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One of the many benefits of our venture studio model is the close collaboration the 19days team maintains with our founding venture teams post-launch. However, time is a scarce resource for early-stage ventures. For venture studios like ours, where we partner closely with founders to accelerate their success in the make-or-break post-launch months, the time we spend together must be intensely focused, strategic, and impactful.
After four venture launches, we’ve refined a communication strategy that ensures our limited face-to-face time is spent making crucial progress, while routine updates are handled asynchronously via email. This approach has helped us maximize the effectiveness of what we’ve dubbed our Founders’ Strategy Sessions.
Every session is an opportunity for a breakthrough—whether it’s overcoming a major obstacle or discovering a new strategic opportunity. To ensure that these meetings are always productive, we’ve developed a structured approach that fosters transparency, accountability, and action.
A few core principles for effective founders’ sessions
The purpose of these weekly sessions is simple but powerful: to focus relentlessly on the biggest challenges and solve them with radical transparency free from egos. We’re here to dig deep, face reality, and make smart decisions.
To ensure everyone is on the same page, we ask all attendees to agree to a core set of principles:
1. Focus on Big Challenges and Strategic Opportunities
Every session should prioritize the most critical challenges and explore strategic opportunities. Conversations must be relevant and forward-thinking, always aimed at the issues that will have the biggest impact on the venture’s success.
2. Radical Transparency and Honest Feedback
Open, candid communication is essential. Feedback should be transparent, with no one holding back critical insights. These meetings must foster a culture of trust where difficult conversations are had constructively, with a shared commitment to growth.
3. Solution-Oriented and Action-Driven
The focus should always be on problem-solving, not reporting. Every discussion must result in actionable next steps with clear ownership, ensuring that the meeting drives real progress and accountability.
4. Continuous Alignment on Vision and Goals
Regularly revisiting the venture’s strategic goals ensures that short-term actions align with long-term success. Every conversation should connect back to these larger objectives, keeping the team focused on what matters most.
There’s still a time for updates – on everyone’s own time
In some schools of thought – like that of Jeff Bezos – in-meeting reading time is a staple. But in the venture world, when every minute is precious, we’re committed to making the pre-work, work. Because after all, if you can achieve the tall task of aligning a handful of schedules for 15 minutes for group reading, it’d be exponentially more valuable to spend it unearthing and solving issues.
To maximize problem-solving time during the meetings, routine updates are handled asynchronously via a weekly email. This email, sent the evening before the Founder’s Strategy Session, provides a snapshot of key metrics and discussion topics, allowing us to dive straight in during the session. Of course, big, celebration-worthy news like new customers are still welcome at in-person meetings, and give us even more energy to tackle the toughest issues.
A good update email looks something like this:
- OKRs: Status (on track/off track) with a one-sentence update for each.
- KPIs: Week-over-week scorecard.
- Discussion Topics: Name of topic and owner.
- Action Items: A list of tasks from the previous meeting, tracked for accountability.
By handling updates this way, we minimize process overhead and ensure that the meeting is focused on solving the most pressing issues.
Now it’s time for the big event: solving problems
At the heart of our problem-solving approach is the IDS process—Identify, Discuss, Solve—of the EOS approach. This is a simple but effective way to keep the most pressing issues at the forefront of everyone’s minds and ensure progress is made on each of them in and outside of these sessions.
We recommend the following agenda to keep momentum and focus:
- Settle in (5 min)
- Review last week’s action items (5 min)
- Review discussion topics and choose priority (5 min)
- IDS (see below) (45 min)
- Review new action items (5 min)
Identify
Throughout the week, each team member adds issues to a shared Issues List. The meeting begins with the CEO reviewing this list and selecting the most pressing problem(s) to address. The owner of the chosen issue clarifies the problem, ensuring everyone understands it fully.
Discuss
The CEO drives focused, time-limited discussion. Founders and 19days partners share insights, ideas, and challenges, with an emphasis on honesty and transparency. The goal is to uncover the root cause of the issue without assigning blame. Often, more time is spent diagnosing the problem than solving it, as a well-understood problem is halfway solved. (True to the 19days name!)
Solve
Once the issue is fully understood, the team discusses potential solutions. The group decides on the best course of action, ensuring that the solution drives the venture toward success. If a solution can’t be found, we find a way to move forward with clear next steps. Mediocre solutions won’t suffice; the only acceptable outcome is one that moves us closer to winning. Action steps and ownership are documented and tracked for follow-up in the next meeting.
Disclaimer: for this to work, you need a culture conducive to solving problems
The effectiveness of these sessions depends not only on the process but also on the relationships and conversations we foster. We aim to create a partnership between founders and our team that is built on mutual trust, accountability, and shared responsibility. This is not a hierarchical dynamic but a true partnership, where both sides bring valuable insights and leadership to the table.
We encourage our founders to embrace this mindset. We want them to feel confident bringing up both successes and struggles, knowing that we are here to help, not to judge. After all, these meetings aren’t intended for founders to boast their latest wins or ‘validate’ our decision to bring them on board. Nor is it a time for 19days partners to assign blame for the issues in question.
Instead, these sessions serve as a dedicated time for solving the meatiest and most pressing issues to drive real momentum. Much like a submarine crew with limited resources and a lofty mission, when there’s a problem, we all – founders and partners – run toward it. We recognize unchecked problems can mean life or death for our venture, so everyone is committed to seeing actions through to completion.
As we continue to refine our collaboration with founders via Founders’ Strategy Sessions and more, we remain committed to learning, adapting, and improving—just as we expect our ventures to do.
