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Commercial Real Estate · Coaching
Coaching
Commercial Real Estate · Coaching
A commercial real estate MD went from AI skeptic to sending AI-drafted investor letters in three sessions
He had passed on AI once and called back to say so. Three coaching sessions later, a colleague's two-paragraph draft became a formatted, investor-ready project letter in under five minutes, and he printed it and texted the colleague on the spot. Sessions are expanding to his firm's teams.
Engagement
CoachingWeekly 1:1 sessions, expanding to team sessions
The problem
A managing director at a roughly 45-person commercial real estate firm, with millions of square feet under management, had initially waved AI off. He reopened the conversation himself, embarrassed by his first pass and convinced the firm was "really missing out." The question was where AI actually fits in a relationship business built on deals, documents, and investor trust.
What we built
- A personal AI assistant reachable over text message: voice-note a schedule and get it organized, ask for a pre-meeting brief, get restaurant research for an investor dinner, all from the phone he already lives on.
- AI connected to his calendar, email, and files: a daily meeting brief every morning and follow-up emails drafted into his inbox ready to send.
- Deal-document review: AI read a live letter of intent and flagged a contradictory closing period, typos, and ambiguous language a tired human eye slides past.
- The moment that converted him: a colleague's two-paragraph draft about a development project, expanded by AI into a fully formatted investor letter with timeline, capital structure, leasing status, and outlook, in under five minutes. He printed it and texted the colleague immediately.