When Your Best Rep Doesn’t Play by the Rules: Making room for your Maverick

A CEO in my Mastermind group asked me this point-blank question: “What do you do with the Maverick sales rep?” Following my own advice, I didn’t answer right away. I asked: “What do you mean by Maverick?”

What followed was a portrait I’ve heard before and that I’m sure you have witnessed. On one hand: outstanding results, deep client relationships, and a creative instinct for finding angles nobody else sees to close deals everyone else wished they had. On the other hand: a CRM that’s always behind, urgent finance approvals that land at the last minute, and a habit of skipping important team coordination meetings. Nobody would call this person difficult but their unorthodox methods are noticed by everyone, and they quietly frustrate both peers and other supporting members from other teams like operations or product management.

What my mastermind colleague was really asking was: “How do I challenge a top performer to follow everybody else’s rules without affecting their outstanding results?”

That’s the tension every sales leader eventually faces.

My recommendation was to stop trying to fit them into a mold and instead define a wider lane for them. Give the Maverick room to succeed but put guardrails on both sides and clearly define where those boundaries are. I asked her to identify three non-negotiable must-do’s and three firm never-do’s: the behaviors that are truly required and the ones that are genuinely unacceptable, regardless of the results being delivered.

She paused. After a moment, she had one of each: (1) always have your weekly forecast loaded in the CRM by Monday at 8:00 AM, and (2) never miss the Friday morning sales team call. The rest of the guardrail conditions went home as homework and that pause told me everything. Even the leader asking the question hadn’t fully defined where the line was. You can’t hold someone to a standard you haven’t clearly defined and communicated.

We all bring ourselves to work, and great leaders must leave room for people to succeed in their own way, using their own strengths, and applying their unique winning formula. The Maverick’s methods will look different from the rest of the pack’s, but their top results also speak loudly. Your job isn’t to make them like everyone else it’s to be clear about what is and isn’t negotiable, and then get out of their way.

So here’s your challenge: Who’s the Maverick in your team? What would your list of must-do’s and never-do’s actually look like? And before you have that difficult conversation with your Maverick, role-play it with a friend first.

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