My 10 Day Experiment In Keeping In Touch

Relationships are both fun and valuable. That’s my takeaway from Business of Software this year.

Not that I didn’t know it before. But this year I hit my stride. I connected with more people, more deeply, than I ever have before.

Yes, I flitted around, trying to meeting new people—sometimes successfully, sometimes not.

But this year I had the specific aim of deepening my existing relationships. 

I spent time catching up with people and getting back in touch. I hosted a dinner Saturday night to spend intimate time with a smaller group. I reached out before and after to people I knew.

But the reality is that after a conference, life takes over.

Swept up in the whirlwind of trying to run a business, have a life and pursue exciting projects, I forget to stay in touch with people. And so those relationships that could be so much more fade a bit. We’re still connected, but the energy is lost.

The value of a conference like Business of Software is the people.

It’s a small conference—capped at 400 attendees—and everyone there is facing similar challenges running a software company. Being around others facing the same challenges as you, who speak the same language, energizes you—even if you’re an introvert like me (or maybe especially so). Wouldn’t it be great to keep that energy high throughout the year?

It’s not restricted to Business of Software. Every time I visit Boston or another city, I meet fantastic people I’d like to stay in touch with. And then, inevitably, I don’t.

Part of the problem is that I don’t like contacting people.

I dread phone calls and procrastinate e-mails. I’m fine in person when I can see and react to someone, but don’t like low bandwidth communication with those I don’t know. Not that I don’t do it all the time for business. But it’s not my preferred method of maintaining relationships.

Today I aim to change that.

In the vein of starting small, I’m starting a 10 day experiment. Each day I will spend 10 minutes contacting 1 person in my LinkedIn contacts. I’ll say hi, give them some useful piece of information and ask them one question.

The useful piece of information might be something I recently learned that I think they’ll find valuable or a link to an interesting article.

The question will be something to help deepen our relationship. Potential questions might be:

  • Is there anything I can do to help you in your business or life right now?
  • What’s something interesting about you that I don’t know?
  • What is the passion that drives you to wake up each morning?

I expect at least half the people I e-mail will be too busy to respond. But the other half—well, maybe I’ll start to get to know them better.

And maybe, just maybe, I’ll start developing a habit I can continue throughout the year.

So next time I see someone in person, it’ll be a continuation of an ongoing relationship rather than catching up with someone I lost touch with.

Who knows, this might be the beginning of some beautiful friendships.


  1. Michele says:

    Trevor, I love this idea. So thoughtful and purposeful.

    Hope you are well and happy!

    1. trevor says:


      Thanks. We should grab lunch sometime and catch up. I may need to create a separate list for lunching with locals. :-)

      Hope you’re doing well.


  2. Hermione says:

    Trevor, thank you so much for your kind words about BoS. Yes, the people there are awesome – it’s why running it is such a pleasure. Can I share this with the rest of the BoS group on Linkedin? I know your experience isn’t unique and I have plans to try and make it easier for BoS alumni to stay in contact.

    The LinkedIn idea is outstanding, I’ve made a practice of doing something similar for a while now and it has all sorts of unexpected benefits. LIke all habits, there are days (weeks) when it gets drowned out, and I expect that might happen to you, too. But I always go back to it, because the human connection makes me feel good.

    1. trevor says:


      Absolutely. Share as you like.

      On the alumni experience, I’ve thought about hosting BoS alumni dinners when I visit a city as a way to reconnect with people, and possibly meet people I missed meeting.

      With one day down, my experience has rocked. I had an awesome e-mail conversation and connection. Looking forward to a lot more.

      And, guess what? You just got added to the list. :-) I always have great conversations with you at BoS and it’d be great to get to you you better too.


  3. Mark Littlewood (@MarkLittlewood) says:

    Interesting and thoughtful post Trevor and thank you for kind words about BoS. Putting on conferences can be hard work but the thing we always know is we get to meet such cool people when we are they.

    1. trevor says:


      Thanks for your leadership of BoS. You’ve kept the spirit and the culture of the conference alive, which is not trivial when taking over from founders. I appreciate it a lot.

      Meeting in-person is so much more powerful and fun than online. Both have their place, but conferences like these are critical to developing powerful and deep relationships with others like us. So thanks again.


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