Four communication hacks that help me survive as an introverted CEO

Doing effective, meaningful work in my role as CEO for a small startup requires a lot of communicating and interacting with other people. There’s team meetings, customer interviews, sales calls, conferences, board meetings, pitching in on support, and dealing with the daily flood of emails in my inbox. It’s all important, and generally satisfying when I get done with it, but it’s a lot!

I struggle with it because I’m generally a bit of an introvert. Okay, that’s an understatement. I’m incredibly introverted, so I really struggle with it.

For me, dealing with so much input and the interactions that come with it is intimidating and overwhelming. So I’ve had to come up with a playbook of tools, tricks and strategies to help compensate for the more social parts of the job that just don’t come naturally to me. Here’s a few that have been particularly useful.

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Networking hack: Effectively connect with people without business cards (ew!)

Me at meetups and conferences

I will never get used to professional networking. I feel super awkward and out of place at most conferences and meetups, and constantly fight the impulse to go find a corner and bury myself in my phone, looking busy. Unfortunately, I haven’t found any magic bullet that makes talking to strangers any easier, but I have figured out an effective way to avoid one of my least favorite parts of it. I hate, hate, hate x 1000 the “hey let’s keep in touch and trade business cards” shuffle. It’s super inefficient, and it feels like an insincere formality. It’s like “Here, take this piece of garbage with my email address on it. Have fun throwing it away later!” Mainly though, it just feels totally unnatural to me in a way I’ve never been able to get past. Not sure how to describe it other than it’s like I’m playing a role that I’m not prepared for. I’m likely over analyzing the nuances of it, but hey, that’s what introverts do!

Obviously, opting out of exchanging contact information with people isn’t a realistic option. So I came up with an arguably over-engineered solution that lets me take it in a different direction, makes follow-ups easier, and increases the quality of the connections I make.

Instead of business cards, I use a Google Form to collect a name and an email address (nothing more or it gets weird), and then use Zapier to send an info-packed intro email that I’m also cc’d on. No filing the card for later, no worrying about how to word the “hey, remember me?” follow-up. We’re both instantly in each other’s inboxes, and I’ve given a lot of context for directions we can take the conversation in the future. Here’s what it looks like:

Hello! Great chatting with you today! This is an automated email (sorry!), but it will help us connect in the future. I'm Robby. I'm the CEO of RescueTime. We help people do more meaningful work by giving them a way to manage their time and attention. If you'd like to give RescueTime a try, here is a code for three months of premium service. We've recently launched a new way for RescueTime to help out entire teams. I'm pretty excited about it. Here is some information if that's something you'd like to learn more about. If there's anything else that would be fun / useful / helpful for us to talk about, just let me know! Otherwise, I've added some general connection info below. Thanks for taking the time to talk to me and have a wonderful day! Robby Macdonell CEO, RescueTime.com www.rescuetime.com

The interaction works like this: When someone tries to give me a business card, I politely decline and tell them I have something that works better for me. If I’m initiating things, I ask if it would be OK if we trade contact info so we can keep in touch later. It’s good to ask, but if I get to the point in a conversation where I’m asking, the answer is almost always yes.

Then, I just pop open the form (I have a bookmark on my home screen), hand them my phone, and ask them to put in their name and email, explaining what will happen when they fill it out. Interestingly, the act of handing over my phone to them seems to add a nice personal connection to the interaction. It’s a little thing that I didn’t plan for, but multiple people have pointed it out to me.

Outcome:
This gets a way better response than handing someone a business card. It’s memorable, actionable, and gives context in a way that business cards can’t. Also, people seem to really appreciate it, which I hope means that I’m not the only weirdo that finds the whole ritual of business cards absurdly off putting. It’s easily doubled the meaningful, lasting connections I get from networking events.

If you’re interested in doing something like this, here’s how to get started.

  1. Create a Google Form with whatever intro questions you want to capture (again, I recommend keeping this extremely lightweight. Name and email only). Make sure the results are saved to a Google Sheet.
  2. Use Zapier to connect your spreadsheet to Gmail (or whatever email provider you use.)
  3. Create your own version of an intro email, written with the goal of giving people all the information they need to take the next step in a meaningful conversation.
  4. Bookmark the form on your phone, so you can get to it quickly when you need it.

Scheduling Hack: Completely automate the back-and-forth of getting things on a calendar.

Using Calendly to take myself out of the scheduling process

There are a lot of subtle social anxieties that stack up on me when I’m trying to schedule a meeting or a phone call with someone I don’t know. How packed is their calendar already? Am I proposing a bad time? What if the time that works for them doesn’t work for me? Did you mean 2pm in my time zone or yours? How much am I willing to shuffle things around to be accommodating?

Those “let’s find a time” email threads drag out, and cause distractions while I’m trying to focus on other things. Even worse, sometimes while trying to be accommodating, I end up double booking or bumping an existing commitment because it’s the only convenient time for the other person.

I suck at managing a calendar. So as much as possible, I automate myself out of the process.

By setting up predictable times that I’m available and using a scheduling tool that lets other people schedule themselves within my framework, I solve two important problems:

First: there’s only ever one email—“Sure, let’s talk. Here’s my calendar. Pick a time that works for you.”—instead of a back-and-forth trying to pin down a mutually convenient time.

Second: I insulate myself from the bad decisions I make when trying to negotiate that stuff on the fly. People get to choose a time that works for them, and I stay out of the process until it’s time to show up and talk.

Scheduling a coffee meeting

I use Calendly for this, and they make it easy to set up different event types for different circumstances. I can send one link out for a 15 minute phone call, and another for a chat over coffee. It handles time zone conversion, and I can even ask screener questions so I have all the correct information when it’s time to meet.

