Asking Amazing Questions

Questions are insanely powerful. Jedi mind-trick powerful. They're more influential in teaching, learning, negotiating, serving, delivering amazing work, and leading others than most people will ever know. That's because most people don't ask nearly enough questions, and when they do, they ask terrible ones.

One of the first conversations in the biblical Old Testament was a question and answer session between Adam and Even and God, who, I think it's safe to assume, knew the answers to the questions he was asking:

8 And they heard the voice of the Lord God walking in the garden in the cool of the day: and Adam and his wife hid themselves from the presence of the Lord God amongst the trees of the garden.
 9 And the Lord God called unto Adam, and said unto him, Where art thou?
 10 And he said, I heard thy voice in the garden, and I was afraid, because I was naked; and I hid myself.
 11 And he said, Who told thee that thou wast naked? Hast thou eaten of the tree, whereof I commanded thee that thou shouldest not eat?
 12 And the man said, The woman whom thou gavest to be with me, she gave me of the tree, and I did eat.
 13 And the Lord God said unto the woman, What is this that thou hast done? And the woman said, The serpent beguiled me, and I did eat.

I know plenty of leaders and parents who would struggle to have a similar conversation to hold someone accountable for their actions.

When should you ask questions?

You should ask questions of yourself and others all the time, everywhere. And no, this is not annoying, actually it's exactly the opposite if you do it right. Here are four places you should ask more questions:

  1. Giving feedback: Giving is not about telling. Telling someone is not nearly as powerful as having that person experience an epiphany for themselves. "You did that wrong and this is why" is useful feedback, but it already puts the individual in resistance mode, it's emotionally charged. "How did that work out for you?" Is a much better question that opens up possibilities and engages the other person to deep thinking. "Could you have done it a different way?" Helps people solve their own problems. When the individual runs out of answers, if the situation is important to them, they will ask you "what do you think", and then they're completely ready to listen to your constructive feedback and it's their idea, not yours.
  2. Negotiating: Negotiation is an emotional activity, not a logical one, as the FBI has learned over the past couple of decades. Questions deepen emotional connection while also co-opting the other party to solve your problems on your behalf. They allow you to say no without loosing rapport. Try questions such as "How can we do that?" and watch while your adversary solves your problem for you.
  3. Leading: The outdated model of leadership is directive, the commander-of-the-ship approach. I can't actually think of any management expert or successful leader today that advocates this tack, yet such behavior still infests corporate America. The thinking here is clear: instead of telling your people what to do, try asking them what they think they should do. Then you will know what gaps they have, and you can make suggestions where they're needed. You build more rapport, have happier employees, get better solutions, and save time. Why would you do it any other way?
  4. Nailing it: When I see poor performance from any employee anywhere in the world, there is almost always one root cause: the employee is running their own agenda. This leads to missed deadlines, delivering the wrong things, cultural and organizational faux-pas, and interpersonal conflict. Although this is a complex issue, the solution is a simple one: ask more questions. When you assume you know why something needs to be done, you can mis-prioritize it, or tailor it wrong in an effort to please. There's nothing daft about understanding the what, why, when, and how of any task, at any level.

So, how do you ask great questions?

Five tips on how to ask better questions:

  1. Ask open-ended questions that provoke thought. Avoid anything that can be answered "yes" or "no." Rather, great questions usually start with "how" or "what" and sometimes "why."
  2. Embrace silence. Whether in a 1-1 setting or a group, silence is golden because it means people are thinking. Don't be afraid to sit in complete silence, the other party feels it more keenly than you do, and the longer it goes on, the more engaged they'll be.
  3. Really listen. This is easier said than done, because most of us are thinking about what we are going to say next. One way to deepen listening is to mirror back what was said. "I think you should put more detail in the presentation" can be mirrored with "more detail?" You get more insight, but in a way that makes the other person think it was their idea. It deepens your relationship and gives you what you need to know.
  4. Care. The more you genuinely care about the other person, the better answers you will get. Depending on your corporate culture, this may sound hokey, but seeing the other person as human and genuinely connecting with them will go a long, long way to getting deep insight from them. Generally people  don't open up to adversaries, and they withold the best stuff from neutrals.
  5. Subsume your ego. Most people don't ask questions because they don't want to appear stupid or ill informed. For some reason the idea has crept into certain circles that it's better to guess than ask. This is insane.


In conclusion: ask great questions and your life will improve just about everywhere.

Was there a time you asked a great question that changed everything? (Or you didn't but should have, and that changed everything.)