Dear Calcy: Getting Managers on Board Before Plans Fall Flat

Dear Calcy,

Our team puts a lot of time and effort into building thoughtful, impactful comp plans for our sellers, but we’re finding that when it comes to rolling them out, there’s a breakdown at the managerial level – some misinterpret key mechanics while others don’t put much effort into reinforcing goals and expectations to motivate the right outcomes.

How should we rethink getting managers aligned from the beginning to improve plan communication and performance?

Sincerely,
Don’t Blame the Messenger

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Dear Don’t Blame the Messenger,

You’re right to raise such a critical (and often overlooked) issue.

Even the best-designed plan falls flat if it’s poorly communicated. While it’s tempting to keep the focus squarely on sellers, managers are your enforcers, so getting them aligned and on board early will help amplify the results of the whole program.

Here are some top tips I’ve seen teams help bring managers in early and get them up to speed (and up to snuff):

1. Treat Managers as Strategic Partners

Too often, managers are the last to know — handed a PDF at kickoff and told to “cascade it down.” Flip that. Involve them in the design or validation process so they understand the “why” behind key decisions. When managers feel ownership, they become better advocates and better translators.

2. Arm Them with the Right Messaging

Managers don’t need a 20-slide policy deck. They need clear, concise talking points:

• What’s changing and why
• How the plan supports company and team goals
• What success looks like under the new structure
  

Consider creating a one-pager or internal FAQ they can reference during team meetings or 1:1s.

3. Clarify How to Coach with the Plan

Most managers know how to coach skills or pipeline — but not comp mechanics. Help them connect the dots. For example, show how certain behaviors (discounting discipline, product mix, deal timing) translate into compensation outcomes. When managers can coach through the lens of comp, reps start making smarter decisions.

4. Train for Consistency, Not Just Compliance

Rollout meetings are just the start. Host manager-specific trainings that go beyond “what’s in the plan” to “how to talk about it.” Encourage open discussion, field their questions, and role-play tough conversations. Consistency builds confidence — and prevents misinterpretation from spreading across teams.

5. Create Feedback Loops

Finally, give managers a seat at the table year-round. They’re often the first to see issues in quota fairness, comp confusion, or behavior misalignment. Regular check-ins, surveys, or rep-level analytics reviews can turn their insights into actionable input.

When managers fully understand the plan, believe in its ability to drive the right results, and can explain the “what”, “why”, and “how”, clearly, the whole system works better – and your sellers are set up for success. Ultimately, when you empower the managers, you’ll empower your sellers, too.

Here’s to Clearer Communication!
—Calcy