Jeremy Koudri: Coaching Questions for Every Situation

Coaching questions

What matters when questioning is not simply what is said, but how, when, and why it is said as well. Context and motives.

Coaching is goal-oriented, non-directive, and learner-led. In the words of the coaching pioneer and writer Sir John Whitmore, coaching is about unlocking an individual’s potential to maximize their own performance.

When coaching someone, remember that, if they say or think something, then that is their reality.

In the context of coaching, questioning is the route to progress.

Some fundamental – almost universal- questions are:

What is your ideal?
What is your goal?
What are your options?
What is the best (or least worst) option?
What is stopping you?
What can you do about that?
Why do you think that? How do you feel about it?

The GROW model is about goals, reality, options, and a way forward.

Questions regarding goals:

What is your goal? What are your priorities? What are you trying to achieve?
How will you know when it has been achieved? What will success look like?

Questions regarding reality:

To what extent you can control reality?
When do you want to achieve the goal by? Are there any milestones?
Who is involved and what effect could they have?
What are the major constraints?

Questions regarding options:

What options do you have?
Which is preferred and why?
If you had unlimited resources, what would you do?

Questions regarding the way forward:

What are you going to do? By when?
Who needs to know?
Do you need support?

Personal coaching questions

Questions about you

The Leader’s Shadow:

What I say – how I set context and frame issues.
How I act – my behaviors, symbols, relationships.
What I measure – the things I look at and take an interest in.
What I prioritize – whether disciplines or routines.

Some questions:

What does good look like?
Where do you spend your time?
What gets followed up?
What is forgotten?
What do you want to do more, or better?
What do you want to do less, or stop doing?
How well do you know yourself?
What are you afraid of?
What qualities do you admire, and why?
What are your biggest challenges/concerns/priorities currently?
How and when do you cause negative feelings in others?
What are you known for?
What do you aspire to achieve?
Are there any limiting beliefs?
Which areas are strengths for you? Is this view shared by your colleagues?
What are your weaknesses or areas for development?

Personal effectiveness questions

Time has two meanings when setting goals: first, it can mean time-bound – constrained by a deadline; second, it can mean timely – delivered at the right (most) appropriate time.

Some questions:

Are you trying to be a perfectionist?
Have you done enough to determine when it is necessary to deliver a perfect outcome, and when you need to let go?
Do you know what is inside and outside your control?
Can you distinguish typical patterns of behavior from unusual ones?
How will you apply what you have learned?
How will you assess and measure your progress?
What will it take to succeed?
Does the goal reflect the right priorities? Is it engaging and exciting? Is it the end goal or performance goal?
What is the difference between a good and a great outcome?
Would it be useful to have interim measures?
Is this the right goal at the right time?
Are you sufficiently positive about the benefits of the objective?
Would it help to use the STAR (situation, task, actions/activities, results) approach when setting goals for someone else?
Are you moving towards something exciting, or are you moving away from something negative?
Have you mapped the likely sequence of events, stages, or milestones?

Emotional intelligence questions

Goleman builds on the work of Howard Gardner and Peter Salovey. Emotional intelligence is evident in five areas:

Knowing one’s emotions.
Managing emotions.
Motivating people.
Recognizing emotions in others.
Handling relationships.

Some questions:

Which relationships do you value – and why?
Which relationships could you improve?
Which emotions do you need to manage more or better?
What are you passionate about?
How well do people know you?
Could you do more to draw people towards you?
What is your greatest fear?
What do you really want?
How good are you at taking advice?
What will help you push harder?
How would I know that you trust me?
How do you build your credibility?
How will you engage someone’s heart?
What could you say about yourself that would help others understand your more personally?
How do you want to be remembered?

Learning questions

Mark Twain: “It ain’t what you don’t know that gets you into trouble. It’s what you know for sure that just ain’t so.”[1]

Three potential pitfalls when assessing your own skills and behavior: regarding a personal failing as a situational problem, avoiding the new and unfamiliar, suppressing doubts and acting with certainty.

Some questions:

Whose feedback do you value?
How will you learn and develop new skills?
What skills do you need to develop to succeed in your current role?
What are you good at?
Where, when and how often do you apply your strengths?
What are the top three priorities for your development?
What is the timeframe for development?
How will you develop your skills?
How will you develop the right thinking and mindset?
How will the result be integrated into workplace activities?
What will you stop doing to make time for: learning activities and new habits?
Whose support do you need?

