Cowork Capabilities and Limitations

When not to reach for Cowork. PE-anchored examples on the misses, so you spot them before you waste an hour. About 30 to 40 minutes.

TourTBC, week of May 25

What we cover

Weak fit, real-time licensed data: Pitchbook, CapIQ, anything where the platform's ToS locks the data behind their UI
Weak fit, precision math: LBO mechanics, returns waterfalls, scenario analysis. LLMs are pattern matchers, not calculators. Use Excel.
Weak fit, anything requiring perfect accuracy without a verification step: legal review, compliance attestation, anything with regulatory consequence

Why it matters

By now you have seen what Cowork can do. The leverage here is the inverse: spotting the moments when Cowork is the wrong tool, before you have spent 30 minutes producing output you cannot trust. The three weak fits below are the ones that bite a PE team most often.

Hands-on moment

Each tour stop has a proof point or short discussion. You watch Cowork stumble (or be honest enough to refuse) so you remember what the stumble looks like before you trust the next answer.

Agenda

Weak fit: real-time licensed data

Cowork cannot scrape Pitchbook, CapIQ, or DealCloud through the back door. Those platforms lock APIs and their terms of service prohibit scraping. The right move is to use the platform's native UI for the data pull, then bring the export to Cowork for synthesis.

Room prompt

Ask Cowork: "Pull me the comparable transactions for X in the last 12 months from CapIQ." Watch it either refuse or invent. That refusal (or the invention) is what you want to recognize before you trust the next answer.

Weak fit: precision math

LLMs hallucinate numbers. LBO mechanics, returns waterfalls, multi-step scenario analysis, anything where one wrong cell breaks the whole model. The right tool is Excel. Cowork can describe the model, walk you through the assumptions, and read the output, but it should not be the calculator.

Room prompt

Ask Cowork: "Run a 5-year LBO with 5x entry multiple, 60 percent leverage, exit at 8x." Read the answer carefully. Spot at least one number that does not pencil. That is the muscle you want to keep flexed.

Weak fit: legal and compliance review

Anything requiring perfect accuracy without a verification step belongs with a human. Legal document review goes to Kira or Luminance plus a lawyer. Compliance attestations go to a real signoff. Cowork can help you read a contract; it cannot tell you to sign one.

Room prompt

Hand Cowork an NDA paragraph and ask: "Flag anything unusual." Read the output as a starting point for your own review, not as the review itself. The framing-only exercise here is recognizing the line.