Leading from the Messy Middle

Every organization relies on strong middle leaders. Few prepare them for the realities of the role.

About the Program

Middle leaders carry the hardest job in most organizations: turning strategy into action, keeping teams motivated, influencing across departments, and juggling competing demands. They're balancing expectations from every direction, often without the authority to solve every problem.

This interactive workshop helps leaders better understand the structural pressures of leading from the middle and develop practical strategies to respond with greater clarity, confidence, and influence.

Rather than trying to do more, participants learn how to focus their energy where it has the greatest impact, strengthen relationships across the organization, and make better leadership decisions in complex environments.

Workshop Format

This highly interactive workshop combines facilitated discussion, practical frameworks, reflection, and real workplace scenarios. Participants will work through current leadership challenges, learn from their peers, and leave with actionable strategies they can begin using immediately.

Coaching Add-On

As an additional offering, we provide personalized leadership coaching to further support individual growth and development.

This coaching option is designed to address specific leadership challenges, provide tailored feedback, and help participants implement the skills learned in the program.

To purchase the coaching add-on ($225 + GST per coaching hour), please connect with kaley@reimaginework.ca to arrange after you've purchased your ticket.

Date + Location

  • October 6, 2026

  • KWENCH Co-Working + Culture Club (2031 Store Street, Victoria, BC)

Pricing

  • $165 + GST per ticket

Participants will:

  • Understand why leading from the middle feels uniquely challenging

  • Learn to distinguish between what they can control, influence, and release

  • Recognize how organizational systems shape everyday leadership challenges

  • Strengthen their ability to influence without relying on positional authority

  • Build practical habits that reduce reactivity and increase effectiveness

  • Leave with tools they can apply immediately with their teams

Who This Is For

  • Middle managers

  • Supervisors

  • Team leads

  • Program managers

  • Department managers

  • Leaders responsible for guiding people while balancing organizational priorities

REGISTER NOW!

Meet the Facilitators

  • I have spent more than 15 years as a Human Resources and Program Management generalist with experience in recruitment and selection, terminations, return to work, policy development, and performance management.

    I am a passionate Human Resources Consultant and Career Coach (not a formal therapist with a couch). This gives me an objective, professional, fresh viewpoint to help clients unveil their career aspirations and work through challenges.

    For me, nothing is more rewarding than connecting people to meaningful work and the workplaces they will thrive in. I also love supporting good workplaces as they transition into great ones. Building on my vibrant and diverse background in recreation and youth leadership development, human resources, and career development, I bring high-level energy, a wide range of experience, and laser focus to every workday. I am dedicated to helping people pursue their dreams, to fostering purposeful connections within teams, and to linking organizations with the best candidates for their positions.

    After completing my Bachelor of Arts at the University of Victoria, I went on to train as a Professional Certified Coach (PCC) with the International Coaching Federation and Certified Career Development Practitioner (CCDP). I have been a coach, recruiter, and facilitator for over 50 different local and international organizations.

    I am an active volunteer in my community and enjoy participating in a number of charities. I love running special events such as Soul Sessions and facilitating the mentoring portfolio for the Chartered Professionals in Human Resources (CPHRBC). In my free time you will find me on a Hornby Island beach or somewhere outside with my family.