The Stakeholder Type Most CSMs Get Wrong

Early in my career, I misread assertive stakeholders. I read them as aggressive and

difficult to handle.

I correctly identified them as assertive, but misunderstood what that meant.

Christopher Voss maps this well in Never Split the Difference. He identifies three types

of negotiators, and CS professionals already have the soft skills to spot all three.

The Analyst - Data-driven, methodical, deliberate. This is CSM’s comfort zone. We are comfortable with data and leveraging it to promote value and drive customer growth.

The Accommodator. Relationship-first person, dialogue-driven. Familiar territory, too, as CSMs are relationship builders, but watch the risk: they overpromise without the authority to deliver. Classic scenario: You build a strong relationship with someone who can't sign the renewal.

The Assertive. They want to be heard. They seek immediate solutions. They want to win fast.

This is the type most CSMs struggle with. We're built for empathy and collaboration, and

the Assertive operates on different terms. Beyond their personal characteristics, what they say during negotiations and difficult conversations is filtered through the lens of how it will be received when they walk back into their organization.

Once you see that, the approach changes.

CSMs can prepare by understanding the definition of success that the assertive stakeholders have in mind. In other words, what does winning look like for them internally? Then drive the solution toward that win.

An Assertive person who feels like they won will close the deal, approve the renewal, and push the expansion through.

Two things to take from this.

First, identify the type of negotiator you're dealing with and adapt accordingly. That's CS instinct applied to negotiation.

Second, for the Assertive specifically: lead with curiosity about what success looks like inside their environment, then plan your activities and discussions around getting them there.

Practitioner Tip for TheCSCycle Readers

Before your next renewal conversation with an Assertive stakeholder, find out what they

need to report upward, not what they need from you.

Ask directly: "When you take this back to your team, what does future successful engagement look like?"

Write the answer down in your account notes, word for word. Then build your agenda

backward from that answer, not from your renewal checklist or predefined renewal playbook.

This is one of the frameworks I explore with CS executives and CS professionals inside TheCSCycle.

If this resonates with where you are today, visit thecscycle.com to learn more.