I have a persistent, steady sense of dread and obligation when meeting someone for the first time. I would constantly question the value. I would factor in the time it would take to drive, the awkwardness on timing. I know I'm not alone, I was once asked, "If I'm meeting someone for coffee and I get there first, do I buy my coffee or wait and we order together?" That's an important question!

I didn't like that I didn't like meeting interesting people. It was holding me back. I resolved to improve. I believe any improvement must come from practicing very specific tactics and feedback. I needed to measure the value of the meeting and ensure the other person felt their time was respected. Fortunately with the advent of Google Hangouts and Skype, I didn't need to worry much about coffee buying.

Each meeting I had different ideas to try. Many of my ideas didn't stick or didn't seem to have a place, some were even awkward. After the first 5 or 6 conversations I had (out of 20 or so emails asking to talk to strangers) something simpler emerged. The simplicity boosted my confidence and made it easier to follow along.

I'm no social butterfly and I often want nothing more than to cancel and run away. Improving the experience of the meeting has changed this, though. Now it's not unusual to eagerly look forward to a conversation. Trying other ideas, guides and manuals, struck me as too superficial; they targeted selling or brokering a deal. That didn't help me overcome the discomfort that was keeping me away. I didn't need tactics reminiscent of pick-up artists. I wanted guidelines to feel I was respecting everybody.

Rule 1: Humanity first.

For years I thought the most important thing about any meeting was the topic to discuss. I would jump straight in, make a splash! Each time I would completely bypass the person across the table. Alienating them in this way ruined a lot of opportunities. The best way to get a second meeting is to enjoy the first.

When meetings have a specific purpose, definitely respect the purpose. Be aware that the purpose may be a small percentage of the total time available. With that in mind show the human connection first. Start with something interesting, talk about the important matters, end with something interesting.

For a long time I failed at this and made a lot of excuses. Recently a friend helped articulate this:

  1. Always have something more interesting to talk about than what needs to be discussed.
  2. Learning even basic information about people, companies, and ideas is very easy in today's world and has a powerful effect.

With Twitter's ubiquity and Google's reach, it is absurdly easy to find where people's interests lie. Finding out mutual interests not only helps conversations, it helps to see people as people. Mutual interests may improve an opportunity into a friendship and an opportunity.

One of my favorite quotes is, "People don't quit jobs, they quit managers." People. It's a lot easier to turn down a second meeting than quitting a job. For optimal encounters, connect to the person before anything else.

Rule 2: Know why we're here.

I don't mean in a cosmic sense. Everyone should understand why they have been invited to a coffee shop or a Hangout. It can be uncomfortable to sit down with someone and not know why. This discomfort is what kept me away from initiating these conversations to begin with. Even when the context of the discussion is presented, the specific reasons why that one, single, special person was invited isn't always known.

The purpose of the discussion should be easily understood and not very complex. I've invited people to coffee for the purpose of asking one, single question. Overkill? Maybe. When combined with Step 1 I've created really wonderful relationships and got answers. The best part is an honest answer, from a specific and unique perspective. Always strive for a simple purpose; simple purposes yield complex results.

Now that I've been on the receiving end of a few disjointed conversations I can confirm the bewilderment. It's bad for everybody if when someone walks away wondering "why did they want to talk to me?". Most importantly, I wouldn't agree to any follow up conversations. That's probably where the real purpose would be revealed, but I'll never hear it.

Rule 3: No surprises.

Nobody wants to be a deer in the headlights. This can be prevented with a few minutes of work on both sides. You can't force other side but always do your part (This is rule 3b). Make sure you study up on who you are talking with, what they are interested in (Rule 2). Be ready to articulate any requests (see Rule 1). Send as much information as you can ahead of time, and be prepared by anticipating likely questions.

Sharing the specific purpose allows people to have time to think and reflect on what you're asking. The decisions and thoughts made after a good nights sleep will almost always be better than those made quickly, in the moment.  If the person isn't familiar enough with the subject matter, it gives them an opportunity to read up and come up with a few high quality questions.

I had a fear that if I explained why I wanted to chat, people would just reply over email and I would lose that face to face (or screen to screen, more likely) opportunity. The opposite has happened.

I have found more people have accepted, and replied to cold emails, when I lay out a very specific question or request for them. It also helps the conversation along, as there is less time evaluating why and more time discussing the "how".

Key Takeaways

Always come into an encounter with expectations and practice expressing them. If someone comes to you for help, determine how far you would be willing to go. If you are requesting help, articulate that well and comfortably.

Aim to discuss something more interesting than the purpose of the discussion. This builds the human connection which will matter more in the long run. The conversation should always be about the human across the table first.