Whether you’re looking for books to give as gifts this holiday season or to read yourself as we head into a New Year, our executive coaches have you covered for top leadership book suggestions.
Books are great presents for the leaders on Santa’s nice list (and hey, perhaps even more appropriate for a leader on the naughty list!). From seasoned leaders to young adults you’d like to see succeed in life, our top leadership book picks have something for everyone.
We surveyed our experienced team of executive coaches for their favourite reads (our blog with our Padraig team’s thoughts on leadership was one of our most popular in 2023!). In no particular order, here’s what they recommend you buy to give to someone you care about or add to your personal reading list:
Four Thousand Weeks: Time Management for Mortals
By Oliver Burkeman
Kathleen Cameron, Certified Executive Coach (PCC) and Padraig Facilitator, recommends this New York Times bestseller because it challenges us to think differently about time management and productivity.
“Time management is a common theme that comes up in coaching,” shares Kathleen. “Often, our clients are struggling to juggle demanding workloads and competing priorities. What I enjoyed about this book is that the author challenges us to look at some of the fundamental ideas that influence how we think about time management and productivity differently.”
She says Burkeman pokes at some of the ideas that keep us focused on trying to get more done in less time: “He claims it is a fallacy that we will ever get to the end of our to-do list. Rather, we want to explore our motivation and approach to productivity. Does it actually serve you to do more? Are we deceiving ourselves into thinking our to-do lists are finite and achievable?”
Burkeman encourages us to embrace the notion that we can’t get it all done.
“When you release yourself from that pressure, your experience changes,” says Kathleen. “You focus on what’s important and let go of the rest. It’s an interesting read. I encourage you to try on some of the ideas and see if anything shifts for you.”
Pro tip: Feeling too busy to read? Download the audiobook version and listen while you commute, work out at the gym or go for a walk.
Coach’s Book Questions: How do your thoughts on time management and productivity influence how you approach your to do list? If it was impossible to get all of your work done, how would you prioritize your time and focus?
The Coaching Habit: Say Less, Ask More and Change the Way You Lead Forever
By Michael Bungay Stanier
Ryan Quesnel, Certified Executive Coach (ACC) and Padraig Facilitator, says this was the first coaching book he read when he was in a leadership role.
“It had a profound impact on how I was leading my team,” says Ryan. “I circled back to the book again when I was training to be an Executive Coach, and the second time reading it, I had many more ‘ah-ha’ moments.”
He says that themes that stick with him include common traps leaders get into with their team members, the importance of curiosity and learning to lead yourself before you lead others. Additionally, this book helps leaders learn to confidently lead from a coach-like perspective instead of advising what to do.
Coach’s Book Questions: What motivates you to do things for others on your team instead of letting them figure things out? Are there ways you could shift your lens around leadership situations? What can you do to be more adaptable in leadership situations?
Think Again
By Adam Grant
Ryan also recommends Think Again as a top leadership book. It explores the concept of rethinking and embracing a more flexible, open-minded approach to our beliefs and decision-making through a neuroscience lens of neuroresilience.
“This is a great stepping stone for a leader interested in Emotional Intelligence, covering the neuroscience behind topics like psychological safety and the mental mechanics of conditioning, belief systems, biases and coping with triggers,” he says.
Additionally, Ryan shares, Think Again helps you discover self-awareness check-points that alert you throughout your day that you are either off-track—needing to come into the present moment and refocus—or become aware of a “gratitude alarm” as an opportunity to be grateful for what you’ve accomplished.
Coach’s Book Questions: When did you last consider your wellbeing and mindset? What do you actually need to achieve the goals you have? How do you start to move forward, especially if you’re overwhelmed?
Quiet Leadership: Six Steps to Transforming Performance at Work
By David Rock
and
Change Your Questions, Change Your Life
By Marilee Adams
Janet Wright, Certified Executive Coach (PCC) and Padraig Facilitator, says these books are two of her favourite leadership books. She recommends them a lot to coaching clients.
“They’re old, but I still like them. The first because it emphasizes the importance of leaders investing time to develop employees through a coach approach instead of telling and telling,” explains Janet. “The second I like for the same reason; it’s about asking and listening instead of telling and assuming.”
She says that some leaders seek to “fix” people who aren’t doing what they’re supposed to be doing. Frequently, the leaders spent very little time with their employees and asked very few questions.
“In pretty much every instance, it turned out the leader was at least part of the problem, which was unsurprising to me but unwelcome news to the leader.”
Coach’s Book Questions: What assumptions may you have been making about your employees’ behaviour? What might you be missing by not asking good questions? Is it possible that there is something that you don’t know about that is affecting what you’re seeing in your employees’ behaviour? What’s getting in the way of you having more meaningful conversations with your employees?
