Leaders | Executives | Boards | Founders
Brave ideas.
Deep listening.
Breakthrough advice.
Ethical, empathetic support trusted by 200+ leaders.
Navigate complexity, ambiguity, or change
Grow your social purpose, business, and career
Better your relationships, teams, and communities
“Jonathan operates from a place of decency. He is thoughtful, helpful, and once he is invested in your success, he’s all in. I don’t know how I would have navigated my path without him.” — Hon. Maryam Monsef, CEO, Onward | Former Minister of Women and Gender Equality, Govt. of Canada
Experienced.
“My clients—individuals, teams, boards—span industries and time zones. But they are all driven by a common, yet deep, hunger—to evolve as leaders, excel in their roles, create meaningful impact, contribute to their communities, and ultimately thrive.” — Jonathan
One-One and Group Coaching (3 month, 6 month, 1 year)
Trusted Advisory Services and Annual Retainers
Keynotes, Team Facilitation, and Strategy Sessions
Governance Supports, Team Trainings, and Workshops
Join these progressive leaders who believe better is possible.
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Rhonda Barnet, Chief Executive Officer, Palette Skills
“Working with Jonathan? It’s like having a stronger inner voice sitting on your shoulder to guide you through difficult situations faster, better, stronger and with more confidence. He offers candour and the firm but gentle push needed to dig deeper into issues and ways of thinking or approaching difficult situations and conversations.”
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Payam Pakravan, Co-CEO, Inner City Health Associates
"Jonathan is a great listener and highly effective executive coach. He creates a positive, welcoming space that felt perfectly suited to where I'm at in my journey. He probes rigorously but respectfully, on areas that require further clarity, and helps ensure that reflection is followed by action. He is warm, genuine, and insightful. He takes the time to find out where you're at and what sort of exploration would be most helpful. He draws on his knowledge and experience carefully and appropriately to provide examples, options and comparators that help enrich your own process of self-reflection."
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Kathryn Henderson, Chief Engagement Officer, YW Boston
“It was easy to work with Jonathan. He is an attentive listener and asks questions that really help to clarify. While focused on career goals, he took time to understand broader themes, priorities, and challenges in my life that could affect what we were discussing career-wise. After spiralling about if/when to seek a new role, working with Jonathan finally interrupted that spiral and got me moving along a path forward.”
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Jennifer Ballentine, CEO, Coalition for Compassionate Care of California
“Jonathan was extremely skilled in cutting through a lot of extraneous context and confounding detail and isolating the core issue and then helping me think it through in my own terms. He offered affirmation and pushback in appropriate measures -- never pushing a conclusion but helping me get to it on my own. He taught me techniques for corralling the chaos and keeping priorities straight. It was exactly what I needed to get my feet under me in a new executive position. 10/10.”
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Roslynn Baird, Executive Director, Indigenous Diabetes Health Circle
Coaching and Consulting: "Coaching was something that I first thought was just something else I had to fit into my already busy schedule. However, it quickly become a session that I looked forward to. I can highly recommend the coaching provided by Jonathan Bennett. He is an amazing listener and has provided me with suggestions to improve my management skills as well as my interaction with the board of directors.."
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Misha Munim, Lawyer | Equity, Diversity, Inclusion Consultant
“Jonathan's leadership coaching has been invaluable to me. As I became a new business owner, his sound, trustworthy advice and encouraging messaging throughout my journey served as cornerstones to my company's growth. I'm so grateful to have had Jonathan in my corner; his expertise spans across multiple areas and he's great at understanding people. I highly recommend Jonathan as a leadership coach: he is wise, intuitive, and always helpful.”
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Cynthia Weaver, COO, Kinark
“The comfortable nature of Jonathan’s personality and questioning offered different perspectives and stretched my thinking. His use of social media helped me to better represent myself as a leader. He has good knowledge and insights into NFP work, leadership skills and governance. I would describe working with Jonathan as professional, confidential, insightful, and energizing.”
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Janet Brown, Customer Care and Engagement Leader, NYC
“[Jonathan’s] calming nature and insights allowed me to open up and see what was causing anxiety within me. He drew on the strengths that were already present…to plan a strategy to achieve my goal. Self-doubt, anger, and fear can overwhelm a person. However, Jonathan helped me to see that my ability to show empathy despite how I was feeling was the right course to take. I was then able to handle the situation with greater clarity.”
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Paul Hurley, CEO, Engage Engineering
Coaching and Strategy: “Drawing on his personal experience as a business owner, along with his uncanny ability to listen and truly understand the heart of the issue, Jonathan was able to achieve in a few coaching sessions what would have taken us many, many months.”
