People break things, like always
In the early days of Textio, our office was in a condo that was not zoned for business. Since we were a software company rather than a brick and mortar store, we persuaded the landlord to let us rent it anyway. There were five of us "roommates" on the lease, ten by the time we moved out.
There are many aspects of that time period I remember fondly, but the best part was how our team talked every day. Not in scheduled meetings, because we didn't need them, but just whenever someone had an idea. It was easy to stay in sync because we never had the chance to get out of alignment.
We grew rapidly after that. Our next 30 hires were by and large exceptional, but we never again had this effortless connection.
Comms whack-a-mole
Up until Textio had about 50 people, you could ask anyone on our team about vision, values, and priorities, and people pretty much said the same thing. I saw this play out both firsthand and in anonymous surveys from employees. If anyone was ever confused or had a countering opinion, they could raise it quickly and we would talk it through and get aligned again. It was delightful.
But once we reached 50 people, I started hearing the same baffling comments over and over again. What do you mean, you don't know our vision? We just talked about this in the all-company meeting! How do you not know what the product team is working on? It's right there in Slack! Wait, you didn't know customers hated that feature? I've had five meetings about it this week!
We tried many strategies to address the gaps. I published weekly kickoff notes, we had weekly all-hands meetings, and an employee committee set out guidelines for our use of Slack and other tools. These measures helped some. But no matter what we did, the chorus never entirely went away.
These aren't the droids you're looking for
I've worked with a lot of companies since stepping down as Textio's CEO. Once a team passes ~50 people (15-20 if the team is distributed rather than co-located), internal comms falls apart. Employee complaints are the same across industries, employee bases, tool choices, and leadership styles.
It's tempting to hope that AI can solve for this, and plenty of AI productivity tools are trying to help: Auto-summarizers, personalized alerts to tell employees what they need to focus on, AI-powered search tools to help people track down key info, semi-creepy listening services to anticipate employee confusion, and more. I haven't seen any tool that makes a meaningful difference.
In the end, I've found that only three things help, and even they don't fix it entirely.
#1: More time in person
Man, do I love typing words on the internet! I would much rather write stuff than have a meeting. Unfortunately, where alignment is concerned, typing isn't the same as spending time with your colleagues. No amount of Slack updates or vision docs or slide presentations (or zoom meetings, sorry to say) can substitute.
Spending time in person allows for the spontaneous, real-time exchange of perspectives that allows you, and everyone else, to be heard.
#2: You just need fewer messages
As a CEO, I sometimes inundated my team with vision memos, product docs, customer data, and written feedback on our projects. A few people on the team loved it and appreciated the deep context. Everyone else hated it, because they had no idea what to pay attention to.
When you're constantly talking, no single message is important enough to cut through the noise.
#3: If you're not repeating it in every single conversation, you're not saying it enough
I'll never forget the quarter when I rolled out a re-articulated vision for Textio. I spent two months before annual kickoff with the leadership team perfecting it and dozens of hours preparing my talk for the company to roll it out.
We had the kickoff meeting and it went great! I was psyched! Right up until my 1-1 with the VP of Customer Success a week later. "We need a clear vision," she told me. "Not having one is holding my team back. They complain about it constantly."
Wait, what?!?!?!
Not only had her team not internalized the vision we had just rolled out, their VP (who had literally been in the room for gazillions of hours of discussion about the vision!) hadn't internalized it either.
It was a total fail. Though I felt like I was talking about nothing but the new vision, the simple fact is that I just hadn't repeated it often or clearly enough. And because the VP hadn't internalized it, she couldn't possibly repeat it often enough for her team. Because ultimately, most people look to their managers for guidance and vision, not their CEO.
You can repeat it until you're bored out of your mind, in big meetings and small meetings and 1-1s and in writing. You can train your managers to talk about it seven ways from Sunday. If it's important, you're still probably not saying it often enough.
The bottom line: I am pretty good at comms, and I still made mistakes. You can do everything right, and if your team is big enough, your internal comms will still be broken. The work to fix it is ongoing and constant. It's also one of the most important parts, maybe the most important part, of a leader's job. It's at the core of your organization's ability to succeed, so you gotta keep doing the work. As long as you have human employees, AI tools are not coming to save you.
Kieran
I've coached tons of fast-growing companies on how to build teams that continue to thrive as they grow. Join my summer 2025 waitlist!
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