Part of the Strategic Leadership program

LEADERSHIP SCENARIO

The Reorg

3-5 day simulationAdvanced

DataFlow is pivoting to enterprise. Your VP wants you to restructure your org to free up headcount — and he wants a proposal by his deadline. You manage three engineering managers. None of them know yet. The rumor mill is already turning.

From
Jordan Ellis
Subject
Enterprise push - your org

Quick one. The enterprise push is real and it's moving fast. I need your org to restructure to support it — we need to free up headcount and align your teams to the new priorities. I'm not going to tell you what shape this takes. You know your people and your teams better than I do. But I need a proposal on my desk by the deadline. Think about it. What does your org need to look like to support enterprise? What's working, what's not, and what needs to change?

THE SITUATION

Every option has a human cost

The enterprise pivot is real and it’s moving fast. Jordan Ellis, your VP, has given you autonomy — and a deadline. He wants a restructuring proposal, but the shape is yours to decide.

Nina Petrov runs Product Engineering — politically astute, execution-focused, already angling for expanded scope. Raj Mehta leads Platform — quietly respected, won’t advocate for himself, but his team does foundational work nobody else understands.

Amara Osei manages Developer Experience — sharp, still growing into her first management role, protective of a team whose mission could easily be absorbed. The hallway chatter is already ahead of you.

Every restructuring option benefits someone and costs someone else. The question isn’t whether someone gets less than they wanted — it’s whether you can make the call and defend it.

WHAT YOU'LL PRACTICE

4 leadership skills, one scenario

Restructuring with competing stakeholder needs

Three managers, three valid perspectives, and a business need that can’t accommodate all of them equally.

Consulting without abdicating the decision

You need input from the people affected. But asking everyone’s opinion isn’t the same as making a decision.

Distinguishing political maneuvering from legitimate concerns

Some feedback is about what’s best for the org. Some is about what’s best for the person giving it. Learn to tell the difference.

Making a decision you can defend

When someone gets less than they wanted, they’ll ask why. Your reasoning needs to hold up under scrutiny.

HOW IT WORKS

From inbox to insight

1

Receive Jordan’s directive

A restructuring mandate with autonomy and a deadline. The shape is yours to decide.

2

Reply with your approach

Your real email, your real words. How you respond signals whether you’ll consult or command.

3

Nina, Raj, and Amara respond

Each manager reacts based on what you share, when you share it, and whether they feel heard or managed.

4

Navigate competing interests

Every conversation narrows your options. Promises made to one person constrain what you can offer another.

5

See the outcome

Your proposal lands — and everyone learns what you chose and who you chose it for.

6

Get your debrief

A personalized coaching assessment: how you balanced consultation with decisiveness, and what your process reveals.

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Three managers are about to hear the news

You can consult or you can command. You can be transparent or strategic. But by the deadline, you need a proposal — and everyone will know what you chose and who you chose it for.

Start The Reorg

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