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Useful Questions

Planted 02021-06-28

Quick answers

A list of ways to answer a question, in order of low to high leverage:

  1. Answering one person’s question in a direct message (so only the person asking the question benefits)
  2. Answering one person’s question in a public channel (so anyone else following the channel that day can benefit)
  3. Answering one person’s question by documenting the answer and sharing the link with them (so anyone searching the docs in the future can benefit)
  4. Take action (fix a bug, add automation, etc.) to make the question obsolete so nobody ever asks it again

The Seven Essential Questions

From The Coaching Habit.

1. What’s on your mind? It’s a question that says, Let’s talk about the thing that matters most.

  1. Project side → any challenges around the actual content
  2. People side → any issues with colleagues/bosses/customers/clients
  3. Patterns → if there’s a way that you’re getting in your own way, and not showing up in the best possible way.
Where should we start?
2. And what else? “There is nothing else” is a response you should be seeking. It means you’ve reached the end of this line of inquiry. Take a breath, take a bow and go on to another question.

  • “And what else could you do?”
  • “And what else is a challenge here for you?”
  • “And what else might be possible?”
  • “Is there anything else?” → invites closure, while still leaving the door open for whatever else needs to be said
3. What’s the real challenge here for you? Emphasis on real and you. Adding “for you” to a question helps people figure out the answers faster and more accurately.

Proliferation of challenges
“If you had to pick one of these to focus on, which one here would be the real challenge for you?”

Bitching and moaning – Gossiping
“I think I understand some of what’s going on with [name of the person or situation]. What’s the real challenge here for you?”

Abstractions and Generalizations
“I think I understand some of what’s going on with [name of the person or situation]. What’s the real challenge here for you?”
4. What do you want? What we want is often left unknown or unsaid.

  • Tribe → Are you with me or against me?
  • Expectation → Do I know the future or not?
  • Rank → Are you more or less important than I am?
  • Autonomy → Do I get a say or not?
5. How can I help? These three labels aren’t descriptions of who you are. They’re descriptions of how you’re behaving in a given situation. They are roles we end up playing when we’ve been triggered and, in that state, find a less-than-effective version of ourselves playing out.

The Drama Triangle

  • Core belief → “My life is so hard; my life is so unfair. ‘Poor me.’”
  • Dynamic → “It’s not my fault (it’s theirs).”
  • Benefits → No responsibility for fixing anything; you get to complain; you attract Rescuers.
  • Price → You have no sense of being able to change anything—any change is outside your control. You’re known to be ineffective. And no one likes a whiner.
  • Stuck → “I feel stuck because I have no power and no influence. I feel useless.”
  • Core belief → “I’m surrounded by fools, idiots or just people less good than me.”
  • Dynamic → “It’s not my fault (it’s yours).”
  • Benefits → You feel superior and have a sense of power and control.
  • Price → Responsible for everything. You create Victims. You’re known as a micromanager. “People do the minimum for you and no more. And no one likes a bully.
  • Stuck → “I feel stuck because I don’t trust anyone. I feel alone.”
  • Core belief → “Don’t fight, don’t worry, let me jump in and take it on and fix it.”
  • Dynamic → “It’s my fault/responsibility (not yours).”
  • Benefits → You feel morally superior; you believe you’re indispensable.
  • Price → People reject your help. You create Victims and perpetuate the Drama Triangle. And no one likes a meddler.
  • Stuck → “I feel stuck because my rescuing doesn’t work. I feel burdened.”

“How do I [insert query most likely to sucker you in]?”

“That’s a great question. I’ve got some ideas, which I’ll share with you. But before I do, what are your first thoughts?”


“That’s terrific. What else could you do?”


“This is all good. Is there anything else you could try here?”

And then, and only then, you can add your own idea into the mix if you wish. And of course, if the conversation is going well, keep asking “And what else?” until she has run out of ideas.

Curious, “What do you want from me?”
6. If you’re saying yes to this, what are you saying no to? “Let’s be clear: What exactly are you saying Yes to?” brings the commitment out of the shadows. If you then ask, “What could being fully committed to this idea look like?” it brings things into even sharper, bolder focus.

  • What projects do you need to abandon or postpone?
  • What meetings will you no longer attend?
  • What resources do you need to divert to the Yes?
  • What expectations do you need to manage?
  • From what Drama Triangle dynamics will you extract yourself?
  • What relationships will you let wither?
  • What habits do you need to break?
  • What old stories or dated ambitions do you need to update?
  • What beliefs about yourself do you need to let go of?
Saying Yes more slowly means being willing to stay curious before committing. Which means asking more questions:
  • Why are you asking me?
  • Whom else have you asked?
  • When you say this is urgent, what do you mean?
  • According to what standard does this need to be completed? By when?
  • If I couldn’t do all of this, but could do just a part, what part would you have me do?
  • What do you want me to take off my plate so I can do this?
The Other Five Strategic Questions
  • What is our winning aspiration? What impact do you want to have in and on the world?
  • Where will we play? “Boiling the ocean” is rarely successful. Choosing a sector, geography, product, channel and customer allows you to focus your resources.
  • How will we win? What’s the defendable difference that will open up the gap between you and the others?
  • What capabilities must be in place? Not just what do you need to do, but how will it become and stay a strength?
  • What management systems are required? Measuring stuff is easy. It’s much harder to figure out what you want to measure that actually matters.
7. What was most useful for you? Advice is overrated. I can tell you something, and it’s got a limited chance of making its way into your memory. If I can ask you a question and you generate the answer yourself, the odds increase substantially.

Five useful questions

Seth Godin, Five useful questions

What’s the hard part? Which part of your work, if it suddenly got much better, would have the biggest impact on the outcome you seek?
How are you spending your time? If we took at look at your calendar, how much time is spent reacting or responding to incoming, how much is under your control, and how much is focused on the hard part?
What do you need to know? What are the skills that you don’t have that would make your work more effective?
What is the scary part? Which outcomes or interactions are you trying to avoid thinking about or interacting with? Why?
Is it worth it? After looking at your four answers to these questions, you might have a better idea of what it will take for your project to reach its potential. Does the outcome of the project–for those you serve and for you–justify what it will take to get it there?