ESO Summit 2026 ยท 16 Tech
Practical AI: Five Smart Decisions, Five Useful Tools
Everything from Practical AI: Five Smart Decisions, Five Useful Tools at the 2026 ESO Summit at 16 Tech on Tuesday, November 10, lives here: the five principles, five setup prompts, the connector map, the use case generator with starter prompts for the work founders bring you, a sample blueprint, and a free 30-minute use case strategy review. Copy a prompt, paste it into your AI tool, and read the answer before you trust it.
AI Office Hours (event day only)
12:50 to 1:25 p.m. in room H138. Bring a laptop and a real task. The BiG table is in the Alleyway, in front of Submit and Lake City Bank, all day.
You have two AI jobs
Inside
Inside: five principles
- No 100% adoption. Twenty-five to thirty-three percent of staff actively using AI is the healthy range. Past it, productivity declines. (BiG Impact Group observation from client engagements, not a published study.)
- The 80/20 rule. Twenty percent of your people deliver eighty percent of the value. Start with executives and centers of influence, where problems go to get solved.
- Stay in your lane. There are things that could be done and things that should be done. AI amplifies; if you have dysfunction, it amplifies that too.
- Grow in your lane. Let people use their own skills, reasoning and judgment, and discover how AI extends their impact where they already work.
- It's all about problems. Name them, rank them, point the tools at them. Eighty percent of your paycheck is solving problems.
Inside
Inside: five setup steps, one prompt each
1Choose the model
The frontier five: ChatGPT, Claude, Gemini, Microsoft Copilot, Grok. You won't go wrong with any. Microsoft 365 shop, start with Copilot. Google Workspace shop, look at Gemini. Most organizations land on ChatGPT or Claude.
2Personalize it
Most people never take ten minutes to tell the tool who they are, who they serve and how they write. Find it under Settings: personalization, custom instructions, memory.
Help me write my profile for this tool. First tell me what you already know about me. Then ask up to five questions, one at a time: my role at my organization, who we serve, the programs I work on most, how I like answers, and what I never want you to do. Draft three to five lines I can paste into Settings and show me before I use them.
3Connect your tools
Same idea, five names. The top five connectors for an ESO: email, calendar, files, your CRM, and billing. There's a learning curve to trusting them. The gain is worth it.
Connector map (checked November 2026; MCP is the Model Context Protocol, the open standard most now use):
| Tool | Connectors | Bundles | Custom MCP |
|---|---|---|---|
| ChatGPT | Apps (formerly Connectors) | Apps SDK apps, custom GPTs | Developer Mode, mainly Business, Enterprise and Edu |
| Claude | Connectors | Plugins (skills, connectors and commands in one install) | Custom connectors from a remote MCP server |
| Gemini | Apps (formerly Extensions) | Gems, Gemini Enterprise connectors | Custom apps from a remote MCP server URL |
| Microsoft Copilot | Copilot connectors | Agents with actions (formerly plugins) | Declarative agents and Copilot Studio |
| Grok | Connectors (since May 2026) | Third-party connector catalog | Bring your own MCP connector |
Swipe the table sideways to see every column.
4Build skills
A skill is a micro SOP: saved, reusable instructions the AI follows on demand. Best candidates are high-volume, repeatable work with a clear good result. Five worth building first at an ESO: your voice, your preferences, a founder session recap, a resource referral match, and a program report.
Explain, in plain language for someone who runs programs at a nonprofit, what a saved skill or instruction set is in this tool, what it is good for, and what it is bad for. Then give me three examples from entrepreneurial support work: a founder session recap, a funder report narrative, and a referral note. Keep it under 200 words.
Interview me to find the three tasks I do every week that would make good saved skills. Ask one question at a time: what I do on repeat, which of those I would recognize instantly if it came back wrong, and which ones never need a founder's name or financials to do. Then rank the three and tell me which to build first and why.
Help me build a reusable instruction set for a founder session recap. Ask me for one set of raw notes with the founder's name replaced by Founder A. Then write the instructions: what to produce (a three-line recap, the founder's commitments, my commitments, and a referral flag), the tone, what to leave out, and the check I should do before sending. Show me the instructions and a sample output side by side.
5Keep training
The tools change every few days. Skip the hourly feed. Have a small committee review tools monthly or quarterly against your problems.
Act as the small committee that reviews AI tools for our organization once a month. Ask me for the list of problems we are trying to solve and the tools we use today. Then give me a one-page review format: what changed in the tools this month that matters for those problems, what to try, what to ignore, and one question for leadership. Keep headlines out of it.
Outside
Outside: what founders come to you for
- Resources and navigation. Where do I go, and what applies to me?
- Funding and capital readiness. How do I finance my next step?
- Connections and mentorship. Who can help me move forward?
- Business planning and practical skills.
- Customers and market access.
Five starter prompts, one for each. Each asks for what it needs and never asks for a founder's name.
Act as a resource navigator for entrepreneurs in our region. Ask me to paste our public resource directory and our eligibility rules. Then, for a founder I describe in generic terms (stage, sector, county, what they are asking for), return the two best next steps, who to contact, and the one question to ask before referring. Never ask for the founder's name.
Help me write a loan readiness checklist and a plain-language gap letter for a founder. Ask me for the founder's situation in generic terms: stage, revenue band, the ask, and collateral type. Then list what a lender will ask for, the likely gaps, and a short letter the founder can act on this week. No financial statements go into this chat.
Help me match a founder to a mentor and write the introduction. Ask me to paste mentor profiles described by skill, sector and availability with no contact details, and the founder's need in generic terms. Rank the three best matches with reasons, then draft a warm introduction in my voice that explains why.
Turn a workshop into a take-home worksheet. Ask me for the session outline and the three things a founder should be able to do afterward. Then write a one-page worksheet with the steps, a filled example, and a checklist the founder can bring to the next coaching session.
Help a founder find their first ten customers. Ask me to describe the business in generic terms: what they sell, to whom, where, and the price range. Then list ten specific places or channels in our region to find those customers, the one message to lead with for each, and how to tell in two weeks whether it is working.
The use case generator
The generator builds use cases for your role, inside and outside, five at a time, using your organization's website as context. Type a number to see the full write-up, keep the ones you want, and type submit. Your use cases arrive in your inbox and ours, and that submission is what we work from in the review. No account needed. Keep founder names and financials out of it; describe them in generic terms and it will do the same.
What a blueprint looks like
When a leadership team runs the generator, the submissions become a blueprint: every use case scored on a five-part rubric, placed on a quick-win and strategic-bet map, grouped into programs, and sequenced across three quarters with a data policy, a governance committee and gate decisions. We built a sample for Crossroads Venture Network, a made-up five-county ESO with five leaders and five use cases each, so you can see what yours would look like.
Free 30-minute use case strategy review
Bring your use cases and anyone from your team who ran the generator. In thirty minutes we tell you which three we would pilot first, what each would take, and what to keep out of the tools. No preparation needed beyond your submission. Trent Decatur runs the review and John joins.