My System for Virtual Coffees: Building Meaningful Connections Without Calendar Chaos

The Trademark 'Smooth Operator' Cog in light sage green.

Note: This is part of my “My System For…” series, where I share systems I’ve designed that work for me. 

Remember, every system is perfectly designed to get the results it gets—so if you don’t like the results of your current systems, you can change them. I’m not saying my approach will automatically work for you. I’m also not saying that other systems are bad. My goal is to share how I apply systems across my own business to spark ideas for your own! 

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Ever since I started my business in 2017, I’ve heard a common refrain: if you have a B2B services business, your best way to grow it is by networking. 

I’ve always worked virtually, so ‘networking’ has always looked specifically like a combination of in-person or virtual events and what we like to call ‘virtual coffees.’ Most of us have done hundreds of these. In-person networking, LinkedIn connections, introductions, and virtual group meetings all funnel into the same place – a virtual 1-on-1 conversation. 

Averaging about 3 networking events or conversations per week for my nearly 8 years in business, I estimate that I have attended over 1,000 networking events or meetings, which has turned into over a year of working hours. 

Here’s the deal: relationships matter deeply to me. And, I’ve known for years that something has to give.

When I Knew I Needed a New System

Have you ever looked at your calendar going into a new week and groaned inwardly at the slog of meetings and events that you’re already committed to? I have. 

Beyond that, I knew I really needed to change something when:

  • Sick kids (or God forbid, a sick me) would turn into a flurry of rescheduling and needing to ‘catch up’ from missed meetings. I’ve emailed people to cancel meetings while in labor and from an ER waiting room
  • I would have five or more virtual coffees on a single day, despite working only 25 hours a week and being a serious introvert (making these meetings even more expensive as a percentage of my time and energy)
  • Time out of the office would turn into the weeks before and after being even MORE stacked with meetings
  • I set a goal of having fewer than 15 meetings a week and consistently failed to achieve it 
  • Even best-case scenario conversations with really cool people turned into an ongoing pressure for both of us to “stay in touch,” which usually led to us not talking for years and then forgetting we ever met

Why I Was Resistant to Change

I’ve tried changing my approach to virtual coffees many times over the years. A few things kept tripping me up:

  1. I’ve been told networking is essential. Over the years, I’ve heard that virtual coffees and networking in general are the best and most powerful way to build a B2B services business like mine
  2. I’ve had genuine success with them. I have met incredible people who have become meaningful friends and clients through virtual coffees over the years. A lot of these conversations have been life-giving and interesting
  3. Saying “no” feels personal. If I decline virtual coffees, it can feel like a personal rejection to folks, and we can feel like we’re at a complete loss about what to do next in terms of building a relationship
  4. Other options don’t always work as well. Especially with new connections, people who ask to schedule a 30+ minute meeting with me will not reply to alternative options, ending the conversation before it even begins
  5. People don’t like it. Several times, I’ve tried cutting back on virtual coffees and then ultimately gone back to them because my response made people uncomfortable or even annoyed. It can strike people as high maintenance or even snooty, like I am playing some queen who won’t deign to speak to them

What I Needed From a New System

A good system always starts with the outcome you want and the core principles you want it to rest on. To make a change and finally stick to it, I needed to articulate mine:

  • Meaningful human connections. I need a way to build genuine personal relationships with people
  • Sustainable meeting load. I need to hold to my goal of fewer than 15 meetings a week (including all client and team meetings) to have a business that feels sustainable and joyful
  • Accepting the relational costs. I am willing to accept the discomfort that comes with doing things differently, even if it means not having conversations with people I otherwise could
  • Accepting the business costs. I had to really face the possibility that real opportunities may pass me by when I hold this line. I ultimately had to realize that I need to build a business I can sustain, and that means it has to be one that works on fewer meetings
  • Flexible options. I want approaches that work for people who operate differently from I do

My Current System

Here’s how I handle virtual coffee requests now:

The Initial Response

My executive assistant is new, but one of my goals is for her to reach out to folks who express interest in a virtual coffee with a template that explains how I operate, why I’ve made these choices, and what options are available for us to connect meaningfully.