Calendly works great for me, but there are other services that do similar things, like Doodle, or Google Calendar’s Appointment Slots feature.

Outcome:
I am able to remove myself from a process that makes me uncomfortable and I don’t feel like I’m good at anyway. Other people seem to really enjoy the control and flexibility it gives them as well.

Brainpower Hack: Regular journaling helps me process conversations, decide on next steps, even think through how to respond to things I’m unsure about.

Daily journal entries

I spend a lot more of my time these days talking. Talking with new customers, users in research sessions, coworkers, partners… So many conversations! I don’t hate it, but I don’t feel like I’m very good at it. All the input can be overwhelming, it’s too easy to forget details, and I feel like I put my foot in my mouth more often than I’d like. And the worst part is I feel worse at it the more I do it! If I spend too much time in always-on communication mode, I start feeling burnt out and unprepared for new conversations.

The antidote to that is regularly taking some time to write privately. Nothing elaborate, just opening up a Google Doc and letting whatever is in my head flow out onto the page. I make zero attempts at editing, because this is just for me.

There are a lot of benefits to a regular journaling habit. The best part about it for me is a chance to digest past conversations and think about which things are really important. It really helps my interactions with other people as well. Being able to work out, ahead of time, why a meeting relates to an important goal helps me feel more confident, and better able to direct the conversation. It also helps me look at things through the eyes of the other people I’m working with. Writing about how I think an interaction is going to play out is an amazingly effective way to spot problems with the way I would otherwise communicate. On-the-fly communication isn’t my strong suit, so the chance to work things out ahead of time is great.

It also serves as an extension of my brain that I can go back and dig through later when I’m trying to remember what was important about an interaction. For me, journaling is a lot more effective than taking notes during a meeting because I will write about how the discussion made me feel, rather than just scribbling down key words in real time.

Outcome:
I feel way more centered when I take the time to write to myself daily. I feel like I’m better prepared, more creative, and it almost always brings my stress levels down.

The problem with journaling is that it takes time. Not much, but it’s an effort investment. It’s one of those things that I find incredibly valuable when I’m able to do it, and really miss when I can’t keep it up, but I still struggle with making time for it. I’m still working on how to make it a more consistent part of my daily routine.

Mental-health Hack: Establish an email rhythm that leaves room for me to breathe.

Total time per week in email

I really miss the days when I could focus for long stretches of time on a single problem! Keeping up with constant input and being responsive is really draining. Some of this is self imposed. I regrettably admit to sometimes spending 45 minutes trying to word a 3 sentence email correctly. My responsiveness tends to fluctuate wildly, and I really hate either end of the spectrum. Either I have a weight of 1000 emails in my inbox crushing me, or I feel like I’m not getting anything meaningful done because I’m too busy getting back to people right away.

Managing my inbox is always going to be a struggle, but one thing I’ve discovered that has really helped me feel more balanced is to define what my comfort zone actually is and setting expectations with that in mind. I’m not ever going to be instantly responsive, and hate trying to be. At the same time, I fret a lot about leaving people hanging.

To find a compromise, I’ve worked really hard to instill a rhythm of a 24-48 hour response cycle for emails. Once I got it established, it relieved a huge amount of pressure.

I do my best to do a pass on email once a day, usually in the morning. If things come in later in the day, I’ll often intentionally push them off until the following day, even if they just need a quick response. I’m intentionally creating space where it’s OK not to worry about what’s looming in my inbox.

My process is pretty simple, and it’s based on Tony Hsieh’s Yesterbox technique. The important first step is to bulk-select the emails I plan on dealing with today and label them ‘@processing’. Once that’s done, that’s my inbox. I hide everything else and nothing new comes in to push the older emails out of the way. I just have a single static list to churn through. That’s important, because it turns email into a finishable task, rather than an ever-replenishing monster.

If there’s more in my inbox than I can handle, that’s OK. I only add a chunk of it to the @processing queue and save the rest for another day. This means sometimes my backlog falls behind by a day or so, but I can usually catch up pretty quickly. Even with the occasional 48 or 72 hour response time, I’m way more responsive in total than I was when I’d try to scan the hundreds of messages in my inbox for the threads that were important enough to pull me away from whatever else I was working on. That was my old way of processing email, and I would regularly have my response times slip to the ‘weeks-to-never’ range.

There are two tweaks I’ve made to Gmail to make this easier.

My Gmail inbox settings

First: items labeled ‘@processing’ show up at the top of my inbox and I’m able to collapse everything else. This makes it easy to focus on just the things I said I was going to focus on. Under the inbox options, I can set the @processing inbox to disappear when it’s empty, so it gets out of the way when I’m not using it.

Second: I have my inbox set so that only unread messages show up in my inbox (Inbox section #2 in the image above). This adds some immediacy to dealing with an email. If I open it, it’s getting archived by default unless I intentionally mark it as unread again.

Outcome:
This process works great for me. I don’t cringe when I look at my inbox any more because I know I have a process to get out of whatever pile is in there. I’ve also noticed that no one has ever complained about a 24 hour response time, so knowing I can put things off until later is a huge weight off my mind.


I can say without exaggerating that these hacks have helped me be way more effective with the interactions I have with other people. Some of them may be finely tuned to my own personal quirks and introverted tendencies, but I suspect some of the things I wrestle with are fairly universal. Hopefully they’ll help you, or at least get the gears turning about your own strategies for dealing with the parts of work that aren’t totally in your wheelhouse.

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Robby Macdonell

CEO at RescueTime

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