Question Everything

How to ask questions that rock the boat, without sinking yourself

One of top three skills for being a disruptive hero in 2017. See here, here for more.

1. Find Your Core Set of Questions

These are your go-to questions that are helpful in most any situation. Limit your core questions to 3—5. For me as a business consultant, I almost always begin with…

• How do you define success? Or: If we were super successful and we asked 100 people for their reactions, what would they say? This puts the person you’re speaking with in the customer’s/client’s/audience’s shoes.
• Why? Journalists are taught to ask variations of Why? up five times until they get to the real truth. (Most people haven't explored Why? until asked multiple times.)
• Time/Quality/Cost: Pick Two. You can’t ask this directly. Everybody will always respond that all three are equally important. But they never are. One of these three is always the deciding factor. (And cost is often a lot more flexible than we’re led to believe.) You will need to ask this question indirectly multiple times in order to uncover which one it is.

Some additional suggestions…

• What is our (company, team, store, etc.) core purpose on earth? Variations of this question always quickly get to “Why are we really doing this? What’s the ultimate purpose of this?”
• What should we stop doing?
• If our (company, team, store, etc.) didn’t exist, how would we approach this?
• How could we do this differently?
• (Adapted from Warren Berger, host of the blog A More Beautiful Question)

A few more suggestions…

• What if there were no rules for this? What would we do?
• What would we do if we wanted to have no regrets?
• Is this the hill we want to die on? (Is this really that important?)
• What’s the difference between what they want and what they need?
• What really matters in this situation?
• (For even more great questions, go here)

2. Practice, Practice, Practice

To accomplish the next step, Step 3, you will need to practice your core set of questions constantly. In most every meeting, in most every exchange.

3. Sense the Tipping Point

At some point in the exchange, the vibe will change. If you pay very close attention, you will begin to sense the exact moment where the vibe switches from “OK, I will give you some discovery time…” to “Let’s move on to getting stuff done.”

For example, many of my new business opportunities occur during teleconferences. Assuming a one-hour call, the tipping point is usually between 20 minutes and 40 minutes into the call. I then quickly switch into “Here’s what I’d recommend we do” mode. Your goal is to push right up to the edge of that tipping point (maximizing discovery time)… But never go over it (the point at which just one more question will annoy others).

4. Get to the Point… Fast!

After you’ve questioned as much as you can, jump quickly into getting stuff done.

• Make sure your actions/recommendations are built upon how people just answered your questions.
• Get to the point fast! Spell out recommendations and action items clearly and succinctly.

5. Repeat: Going Further Each Time

Push as far as you can with one round of questions… Execute based on what you learned… Then, the next opportunity you have, push a little further with even more questions or more probing questions.

(Adapted from, Click, the How To Addendum to Disrupt! Think Epic, Be Epic)

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Bill Jensen Site, Twitter, FB. Bill’s latest book, Future Strong, is about the five deeply personal choices each of us must make to be ready for all the disruptive tomorrows heading our way.