The toughest questions

Some questions:

What does achieving this goal mean to you?
Why is it important?
Of the things you want to change, what do you want to change most? (And why? How? When?)
Who has most profoundly affected you – and how did they affect you?
What is the most significant event in your life?
What gives you energy?
What drains you of energy?
What would you like your obituary to read?
What qualities do you admire?
What is your greatest achievement?
What is your biggest disappointment?
How would close friends describe you?
What would you like colleagues and contacts to do more, less or better?
What gets you out of the bed in the morning?
What sustains you during challenging times?
What is your best kind of day?
What is your worst kind of day?
What do you need to unlearn?
How will you sustain your focus, energy and your spirits?
Who can you learn from?
What are you worried about?
What is the benefit – the reason for making this change?
What is the risk of inaction?
What will you do first?

Resilience and emotion questions

One of the most effective ways to coach someone to develop resilience is by focusing on four issues:

What they give their attention to.
What they think.
What practical action they take.
What engages and motivates them when dealing with life’s events.

Churchill: “Success is never final; failure is never fatal; the only thing that counts is courage.”[2]

Some questions:

What do you think when something positive happens?
What happened?
Why did this happen?
Was it predictable?
What was the impact of this event – the consequences?
Is it possible that while you feel empathy and compassion, you could do more to show it?
Do you have a go-to activity that increases your energy?
What is it about you that sparks a deep emotional connection and feelings of respect?
What makes you smile?
What issues, situations and behaviors bore you?
What do you like? What do you need?
What are your addictions – do these need to change?
What shocks you?
What concerns do you have?
What can you learn from the past (your past)?
What would you like to do or find again?

27 distinct categories of emotions according to Alan S. Cowen and Dacher Keltner:

Admiration
Adoration
Aesthetic appreciation
Amusement
Anxiety
Awe
Awkwardness
Boredom
Calmness
Confusion
Craving
Disgust
Empathetic pain
Entrancement
Envy
Excitement
Fear
Horror
Interest
Joy
Nostalgia
Romance
Sadness
Satisfaction
Sexual desire
Sympathy
Triumph

Decision-making and problem-solving questions

Five big questions to help develop your decision-making style:

Are you going to solve the right problems with your decision-making?
Are you framing your decision-making in the most appropriate way?
Are you making the right assumptions?
Methodology – are you balancing intuition with data?
Reflect on experience – is there a precedent or a lesson to be learned?

Bad decisions usually happened when the alternatives were not clearly defined, the right information was not collected, and the cost and benefits were not accurately weighed.

Some decision-making traps:

The anchoring trap.
The status quo trap.
The sunk-cost trap.
The confirming-evidence trap.
The framing trap.
The overconfidence trap.
The prudence trap.
The recent event trap.
Bolstering – an uncritical emphasis on one option.
Shifting responsibility.
Cultural flaws: fragmentation and groupthinking.

Grey rhinoceros events (high-probability, high-impact, yet neglected threats) or black swan events (low-probability, high-impact).

Some questions:

What is the core issue you need to resolve?
What are the implications?
What related issues also need resolving?
What lessons are to be learned?
Do you have enough information or resources to tackle this issue?
Can you reframe the problem or issue in a more positive or productive way?
How will you know when it’s been resolved?
Who needs to know about the issue?
What do we know and recognize?
What data do we have available?
What is unknown and unfamiliar?
What do we know but can’t prove?
What are the obstacles to the ideal solution?
What is not optional – what are the essentials?
How will you learn from the decision?
What exactly, are the risks of staying the course for too long?
What are the risks of trying a different approach?
What is stopping you from changing the course at the right time? What would help?
Do you look for evidence to justify a decision rather than comprehensively reviewing the decision?
Do you consistently apply common principles, values and perhaps even a guiding vision when making decisions?
Would it help to start with a meta-decision: decide the way you are going to decide?

Questions on purpose

It is purpose that provides the focus, encouragement and drive needed to succeed.

Some questions:

What do you feel you are meant to do in the world?
What did you want to be when you were child?
What are your talents and natural abilities?
What are your three most significant weaknesses?
If you had only one year to live, what would you focus on?
What have you done that you would like to do again or more often?
How is your work and career path intertwined with your destiny?
What have been your greatest career accomplishments?
What key skills have you picked up that are of most value to you?
What have all your failures prepared you for?
What specific life experiences have had the most meaning?
What would you do if you could not fail?
What would you regret most not doing?
What would your ideal life look like?
What lasting legacy would you like to leave behind?
What do you care about that is bigger than you?
What will you do first?

