Lately, we’ve been thinking a lot about work-based relationships. For many at Workomics, some of our most cherished friendships got their start in the workplace. As workplaces continue to adopt hybrid-remote models, we wonder if the depth of work-based relationships will suffer. One can absolutely establish deep and trusting relationships through interactions that are mostly happening virtually. But back when everyone was in the same physical space every day, that depth and trust could be established without deliberate effort, and 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 research* 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 ones†. 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.

We think that this 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.”‡ 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.