Dare To Lead: Brave Work. Tough Conversations. Whole Hearts.
By Brené Brown
Jim Simms, Certified Executive Coach (PCC) and Padraig Facilitator, says this book was impactful for him for many reasons.
“It’s particularly powerful for those who have spent years in large organizations, such as the military or a large institution that is hierarchical,” says Jim. “When you’re trying to be what the organization wants you to be instead of embracing your own leadership brand.”
He says one part of the book he often uses as a warm up for coaching clients contrasts an armored leadership style against a more daring leadership that embraces vulnerability. In armored leadership, the leader wants to be in the know instead of sharing the knowledge. They’re collecting stars instead of giving them out.
“It hit home and made me do some re-look at how I wanted to show up authentically as a leader,” says Jim, who says he appreciates how Brown shares her personal struggles and brings science into the discussion as well.
Coach’s Book Questions: How do you lean into vulnerability in your leadership practice? How are you investing in developing the hearts and minds of leaders? How might you embed the value of courage in your culture?
How Women Rise
By Sally Helgesen and Marshall Goldsmith
and
The First 90 Days: Critical Success Strategies for New Leaders at All Levels
By Michael D. Watkins
Eve Gaudet, Certified Executive Coach (PCC) and Padraig Facilitator, says these two books are her go-to books.
“I have used them over and over again with clients,” says Eve. “I have found them to be—and my clients have found both of them to be—very useful.”
How Women Rise offers a very practical way of highlighting 12 different habits that hold women back in their leadership as they grow and develop (things such as overvaluing expertise, the disease to please and focusing on perfectionism) and ways to overcome them.
“I have recommended or sent it to a lot of female clients and it’s good for men to read, too. It’s an opportunity to look at whether we’re doing some of these things and learn how to shift out of those less than useful habits.”
The First 90 Days, says Eve, is a very practical book written for when you are moving into a new position—particularly a senior position—as a leader.
“It overviews where to put your focus of learning and your priorities. So, for example, you don’t go in and start making changes. You start by preparing yourself mentally into the change and understanding the challenges and the onboarding,” explains Eve. “It’s about how to accelerate your learning to deeply understand the organization that you’ve moved into—not just a new boss, but with a new team, stakeholders, everything. By securing early wins, you’re building credibility and vision.”
Coach’s Book Questions: What habits might be holding you back right now? What’s a step you can take to shift that habit? As you transition to a new role in leadership, what are you taking with you? What do you need to leave behind? How can you ensure you make the mental leap into a new position?
Systems Inspired Leadership: How to Tap Collective Wisdom to Navigate Change, Enhance Agility, and Foster Collaboration
By Frank Uit de Weerd and Marita Fridjhon
Katharine Cherewyk, Certified Executive Coach (ACC) and Padraig Facilitator, highly recommends this book about systems-inspired leadership.
“This book focuses on listening and learning from the collective intelligence inherent in any system. It’s full of tools to use with your team to tap into the wisdom of the individuals and provides a road map for leaders to optimize results through collaboration. The main idea is that leadership is shared at all levels of an organization and should take the pressure off a leader to know it all,” says Katharine.
“Tools are shared to help a leader reveal the system to itself so that a team can get curious about what’s really going on between components of that system. For example, what is our excitement for change saying right now? What is our silence saying? What kind of conflict protocol is needed here? This book provides tools for diving into change management by understanding all of the forces that are acting upon a system.”
Katharine says: “When what you’re doing isn’t working, you can double-down and try harder doing the same things, or you could try something different.”
She says this book is worth the read if you want to challenge your assumptions and learn some easy and practical tools you can use with your team immediately.
“One of my favourite takeaways from this book is how I look at conflict or tension in a system. It doesn’t need to get labelled as good or bad — it just means something is trying to happen. This book helps leaders get curious about that question in ways that allow for answers to come from all components of their team.”
If you want to go fast, go alone.
If you want to go far, go together.
~ Ubuntu Saying
Coach’s Book Questions: What if you, as the leader didn’t have to have all the answers? What do you notice about the current relationships within your team? Who is speaking? What is silence trying to say? What’s possible if you could pull more knowledge and leadership from the collective wisdom of your team?
7 Habits of Highly Effective People
By Stephen R. Covey
Ever since Tom Newton, Certified Executive Coach (PCC) and Padraig Facilitator, read this bestseller, he has highly recommended it to everyone from coaching clients to friends and family—including his young adult daughter.
“Even though it’s more than 30 years old, I only read the book about three years ago—after I had become a coach,” confesses Tom. “The reason I’m suggesting this is because so much of it is a cornerstone of what we as coaches do. Habit #5 specifically comes up in every single coaching engagement that I do – seek first to understand and then seek to be understood.”