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Dr Helen Scott, Assistant Professor, Dalla Lana School of Public Health, University of Toronto; Consultant, PMNCH, World Health Organization
“When I was launching my career as a not-for-profit founder and executive, Jonathan was instrumental in providing pragmatic and practical advice, grounded in his extensive experience. His approach was simultaneously supportive of me as a leader, while also guiding me to build a successful, sustainable organization.”
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Kristy Hook, Administrative Principal, Lett Architects, B Corp.
“Jonathan was able to ask the questions I had not yet thought of to ask myself. Exploring and discarding options is a helpful process to follow when deciding the correct way forward. Jonathan has a unique ability of cutting through the noise and distraction to get to the core of the issue. His perspectives were invaluable.”
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Kate Edwards, CEO, Access Copyright
Group Coaching: “I would tell those considering coaching with Jonathan to come prepared to explore opportunities they might not have known existed, all within a supportive, safe environment.”
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Laura Click, Founder and CEO, Blue Kite, Nashville, TN
“Working with Jonathan is like having an extremely wise, empathetic friend who can guide you through the ups and downs of entrepreneurship. He's kind and validating, while also offering practical, actionable advice that you can implement right away. I always left our calls with an action plan that gave me confidence on how to move forward. His support and guidance was exactly what I needed in this season to help me grow my business.”
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Tosh Sondh, Director, Information Technology, Palette Skills
Workshops and Group Coaching: “Even though I knew what Jonathan was doing, the way he conducted the one-on-one chat at the end and by the questions he asked, made me feel really comfortable. I found it very easy to talk to him, almost forgetting that others were watching me. It was like talking to an old friend. Personally, I would like more one-on-one coaching sessions like this.”
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Danielle Belair, Executive Director, Community Care
Group Coaching: “Coaching was a great opportunity, and gave me the time to express myself, all the frustrations, dilemmas, successes, goals. I felt understood somehow. It was a great experience.”
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Cathy Mann and Anne LeMesurier, Fundraising Lab
“Jonathan, your gentleness allowed us to bring our full and vulnerable selves to coaching. Your straight-forward approach kept us pragmatically on track—it was the beginning of an important change.”
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Patrick Rainville, CEO, and Consultant at The Foot Health Network
“I enjoyed the fact that he was able to feel the pulse of the group and was able to extract what was needed at that moment in time. I benefited by having a completed session with a clear direction of where the group was going. I would tell someone looking to work with Jonathan to keep an open mind and be prepared to change for the better.“
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Heather Norris, CEO, Ottawa Network for Education
"Jonathan is easy to talk to. He provides valuable insight, advice and helps me lead effectively through difficult situations. He's a great listener, asks the difficult but necessary questions and provides focused feedback. I laugh and cry with Jonathan and at the end of the day his input and guidance builds my capacity and confidence. I have much respect for Jonathan and his approach to executive leadership.”
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Kim Blackwell, Artistic Director, 4th Line Theatre
“I went into my time with Jonathan feeling very overwhelmed by leading my organization. Jonathan was able to let me know I was not alone in what I was struggling with. He helped me to identify what I needed, gave me tools, and helped me to break free from old patterns of thinking and move forward in a very meaningful way. Working with Jonathan was both effortless and tough. Jonathan has an easy and supportive manner. And along with that, I was required to put in the hard work towards my own success.”
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Terri Forman, Executive Director, First Graduate, California
Group Coaching: “The coaching was very helpful--and easy (meaning, it was not hard to see and apply the thought process), so it was coaching with a light touch that felt empowering. Coaching with Jonathan is like having a very wise friend or colleague that you want to hear more from. There are no "shoulds" or "coulds"; only the best kind of questions, like "what if?" and prompts like "tell me more".”
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David Leonard, CEO, Writers' Trust of Canada
“Jonathan's approach is warm, sensible, and filled with valuable insights. Having someone who has experienced many scenarios himself, but who can also game out situations live in real time, was tremendously helpful. Having Jonathan as a coach is like a trusted friend. He's not afraid to challenge you on areas where you need work, but he's also very good at validating areas where you are strong. His broad perspective and solutions-focused approach is very versatile and was immeasurably helpful.”
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Nancy Johnston, Executive Director, Cornerstone Family Violence Prevention Centre
“I will be forever grateful for the transformative impact Jonathan has made on my leadership journey. One of Jonathan’s unique gifts is his ability to listen deeply and listen for meaning. Jonathan asked me the tough questions in a way that created a welcoming and safe space for me to dig a bit deeper. As an Executive Director, I spend most of my time looking outward. This vantage point comes with the job. What I realized through coaching is that I need to balance looking outward and looking inward. I will continue to turn to Jonathan for coaching and know that I can rely on his candid, caring and authentic approach.”
