personal life. The two platforms give you a more complete picture of a person.
Scrolling through someone’s Instagram shows me what inspires them. It shows me what they care about. It shows me who they love. It shows me what they like doing. It shows me where they deploy their finite levels of energy and passion. I never want to just research someone on a business level.
You need to research a person before you talk to them. Otherwise, you’ll limit the opportunity to fast-track the conversation to a position of rapport.
Rapport makes the two of you connect.
Connection leads to relationships that can last a lifetime.
Use honest persuasion
Liars are everywhere. Bragging is a given.
That’s why I change up conversations with honest persuasion. If one of my goals is to get someone to do something, I use high levels of honesty. I tell them a lot about the downsides. I tell them what I think about them in a constructive way that doesn’t offend them.
People eventually find out the truth. So if you lead with the truth, you’ll persuade people even more when they find out for real how honest you were in the first place. Honest people are insanely likeable.
Writer, Tom Kuegler, did this to me in 2016. He told me that the bags under my eyes in a particular photo made me look tired. He suggested I change my profile picture. Given I hardly knew him at this time, that was a huge risk. Yet, it’s the reason today that I have so much time for Tom.
Honest conversations are effortless.
Let the heat die down. Then try again
Some conversations can reach their peak and go nowhere. This has happened to me a lot. One technique I use is to let a conversation cool off.
I allow a four-week gap and then reach out to the person again for a chat. It’s amazing what those few weeks do. The person completely forgets where we left off.
Gaps of blank space allow a conversation to grow on someone.
Some people need time to think after a conversation. Things can easily become heated in a conversation, accidentally.
I’m surprised how forgiving I can be after a few weeks have passed following a difficult conversation.
Heat a conversation up. Let a conversation cool down. Re-enter the conversation when it’s still lukewarm.
Ask for permission to say certain things
“A colleague of yours said you hate bullshit. Can I have your permission to be a little informal?”
I said that last week. Using this technique makes me feel superhuman in a conversation. Asking for someone’s permission makes a person feel like you respect their opinion. Once you have permission, you can really let loose and build enormous rapport much faster.
Say this: “Can I have your permission to be…”
Name-dropping isn’t evil. Mentioning the right names makes all the difference. It’s all about how you name-drop.
If you drop a name because they’re famous or successful or stinking rich, you’ll confuse a person. If you mention the name of someone they know and respect (because you’ve done your research) you’ll have a person you can build a conversation around.
It’s hard to ignore someone who is talking about a person you respect.
Rather than highlight their achievements or status in society, highlight why you enjoy spending time with them or how they make you think differently.
Conversations that drag on feel like you’ve got a boat anchor chained to your gorgeous neck.
Get to the point.
How? Well, if you’ve done your preparation then you’ll have your 2–3 key dot points to speak about. A good conversation starts before the chat.
You can put conversations in a person’s calendar and think carefully about how much time you allocate. You can frame the length of the conversation at the start of the chat. Or you can be quiet, say nothing, and just let them talk the entire time until they run out of things to say (a highly successful strategy).
Less is more in a conversation.
You can always take what you didn’t cover and insert it into the next call.
The goal is a genuine connection — not a one-time call that ends due to a lack of it.
Give people back 5–10 minutes. It’s better than gifting them a nice diamond watch
I swear to you this technique can work wonders. I generally allow a chat to go for 30 minutes on average. My goal is always to end the conversation with 5 minutes to spare.
The level of respect you show a person when you give them time back in their busy calendar is almost unexplainable. It’s such a pro strategy because very few people do it.
Respecting someone’s time is respecting a person. That level of care can make you far more likable than the twat who can’t shut up and always goes overtime.
Aconversation is effortless for a person when you aim to be relatable, follow up with a next conversation, respect a person’s time, start with a personal question to make it personal, prepare, do your research, let a conversation cool off, be succinct, and give people five minutes back at the end of the conversation.
Each of these techniques (when combined) can help you have better conversations that become effortless for both sides. At the same time, your ability to hold quality conversations will make you unique because it’s so rare.
Hard-to-reach people are near-impossible to contact — you can reach them when you leave behind the herd of sheepish braggers, impressers, and people that can’t stop talking about themselves and their wonderful life.
When you feel cared for in a conversation, you act differently.
Be the caring person in a conversation.
This article first appeared on Medium.