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    the more you know, the worse you sound

    2026-05-28

    Three weeks. Maybe four. Depends on how clean their data is. If the annexes apply differently we might need an extra week, and there's a question of whether the BSI guidance from March has actually been internalized on their end.

    That's what I said on a call last week. Every word true. Every word, I thought, useful.

    The buyer heard: this guy isn't sure.

    The Big 4 partner who walks into the next meeting says "yes, absolutely, we handle that all the time." Less informative. Zero specifics. Reads as confident. Wins.

    I've been chewing on this for a few days. The mistake isn't honesty. The mistake is what I was being honest about.

    The buyer isn't asking "can you do this." They're asking "will I look stupid if I pick you." Two different questions. I keep answering the first one. They keep needing the second one answered.

    When I list the conditions, I'm giving them information they can't use. They don't know which conditions matter. They don't know how to weight "if the data is clean" against "three weeks." All they hear is the texture of doubt. Doubt is the only signal they can read.

    The Big 4 partner sounds confident because she's not surfacing anything the buyer can't process. The information loss is the feature. She knows the buyer's job is to pick a vendor without looking dumb, not to evaluate timeline risk. So she removes everything that complicates the pick.

    I was doing the opposite. Optimizing for the buyer's understanding of the project. They don't want that. They want to be relieved of the project.

    things I'm trying

    Answer the category, not the instance. "Yes, this is exactly what the platform does." True. Doesn't open the instance-level can of worms until they've already said yes and we're in scoping.

    Move hedges from the headline to the footnote. "Three weeks. We confirm scope in kickoff." Hedge is still there, just not leading.

    Stop pre-disclosing risk. I kept surfacing things that might go wrong because I'd want to know. They don't want to know. They want me to handle it. If a risk shows up, I address it then. Pre-disclosing risks the buyer can't act on is competence punishing itself.

    Speak from the platform, not the labor. "The platform handles that" sounds like infrastructure. "I'll build that" sounds like one tired guy. Same code, different frame.

    Use the doctor frame. Doctors don't walk you through their reasoning unprompted. They say "it's strep, take this." The reasoning is in reserve. They deploy it if you push back. I was deploying mine before anyone asked, because I find my own reasoning interesting. The buyer finds it scary.

    the underlying thing

    I was optimizing for being correct about myself. The right thing is to optimize for the buyer's decision. Counterintuitively, a clean yes is often better information for them than my hedged yes, because they can't weight my hedges. The hedge just adds noise. They make a worse decision with more accurate data.

    The line where this becomes lying: claiming capability I don't have, or hiding a real dealbreaker. "Three weeks" when I know it's six is a lie. "Three weeks" when I'm 70/30 on three vs four is confidence. I was conflating those two and over-correcting into hedging everything.

    the drill

    After each call, write down every hedge I used. For each one, ask: did the buyer need this to decide today, or could it have lived in the SOW after they said yes?

    Most of them could have waited.

    Those are the ones to cut.

    — Simon