I was waiting for my son's basketball game to start this weekend, and with the morning's emails all drained, I turned to Twitter and saw this Tweet from Marshall Kirkpatick:

I consider Marshall a business friend. A fellow thinker and tinkerer of technology. Somebody I respect. And like. But here's the thing -- I honestly can't remember how many times I've actually met Marshall in person. I know him really through being online, and from that we've had phone calls to debate his business and such.

It's an online relationship, and I actually believe that as of 2015 I've met more of my close connections in the past five to seven years online before offline. Brad Feld. Fred Wilson. Tristan Walker. And many, many more. Some through blog comments -- your place or mine. Some on Twitter.

I responded to Marshall's obvious comment bait :) with "I'm always surprised more people don't engage." So many friendships or acquaintances start online.

I was reminded of that when Shafqat Islam weighed in:

It's true. I knew Shafqat as a reader on my blog and then I was introduced to him on a trip through New York. His personality is infectious and we instantly became friends. I've seen him over the years at several cocktail parties and have him on my short list of people "I wish I had known in time to invest in his A-round" but have down to meet early on NextCo.

Figuring out how to engage is tricky. You want to be respectful. You want to say something informed. You want to toe the line between friendly public comment and being smothering.

1. Blog is best.

The best way to engage with anybody you want to build an online relationship with is their blog if they have one. If they are not the kind of person that reads their blog comments then they probably aren't the kind of person who would build an online relationship anyways. Most bloggers I know read most if not all of their comments. I recommend you keep comments brief unless it's the perfect topic for you and you want to add to the story.

I read almost every comment made within the first week or so (I often don't go back after a week to see who's commented). I try to respond to many comments but not all. But over time I've seen the same names through the years, and I know all of these people by name if not by face. If somebody like Cookie Marenco or Phil Sugar ever pulled me aside at an event, I wouldn't know what they looked like, but by name I'd immediately chat with them. I feel like I've "known" them for years. Or Fake Grimlock. Or Startup Jackson.

2. Don't go immediately for the kill.

There are times where you don't know somebody but you engage just to get a conversation started or be polite. Sometimes these people immediately try to friend me on Facebook, send me a deck or tell me they want to pitch me a company. I don't recommend coming on that strong. You need to earn some name recognition and engagement before moving your relationship to the next level.

3. On Twitter add value, be funny, link or be brief.

I like engaging with people on Twitter. It's a chance to get to know new people and you aren't locked into a 20-minute conversation to do so. You can watch who comments with whom frequently and get a sense of who knows whom. It's fun.

I also remember early on Twitter there were some well-known people who never responded to anybody. I felt like they were doing it wrong. Twitter is best when it removes the barriers and the bubble and puts you in direct contact with people who want to know YOU and people you want to know.

As with blogging, there are those who engage from time-to-time that I feel I know. And there are people who come on too strong or pretend they're your best buddy. I don't recommend that.

It's ok to be funny. I recommend being brief unless they talk back at you a lot or if you're engaged in a good conversation. Respond from time-to-time but not to every one of their Tweets. It's an art, but surely you have enough of a filter to know not to be a creep.

4. Don't hop into conversations with people you don't know. 

I saw an interesting response to Marshall and my back-and-forth from David Senior:

I thought in this case it was perfectly appropriate because it was a public question from Marshall and therefore responded to my response was fair play. But sometimes you might see a conversation between Marc Andreessen, Hunter Walk and Semil Shah on Twitter where they're clearly talking with each other about a topic. If you don't know one of them it can be a bit inauthentic to hop in, reply and copy all of them. People do, but it strikes me as in bad form.

It's one of the things I think Twitter needs to eventually fix. How people have a closed conversation while allowing others to witness the results. It's really a magical component of Twitter to see public conversations but the lack of tools I believe discourages this.

5. Be subtle, be occasional.

Play the long game. Don't try to be noticed in your first engagement. Say something and then move on. Re-engage. But it doesn't have to be every time or all the time. Blogs you can comment frequently but Twitter you need to be careful until you know them better.

6. Don't assume engagement = knows you.

I often find somebody at a conference will say "I comment on your blog from time-to-time." Usually I will recognize the name and I like that. Or there are the people on Twitter with whom I've been talking to for years and know their names. But often somebody will approach me and say, "Hey, I'm so-and-so. You wrote me on Twitter." Crickets. I write lots of people on Twitter. FWIW: I usually click on people's names and read the bio, which is why it's worth updating yours. But unless I've been doing it for years I simply don't remember each person I said "hey" to.

7. Find a subtle way to close the loop.

Eventually it is nice to close the loop. This can be at a conference, via an intro from a mutual friend or similar. It's always good when you do this because then future online conversations come from a position of knowing that person better. You don't necessarily need to spend 45 minutes standing by them at a conference. You just need to close the loop, be subtle, and build the relationship and trust over time.

8. Well known people should engage, too.

There are well-known actors, musicians, VCs, bloggers, politicians, you name it, who engage with random people on Twitter. Twitter magic. But I see some people in our community who really only use Twitter to publish their media or have a one-way conversation or at best reply only to people they know. I won't say this is doing things wrong. But this is doing things wrong. I've seen it directly through data. Every social media analytics platform, video platform with data or similar that I've seen show the same phenomenon. People who publish and don't respond get some take up. People who publish and respond to "fans" get massive engagement and earn followers. Channel your inner Gary V. He's the boss.

This article was originally published on Mark Suster's blog, Both Sides of the Table.  

Published on: Jan 26, 2015