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03 · Professional & Academic · Topic

Questions to ask in business and sales

Discovery calls, client kickoffs, vendor selection and investor meetings all turn on the questions asked in the first ten minutes. These sets are written for the person running the conversation.

82 sets · 1,808 questions · each with a note on why

A few to start with

  • What are we depending on that we do not control?

    Vendors, another team's release, a data feed, a procurement cycle, an external approval. External dependencies fail differently from internal ones because you cannot escalate your way out of them, so each one needs a named owner and a date you have confirmed yourself.

    From: Questions to Ask Stakeholders for a Project

  • What do you do once you realise you have the wrong person in a senior role?

    The interesting variable is time. Most leaders will admit they waited too long at least once, and how they describe the delay says a lot about whether they can act against their own sunk cost.

    From: Questions to Ask Business Leaders

  • If we hit a problem halfway through, how would you want me to raise it?

    Some clients want a call the same day; others want it framed with options at the next meeting. Establishing this while things are calm makes the difficult conversation survivable.

    From: Questions to Ask a New Client

  • Where does your work come from now: referrals, repeat customers, advertising, cold outreach?

    This is the answer most worth having, and most businesses are more dependent on referrals than they realise. Ask what would happen if that one source went quiet for three months.

    From: Questions to Ask an Entrepreneur

  • Do you work on landing pages, or is that our side?

    Campaign performance is capped by the page it lands on, and this is where responsibility most often falls between two parties. Settle it before results are disputed rather than after.

    From: Questions to Ask a PPC Agency

  • How should I store and use what I express?

    Handling rules differ depending on whether milk goes in the refrigerator, the freezer, or straight into a bottle, and on whether the baby is premature or unwell. Ask for the version that applies to your baby rather than the general one.

    From: Questions to Ask Lactation Consultant

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