1:1 ADVISORY SESSIONS FOR ORGANIZATIONAL LEADERS
Empathetic advice and strategic guidance for leaders. Anchored in decades of organizational experience.
And tailored to the realities of your day-to-day.
✔ As an experienced CEO turned advisor and strategist, I get to know you—the person and the leader.
✔ Then, give you the balance of support and pragmatic guidance only someone who’s been there can give.
Not to be dramatic, but it’s lonely at the top.
(Especially when you’re new to it. Or the landscape has changed. Or you’re the first person like you to claim that seat.)
✔ You often face challenges you’ve never seen before or are in situations made up almost entirely of grey areas.
✔ You have no clear description or manual for what to do.
✔ The day-to-day needs of the board, your staff, key stakeholders, and your loved ones never stop coming.
✔ You’re under constant pressure as everyone watches to see what you can do.
✔ And you’re never sure who to turn to for guidance.
THE IRONY ISN’T LOST:
Thinking big-picture is more important than ever.
But it’s also harder than ever.
(This is where I come in.)
IF WE HAVEN’T MET, I’M JONATHAN BENNETT
Leaders turn to me when they’re stuck in their heads or getting lost in the day-to-day.
My goal is to 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 a way through.
I’m here to give you what you need at any given moment, whether that’s accountability, a gut check, a needed nudge, the unvarnished truth, a new idea, the space to plan, a problem reframed, a cautionary tale, the permission to change, or simply someone who gets you and will listen.
THIS IS WHERE LISTENING AND EMPATHY MEET ACTIONABLE BUSINESS ADVICE
Tell me what feels heavy. I’ll help you figure out why.
(And what to do about it.)
With a unique combination of deep listening, experience-based business advice, and leadership development techniques, I won’t just help you understand your work issues, I’ll help you solve them.
Here’s how it works
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STEP 1
Connect with me
Reach out and book a complimentary intro call with me, so we can get to know each other and make sure we’re a fit.
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STEP 2
Make a plan
Together, we’ll identify the key issues, projects, of opportunities you’d like my support on and decide on the best way forward.
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STEP 3
Do the work
This isn’t paint-by-numbers. For the breakthroughs you want, we dig deep. We’ll focus on change, results and outcomes. Together.
“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.” — Rhonda Barnet, Chief Executive Officer
Executive Counsel or Professional Mentorship
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1. Trusted advice for experienced execs
For senior leaders navigating complex issues with lots of ambiguity, high-stakes decisions, and potential paths forward—but no playbook to follow.
My trusted advisory services will help you:
✔ Manage crises or complex, shifting situations
✔ Drive performance and results
✔ Build psychologically safe and accountable teams and workplace cultures
✔ Navigate management change and ambiguity
✔ Scale your business or prepare for acquisition
✔ Prepare for difficult conversations with colleagues, stakeholders, government
✔ Improve governance and build a better board
✔ Manage HR, succession planning, and restructuring
INVESTMENT: Packages starting at $3-6k
TIMELINE: 3-6 Months
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2. Professional mentorship for newer 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 as a result.
Through professional mentorship, I can help you:
✔ Hone delegation, decision-making, performance- and time-management skills
✔ Set goals and make strategies for personal growth
✔ Plan, create, and implement new projects or ventures
✔ Develop your personal leadership brand and communications skills
✔ Practice having hard conversations that deliver the results you need
INVESTMENT: Packages starting at $3k
TIMELINE: 3-6 Months
Reconnect with your purpose and
carve out time to think big-picture.
OUR SESSIONS WILL GIVE YOU DEDICATED TIME AND MENTAL SPACE FOR:
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Personal Growth
Spark personal goal setting and set strategies for your growth as a leader.
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Professional Development
Learn to delegate, manage your time, and motivate and inspire your team.
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Big-Picture Planning
Think clearly and calmly as you plan and implement new initiatives.
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Debriefing & Support
Let off steam and vent within a safe, constructive, confidential space.
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Preparation & Practice
Prepare for and practice difficult conversations that must be had.
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Your Leadership Brand
Hone your personal leadership brand and communications skills.
Like executive coaching,
only nothing like executive coaching.
Coaches are great (they ask the best questions)—but they stay on the sidelines. I use coaching tools. I also jump in with sound advice, gamed-out scenarios, trustworthy direction, decision-making support, and the kind of guidance only someone who’s been where you are can offer. Yes, I can help with that budget, the marketing campaign, that HR issue, your own CV…you name it.
I’ll walk with you through complex, ambiguous, and novel leadership challenges.
Together, we’ll come up with elegant solutions to anything that comes across your desk or keeps you up and night, like:
✔ 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…
FAQs
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Yes. We sign an agreement that outlines all the terms and conditions around confidentiality and our shared obligations.
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You can stop our sessions anytime without penalty if unforeseen circumstances occur. I also allow last minute re-scheduling—because I know you are busy and life happens.
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On average, my clients invest between $3-12K over a three- to six-month period. Everyone is different. We design a package that works for you before we begin. Some start with a block of sessions. Others go on retainer. There are no surprises. Ever.
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Yes! I facilitate strategic planning sessions, lead team training and workshops, offer annual retainers, and host monthly group sessions. Reach out—let’s talk.
Lead with confidence, clarity, and compassion.
It's hard to be a sturdy leader when you’re overwhelmed and in the weeds.
With me, you will:
✔ Get immediate advice and elegant solutions for the complex leadership issues that make it feel like “the house is on fire.”
✔ Carve out space to reflect, dig deeper, and get to the core issues that keep coming up at work.
✔ Set clear priorities, think big-picture, and move forward meaningfully.
IF YOU’RE HERE, YOU’RE READY.
Still have questions? Reach out!
You can DM me on LinkedIn, or email me here
I believe in making educated decisions. If you need more information, please reach out.