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Jesse Maher, Director of Marketing and Strategic Partnerships, Chicago, IL
“Jonathan was immensely helpful in getting my mindset in the right place as well as working on my strategic narrative. I landed the job…. I know that his insight helped tremendously! I went in with more confidence than ever because Jonathan prepared me to think differently and provided insight unique to my specific situation. For this, I am grateful and highly recommend speaking to him for executive coaching.”
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Jeanny Scantlebury, Vice President, Surrey Place
“Jonathan's breadth of knowledge and experience enabled him to provide me with coaching across a wide variety of areas, from running engaging meetings, to working with Indigenous partners, even setting up a LinkedIn personal brand.”
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Meaghan Macdonald, Executive Director (former), Habitat for Humanity Northumberland
“Being coached by Jonathan was an empowering and reflective experience. Jonathan is supportive but challenges you to think differently. He listens intently and allows you to work your way through an issue with his careful and kind guidance.”
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Nicole Wood, Executive Director, Rebound
“Jonathan helped me to approach my challenges in a way that worked to my strengths - never really providing the answer, but always helping guide me along my path to finding a way to approach the challenge that would work for me. At the end of every conversation I felt renewed and invigorated, ready to go back and look at what I was facing through a different lens.”
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Scott Pepin, CEO, Five Counties
Workshop: “The flow of the event was perfect. It didn't feel rushed or drawn out. Jonathan wasn't only a facilitator he provided great input and guidance that helped move the discussion forward. Jonathan was professional, responsive and easy to work with. 10/10.”
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Dawn McColl, Assistant Executive Director, VCCS
Group Coaching: “I liked that the coaching techniques provided an opportunity and a space for individuals to explore the challenges they faced at a deeper level…it gave us tools to try and supported us to work through the process. Also all participants are encouraged to refrain from coaching or "fixing" which I learned that many of us spend a lot of time doing!”
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Mary Ellen French, Board Director, Entrepreneur
Governance Training: “Good pace, information in manageable chunks and well explained. I particularly appreciate governance examples that help to clarify points of information. Jonathan’s presentation and questions gave me lots to think about both in terms of reflection and thinking forward. I would tell others that Jonathan is very knowledgeable as well as relatable (eg examples from his own experience of being a Director on a Board). 10/10.”
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Chris Farley Ratcliffe, Manager, Specialty Support, Royal College of Physicians and Surgeons of Canada
“Jonathan helped me discover and recognize that I was ready for new challenges and opportunities….this has given me greater focus in my daily work….I like what Jonathan said in our first meeting about what he does. He described it as "work therapy" and I think that description is what I would use when explaining the experience to others.“
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Louise Campbell, Administrator, Trent University
Governance Training: “Jonathan is approachable and easy to ask questions of. I benefited by now having an advanced understanding of my responsibilities on the governance board. I would tell others as I did a few times already since this session that Jonathan is easy to work with, has an advanced knowledge of leading boards and that their time and money would be well spent.”
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Holly Petersen, Founder
“Collaborating with Jonathan has significantly contributed to both my personal and professional growth. He generously shared his wealth of knowledge, encouraging me to step out of my comfort zone. Under his guidance, I made strides in enhancing my networking skills, consistently publishing my thoughts on a monthly basis, and successfully dispelling unproductive narratives I had previously held onto.”
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Galen Eagle, Communications Leader
Board Facilitation: “Jonathan kept us on topic and led a thorough visioning exercise that brought us naturally to some short, medium and long-term objectives we could all agree upon, all within a single morning session. He helped create a safe environment for thoughtful discussions and facilitated a process that flowed easily from one topic to the next.”
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Rose Goodall, Marketing Leader, Part Time CFO Services
Governance Training: “Jonathan is someone who takes the time to connect with each individual and understand the workings of your organization or group. Because of this, he is good at identifying processes that are being done well and those that have issues and need to be addressed.”
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Rebecca Finley-Schidlowsky, ICD.D, Management Consultant, Finley & Associates
“Jonathan does a great job at meeting you "where you are at" during each coaching call. He builds rapport quickly and you can tell he really cares about his clients. He has such a wealth of knowledge; I really enjoyed our sessions. I’d describe coaching with Jonathan as awesome experience that is a jolt of energy and clarity to your thinking. Jonathan provides a great external perspective that challenges and invigorates you to want to do more and be better.”
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Jerad Spry, General Manager, Ontario Line Clearing
"Jonathan gives great advice--at times when I felt like I was just ranting he was able to pick apart what the actual issues were and then helped me work through them. He has a calming presence and encouraged me to really evaluate how I was feeling and how to come to a solution. I would encourage anyone who is struggling in a leadership role to work with him to find out what you need most to succeed and build a game plan of how to get there."