Words Matter… But Context and Serendipity Matter More

Audible version featuring Theo Lau and Matthew Halliday

A few weeks ago, Theo Lau (@psb_dc) – founder of @UnconventionVc and someone who enjoys amazing tiramisu baked by her superhuman kids – tweeted about a couple of LinkedIn connection requests that she flat-out rejected:

At the time, I was thinking a lot about the interplay between words, context, and serendipity – and then it struck me… What a perfect opportunity for an experiment! 

You see, Theo and I talk to each other on Twitter frequently, but I cannot recall how or when it all started. Her tweets about the oddball connection requests made me realize we weren’t connected on LinkedIn yet. Time to remedy that.

Here’s my LinkedIn connection request:

As you can see, my choice of words was questionable. I intentionally used the same phrases that failed spectacularly earlier that week. The context and serendipity, however, were excellent. Would that be enough?

The conversation quickly moved to Twitter and others joined in as well. Click to see the full context.

Listen Intently

The lesson here is the importance of listening. Since I had already taken the time to get to know Theo, I had the necessary context: she values non-creepy connection requests on LinkedIn and also has a great sense of humor. I had also been keeping up with the relationship for quite some time, mostly interacting over Twitter, which made serendipity possible. 

While this was an intentionally humorous stunt of sorts, I believe it makes an important point:

People painstakingly obsess over word choice when trying to share their worldview or passion with others. But there is no such thing as the “perfect” wording. It makes no difference whether you are evangelizing a product or an ideology. The perfect words for one person are often the wrong words for someone else. 

Words alone, do not win hearts and minds. Words matter, but it’s context that does the heavy lifting and serendipity that opens the door.

Enterprise sales reps understand this truth better than most. It’s the reason why they always want to meet with customers and prospects in person. Not because they think a handshake or hand-delivered plastic of crap that ultimately just ends up in our oceans actually closes deals – it’s all about laying down context and teeing up serendipity. Walking the halls in person means bumping into people, starting conversations you can build upon later, building social credibility, and – most importantly – listening.

Why does that matter? In sales, you don’t land big meetings with important people who you barely know by sending a LinkedIn connection request or cold-calling and leading with, “I need a big meeting with you.” No way. You have to become a part of their world first – and that requires taking the time to listen and get to know the other person. 

The same holds true for building relationships of any kind. At a dinner party, for instance, you wouldn’t walk up to a group of people and just start talking at them about whatever is on your mind. No, that would be obnoxious and get you nowhere. You listen first – figure out the topic of conversation, what’s already been covered, the group dynamics, and so on. Once you have that context, you can start to offer comments, share insights, ask questions. Before you know it, you are fully immersed and new relationships are being built.

WFH = Serendipity Lost? Nope

With Covid-19 keeping many offices closed (including Incorta’s), opportunities for serendipitous encounters have seemingly evaporated. I see people trying to recreate these moments of serendipity remotely with apps like Donut on Slack, but it’s not the same. Most of the time it feels too scheduled, too structured. That serendipitous feeling is lost. 

Joe McKendrick (@joemckendrick) has written extensively about this phenomenon and the implications of digital experiences killing serendipity – especially with respect to innovation. I wholeheartedly agree. The struggle and the risks are real. 

That said, however, I do believe there is a digital space where serendipity can still be found in spades: Twitter. 

A lot of people assume that LinkedIn is the place where professionals connect, and that is true to some extent, but Twitter is where the real action is happening. It’s like hundreds of conferences and trade shows happening all at once, twenty-four hours a day, seven days a week. And now that most in-person conferences and trade shows are going digital, there’s even more happening on the platform. It’s amazing. 

While people are quick to bemoan the short-form nature of tweets as too limiting, or the never-ending firehose of commentary as too much to keep up with, that is exactly what makes Twitter such fertile ground for serendipity. Twitter – far more so than Facebook, Instagram, LinkedIn, or any other social network for that matter – gives you an endless stream of opportunities to jump into conversations, meet new people, and build relationships. 

At the same time, Twitter also helps you connect with people on a deeper level by offering a more multifaceted view of an individual – who they are, what they like, what they are passionate about, how they spend their time during the day, etc. Granted, absorbing all of this context and acting upon it requires time and effort, but for those who are in it for the right reasons – i.e. building relationships, not just lead flow – there is no better place online today to do it.

Making Lemonade on Twitter & Beyond

Twitter can help you rediscover serendipity during the Covid-19 pandemic, but to get there you have to take the time to listen and really get to know people first – just like you would in real life.

I see people get impatient on Twitter all the time, thinking they can just sign up, follow a bunch of people, retweet a few things, and then – boom – instant relationships! But it doesn’t work like that. There are no shortcuts. It takes time, a track record of valuable contributions, and a whole lot of listening.  

In this way, I think Twitter offers a much-needed sandbox for retraining our minds about how to build relationships in an increasingly digital world. When we plug into digital networks and platforms, we tend to disregard the relationship building skills we’ve built up over decades in the real world. We assume that just because we can find and connect with someone so easily, that we can build a relationship with them easily as well. But that’s not how it actually works. Relationships run deeper than the technology used to facilitate them. 

More on that in my next article, Your Grandparents Can Probably Give You Better Relationship Building Advice Than Digital Marketers

Disclaimer: I recognize that being a co-founder of a fast-growing data analytics company, as well as an early Twitter user with a fairly large and long-standing community, makes it easier for me than most. Nevertheless, I believe the suggestions for relationship building offered here are universal and timeless.

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Published by Matthew Halliday

Co-founder, EVP of Product Strategy at Incorta. Passion for design, UX, data, stories, and making beautiful things.

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