Coaching - helping others find insight

book-notes , emotional intelligence , manager

Coaching is like midwifery. A midwife can not give birth to the baby, she facilitates the birth. Similarly, a coach can not give a solution, she must give birth to the insight from within the coachee. Coaching is asking questions, guiding, and facilitating understanding, and this post collects my studies on the topic.

The coaching mindset

Real understanding comes from within, and is not imparted by someone else. Ask questions, guide, and encourage. When you ‘tell the solution’ at best the solution is forgotten, at worst it offends and shutdowns down the coachee, damaging the relationship.

When being a coach maintain the following mindset.

  • Ask permission to be a coach. (Avoid forcing them)
  • Check-in with yourself to maintain the coaching mindset (Avoid forgetting your role)
  • Let your coachee do most of the talking. (Avoid cutting them off)
  • Keep questions open ended. (Avoid Yes/No questions)
  • Test your understanding (Avoid assuming you understand)
  • Be accepting, compassionate, and curious (Avoid judging and evaluating)

Frequent coaching situations

Some coaching situations are common, so I have deep dived into them.

The 7 goto coaching questions

When folks have questions or appear stuck, that’s a great time to provide rapid in the moment coaching. These 7 questions are a great starting point to help coachee build the required insights for solving their own problem:

  • Open: What’s on your mind?
  • Expand: What Else?
  • Focus Problem: What’s the real challenge here for you?
  • Focus Need: What do you want?
    • Do not ask why, it makes people defensive - you’re question their ability by asking why.
    • Want vs Need
  • Focus Request: How can I help?
  • Focus Trade off: If you say yes to this, what will you have to say no to?
    • Omission - automatic no
    • Commission - what you must give up to make it happen (relationships/projects/)
  • Close the loop: What was most useful for you in this conversation?

Questions for specific situations

Depending on what insights you want to provide, you need to use different questions. Some questions are below, Decisive has a plethora of other questions.

To clarify thinking

  • Help me understand that?
  • Tell me more?
  • Unpack that for me?
  • How did you come to that realization?
  • I’m having a hard time understanding, can you give some examples?

To challenge assumptions

  • Is that always the case?
  • What would it look like if that was false?

To gather more evidence

  • What makes you say that?

To find more alternatives

  • What is the counter argument?
  • What other options have you considered?
  • What would happen i this option dissapeared?
  • What is the next best use of resources?
  • How can you do A and B?
  • How would you decide if you had double the resources?
  • How would you decide if you had half the resources?

To build strategic insight

  • What does success mean?
  • What is our scope (who/where)
  • What will be our differentiator/moat here?
  • What capabilities/assets will need to achieve this?
  • How do we measure success and provide feedback?

To increase productivity, effectiveness, and efficiency

This request often comes in as the wrong question, need to deep dive into where the problem is coming from.

  1. Find the right thing:

    • The top optimization is spending zero time on the wrong thing. How often do you feel your spending time on the wrong thing?
    • Taking time to explore is important, how are you splitting time between, learning, exploring and doing?
    • What does success look like, how is your work supporting that success?
  2. Test for motivation:

    • On a scale of 1/10 how energized are you doing this work?
    • When are times you’re most energized and most drained? Any patterns
  3. Realistic Expectations + Estimations

    • Anxiety is the difference between expectations and reality. How are you validating your estimates/expectations are reasonable?
  4. Having the required resources

    • How often are you getting blocked?
    • What things would help you get done this faster?
    • Are there things that if you had, would speed you up?
    • What resources would make you more efficient?
  5. Doing it Efficiently

    • How often are you stuck?
    • How are you going about getting help?

The hows of coaching

Coach for task completion vs insight

Coaching applies to different time frames, keep them separate:

  • P: Project - Immediate task and new skill
  • P: People - Relationship
  • PC: Pattern - Help person get better.

Keep people safe while coaching using human safety models


  • Tribe: Tribe, ‘us’ vs ‘them’ - be us.
  • Certainty: People dislike ambiguity/uncertainty.
  • Rank: Do I move up or down the social ladder
  • Autonomy: I have control

SCARF - More details in Search inside yourself - Leadership and social skills

  • Status: Where am I in the pecking order
    • BUILD: Give credit, and feedback, ups peoples status
  • Certainty: Do I know what what’s going on.
    • Build: removing ambiguity, and giving people certainty on things that matter.
  • Autonomy: Do I have control over the situation?
    • Build: making clear it’s people’s choice, not yours.
  • Relatedness: Is other person friend or foe.
    • Build: by taking time to know people.
  • Fairness:
    • Build: making clear that you’re being fair.

Soften your coaching: How Can I help

  • Out of curiosity
  • Just so I know
  • To help my understand better
  • To make sure I’m clear
  • That is a hard problem
  • Not alone, lots of people struggle with this.

Encourange trying to solve own problem: How would you handle this

Great question, I have some ideas, but first, how would you tackle this? What else?

Say No: Say yes slowly

  • Why are you asking me?
  • Whom else have you asked?
  • What you say urgent what do you mean?
  • What does done mean?
  • If I could only do one part, what part would you have me do?
  • What do you recommend I take off my plate to get this done?want done?
  • If you still have to say no Make sure you’re saying no to task, no to person.

Focus feedback on you, not them

From the superb HBR article: The feedback fallacy. If you don’t read the article (which I’ll also summarize) take this high order bit of focusing the feedback on “you” not on them. E.g. feedback should be “I expereinced X” instead of you screwed up X.

Easy way Effective Way
Can I give you some feedback? Here’s my reaction
Good job! Here are three things that worked for me. What was going through your mind when you did them?
Here’s what you should do. Here’s what I would do.
Here’s where you need to improve Here’s what worked best for me, and here’s why
That didn’t work. When you did x, I felt y or I didn’t get that.
You need to improve your communication skills. Here’s where you started to lose me.
You need to be more responsive. When I don’t hear from you, I worry that we’re not on the same page.
You lack strategic thinking. I’m struggling to understand your plan.
You should do x [in response to a request for advice]. What do you feel you’re struggling with, and what have you done in the past that’s worked in a similar situation?

One on One Questions

See the One on One Sections And One on One prompts in the manager book

Situational coaching

As people learn new skills they experience a learning curve, which requires different support at different points on the curve. Situational leadership describes this in detail, but in a nutshell, while learning new things, people go through this grid from 1 to 4.

Competent/Confident Confident Scared
Incompetent 1. Foolish Novice - Thinks they can do it, but can’t 2. Novice - Knows they can’t do it, and feels bad
Competent 4. Expert - Know they can do it, and they’re right 3. Journey man - Thinks they can’t do it, but actually they can

Each stage requires different types of support

Competent/Confident Confident Scared
Incompetent 1. Instruct and Explain - Tell them what to do 2. Guide and Encourage - Show them how to do it
Competent 4. Empower - Explain Why Not 3. Facilitate - Explain Why.

Other coaching tools

Other coaching ideas to develop.

  • Using a scale question for relative improvement not for calibration. E.g. on a scale of 1 to 10, how do you rank yourself on X! Great, why do you say that?, Great - what would you need to do to move up a point on the scale?

  • Imagery cards - Use cards with images on them to illicit from people what picture represents what concept, then have a discussion. E.g. which of these pictures represents leadership to you? OK, help me see how that shows a leader to you.

Fantastic video on coaching, improvement, and discomfort