Ask the Tough Questions

Working Down Under, I had the opportunity to ride shotgun with one of ThoughtWorks’ top professional services salespeople—a gentleman by the name of Keith Dodds. One of the many things Keith taught me was the importance of asking the tough questions at the start of any new engagement or sale.

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You see, in the beginning of any new engagement or project, you have a lot of leeway in the questions you can ask with little to lose. You can ask wide-open questions like the following:

  • How much experience does your team have?

  • Have you ever done this type of thing before?

  • How much money do we have?

  • Who’s calling the shots ...

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