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The Art of Asking
Boardroom Questions
Prepared for
Atlas Leadership Series, OnBoard
By Lyn McDonell, MA, FCMC, C. Dir.
25 October 2023
1. Introduction
2. The Role of the Board and its Perspective
3. Tips for Asking Questions Effectively
4. An Oversight Framework
5. Your Questions
We’ll cover
Asking Questions
For Deeper Exploration
• 2nd and 3rd Edition
cover this topic in
more detail
• One can pre-order
the 3rd edition
now.
1 | Introduction
Directors Who Make a Difference
What is one main reason
why many directors don’t
ask questions?
Poll
Main Reasons why directors
don’t ask questions
1. Fear of asking a “dumb question”
2. Board culture doesn’t welcome debate
3. Not wanting to make others feel uncomfortable
4. Everyone else is fine with what was presented, so…
5. Not enough time on agenda
6. Don’t feel sufficiently prepared to engage
7. Other?
What Questions Do
▪ Gather essential information
▪ Clarify what is bring said or proposed
▪ Test assumptions
▪ Empower ownership and engagement
▪ Generate change, improvement, solutions,
opportunities and innovation, and
▪ Shift focus of the conversation
Effective Questioning
▪ Makes a meeting come alive, have relevance
▪ Sparks unscripted dialogue
▪ Enhances everyone’s understanding
▪ Helps avoid group-think and psychological traps
(so better decisions)
▪Board models a constructive learning culture
▪Management feels safe to share its challenges
2 | The Role of the Board and its
Perspective
Organizational Progress
and Accomplishment
Board Accountability
A
Purpose
B
Future &
Impact
Board Responsibilities
The Context of Questions
▪ Establishing Identity and Direction
▪ Ensuring Capacity/Overseeing Management
▪ Overseeing Performance/Impact
▪ Overseeing Risk
▪ Ensuring Financial Stewardship
▪ Ensuring Stakeholder Accountability
▪ Developing Good Governance
Roles and
Perspectives
Pause before we Pivot
3 | Tips for Asking Questions
Effectively
1. BEFORE the Meeting
1. Do a flyover. See what’s in package
2. Review the agenda. Note key discussions
3. Use a highlighter/underline essential points
in items. Trace logic paths…
4. Source your own knowledge/insight/gut. Imagine
what needs to go right, who is affected, what this
will change, etc.
5. Write down your comments/questions
2. DURING the Meeting
1. Tune in. Be present.
2. Listen with a Beginner’s Mind…
3. Does everything make sense? Anything fuzzy, or
potentially “spin?” Something left unsaid?
4. Show respect for others, the presenters, and the role
of the Chair
3. ASKING a Question
1. Tune in.
2. Be present.
3. Repeat.
TIPS for Asking Questions 1/2
▪ Be clear as to what you are asking. Don’t start
talking until you have your question framed
▪ Lead into it; maintain flow
▪ Be neutral & conversational
▪ Don’t add emotions or opinions; these
“hitch-hikers” distract and trigger
TIPS for Asking Questions 2/2
▪ Convey encouragement, inquisitive energy,
and not criticism
▪ In it together. Avoid using “you.” Say “we” instead
(less threatening)
▪ Instead of giving advice, phrase it into a question
▪ Face forward. Ask questions about the future
more than the past
4 | An Oversight Framework
The Oversight Framework
Board Accountability
A B
Intent
Purpose
and Values
Plans
Strategy
Action
(Actual)
Impact
Value
Created
ROI
Wise Use of
$ and People
Standards
Compliance
and Quality
Trust
Relationships
Reputation
Sample Questions in the Governance
Perspective
• 3rd edition
|
What one point or tip
will you remember?
Connect: TheAccountabilityGroup.com
The Accountability Group
The Accountability Group (TAG) provides
professional development in governance
for boards and senior leadership across
sectors that readies them for addressing
contemporary issues within a whole
systems approach. TAG is a leader in
advancing the regenerative governance
perspective. The firm is based in Toronto,
Canada and networked globally.
What We Offer
TAG works with Chairs and CEOs to
ensure that boards understand their role
in strategy, and that directors have the
capability to ask effective questions and
participate in meaningful dialogue. TAG
introduces regenerative governance—a
perspective that grafts onto conventional
governance—as an essential 21st century
board shift to prioritize organizational
contribution to whole systems vitality,
and navigate towards thriveable futures.
Lyn McDonell MA, FCMC, C. Dir.
President of The Accountability Group,
Lyn has served as CEO, COO, Board Chair,
and Director. She is a Fellow of the Ontario
Institute of Certified Management
Consultants and a Chartered Director. An
experienced facilitator and adjunct faculty
at York University, Lyn applies systems
thinking to organizations and is active in
communities of regenerative practice
Let’s shift Board
conversations to
the new reality.
Regenerative
Governance is
a living system
perspective grafted
onto conventional
governance.
Thank you.
