The Problem With Remote 1:1s

Let me start with the assumption I make that underpins my entire methodology…

As a manager, everything you do is downstream of your relationship with your direct reports. 

If your direct reports have an open and trusting relationship with you, you’re far more likely to be effective. If your direct reports distrust you or hide the truth from you, you’re almost guaranteed to be ineffective.

I don’t believe this is a new phenomenon. I believe this has always been an underpinning of effective management, but the transition to a remote environment has changed the methods required to achieve this outcome dramatically.

In an in-person environment, establishing a trusting relationship tends to happen more organically. A thousand small structural forces conspire to help you… Everything from the location of your desks to the natural watering hole of the coffee maker creates the infrastructure for relationship building. This is why companies invest millions of dollars into office design. They know that the soft elbow rubbing that happens in these spaces forms a relational bond that creates a culture. This isn’t new information, we’ve known this for decades.

But what happens when all of that infrastructure disappears overnight? There is no more water cooler or coffee maker. You can’t look up from your monitor and make a passing joke to your colleague. You’re not making small talk on your walk-in from the parking lot. You aren’t getting lunch or an after-work beer with your colleagues.

Simple. Trust erodes. 

Slowly, over time, you see your colleagues less as three-dimensional people with families, lives, and interests outside of work and instead begin to see them as avatars for their roles. This makes it harder to see their side of a disagreement or give them the benefit of the doubt after a hard conversation. This turns a team-oriented culture into a culture of heroes and villains and eats away at the fabric of the organization itself.

There is one group that can prevent this… The managers. The overlooked, under-appreciated, and often completely untrained “middle managers” are the one group of people who have the power to prevent this.

Their secret weapon? The 1:1.

The Old Way of Doing 1:1s

I’ve long believed that 1:1s are the most important tool managers have in their toolkits. Everything you do is downstream of your relationships with your direct reports and there’s no better way to build a relationship than dedicated one-on-one conversations.

In the old world, 1:1s were shape-shifting meetings that often included progress reports, status updates, blocker resolution, coaching, and professional development. Some managers might give you five minutes up top to talk about your personal life, but this was a work meeting and it was treated as such. We’ll talk about your kids at the water cooler. Time is precious and we have to get down to business.

In an in-person context, this structure worked well! It was efficient and productive while providing little room for the soft relationship-building that makes the best managers effective. But what happens when we can’t talk about our kids at the water cooler anymore?

Now, this meeting feels less like a working session and more like a hot seat. I haven’t talked to you all week and the first thing I hear from you is “What is the status of this project?”

Yikes. Trust erodes.

Time for a change. 

Remote-First 1:1s and Building Trust

Both synchronous and asynchronous communication have superpowers. To be effective in a remote-first setting, we need to deploy each method of communication in a way that will lean into those superpowers. 

Asynchronous communication is amazing at things like status updates, project briefings, and resolving blockers. Unlike its synchronous counterpart, asynchronous communication has a long memory and a robust paper trail, which is a cheat code for management. 

Synchronous communication on the other hand has a superpower for relationship building. As such, I recommend that remote managers use 1:1s primarily as a relationship-building tool and not as a tool for status updates and project work.

The word primarily carries a lot of weight in that sentence, so let me elaborate.

Sometimes the best thing you can do to build trust in your relationship is to do the work. When my team is deep in the trenches of a very involved project, we may need to use the majority of our 1:1 to work through blockers. That happens. I’m not saying that’s inherently bad or unacceptable. I’m saying that in a remote-first context, this needs to be the minority of your 1:1s with your direct reports. Most of your time in your 1:1s should be focused on relationship-building and establishing personal bonds. If you’re unable to do this, it means that you haven’t established the asynchronous communication structures necessary for your team to thrive in a distributed environment. 

In the coming weeks, I’m going to dive deeper into these asynchronous communication structures and share how you can set up your distributed team to thrive, but the foundation of all of it is your relationships. If you only get one thing from my Substack, I hope it’s this… Establishing trust with your team in a remote-first setting requires a complete reset of your managerial mind.

I hope the insights I share can play a small part in helping you with that reset. 

My Challenge For You This Week

If you’re a manager, I want to challenge you to find 30 minutes for at least 3 of your direct reports where you can have a dedicated, non-work conversation this week. Here’s a list of potential conversation starters… Pick your favorite and run with it:

• What is your favorite thing that you’re watching/reading/listening to right now?

• What’s something non-work related you’re excited about right now?

• How has your family been?

• What’s a hobby you have that you wish you had more time/energy to focus on? Tell me more about that.

• How about them (insert their favorite sports team here)?

• What’s a funny story from your past that you’ve never shared with me?

Once you’ve got them talking… For the love of God, engage. Your direct reports aren’t stupid and they can tell when you’re smiling and nodding to feign interest. You may not share every single interest of your direct reports, but I’m certain you can find something that the two of you have in common. If you can’t find a way to earnestly engage with their personal lives and interests, it’s time to look at yourself in the mirror and ask why.

After you’ve completed this challenge, reply to this email and let me know what you learn… not about your direct reports, but about yourself as a leader. I look forward to hearing from you. 

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Tim Hickle is a marketing leader who helps high-growth startups and scale-ups get unstuck and hit their goals while embracing AI and the future of work. To learn more about how Tim can help your organization grow, visit TimHickle.com