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Scary questions can be helpful

Scary questions can open you and the person you’re talking to up to some big collective insights.

Or at least that’s been my experience in my own consulting activities (and life generally really), when I’ve been bold enough to speak up.

I encourage you to ask your clients and prospects the scary questions. Ask them things that seem counterintuitive to getting the project.

Don’t assume anything. e.g.

  • Why is this project important to the organization?
  • Are you sure you have budget to pull this off?
  • Will anyone else be involved in the decision?
  • How will you know success?
  • What will you do instead if this is too costly?
  • Is there a reason you haven’t done this already?
  • Why do you think you need me?
  • How did you arrive at that budget figure?
  • If this were to fail or be impossible, what’s your ‘Plan B’s?
  • Are you married to this particular path for achieving your underlying goals?
  • Which of the discussed objectives are ‘soft goals’ and which are ‘hard (firm) goals’?
  • What resources do you have internally to dedicate to this project?
  • Of your top ten priorities, where does this project rank over the next quarter or two?
  • What are your top three priorities right now and if this project isn’t one of them why are we talking right now?
  • What is the real basis for that timetable?

The scarier the better. It’ll improve your consulting work. The answers may surprise you. And they may surprise the person giving them as well. You’ll gain better insights. You’ll be able to be more helpful.

And, counterintuitively, the scarier the early questions are … The easier and more productive you’ll be when it comes time to get to work on the project.

By Josh Richards

Josh is a consulting network/ systems/ cloud engineer, freelance high stakes IT project manager, and former technology executive. He has consulted on information technology matters for over twenty-five years. In 2006, consulting became his primary source of income (just before the global financial crisis!). He’s a big fan of craft beer, freshly roasted coffee, artistic burlesque, good food, and applying science and reason to problems and opportunities small and large (and just for fun). When he has time and energy he also likes to get out on his bike or attend a soccer match.

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