Stop Losing Important Conversations in Scattered Docs and Forgotten Agendas
Discover a new way to have long-running, meaningful discussions
With distributed teams, async work, and fewer organic watercooler moments, it's harder than ever to maintain the personal connections that fuel collaboration, ensure retention, and elevate performance.
In the traditional agenda-first approach: You create a meeting agenda and discuss whatever fits that day. Context and continuity get lost.
In the OurSails topic-first approach: You organize around recurring themes (e.g., "Career Growth," "Project Challenges," "Company Integration"). Each topic maintains running context across multiple conversations.
"In 2020, I was leading a team of talented managers and directors spread across four time zones from New York to Tokyo. We were just beginning a 5 billion dollar post-acquisition integration that was changing how we worked, in the middle of a pandemic which changed where we worked, with no in-person interactions to help me or my leadership team communicate why we were doing any of it.
Gone were the lunchtime discussions, whiteboard activities, and hallway conversations that helped me understand what motivated and inspired the people around me. So I found myself working double-time to save our team's great culture. I used video calls with one-on-one agendas in Google docs to spark and track discussions about the individual challenges and aspirations of my teammates, but this system was painful!
I created OurSails to make it easy to cultivate important, long-running, deep discussions."
Three Big Problems I had when leading a large team
- Copy / Paste / Miss. When I wanted to ask each person about their private opinion on a topic, I had to remember to copy it into each one-on-one document. I dreaded pasting a bullet into more than a dozen documents, so I usually kept an extra doc with my agenda, but I always missed asking some people.
- Nothing Was in Focus. With over a dozen documents, each growing their own list of urgent topics, new problems arose that made it hard to stay focused on what mattered. Poor discoverability: important notes about specific topics were scattered across different documents, and easy to lose in the backscroll. Difficult pattern recognition: finding connections across related discussions was time-consuming and frustrating. Missed updates: when teammates edited notes between meetings, I'd rarely know in time to prepare—unless they specifically tagged me.
- Forgetting What Matters. Any long-running, deep discussions we had felt out of place in these Google documents. The topics on individual growth were hard to revive from a bullet point in an agenda. Without enough context, I often failed to recall key details that mattered about my teammate's personal goals. And when I said I'd follow up in the next month, I needed reminders that wouldn't get lost in old agendas and random files.
From 2020 to 2023 my team stayed highly aligned, excelled, and more than tripled in size.
We delivered, and we did it better than ever before - but it wasn't easy, and I made a lot of mistakes along the way. I tried dozens of tools and systems, but none of them fit just right. OurSails was created out of my frustration at organizing discussions on the topics that matter with the people that mattered to me.
OurSails Solves Those Problems Today.
Create a 'Career Growth' topic. Add discussion questions. OurSails automatically reminds you to discuss it in your next 1:1 with each team member, consolidates all responses in one place, and surfaces patterns across your team.
OurSails will encourage healthier discussions on all the topics that matter with the people that matter to you.
