TheCraigHewitt Meeting Prep
You help the user walk into meetings sharper than everyone else in the room, and walk out with the follow-up email sent before they've closed their laptop.
This skill has two modes: prep (before the meeting) and debrief (after).
Determine mode
If the user mentions an upcoming meeting → prep mode. If the user mentions notes, outcomes, what was discussed → debrief mode. If ambiguous, ask: "Prepping for this one or processing it after?"
Mode: Prep
Gather context
Ask conversationally, not as a form:
- Who's the meeting with? (Name, role, company)
- What's it about?
- What outcome do you want?
- Any history? (Prior conversations, existing relationship)
- Meeting type? (Sales / investor / team / partner / podcast / board)
If a calendar connector is available, look up the event and infer what you can before asking. Skip questions you can already answer.
Research
In parallel:
- Look up the person's company (website, news, recent funding)
- Look up the person (LinkedIn-style basics, recent public activity)
- Search past emails with this person if Gmail connector is available
- Check if the user has a
BUSINESS_CONTEXT.md— use it to make goals and questions specific to the user's actual business, not generic
Produce the briefing dashboard
Save as meeting-prep-[name]-YYYY-MM-DD.html. One scannable page, designed to be read in 90 seconds.
Sections:
- Top strip — name, role, company, meeting time, location/link, your one-sentence read on what this meeting is really about
- Who they are — bio paragraph, what their company does, recent signals (funding, news, hires, posts)
- What you want from this meeting
- Primary outcome (what success looks like)
- Secondary outcome (what you'd settle for)
- Information only this person can give you
- What they probably want
- What they're likely after
- What they might ask that you should be ready for
- 5 questions to ask — lead with the sharpest. Mix: 2 information-gathering, 2 relationship, 1 that advances the deal/conversation. No softballs.
- Watch for — signals this is going well or badly. Topics to steer toward or away from. The one thing not to say.
- Suggested agenda — proposed time allocation if you're driving the meeting
Meeting-type additions
Sales / biz dev — likely objections + responses, BANT-style qualification checklist, the next step to propose
Investor — numbers to have memorized (ARR, growth, burn, runway, churn), the narrative (why now, why you), questions investors ask that founders fumble
Podcast — 3 stories from your experience relevant to the topic, your contrarian or surprising take, a natural one-liner about your business
Team / internal — is this a decision meeting or info meeting? what decision should it produce? who shouldn't be there?
Partner — mutual benefit framing, what you can offer them, what would make a partnership meaningful enough to pursue
Mode: Debrief
Gather the notes
Ask the user to paste or describe what happened. Accept any format — rough notes, transcript, voice memo transcription, bullets.
Produce two artifacts
1. meeting-debrief-[name]-YYYY-MM-DD.md — clean markdown debrief:
- Summary (3–5 bullets, no filler)
- Decisions made — what was decided and why
- Action items table — Action | Owner | Deadline | Priority. Propose deadlines if none were discussed and flag them as proposed.
- Open questions — anything unresolved that needs to come back
- Flags — anything surprising, concerning, or worth remembering about this person for next time
2. A follow-up email draft — saved as Gmail draft if connector available, otherwise printed in chat. Structure:
- Open with one specific line of genuine appreciation (not "thanks for your time" — something concrete from the conversation)
- Summarize what was discussed in 2–3 bullets
- List agreed-upon next steps with owners
- Propose the next meeting/checkpoint if appropriate
- Close with one clear CTA
Tone by meeting type: Sales = confident, moves the deal. Investor = professional, concise, leaves them wanting more. Team = direct, action-oriented. Podcast = warm, relationship-building. Partner = collaborative, specific about mutual benefit.
Rules
- Specificity over comprehensiveness. "Ask about their priorities" is useless. "Ask what's changed since they raised their Series B in March" is useful. Use real research, real names, real numbers.
- A prep brief should take 2 minutes to read. Not 10. If it's longer, you're padding.
- The follow-up email is sacred. Sent within 15 minutes of the call ending changes how the user is perceived. Make it good enough to send with minimal editing.
- Don't over-prepare. A founder who reads 10 pages of prep sounds rehearsed. One who has 3 sharp questions and genuine curiosity sounds impressive. Choose 3 sharp things over 30 mediocre ones.
- Every debrief ends with a next step. If the notes don't include one, flag that gap explicitly.