During our weekly intimate roundtables with Engineering Leaders from across the world, we discuss various topics, such as software management, software engineering teams, engineering workflows, and even metaphysical questions that affect our lives!

Last week, one of the sessions was about Coaching & Leadership. The stimulating discussion led one of the Engineering Managers, Nicholas Goodall, to share a list of powerful questions which he uses during his coaching conversations.

Nicholas Goodall, EM at Treatwell, is passionate about coaching and having a positive impact on managers, software engineers and teams as a whole.

In this short blog post, we’re sharing with you the list of questions (and additional resources) that will help you hone your coaching skills!

First things first, what’s Coaching, Mentoring, oh, and Sponsoring?

  • Coaching: here, the angle is more focused on performance, it’s more practical. You will be asking the right set of questions and applying templates to help an engineer achieve his objective (generally in the current job function)
  • Mentoring: the approach is about career development; you are sharing your personal experience with a software engineer to help her/him leverage your experience & knowledge
  • Sponsoring: contrary to the above, sponsoring is about you giving an engineer the opportunities to grow professionally - your concrete action can push her/him on-the-job

Nicholas is focusing on Coaching and in this blog post, we'll share with you a list of curated questions that can help you unlock your coachee. The keyword, indeed, is “unlock”.

“Unlocking a person’s potential to maximize their own performance. It is helping them to learn rather than teaching them.”

In this know definition of coaching, Sir John Whitmore - a leading figure in executive coaching - highlights the basis of what coaching is about. To help learning, questions are the best thing to start with!

Without further ado, the list of questions categorised by topic. All credit goes to Nicholas!


  • When are you working at your best?
  • What do you already contribute to the success of your team and of Treatwell?
  • What are your top three strengths?
  • What are your three most prevalent weaknesses/areas for development?
  • What skills would you prefer to be using?
  • What would you most like to develop in yourself?
  • What would be a stretch for you now?
  • What would take you outside of your comfort zone?
  • What stretch would you agree to?
  • What would you like to do more of?
  • What is the most useful thing you could do right now to take you where you want to go? What action will make the greatest difference?
  • What kind of journey would you like to be on over the next few years?
  • From your list of priorities, which would be your top outcome?
  • What will you have achieved from your career in one, two, five years’ time?


  • Where have you experienced your greatest motivation? What was present?
  • How can you experience that again?
  • What gives you the greatest pleasure and satisfaction in life?

Goal planning

  • What would be a good goal for you?
  • How would this goal be aligned with your values?
  • What would be an even bigger goal?
  • How could you make this into smaller steps?
  • How can you isolate some pieces that will move you towards your goal? What small steps would get you started?
  • What would be an easy first bit?
  • What other choices do you have?
  • What will be different when you have achieved your goal?
  • What is important to you about this?
  • What are you willing to give up / let go of to accomplish this?
  • How will you know you have reached your goal?
  • On a scale of 1-10 how happy would achieving this goal make you?
  • Where have you previously been successful with achieving goals? What can you learn from this?
  • What will you do differently next time?
  • What could be stopping you from taking action? What kind of structure would serve you?
  • Is this goal under your control?
  • What is the cost of going for this goal?
  • What is the cost of not going for this goal? What is the time needed to achieve the goal? How do you know this goal is worth achieving? What might get in the way?

Involving others

  • Who else shares this goal?
  • Who do you know that has taken this path before?
  • Who are the key stakeholders you need to get on board? Who is impacted by what you want to do?
  • Who would champion you on this journey?
  • What would you be prepared to ask them?
  • When will you make this ask?

Commitment and will

  • What could be the effects of achieving this goal?
  • What personal strengths/resources do you bring?
  • What makes you confident that you can achieve this goal?
  • What will get you started?
  • On a scale of 1-10 how committed are you to working on this goal? What will increase your commitment?
  • On a scale of 1-10 how motivated are you?
  • What prevents this from being a 10?
  • What do you need to get your commitment up to 10?
  • What personal resistance do you have to taking these steps? What will you do to eliminate these external and internal factors?


  • What will you need to know, to know that you have achieved it? What milestones will you set up?
  • How will you know you’re on track?
  • Where will you find the resources you need?
  • What is going to help you to stay on track?

About our weekly roundtables
With more than 300 members, discussing & sharing perspectives during weekly roundtables, the community has become a real source of insights for many software engineers and tech leaders!

If you’re looking to join our weekly intimate roundtables to share your perspective on the various topics we’re covering and discover those of your peers, click here. See you soon! 👋