Pushing Through December
Awkwardness, deep conversations, and Christmas prep
This time last year, Mohammed Hussain had a pretty funny twitter thread:
That is me1. I am dying to sleep in. Current projections suggest I will get to sleep in on…December 26th. To be clear this is largely self-inflicted. Who thinks we need three different Advent calendars? Hand-strung popcorn and cranberries on the tree2? Eight different kinds of cookies and a Yule log? Only me3. The only possible explanation is that I think the holiday gauntlet is worth it. And I do.
It’s sentimental and schmaltzy, but once I push through all the prep, I’m rewarded with a few blissful weeks where the regular agenda fades away, and I can devote myself fully to reconnecting with family and friends, quiet times at home, and traversing generations with traditions large and small. And then, come January, I emerge from the end-of-year cocoon, with fresh energy for the new year ahead.
The holidays aren’t a happy time for everyone, I know. But I hope whatever your situation, you find some time to rest, reconnect, and reinvigorate for the year ahead.
Building Trusting Relationships
I’ve been thinking a lot about work-based relationships these past few months. So many of my most cherished friendships got their start in the workplace, and I think that depth of relationship will be one of the things that suffers as we move into a more hybrid-remote work environment. I think you can absolutely establish deep and trusting relationships when most of your interactions are happening virtually. But when everyone was in the same physical space every day, that depth and trust could be established without deliberate effort, almost by accident. When people are mostly or exclusively working remotely, it takes a lot of concerted mindfulness to get to the same level in relationships.
One problem is that relationship work is important, but not urgent. Like all work of that kind, it is so very prone to being pushed to one side when things get busy. And when you’ve got a pile of impending deadlines, of course you’re going to reschedule that discretionary coffee meeting. But the nature of modern knowledge work is that there is always a pile of impending deadlines, and the coffee meetings aren’t so discretionary. If you’re not careful, you’ll look up and four months have passed without your having connected with any colleagues outside the day-to-day grind. That’s especially true when you’re working remotely, because the scheduled meetings are often the only time you have an actual conversation with your colleagues.
Another challenge is having the right kinds of conversations. To build trust and deepen relationships, you need to reveal things about yourself. In her book Remote Work Revolution, Tsedal Neeley talks about what kinds of self disclosures actually build the most trust. She highlights the need for interactions to have depth, breadth, duration, and reciprocity in what people say about themselves. Sharing your opinions and values builds more trust than merely describing events. Basically, you can’t just have small talk — building trusting relationships requires deep and meaningful conversations.
There’s a very real sense in which organizations have been free-riding on the in-person bonds established prior to March 2020. But whether or not the Great Resignation is a real phenomenon, natural turnover means that many knowledge workers have a bunch of new coworkers they have never met in real life. Do we engage with these new employees on a surface-level, sticking to work-related topics? Or do we connect more deeply by making self-disclosures? Our sense of belonging and connectedness in the workplace might hinge on the answer.
Unfortunately, some new research4 shows that our natural instincts in this area are counterproductive. In a series of seven controlled experiments, Michael Kardas, Amit Kumar, and Nicholas Epley found that we both overestimate the awkwardness of deeper conversations, and underestimate the degree of connectedness we will feel from going deeper. Having a deep conversation with another person is a surprisingly positive experience. People report really enjoying them, after the fact. But beforehand, we expect it to be an awkward experience, so we end up avoiding the very thing that could cultivate more meaning and belonging in the workplace.
Fostering a Culture of Pushing Through the Awkward
The solution here, it seems, is to push through the awkwardness and have a deeper conversation than we think will feel comfortable. If we push through the awkward, Kardas et al.’s work suggests there will be a positive reinforcement loop. We’ll update our expectations to more accurately predict how much we enjoy deep conversations and how little awkwardness we actually experience. The more deep conversations we have, the more we want to have.
For organizations, there is a bigger opportunity to actually create cultural expectations around deep talk in coffee chats. The highly-engineered version of this could be facilitating activities based on Arthur Aron’s Fast Friends Protocol, where two people take turns asking and answering questions that gradually delve into deeper waters. By tailoring the questions to explore how individuals relate to organizational values, it can become a way to develop interpersonal relationships while also creating deeper cultural alignment.
But Kardas, Kumar, and Epley’s work suggests you can get to deeper conversations with just by encouraging people to reframe their conversations a bit. As much as we overestimate awkwardness and underestimate rewards of deep talk, people actually have good intuition as to what kinds of questions will facilitate deeper conversation. Kardas, Kumar, and Epley asked research participants to write both ‘standard’ questions to get to know someone new, as well as ‘deep’ questions, and found that the deep questions were meaningfully more intimate than the standard ones5. Kardas, Kumar, and Epley also found that people are more likely to voluntarily choose deep conversations in one of two circumstances:
They are told their interlocutor is caring and considerate
That people tend to underestimate how much others will care about our responses to more intimate questions (i.e. given the results of this research.
To me, that suggests some simple framing might help people connect more deeply: “Here at company X, we’re all a caring bunch, and research shows that people find coffee chats more rewarding when they delve deeper — so try to ask each other questions that go beyond the surface and beyond small talk.6” Messaging like that in calendar invites or donut bots is a low-cost way to boost the chances for meaningful connection that strengthens social ties throughout an organization. There’s nothing specific to remote work about any of these findings, but I think it’s all the more important when we’re losing the casual, serendipitous encounters of face-to-face work.
What I’m Working On
Aside from the part-time job of Christmas prep, I’ve been helping a small Toronto-based company figure out how to take all their pandemic-driven innovation and integrate it with the in-person work they did before COVID, so that the business model is coherent for both employees and customers. There are many wonderful things about working with smaller companies, but I really love getting to see how they’re using new software tools to get work done.
One that has been a particularly helpful on this project is Loom. We’ve used it to record videos that replace detailed walkthroughs of documents or spreadsheet that otherwise would be typed up in an email or covered off in a meeting. You have to overcome self-consciousness from recording your own verbal tics, but it’s worth pushing through the awkwardness. It’s much faster than conveying the same information in writing, you don’t need to coordinate calendars before the real work can start, and you can refer back to the video as needed. The real recommendation here is to make more liberal use of screen capture videos for asynchronous collaboration. But if you’d like to check out Loom specifically, they make it easy for teams to organize and share videos in a workspace, and their free tier allows 25 5-minute videos per team member.
The festive season is just about upon us, and sending out this newsletter is one of the last work things on my 2021 to-do list. Thanks for reading this little corner of the Internet this year. I’m looking forward to whatever 2022 might bring, newsletters amongst the rest. Wishing you all a wonderful festive season, and the very best for the new year ahead.
In comradeship,
S.
Honestly, he’s understating the extent of the operation. I start planning for Christmas on (no joke) Labour Day weekend. I wrapped and mailed all my out-of-town presents in October. The eggnog gets made in November so it has time to age properly. That’s to leave time so I can do things like spend all of yesterday hand-twisting a hundred candy cane cookies for my children to take to school.
Er, my husband actually strung all the popcorn and cranberries this year. Find you someone who will indulge your whims.
Technically, my five year old thinks we need the Yule log. But I am the one agreeing to it, so.
You can check out the full research paper from the Journal of Personality and Social Psychology, or a nice summary the authors wrote up in The Washington Post
They assessed this via Mechanical Turk
This is a riff on the wording Kardas, Kumar, and Epley used for their participants in Experiment 3. They also provided examples of deeper questions in their prompt.
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