Return to site

Is your Career worth copying?

· Leadership,Coaching,Questions


Why would a younger colleague want to emulate your career or seek you out as a Mentor? How have you expanded your Self-Awareness this month? Which question led to most progress? Did you thank the person who asked you? Here are the #Leadership #Coaching #Questions I asked on Twitter in June.


I share this work in progress in the spirit of working out loud. Thank you to the clients, friends, authors and serendipity that inspired the questions. Notice which questions are productive for you and tell me where they take you. You can read more as I post them here. Enjoy the journey.

Can you count the number of teams you have been part of this week?

Who are your stakeholders & how can they measure your effectiveness?

Why not try not preparing?

Which were your good decisions this month?

How humble can your leadership be… and successful?

Is it a good idea to go to the pub with your colleagues?

What can't your mentor do?

What is the first activity you schedule in a new week?

What causes what causes the Stress?

Is it as simple as: leading or leaving?

How is your Behaviour creating value for someone else?

Do you see a correlation between curiosity & energy levels?

Are you empowering or overpowering your people?

Is your HR Leader charting the course?

Is less more?

When is good enough?

What would your 8-year-old self say about what you are doing at work today?

How do you compare two job offers?

What fascinates you?

How could you derail?

Did you push or did they jump?

What are you doing to ensure your talents hold their value?

Which Temptations are you resisting?

What’s the most naïve question you can ask in this week’s Meeting?

Did you show up this week?

How does small-talk make you feel?

Time to think again?

Isn't it obvious?

Are you striving for optimization or availability?

How could you derail?

Take Change or take Charge?

Who will ask the question?

Is Thinking Too Much really a case of thinking too little?

Is it easier to control your words or your actions?

What would you do next?

Is Ambition useful?

How much time do you spend alone?

Do your Mentee’s failures hurt you?

How do you know you are Listening at your best?

When is good, enough?

Do you know what you do not need to know?

How do you sustain your learning?

Who knows?

Does the eye of the storm blink?

How do you sound when you are criticising?

Stepping forward or stepping up: which challenges you more?

Have you prepared what the other party wants?

Do you need a Coach?

Have you found your Ikigai?

What would you delegate to your executive assistant if you had one?

When cars are flying what will your business be selling?

How curious will you be this week?

What is your contribution?

Have you prepared what the other party wants?

Do the same questions come up every day?

If you push, who does not have to pull?

Are you the voice or the echo?

Who will help you next week?

Who did you surprise this week?

When was your last unforgettable experience?

Are you a slacker?

How do you manage a team of experts?

How do they respond when you are happy?

What can Pollyanna teach you?

Who was your first follower?

What stake does each team member have in success or failure?

How often will you smile today?

Are you a great encourager?

Is your career worth copying?

Who will have the last word?

Are you waiting for the deus ex machina?

Would you rather be a natural or work intentionally & know how you succeeded?

What is there to enjoy in the impasse?

Where is the line between on & off message?

Are you a delegate or a representative?

Are your goals clear enough to set you free to succeed?

Are competition & creativity incompatible?

Will you be yourself today?

Bottom-up or top-down?

Does your Big Picture view have a frame?

What do you lose when you find an easy answer?

Who has all the Answers?

Who's your Challenger? Do you show him/her your Appreciation?

Could laughter make a difference?

Can you "express the unspoken collective sentiment”?

Whose bias could you be unintentionally amplifying?

Step up or slippery slope?

Have you faced a similar Problem before?

Have you placed the people around you so they are set up for success?

What good can you find in the bad?

When did you last climb a mountain?

If your staff would repeat you word-for-word, how will you change what you say?

How do they know they can Trust you?

What questions get in the way of solving problems?

How much Time did you spend in Meetings last week?

Are you prepared for the best?

What example will you set this week?

Isn't it obvious?

Did you Risk your Reputation this week?

Would you hire yourself?

Who has the complementary Leadership skills to your own?

Who is feeding the elephant in the room?

When is it the right time to stand alone?

Who can you help today?

What do you do after a meeting?

How does your job benefit from your Sense of Humour?

What's the value of personal development in the gig economy?

Is every question you are asked an attack on you?

Do you own your own behaviour?

What are your interests?


How many new relationships between others have you created?

What is holding you back?

How does Mindfulness work for you?

Can you recall the original cause of your negative feelings about you colleague?

Who did you influence on Monday?

Who put you in the box?

Is your #reputation who you are?

When you help your team, do you make it helpless?

How do you tell a Story?

What part does Social Confirmation play in your Strategy process?

Why are you doing this job at this time of your life?

When will you be ready?

What are the benefits of not being able to remember everything?

Is your feedback specific?

How will you know who is the winner today?

Who did you help on Thursday?

Who will lead in a time of crisis?

Did you start with Why?

What would it take to make it happen?

Who are you trying to change?

Why not do both?

Are you overthinking?

What IS Possible now?

Do you allow yourself to live with Paradox?

Who switched on your light-bulb?

What can the carpet tell you about the meeting?

What is not being said?

Can you do it without a leader?

How much Time do you spend making sense of your Leadership & Experience?

How will you take up your authority today?

A jumping-off point or a dead-end?

How can you move faster?

What are the unknowns?

Whose Truth are you resisting?

How can you accelerate a Meeting?

Which spiral are you falling into?

How many times were you cc'd on emails this week?

Is your CV up-to-date & demonstrating your strengths?

This box your supposed to think out of - what shape is it?

Is second best?

How will you weaken the forces that are holding you back?

Do your peers know your Change story? Do they know how it ends?

What is the worst behaviour you have tolerated?

What’s the value of being the difficult person in the office?

Could your organisation be flatter?

Will your staff read the books you recommend?

Do you want to add value?

When is lack of Focus a benefit?

What are the limitations of your own world view?

Do you have trouble coming up with just the perfect metaphor?

What gets you engaged in a meeting?

Do you get a vision of the future by locking yourself in your office?

Is the concept Business As Usual helpful?

Who led the elephant into the room?

Can you do it alone?

Can you be too good at your job?

Do you need operational experience?

Can you show your past failures compassion?

Is the status quo challenging you?

Does your boss keep you in mind?

Who does not care?

What does Red Amber or Green leave unsaid?

How did you become a manager?

What did you learn about your limits this week?

How can you help you clients by doing less?

Is it time to think in a new box?

When did you last make your boss feel uncomfortable?

Do you dread idleness?

On the way to the meeting you bump into your future self. What will you ask?

Do you miss the memories or the person?

What do your young managers want?

What can you learn from your would-be disrupters?

Are you looking for a fight?

What’s missing?

Is your job to avoid getting shouted at?

Who did you praise on Friday?

What does a bias for action overlook?

Why is Succession Planning such a problem?

Have you been testing the limits of the unknown this week?

What are your hobbies?

Which water-cooler works best for you?

Are you Respected more than you Respect?

How do you practice telling your Stories?

What would your 18-yr old self advise?

Are you working with a malignant Narcissist?

How much time do you spend teaching your colleagues?

Are you a “Constructive Contrarian”?

How can you tell if a Team has a shared Purpose?

How far can you go?

When is your Sense Making at its best?

Are you being heard?

Is it time to feel scared again?

How will you waste your time today?

Does it remind you of a time when…?

Is bigger better?

Is working from home good for Introverts ?

How will you use the word "but" today?

What steps will you take this month to address your skill gaps?

How will you know when you have achieved your objective

Andrew Jones is an Executive Coach and Career Counselor. Please contact Andrew directly to learn more about this topic or subscribe below to hear more from Andrew in the future.