5 | Questions

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The Art of Asking Boardroom Questions

  • 1. The Art of Asking Boardroom Questions Prepared for Atlas Leadership Series, OnBoard By Lyn McDonell, MA, FCMC, C. Dir. 25 October 2023
  • 2. 1. Introduction 2. The Role of the Board and its Perspective 3. Tips for Asking Questions Effectively 4. An Oversight Framework 5. Your Questions We’ll cover
  • 3. Asking Questions For Deeper Exploration • 2nd and 3rd Edition cover this topic in more detail • One can pre-order the 3rd edition now.
  • 5. Directors Who Make a Difference
  • 6. What is one main reason why many directors don’t ask questions? Poll
  • 7. Main Reasons why directors don’t ask questions 1. Fear of asking a “dumb question” 2. Board culture doesn’t welcome debate 3. Not wanting to make others feel uncomfortable 4. Everyone else is fine with what was presented, so… 5. Not enough time on agenda 6. Don’t feel sufficiently prepared to engage 7. Other?
  • 8. What Questions Do ▪ Gather essential information ▪ Clarify what is bring said or proposed ▪ Test assumptions ▪ Empower ownership and engagement ▪ Generate change, improvement, solutions, opportunities and innovation, and ▪ Shift focus of the conversation
  • 9. Effective Questioning ▪ Makes a meeting come alive, have relevance ▪ Sparks unscripted dialogue ▪ Enhances everyone’s understanding ▪ Helps avoid group-think and psychological traps (so better decisions) ▪Board models a constructive learning culture ▪Management feels safe to share its challenges
  • 10. 2 | The Role of the Board and its Perspective
  • 11. Organizational Progress and Accomplishment Board Accountability A Purpose B Future & Impact
  • 12. Board Responsibilities The Context of Questions ▪ Establishing Identity and Direction ▪ Ensuring Capacity/Overseeing Management ▪ Overseeing Performance/Impact ▪ Overseeing Risk ▪ Ensuring Financial Stewardship ▪ Ensuring Stakeholder Accountability ▪ Developing Good Governance
  • 15. 3 | Tips for Asking Questions Effectively
  • 16. 1. BEFORE the Meeting 1. Do a flyover. See what’s in package 2. Review the agenda. Note key discussions 3. Use a highlighter/underline essential points in items. Trace logic paths… 4. Source your own knowledge/insight/gut. Imagine what needs to go right, who is affected, what this will change, etc. 5. Write down your comments/questions
  • 17. 2. DURING the Meeting 1. Tune in. Be present. 2. Listen with a Beginner’s Mind… 3. Does everything make sense? Anything fuzzy, or potentially “spin?” Something left unsaid? 4. Show respect for others, the presenters, and the role of the Chair
  • 18. 3. ASKING a Question 1. Tune in. 2. Be present. 3. Repeat.
  • 19. TIPS for Asking Questions 1/2 ▪ Be clear as to what you are asking. Don’t start talking until you have your question framed ▪ Lead into it; maintain flow ▪ Be neutral & conversational ▪ Don’t add emotions or opinions; these “hitch-hikers” distract and trigger
  • 20. TIPS for Asking Questions 2/2 ▪ Convey encouragement, inquisitive energy, and not criticism ▪ In it together. Avoid using “you.” Say “we” instead (less threatening) ▪ Instead of giving advice, phrase it into a question ▪ Face forward. Ask questions about the future more than the past
  • 21. 4 | An Oversight Framework
  • 22. The Oversight Framework Board Accountability A B Intent Purpose and Values Plans Strategy Action (Actual) Impact Value Created ROI Wise Use of $ and People Standards Compliance and Quality Trust Relationships Reputation
  • 23. Sample Questions in the Governance Perspective • 3rd edition
  • 24. | What one point or tip will you remember?
  • 25. Connect: TheAccountabilityGroup.com The Accountability Group The Accountability Group (TAG) provides professional development in governance for boards and senior leadership across sectors that readies them for addressing contemporary issues within a whole systems approach. TAG is a leader in advancing the regenerative governance perspective. The firm is based in Toronto, Canada and networked globally. What We Offer TAG works with Chairs and CEOs to ensure that boards understand their role in strategy, and that directors have the capability to ask effective questions and participate in meaningful dialogue. TAG introduces regenerative governance—a perspective that grafts onto conventional governance—as an essential 21st century board shift to prioritize organizational contribution to whole systems vitality, and navigate towards thriveable futures. Lyn McDonell MA, FCMC, C. Dir. President of The Accountability Group, Lyn has served as CEO, COO, Board Chair, and Director. She is a Fellow of the Ontario Institute of Certified Management Consultants and a Chartered Director. An experienced facilitator and adjunct faculty at York University, Lyn applies systems thinking to organizations and is active in communities of regenerative practice Let’s shift Board conversations to the new reality. Regenerative Governance is a living system perspective grafted onto conventional governance.