Questions We Didn't Get To
1) Josh mentioned his console was built by 'capturing things like meetings he couldn't attend.' How does that work, did he upload meeting summaries or transcripts, or is Claude somehow connected to a meeting platform?
Great question. I'm not uploading anything. There are no summaries or transcript files that I hand to it. The system is connected directly to our Microsoft 365 and Teams environment, so it reaches the meetings through that connection.
In Teams, I can "follow" a meeting or series without attending it. We record and transcribe nearly every Teams meeting already, so the transcripts exist and only need to be pulled into Claude for processing. Once a day, early in the morning, the system looks at my calendar, finds the meetings I followed but didn't sit in the day before, and pulls the transcript for each one straight from Teams. No forwarding, no copying and pasting, no manual step from me.
From there it reads the full transcript, and gives me back what I care about: the decisions, anything waiting on me, wins, and the sentiment of the room, meaning how the team is feeling about the work. So I stay aware of what's happening in the meetings I can't be in, without watching hours of recordings.
One clarification, since it tends to come up: for meetings I'm actually in, I either use Teams to transcribe those or a recorder (Plaud) to capture the conversation. The system knows that it should favor Teams because it has better fidelity about who is speaking at any point. It then automatically pulls down a Plaud transcript if it exists and Teams is not available for that particular session. But for the "followed" meetings you're asking about, it's all automatic through the Teams connection.
2) You're spending a ton of time teaching it how to think for you, shouldn't knowing what the important points to discuss with the board are be something one can answer on one's own?
Fair challenge, and it's one I actually agree with, in part. Deciding what matters for the board is my job, and it should stay my job. I'm not handing that off, and I wouldn't want to. But that's not what's happening here. I'm not teaching it to think for me. I'm using it as an assistant, the same way a strong executive assistant or chief of staff would help. It doesn't form my judgment. It prepares the ground so I can apply it faster.
Take the board example. Could I sit down and write out the important topics on my own? Absolutely, and I do. But when I ask the system that question, it scans everything that's happened across the company over the last quarter and jogs my memory, so I don't forget to raise something that actually matters. The call on what makes the cut is still entirely mine. What changes is that prep for that portion of the agenda takes far less time, or perhaps it takes the same amount of time but is higher quality.
The point is that I'm getting leverage on my time. I've got a long list of things I'll never get to in a day. If I can compress the prep and the remembering, I free up capacity to do more high-quality work, not less thinking. The thinking is the part I'm trying to protect. This clears the busywork around it so I can spend more of my energy on the judgment calls that only I can make.
So I'd flip the sanity check around. The risk isn't that I think less. It's that without help, I spend my best hours on prep and recall and neglect other things that would benefit from my attention.
3) Are there generalized prompts for the capture and control system being shared that folks can use to start building their own workflows/systems?
Great question, and the honest answer is that I haven't thought that far ahead yet. What I've built so far is a prototype, and the prompts behind them are written for my role and are particular to Endsight's context. If we transplant them into another organization, it probably wouldn't translate to a valuable outcome, at least not without substantial modification.
That said, the pieces underneath generalize very well, and the pattern isn't complicated. It's a set of small capture projects that each do one job, a control layer that coordinates everything, a plain instruction file for each, and a place to give feedback so it gets better over time. None of that is specific to me, and the framework transfers really well. The instructions, though, need to be built out for an individual organization.
Because each instance would need a fair amount of customization, I've thought about running a series of workshops, with starter prompts to get things going and assistance with developing the connections into your data that make it more powerful over time. I'd love your feedback on whether something like that would be helpful, or if you have different thoughts on what would be most valuable.
If you're interested in getting started on your own, the one piece of advice I'd give is to start small and simple. Don't try to build the whole thing at once. I started with a single narrow problem, summarizing meetings I couldn't attend, purely to learn the tool, and it grew from there. Pick one nagging task, get that working, and the ambition and vision will follow.
If it would help you get going, I'm happy to share a starter prompt for the Followed Meeting Capture project I mentioned, so you have a real example to work from instead of a blank page.
Do you have questions?
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Overview
June 30th, 2026
AI Office Hours: Turn AI From Experiment Into Execution
AI has the potential to change how your business operates, and this session shows what that actually looks like in practice.
Many organizations get stuck. Not because they lack interest, but because they lack a clear path forward. They don't need more tools. They need to see what AI looks like when it's working inside a business like theirs.
In this session, Brian Tirado, Director of AI and Automation at Endsight, walks through what changed in the AI landscape over the past quarter: what tools are worth paying attention to, and what's actually driving results for businesses right now. Also featured: Josh Carroll, President and Co-Founder of Endsight, who demonstrates how he built an executive intelligence system using Claude Cowork. The system builds a knowledge base from his emails, meetings, and messages, so AI always has the full context of his world, producing output far closer to stage-ready than anything a general AI could deliver.
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Welcome and introductions
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The AI landscape: 90-day tools update
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AI in action: building a real-world agentic workflow
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Next steps and resources
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Q&A
What You'll Walk Away With- A current view of the best AI tools for business and what actually changed this quarter
- Live examples of AI applied to real work, including agentic workflows
- A sense of where your organization sits on the adoption curve
- A practical starting point, not just inspiration
Resources
- AI in the Wrong Hands - Cybersecurity Risks & Threats Video: https://www.endsight.net/security-shorts/how-hackers-use-ai
- Scenario Library: https://adoption.microsoft.com/en-us/copilot-scenario-library/
- Copilot Lab: https://copilot.cloud.microsoft/en-US/prompts
- Setup Guide: https://setup.microsoft.com/copilot/setup-guide
- Success Kit: https://adoption.microsoft.com/en-us/copilot/success-kit/
- Register for future AI Webinars: https://get.endsight.net/development-webinar
- Register for Office Hours: https://get.endsight.net/cybersecurity/office/hours
- Register for Monthly Cybersecurity Training: https://get.endsight.net/monthly-cybersecurity-fundamentals-training
- Endsight's Video Library: https://get.endsight.net/endsight-video-library
- 365 Tip of the Week Newsletter: https://get.endsight.net/microsoft-tip-of-the-week
- Previous Webinar: https://www.endsight.net/dev/q12026-implementing-ai-in-the-real-world
- OpenAI Data Privacy: https://openai.com/business-data/
- Claude Data Privacy: https://privacy.claude.com/en/
Speakers
Josh Carroll
President and Co-Founder @ Endsight
Josh has worked across nearly every aspect of the business, with a focused emphasis on scaling operations and shaping strategic direction. In his role as President, he champions the thoughtful adoption of AI and emerging technologies, helping businesses navigate how these tools can drive efficiency, reduce risk, and unlock new opportunities, all grounded in clear vision, strong values, and a commitment to delivering exceptional customer value.
Jason Clause
Director of Marketing @ Endsight
Jason has spent the last 18 years working in the managed IT services industry. He has been presenting cybersecurity events for the past several years. He has a bachelor’s degree in Public Relations from Kent State University and is a Microsoft Certified Professional. Jason is certified by Sophos, a worldwide leader in next-generation cybersecurity.
Brian Tirado
Director of AI & Automation @ Endsight
With over 20 years of IT experience, Brian is a seasoned professional who began his career at Occidental Technical Group in 2002 and joined Endsight in 2017 through its acquisition. Since then, he has held various leadership roles, starting as RC Manager, advancing to Director of Pod Operations, and now serving as Director of AI and Automation. Brian has a Bachelor’s in Computer Science from Pacific Union College.