It’s a great resource that will give you a good foundation going forward, says Tom, because every habit goes really deep.
Coach’s Book Questions: How comfortable are you with silence? Do you listen to understand or to respond? How do you know? Could you use listening to be a more effective leader?
Pro tip: For easy reference and portability, Tom suggests buying the online version.
Five Dysfunctions of a Team: A Leadership Fable
By Patrick Lencioni
Tom says he was introduced to this book before he became an executive coach.
“I’ve read a lot of books, but this was the one I got excited about. I connected with it because it resonated with what I was experiencing in the organization.”
The foundation of trust is being able to have a healthy debate.
“This is a great response to when there’s crickets in the room, and you’re trying to make sense of why nobody is talking,” says Tom. “It means people don’t trust each other or they’re nervous.”
This book helps to identify what’s actually going on in the room, so then you can see why you’re not getting results or commitment. It’s about identifying when destructive conflict is damaging your team (and how to encourage healthy conflict).
“The way it breaks it down into layers makes it possible to identify when things are challenging and when they’re good,” says Tom. “Padraig facilitates an intensive program for leadership teams based on this book and it has resounding success.”
Coach’s Book Questions: What does conflict look like in your workplace? Can you identify productive versus unproductive conflict? How can you build trust with and among your team members?
Rocket Fuel
By Gino Wickman and Mark C Winters
Cathy McConnell, Certified Executive Coach (PCC) and Padraig Facilitator, says Rocket Fuel is an excellent book for leaders who are looking for practical ways to draw on senior executives’ strengths and get things done by separating vision and implementation.
“I’ve recommended this to executives who struggle to find time to develop a vision and a strategy. They get caught in the day-to-day operations, and instead of leaving these to their COO or other operational leaders, they get involved, short-changing their focus on the vision,” says Cathy, noting that it’s also beneficial for operational leaders and entrepreneurs in partnerships.
“I’ve had very positive feedback from those leaders to whom I’ve recommended this book.”
Coach’s Book Questions: How would you describe your vision and the way you are executing on that vision? What’s been getting in the way of effectively leading your organization? How did the description of Visionary versus Integrator impact your thinking about your leadership?
Essentialism
By Greg McKeown
Cathy says a client recommended this second book to her because he uses it to guide all of his decision-making to ensure he is making the best use of his time in his work and personal life.
“I don’t think this is just another book about time management. Anyone who is open to living their life in a more effective way, by choosing the essentials that really matter, would benefit from this book,” says Cathy. “It’s an easy read and includes practical time management tips, so we can do the things that matter and accomplish more within the limited time we have.”
Cathy uses Essentialism as a reference often, to remind herself to manage her time better and that it’s okay to say no. “If it isn’t a clear yes, then it’s a clear no.”
Coach’s Book Questions: What’s getting in the way of you being consistently effective in accomplishing what’s most important? What have you said yes to, and later regretted about that decision? What aspect of your life feels short-changed? What are you missing?
Braving the Wilderness
By Brené Brown
“Our inner critic can be such a bully, it sometimes speaks to us in ways that we would never allow someone to speak to us,” says Geneviève Clément, Certified Executive Coach (ACC) and Padraig Facilitator. “This book gives us permission to stand in our own power and to learn to stand on our own instead of trying to fit in.”
Geneviève says she likes this book because Brené always seems to put words to what we’re feeling, and she presents her research in such a human and accessible way. She recommends it especially for anyone who is experiencing imposter syndrome, anyone who is scared to be themselves and anyone who wants to show up authentically with all the things that make us human.
“I love how she shares her process to find true belonging through authenticity, bravery, trust and vulnerability.”
Coach’s Book Questions: What invitation comes up for you as you read this book? Where can you brave the wilderness in your life? How can you remind yourself to show up authentically in those moments you want to hide?
Birds Of All Feathers
By Michael Bach
Geneviève recommends this book as a good starting point to develop a better understanding of diversity, equality, equity and inclusion.
“More and more I’m being asked about diversity and inclusion in coaching sessions and how to do it well at all levels of organizations,” explains Geneviève. “Michael makes it accessible and creates a safe space for people to reflect on the learning and unlearning that we need to do on our equity, diversity and inclusion journey.”
She stresses that everyone can benefit from this book, even those who feel they’re well versed on all things equity, equality, diversity and inclusion.
“You can always learn more or look at things in different ways,” says Geneviève. “Unfortunately, systemic racism and unconscious bias are still routinely encountered in the world; anyone who works with people needs to look at their responsibility to ensure a safe space for those that they walk alongside with.”
Coach’s Book Questions: As you were reading the book, what came up for you? What is the next step that you can take in your organization to positively impact diversity and inclusion?
