BOARDS, ORGS & TEAMS

Strategic Planning, Senior Team Workshops, and Board Training Sessions.

For organizations, leaders, and boards navigating change.

  • Rolling out your organization’s next big change is difficult. Why go it alone? 

  • With strategic planning and training sessions, I work with you to strategize, game out, and execute organizational change. (While helping you energize your team, engage your stakeholders, motivate your board, keep everyone on the same page, and hold on to your sanity in the process.)

TEAM WORKSHOPS AND TRAINING

Uniting your team around a central aim can be messy.

Everyone has opinions. There are critics in the room. And the person tasked with leading feels the weight of the initiative on their shoulders.

These high-stakes, low-structure scenarios result in waste-of-time meetings, exhausting days-long sessions, and rollouts that never get rolled out. (Creating friction and frustration all around.)

I had to watch it happen to my clients’ organizations time and time again. Now, I step in and help.

  • 1. Strategic Planning

    Together, we’ll lead your team through a multi-month, formal strategic planning process, a single-morning offsite, and anything in between.

    Tell me more

  • 2. Training for Boards

    From board “101” governance training and beyond, I can help you develop and lead a meaningful session that produces real results and change. 

    Workshop details

  • 3. Workshops for Teams

    Book a team workshop and unite around culturally relevant topics like inclusion, psychological safety and accountability, and workspace culture.

    Workshop details

Led by Jonathan Bennett

FOUNDER, DIRECTOR, ADVISOR & STRATEGIST
If we haven’t met yet, hi! I’m Jonathan. 

I spent a decade building a management consulting company that served over 200 organizations nationwide and became a proud B Corp. Then, in 2021, I sold up and moved on to my next adventure.

Now, my clients are not the organizations—but the leaders who run them. My goal is clear: stand with fellow leaders 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. 

“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.”  — Jennifer Churchill, Chief Executive Officer, Empowered Kids Ontario

Trusted by organizations like:

Strategic Planning

I’ve led over 100 strategic planning processes.

The old saying is true…if you plan the battle, they won’t battle the plan.

Regardless if you’re embarking on a multi-month, formal strategic planning process (complete with focus groups, surveys, and a retreat) or a single-morning offsite to push your thinking, I can help with:

  • Probing questions & deep listening

  • Expert facilitation

  • Environmental scans

  • Focus groups and surveys

  • Retreats and workshops

  • Strategy development and writing

  • Operational planning workshops and KPI development

Together, we’ll create the conditions for clear,
evidence-based decision-making, and buy-in. And you’ll leave a legacy of profound impact.

Training for Boards

A Chartered Director, with more than 20 years serving on boards, I’ve helped boards of all shapes and sizes across Canada with whatever is most pressing. From Governance “101” to customized sessions, as a seasoned strategic facilitator, I work with management teams and boards to:

  • Set goals and develop a focussed agenda

  • Create and deploy pre-meeting surveys

  • Bring the latest in governance thinking to your board
    (fiduciary, strategic, generative, relational governance)

  • Lead experiential and customized sessions that address
    your board’s real needs

  • Ensuring the session delivers meaningful results

Workshops for Teams

My workshops focus on leadership, inclusion, and creating safe, collaborative workspaces. Topics include:

  • The Art of Delegating Like a Leader (Not a Manager)

  • Workplace Psychological Safety and Accountability

  • Building Trusting Relationships at Work

  • Governance 101” Training for Non-Profit Boards

  • Achieving Strategic Clarity at Your Organization

    DOWNLOAD WORKSHOPS ONE-SHEET (PDF)

Let’s motivate your team and make change happen—together.

Book an introductory call to discuss how I can support you as you lead your team.

If you’re here, you’re ready.

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!