Initiate the Conversation

Back in grade school, I idolized Michael Jordan. I wrote him letters, bought his jersey, wore a Bulls cap (even though I was born and raised in California), and signed up for his mailing list. Letters covered in Bulls logos and a golden embossed MJ signature would occasionally arrive at my house and I’d tear into them, run my finger over that signature and try to convince myself that Michael Jordan had really signed it.

I wanted to believe that he had personally read my letter and spent time crafting a reply, but I knew it was unlikely.

Now that we find ourselves in the D-Rose era, professional athletes don’t captivate me as much they once did, but people who are writing and changing the world certainly do.

I sign up for the mailing lists of travelers, creatives, business leaders, and prominent bloggers, follow them on Twitter, and read their blog posts. I’m a social media fan boy. And one of the many things that has changed since Jordan’s glory days is how those people communicate their brand and foster a following.

Social media has made celebrity’s interaction with their fanbase more direct and personal than ever before. I could Tweet at Michael Jordan today and there’s a better chance of him seeing it than there ever was of him reading one of my letters.

So this year, I’ve challenged myself to reach out to people I admire and respect as I work to learn more about writing and communication. I’ve made a “Connect with…” list and schedule out times to chat.

This process starts the same way every time; I take the initiative. It may be in the form of a reply on Twitter, a message or comment on Facebook, a comment or “like” on Instagram, or whatever. Reaching out to these seemingly far-off people in small ways like this lessens the gap of separation. The bridges are already built, but we’ve got to be willing to walk across them.

One of the most exciting questions I’ve learned to ask this year is, “Would you be willing to entertain a phone call with me about the work you do?” It’s that simple.

Most people enjoy talking about themselves and are excited to share what they know with an admirer.

As I’ve done this more, my confidence has grown and the process becomes less uncomfortable. Before each of these conversations, here’s a mental rundown of how I prepare:

  • Interact with them as a follower or fan. Retweet them, reply to a tweet, comment on a post, share something of theirs with your own following.
  • Read their latest tweets and posts. Know what they have been doing this week. If they’re sharing it on the internet then it’s not weird that you know about it already.
  • Browse through their LinkedIn profile. Brief yourself on the career path that led them to their current position.
  • Have questions prepared. Know what you want to learn from them. Most people will want to help, but if you don’t know what you want then they can’t know how to be of service.
  • Be OK with awkward silences. These silences will become less the more you reach out, but in the meantime, don’t be afraid of them.
  • Be prepared for rejection. The worse that can happen when reaching out is that the person will say ‘no thanks.’ Seriously, that’s the worse that can happen. That’s not so bad at all, so keep reaching.
  • Document everything. You’ve got the person on the phone and they’re sharing valuable insights you don’t want to forget. Take notes.
  • Be grateful. A simple thank you can go a long way. Make sure that the person you’ve spoken with knows that you appreciate their time. Send them a handwritten letter or a postcard. Demonstrate your gratitude.

As the year continues, my list of people to connect with is expanding. I remind myself that they are human beings just like me, so we already have a lot in common. It’s up to me to take the initiative.

Even though Michael Jordan isn’t on the list, I’m confident we could share a great conversation. Maybe I’ll tweet at him.

Student BlogsDane Johnson