Strategic Coaching Questions for Leaders

Hi, I'm Rachael Pickworth from MAD Leaders.

In the Elevate in 90 Days Program we have an entire lesson dedicated to delivering effective 1:1 meetings using a template we provide. 

As a bonus, we also provide a list of strategic coaching questions, to gain deeper insight into how to provide greater leadership to the team.

These are the actual questions asked by a long-term client of mine; a Director who meets with every person in her team twice per year. 

This is a video I posted on LinkedIn in December 2018 with the questions, which you can download below...


Automated subtitles 

Download Questions

"The combination of coaching, team coaching and coaching skills training over recent months has supported our leadership team to move to the next level. We are more aligned, focused and have a better understanding of how to be effective leaders. Thank you for your support."

Stuart Draffin
GM Planning and Development, City of Stonnington

"Through coaching sessions with Rachael I have been able to quite quickly achieve clarity and a sense of purpose around what my goals are. This has made it a lot easier to make decisions on where I should be focussing my time and what career decisions I should make. The clarity has provided a sense of relief by taking away the ‘noise’. I would not have achieved this without Rachael providing guidance and gently challenging and interrogating my thinking."

Kym Myall
Director Risk Assessment and Intelligence, Australian Tax Office

"As a HR Business Partner I have engaged Rachael’s coaching services periodically over the last 5 years. This has included Rachael coaching individual staff (40), delivering goal setting workshops and facilitating team coaching with great success. Rachael has a unique and vibrant way in which she engages an audience and individuals to set and achieve goals and it is always a pleasure working with her."

Donna Durston-McKenna
HR Business Partner, 
Southern Health

"Being on a journey with Rachael is like standing in front of a mirror with a warm hand on my shoulder. Rachael listens intently to every word and takes nothing for granted. She searches for gaps in my facade and won’t let me walk away from where she knows I need to go. And when I get there, she is right by my side. Rachael is direct but kind. She is bold but nurturing. And simply, she makes it her business to see people discover their best selves."

Donna Maloney
Manager Business Partnering, Department of Transport

"Coaching for me is about staying at the top of my game in every aspect of my life. With such a demanding career, whilst being successful at what I do, coaching ensures I prioritise my relationship, my kids, my health and my downtime, in ensuring my life is a success."

Prakash Menon
Director Myer Logistics, Myer Ltd.

"Rachael has worked with a number of colleagues at various organisations for me. Rachael has the ability to take the people ‘out of their comfort zone’. She will ask them to assess, challenge and stretch themselves. By doing this she gets results. I have seen great growth in these colleagues as a result of the sessions they have had with Rachael."

Fleur Delves
Victorian Manager, PKL Recruitment

"The coaching, enthusiasm and insight Rachael provided me throughout my journey, has not only enabled me to discover a great deal about myself but more importantly made me conscious and able to refocus on how I can progress positive change. I have felt comfortable and inspired since our first meeting and the momentum continues today. A motivating learning experience for me – Thank you."

John Karabatsos,
Manager IT Market Interface Solutions, Australian Energy Market Operator Ltd

"You are a legend. Thank you so much for facilitating our goal setting day. I was really pleased with the outcome. I admire the way you ran the day and your perceptiveness to the different personalities. You really do have a gift with people. Thank you again."

Regina McInnes
MD, McInnes Property Management

"Rachael opened my mind to possibilities I hadn’t even considered. The sessions helped me explore my values, understand my personal and professional purpose and be confident that I can make the right choices to balance what I initially felt were conflicting aspirations. Thanks Rachael."

Charles Boorman
Program Planning Specialist, VICRoads

"Just a quick note to let you know how much we appreciated and enjoyed your presentations at our recent WCN networking breakfasts. You might be interested to know that at the May breakfast we had a record attendance with over 160 guests and that you are the first speaker we have asked back due to such an overwhelming interest. The response has been phenomenal and the evaluation forms 100% positive! You will be a tough act for others to follow. "

Kate Wilkins
Member Relations Executive, CPA Australia

50% Complete

If you want to take your leadership to the next level here are 3 things that will help:

Day 1.  Vanessa's coaching questions PDF download

Day 2.  3-Page 'Craft Your WHY' Simon Sinek activity and video to help clarify the purpose of you and your team

Day 3.  The secret of leaders who fast track their awareness, brand, leadership capability & careers: 'STRATEGIC FEEDBACK GATHERING SYSTEM' (PDF download and instructional video)