You go for a walk reflecting on how your startup is doing and you realize you’re moving slower with 8 people than you were with 4.
It makes no sense! You’ve hired smart people, you’ve written good documentation, you’re not burdening people with meetings. Yet somehow, adding more horsepower has made you move slower.
Here are my reflections and learnings from going from 4 to ~15 in a remote team.
The Good Ol’ Days
In the early days of a startup, there’s a handful of people in a room.
You all have total context. Every decision, every new insight is naturally ingested in the process of working together on a single, focused problem. There’s no need to hold alignment discussions as everything is assimilated through proximity and shared experience.
You move fast because everyone just knows what to do. The strategy lives in the air, unspoken but universally understood.
All being well, you get traction and start to scale.
Scaling usually involves adding more humans (at least in 2025). Labor, one of the oldest levers is needed to do more work, build more stuff, and capitalise on a market opportunity.
So you hire a few people.
Initially there isn’t too much of an issue, a couple of good docs are sufficient to compress enough required context into the mind of the new team member.
The culture is still functional and progress is possible.
Then more flux happens.
A few more people join and some of the original people leave.
Despite having good docs, people just don’t seem to say the thing you’d expect when asking them about company strategy.
How could they be so off the mark with their understanding?
Despite our good intentions, we completely forget: this new team mates did not have the same lived experience during the earlier days. They don’t know in depth why we’re pursuing path A instead of B. They weren’t there during the pivots and dead-ends. They didn’t witness the customer calls that killed the most promising feature or the competitive analysis that shaped your positioning.
All of a sudden, your fast-moving, trust and intuition-based culture which was once your greatest strength is now a huge problem. The leverage of labor now starts diminishing and you’re moving slower.
Reflection and Remedy
I fell into this trap, painstakingly writing a strategy document, explaining what we were doing intentionally and articulating the known trade-offs we were making. I assumed it was sufficiently comprehensive and clear.
I shared it on Slack with a thoughtful message, confident that alignment was now solved for at least six months.
Reality is not so simple.
Someone was on vacation. Someone else opened the doc whilst working on another task, then forgot to go back and read it. A third person skimmed it but missed the crucial part in section three. Life is messy and noisy. The document that was supposed to solve everything became just another unread tab in someone’s browser.
Marketing teaches us that people need 7+ touchpoints before they act or internalize a message. Why did I think internal alignment would be any different?
To grow a team without sacrificing speed, the direction and quality of work has to be maintained without any leadership being in the room. And that only happens through deliberate, repetitive over-communication. Especially in a remote environement.
My new heuristic is: repeat the message until I am sick of myself internally for being so tediously repetitive. Then keep going.
In Practice
Some practical approaches I’ve been trying:
- Every doc should restate the mission.
- Every meeting should invite questions about the strategy.
- Every quarter kickoff should reconnect to the why.
- Every 1-1 should invite questions around decision making.
- Every Slack update should reinforce the narrative.
Having only ever worked on startups I have a natural repulsion to anything that feels procedural. It feels like you’re treating your smart, capable team like they can’t remember anything. On the contrary, it’s not about their intelligence or memory. It’s about creating a shared consciousness that can only emerge through repeated exposure.
The transition from natural to intentional alignment can feel like moving backward.
You’ll reminisce about the days when everyone just got it. But those days were only possible because everyone had lived every moment of the journey together.
Alignment is speed.