ABOUT CLEARLYTHEN
Empathetic Support and
Experience-Based Strategy.
For emerging and experienced organizational leaders dedicated to earning
their titles—and rising to the occasion.
LIKE EXECUTIVE COACHING.
ONLY NOTHING LIKE EXECUTIVE COACHING.
You don’t need a cheerleader.
You need an empathetic ear, reminders to think big-picture, and “do this next” advice.
I go deep by listening, pulling at threads and asking questions (traditional coaching approaches). And back that up with real governance experience, financial acumen, and tangible advice (not so traditional in the coaching space).
Leadership is isolating.
I know because I’ve been there.
MY PROFESSIONAL BACKGROUND
1995 - 2011
Executive Leadership
I started my career in book publishing, and at nights I wrote fiction. Published 7 books! Sat on my first Board. Started a family. During the days, I managed people, worked my way up, until I held an executive role at a large hospital—as the Chief Communications Officer, and Director of Planning. I managed people and budgets, was a part of a senior team that led a huge capital project (built a new hospital) and then an operational turnaround. Learned a ton. Was exhausted.
2011- 2021
Entrepreneurship
I struck out on my own, founding a management consulting firm, Laridae. The company grew. We became a B Corp and served hundreds of organizations across Canada. Strategic planning, branding, management and leadership training, governance. I sat on more Boards. Became a Chartered Director. So, 10 years in, and things were great. Except I’d become… unfulfilled. I was ready for a change. So, sold the company to an amazing colleague in a management buyout, sold the building, and I struck out on my next adventure.
2021 - Now
Advisory and Strategy
I launched ClearlyThen—an advisory and strategy practice. Now in the “portfolio phase” of my career, I sit on corporate boards, guest on podcasts, work one-on-one with leaders across North America—and with a network of other consultants—I lead teams and boards in strategy, workshops and training. Since going all in on this, I’ve honed my approach, blurring the lines between advisor, mentor, coach, and strategist and finding my lane. I’ve learned that bringing my whole self to whatever I’m at, is my strength. I’ve simply embraced the “outside the lines” approach that my clients love me for. And it’s worked—for me and the 200+ clients I’ve helped.
IF WE HAVEN’T MET YET, I’M JONATHAN BENNETT
Organizational leaders come to me for understanding, guidance, and an outside perspective. My mission is to help purpose-driven leaders go from being overwhelmed and stuck to thriving—quickly.
Wherever you’re at, I’ll bring 25 years of creativity and leadership success to your situation. You’ll experience humour and empathy and see firsthand why I am known for my deep-listening and breakthrough questions that create insights and new strategies.
Trusted by organizations like:
Together, we’ll come up with elegant solutions to the problems that come across your desk—or keep you up at night.
From HR to crisis comms to safe space to just rant, I’m here. To give you what you need, at any given moment.
✔ HR Issues
✔ GR and PR
✔ Board and stakeholder relations
✔ Organizational structure
✔ Professional growth
✔ Succession planning
✔ Personal brand development
✔ Mentoring & leadership development
✔ Board Governance 101 training
✔ Strategic planning
✔ KPIs & performance management
✔ Custom workshops, and more…
Listen deeply. Answer honestly. Hold yourself accountable.
These values guide me in life, business, and leadership.
Presence
Listening deeply can be the difference between the status quo and a big breakthrough. I listen with intention and empathy, seeking to understand the unspoken, the hesitant, and the heartfelt.
Honesty
I offer unvarnished truths, even when it’s hard. My role is to support, inspire, and sometimes challenge you to confront what needs to be faced in service of your growth and purpose.
Accountability
We have deep accountability to ourselves, one another, our organizations, our communities, and the world. That means I am accountable to you. It also means I’m willing to create accountability for you.
Social Justice
I am a feminist who understands intersectionality, yet I am always learning. Part of my work involves helping leaders identify where biases (internal or external) are coming into play—and calling them out.
Reconciliation
For me, Indigenous reconciliation in Canada is personal, and it means taking action in a good way. Over the past 20 years, I’ve worked alongside, learned from, and grown because of my many relationships with First Nations colleagues.
Inclusivity
I am committed to being an ally to the disabled, neurodiverse, racialized, and LGBTQ+ communities. Because of my own life experiences and family, I believe autistic and trans rights are human rights, and everyone has the right to a safe, full, and healthy existence.
“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 an advisor and mentor: he is wise, intuitive, and always helpful.”
— Misha Munim, Lawyer | Equity, Diversity, Inclusion Consultant
Lead with confidence and compassion.
My goal is clear: stand in your corner and share the calm confidence and optimistic perspective I’ve gained from having been through it before—and knowing there is always a way through.
I CAN HELP YOU GET THERE WITH:
Professional Mentorship
FOR NEW LEADERS
For emerging and mid-career leaders who are confident in their fields but new to leadership. And experiencing self-doubt, imposter syndrome, and overwhelm.
Trusted
Counsel
FOR EXPERIENCED EXECS
For senior leaders navigating complex issues with lots of ambiguity,
high-stakes decisions, and potential paths forward—but no easy
playbook to follow.
Strategy
& Planning
FOR TEAMS & BOARDS
For organizations and leaders
who are planning for, rolling out, and navigating change. And want support to make it impactful—
and make sure it sticks.
Team Training & Workshops
Virtual and in-person. These sessions are the quickest and most effective way to introduce new perspectives, bring everyone together, and move forward with meaning. I’m available for workshops, retreats, and team training sessions.
BUT WHAT’S IT REALLY LIKE?
Hear Jonathan In Action
Experience the essence of the advisory, mentorship and strategy work I do while gaining practical insight you can apply to your leadership journey by listening in on six actual conversations I’ve had with real (and fully consenting) leaders. Listen anywhere!
Our Bios.
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Jonathan Bennett, C.Dir., FNI. Dir., provides sought-after strategic counsel to CEOs, executive teams, politicians, and boards of directors across Canada. With experience in urban, rural, remote, and First Nations communities, Jonathan’s expertise is in social purpose business strategy, governance, branding, change, and communications.
Prior, Jonathan Bennett founded Laridae, a leading management consulting and training firm in its space. As its first CEO, Jonathan grew Laridae from a start up to a leading firm in its space—Laridae is a proud B Corp. He sold the company in 2021.
Jonathan is a Special Graduate Faculty in Trent University’s M.A. Sustainability Studies Graduate Program. An experienced director, he currently serves on two privately held, corporate boards: Accerta (ON) and OwlCrate (BC), and is Co-Chair of a local non-profit, Peterborough Community Health Centre. He is a member of the Institute of Corporate Directors and is a Chartered Director (C.Dir.) and holds a First Nations Director designation (FNI.Dir.) from the First Nations University of Canada. Previously, he has served terms on the Boards of CashCo Financial (AB), and as Chair of Ontario Telemedicine Network (OTN) and the Kawartha Haliburton CAS, and served two terms as a Board Director for the Writers' Trust of Canada.
A widely published and award-winning writer, Jonathan is the author of seven books. Born in Vancouver, grew up in Sydney, Australia, Jonathan lives with his family in Peterborough, Ontario, Canada. -
Catherine is a Remote Executive Assistant providing high-level support to executives and business leaders.
Currently working alongside Jonathan, Catherine helps streamline scheduling, manage priorities, and improve workflow efficiency, allowing him to focus on key business goals. She takes a proactive approach, anticipating needs and handling tasks with precision and professionalism. With a passion for problem-solving and organization, Catherine brings clarity and structure to busy professionals' lives.
Connect with Catherine on LinkedIn: linkedin.com/in/catpaul23