The Problem OurSails Solves

Losing Focus and Missing What Matters

In 2020, I was leading a team of 50 talented individuals 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.

“OurSails takes a meaningful topic-first approach to discussions, rather than a shallow agenda-first approach to meetings.”

Charles Abbott
OurSails Founder

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 for three big reasons:

  • 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 20+ documents, so I usually kept an extra doc with my agenda, but I always missed asking some people.
  • Nothing Was in Focus. With dozens of separate documents continuously scrolling with all sorts of discussion history - it was too easy to forget where I had written down a note about a topic. On top of that, it was painful to find patterns across these discussion notes. And what happened if my teammate updated some of the notes in between our 1:1s? Unless they tagged me, I'd rarely see it in time to prepare adequately to focus on what mattered to them. With dozens of documents mixed with dozens of ideas, nothing was in focus and everything was too easily forgotten.
  • 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. When stored in other documents, the documents were hard to find. I often failed to recall key details that mattered about my teammate's goals and personal objectives. And when I said I'd follow up in the next month, I needed reminders that wouldn't get lost in old agendas or random docs.

From 2020 to 2023 my team excelled and grew rapidly. 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.

OurSails takes a meaningful topic-first approach to discussions, rather than a shallow agenda-first approach to meetings. Our features include smart agendas, but also a single-pane view for all of your reminders and notes on any topic, and personal insights that will encourage discussions on all the topics that matter with the people that matter to you.

Dream Together
Succeed Together

Build trust by dreaming, discussing and documenting what matters with the people that matter to you.

A dream written down becomes a goal. A goal broken down into steps becomes a plan. All plans meet unexpected circumstances - discuss regularly and adjust quickly! Clear goals, flexible plans and consistent action will eventually turn dream into reality.

"Only three percent of adults have written goals, and everyone else works for them." - Brian Tracy