"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."

“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.”

“Jonathan's expertise in governance...was evident and incredibly valuable, helping to guide discussions with clarity and insight. His communication in the lead-up to our board retreat was clear, timely, and thorough, which made preparation smooth and efficient. Jonathan also has a remarkable ability to ensure everyone feels included and heard, fostering a genuinely collaborative environment. Overall, working with Jonathan was a standout experience thanks to his thoughtful and inclusive approach."

"As a young, racialized, woman in leadership, Jonathan and I explored our different privilege and marginalization early on - with Jonathan being open and honest and recognizing these differences. It was re-assuring to have this conversation... Jonathan's coaching method felt a lot like mentorship...I particularly appreciated his method of asking questions and encouraging me to explore the answers instead of just "telling me" the answers. His experience and expertise were greatly appreciated as he was also able to push me to think bigger and faster on some decisions than I would have if left on my own. Overall, it was wonderful working with Jonathan!"

“Jonathan's leadership support 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.”

“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.”

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.."

“[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.”

“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.”

“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.”

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.”

“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.”

“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.”

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.”

“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.”

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.”

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.”

“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.”

“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.“

"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.”

“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.”

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".”

“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.”

“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.”

“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.”

“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.”

“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.”

“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.”

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.”

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!”

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.”

“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.“

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.”

“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.”

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.”

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.”

“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.”

"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."

“I really appreciated my work with Jonathan. He provided me with a very knowledgeable outside perspective which in turn gave me insight into how to handle a variety of situations. He had a way of giving me the tools, but I had to do the work. I always left the call feeling inspired.”

“I was skeptical. I was busy, overwhelmed in starting a new role, and couldn’t see how this one extra thing would be helpful. However, my time with Jonathan was incredibly valuable. He listened with no judgment, guided me as I reflected on the challenges I was facing, and then pushed me to step out of my comfort zone and try new techniques. Each time I was amazed at how well the team responded. Because of his support and suggestions, I was able to bring together a new team and gain a better understanding of the best way to support each unique member. Thank you!”

When I understood how important it was for the Leadership Council to have a conversation about its purpose, membership, and role in the association, I knew we would need the right person to lead this work. There was no question in my mind that you have the skills, knowledge, and creativity to do this. You proved me right. The exercises and discussion moved us toward decisions that are…essential to the association’s growth, responsiveness to our members, and its impact. Thank you for bringing your talents...I’m grateful for your contribution.” 

“I had the privilege of working with Jonathan as a facilitator and executive coach. He listens deeply and offers insightful, values-driven advice tailored to each client’s unique context. Jonathan is a strategic sounding board and trusted advisor, adept at navigating complex leadership challenges. He seamlessly balances listening, coaching, and offering precise strategic insights—always asking the deeper questions that uncover what truly matters. Leaders who partner with him gain clarity, purpose, and a renewed commitment to living their values at work.”