Coaching questions for typical and difficult challenges

Leadership and teamwork questions

Team members can be assessed against four key criteria:

Ability
Attitude and mindset
Relationship
Trust and integrity

Teams have:

The stars
High potentials
Capable movers
Somebody on probation
Low-priority movers
High-priority movers

The stages of team development:

Forming
Storming
Norming
Performing
Reforming

Some question:

In what ways does the vision mobilize people and generate commitment?
Is the vision focused, specific and ‘real-world’ enough to be used as a basis for strategic planning and to guide decision-making?
Do you prefer to learn by immersing yourself into a situation or by observing for a while before taking action?
Have you considered both the importance and urgency of the task that you are delegating?
Are you choosing the right person? What makes them the right person?
Will the task stretch and challenge the individual?
Have you discussed the task, from purpose to completion?
Have you provided all the necessary resources?
Delegation without control is abdication – how much control will you retain, and how will you exert this control?
Do you let the person complete the task in the way they prefer?
Do you let those team members with the greatest insight and understanding take decisions themselves?
Does your team have: a team charter, a guiding vision, a clear set of priorities?
Do team members hold you and each other to account and in a positive, encouraging way?
Does your team share experience and expertise?
Is the team focused on the right things? Is everyone agreed on the priorities?
Are objectives and processes aligned, consistent, and pulling in the same direction?
What sort of things could we do to be more effective?
If you were me, what things would you be looking at?
Are expressions and body language consistent with the words used?

Questions when coaching across cultures

Paying attention to information is part of the art of coaching. When someone mentions something, the question is not, why is this significant, but how is this significant?

We have universalism versus particularism, individualism versus communitarianism, natural versus affective, specific versus diffuse, achievement versus ascription, sequential versus synchronic, internal versus external control.

Transformation and change questions

When you’re under pressure it is easy to forget that employees have varying interests, abilities, goals and styles of learning.

Some questions:

If this issue was resolved, what would the solution look like?
What is the best way to communicate the need for change and establish a sense of urgency?
What will a successful outcome mean for the organization, each team and each individual?
What will people want to know?
What would change first – is there a plan with roles assigned?
How will you use the changes to provide added value?
Tell me, what’s on your mind? I’m keen to understand.
What aspects of work would you like to change?
You aren’t operating at your full potential – for example … Why is this? What’s holding you back?
What do you think you are capable of achieving?
What can I do to help you?

Communication, influencing and engagement questions

Thomas-Kilmann Conflict mode. Dominant and submissive dimensions and warm and cold. Dominant and warm goes about: tell me what’s on your mind?

Some questions:

What is your message?
Why do you want to convey your message?
What response and outcome are you looking for?
What is your intended purpose?
Who is your primary audience?
What are your audience’s priorities?
What is the most appropriate way to convey your message?
What issues do you need to address?
When is the best time to communicate?
Are you listening?
I think you can do better – what is your view?
What obstacles, risks, and concerns will people have?
Are concerns and objections valid?
How will you address and counter likely objections?

Coaching questions for defining moments of leadership

Arrival questions

Share experiences, don’t instruct. Listen to progress, don’t review it. Provide feedback, don’t course correct.

Some questions:

Is there a mentor or coach you could work with to support you during the transition and to help you achieve your aims?
What will success look like for your boss?
What are the expectations of key stakeholders? Are these expectations realistic?
Who will you speak with so as to gain the simplest, most accurate view of strategy and capabilities?
What do financial indicators and other performance measures indicate about the business’s real priorities?
What do outside observers (customers and analysts) think about how the organization is managed?
Who has to be replaced and how will this be done?
Can productivity be improved – if so, how?

After action review and feedback questions

Some questions:

What was supposed to happen? What did happen? Why was there a difference?
What worked? What didn’t work? Why?
What would you do differently next time?
Is there consistency between what top people tell you and what their direct reports say?

Future-thinking questions

Adaptive intelligence is about: the ability to live with uncertainty and change, the ability to embrace change and unfamiliar circumstances as opportunities to understand, learn, and improve, the ability to embrace diversity, and the ability to nurture opportunities for self-organization.

[1] In the book on page 60

[2] In the book on page 91