The Options I Offer

Instead of defaulting to a calendar meeting, I provide several alternatives:

  • Voxer: A walkie-talkie app on our phones for ongoing voice conversations
  • Google Chat: If they also use Gmail, we can chat using audio or text there
  • Video/Audio Messages: Loom videos or audio recordings are great for deeper conversation and getting to see someone’s face
  • Email: While I don’t love spending time writing long emails, I’ve found that for some folks, sitting down to listen to a video or audio is distracting and hard to process. In these cases, I can talk out my response, have AI format it into an email, and send it so they can read it.

Addressing Neurodivergence the “I’ll Come Back to It Later” Problem

We’ve all received a long email or video at a time that wasn’t great for sitting down to respond to it. This often turns into saying, ‘I’ll come back to it later”… and then never coming back to it as it gets devoured by our endless stream of emails. For a lot of folks, this is a real danger for any kind of asynchronous communication. Calendar invites make sure things happen and don’t get lost. 

I completely get this and want to honor it! Something I’ve started suggesting is that people can add a 10-15 minute block to their calendar to watch/respond to my video. This does a few things:

  • They get the calendar reminder they need
  • It still saves significant time over a 30-45 minute virtual coffee 
  • If they don’t feel like doing it when the time comes, they can simply move it
  • They can schedule it for any time of day or night that works for them—no need to worry about my availability

Side note: A lot of folks have ADHD or a whole suite of other circumstances that make sitting down to watch a video not a great fit. Having a live person staring at you through a screen is another benefit that gets lost without a scheduled meeting! In these circumstances, I’ll often default to shorter email chats that might turn into real-life calls on a topic that matters to us both. 

When I Do Take Calls

This doesn’t mean I never have calls with people. But when I do, I want them to include a specific topic (like a potential collaboration, a question, or an idea) that we want to talk about together. I also need to hold to my calendar boundaries, even if that means we have to wait a while to talk. I also really like doing group calls when I can as a way to cultivate a group of deeper friendships over time. 

As Tim Ferriss once said in “Four-Hour Work Week,” we need to think about the smaller ‘bad’ things we’re willing to accept for the sake of a bigger good thing. 

A Side Note About Our Calendar Culture

I think part of the reason virtual coffees are so common is that having something on our calendar makes it more likely to happen, even when not having it on our calendar would save time and make life easier.

Being responsive to our calendars is fine, but it often means we aren’t experiencing the kind of protected creative time we need. It also means we’re spending more time on things we wouldn’t otherwise prioritize to the same extent.

Think about it this way: if I walked up to a stranger on the street and said, “Hey, please spend 30 minutes one-on-one with me with no other agenda than us getting to know each other because we both have businesses,” most people would give me a strange look and then speed walk in the opposite direction. They have full lives and wouldn’t want to spend such a significant amount of time with a stranger for such a vague reason. 

But in the online virtual networking space, that’s incredibly common.

The same folks who might suggest we spend 30 minutes on Zoom together often won’t prioritize watching and responding to a 2-minute video, even though it takes much less of their time. And that’s fine—they’re not required to prioritize me! I’m a complete stranger, and we don’t have a specific mutual benefit to discuss. It’s an easy thing to let fall to the back burner. But it makes me feel okay about sparing both of us the much greater time investment of a scheduled meeting.

Another important thing to remember is that the energy impact of even a 15-minute meeting is deceptively large. If you’ve ever said ‘yes’ to a single meeting on a day off, you’ve felt this. All of a sudden, it’s changing how you dress (will you be video ready?), what the rest of the day looks like (that reservation would otherwise be great but what if we’re not done on time?), and where you go (what if they don’t have service or a quiet environment?). You’re having to keep tabs on the passing minutes and may even freak out every time you lose track of time temporarily. Obviously, it’s not quite as intense on a working day, but it’s important to remember how much energy a scheduled commitment requires. 

I’m just wondering if we can start pushing back on this culture of defaulting to virtual coffees and being ruled by our calendars. When we do, we’re spending lots of time on things that probably aren’t worth that much time – at least not at the beginning. If we need our calendars to make things happen that matter to us, it’s time for us to take another look at our time management/prioritization systems. 

The Bottom Line

Please don’t hear me say that I don’t value human connection. I absolutely do value getting to know people, hearing their stories, learning about their dreams and goals, sharing my own story, and finding ways to collaborate or even become friends.

But I’d love to be part of the conversation about creative ways to do that in a world of virtual meetings and endless to-do lists. We all need more protected time for what matters to us. I don’t believe we have to sacrifice the human touch to get it.

What’s your approach to virtual networking? How do you balance meaningful connections with protecting your time and energy?