Service-Disabled Veteran-Owned

THE FIVE CHALLENGES WORKSHOP

Your best people got promoted. Now let’s help them lead.

One working day. Your new managers learn to lead through others, and stop sending problems back up to you.

The starting point for the Five Challenges. In one day, your leaders learn the framework, find where they're stuck, and start fixing it.

A 30-minute call with Rob. You'll leave with a clear next step, whether or not we work together.

On-site or virtual. Teams of 8 to 30.

TWO WAYS TO ATTEND

Bring it to your team, or join an open session

For your team

A private day for 8–30 people, on-site or virtual, built around your organization.

Contact us

For individual leaders

Join an open Five Challenges session alongside leaders from other organizations. Next open session: coming soon.

What the Workshop Is

A working day, not a training class.

Your leaders work on their real situations and leave with a plan they'll use the next morning.

Built on Rob's book, Crossing the Divide, and facilitated by Rob.

Shaindel Marcus, our Pre-Promotion Specialist, works alongside Rob throughout the day, leading the people side.

  • Full-day facilitated working session (6-8 hours)

  • DISC behavioral assessment for each participant

  • Five Challenges framework applied to your team

  • Structured conversations and breakout work

  • A practical action plan built for your organization

  • 30-day follow-up call with Rob

Workshop Agenda

A day built around five named challenges.

Opening

Challenge 1: Skills

DISC debrief and the skills the new role needs: delegating, deciding and setting clear priorities.

Morning

Challenge 2: Relationships

Building trust across teams, so work moves without you refereeing it.

Midday

Challenge 3: Responsibility

Owning results and decisions without micromanaging or burning out.

Afternoon

Challenge 4: Identity

Making the shift from expert to leader, and holding good decisions under pressure.

Closing

Challenge 5: Teams + Action Plan

A team that carries the work instead of sending it back up, plus a 30-day action plan.

What participants say

Practical insight. Real voices from the room.

"There is no person individually that cannot attend this. He taught us the importance of leadership, mentorship and clarity. The way he lets you know how important your leadership is - it is going to be the basis of your business."

Gigi McMillan

Purple Runway & Kamisole Style Consultancy

"We learned things about each other as a team that will make us better. The community will benefit from this."

Juanita Shanks

CEO, Fail Safe ERA

Start with one day. Your team, or an open session.

On-site or virtual, for 8 to 30 people. Start with a short call about your team.

A 30-minute call with Rob. You'll leave with a clear next step, whether or not we work together.

Strategy, operations and leadership for organizations that are outgrowing how they run.

A Service-Disabled Veteran-Owned Small Business

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