A few years ago, I led a CS team through a major product pivot.
It was a big shift. What we were promising customers wasn’t aligned with what the product could consistently deliver. Leadership knew it. The CS team definitely knew it. And we were all bracing for churn.
One of my senior CSMs asked if we could run a war room. Not a firefighting one. A strategy war room where everyone (Support, Product, Sales, CS) could raise red flags, challenge assumptions, and rework our engagement plan together.
At first, there was resistance.
Some leaders were hesitant to “air dirty laundry.”
Others wanted us to stay positive for morale.
But I knew: the only way out was through.
We ran the session. It was uncomfortable. People disagreed.
But what came out of it was one of the clearest, most executable cross-functional plans we’d ever had. Not because we had better data. But because we made space for contributory dissent. The type of disagreement that drives outcomes forward.
What Is Contributory Dissent?
It’s not about being a contrarian or poking holes in every idea.
It’s about building a culture where people are encouraged and trained to contribute alternative perspectives that improve collective decision-making.
In Customer Success, we see the need for this every day:
- The executive wants one thing. The end user another.
- Product sees a feature request as low priority. CS sees it as critical for renewal.
- Sales is pushing expansion. CS is waving the red flag.
But instead of leaning into these moments, most teams avoid them.
Or worse, sugarcoat the feedback to maintain the illusion of alignment.
And that’s where growth gets stuck.
3 Ways to Normalize Dissent Without Creating Chaos
Train your team to “disagree constructively”
Teach CSMs how to raise concerns with clarity, not emotion. Language like “Here’s a risk I’m seeing that could affect our renewal goals” is more actionable than “This won’t work.” Your team needs permission and structure to speak up.
Model it as a leader
As a CS leader, openly inviting pushback changes the room.
Say things like:
“Where might this fall apart?”
“What are we not seeing?”
“Tell me if this doesn’t make sense from your view.”
When you make dissent safe, your team learns it’s not rebellion—it’s responsibility.
Build it into your culture
Don’t wait for high-stakes moments. Make dissent a habit in postmortems, project reviews, and even QBR prep. Over time, it signals that thoughtful disagreement is not just accepted—it’s expected.
The Real Leadership Opportunity
In fast-moving SaaS orgs, speed can’t come at the cost of insight.
When teams only seek agreement, they miss the nuance that drives better outcomes.
Contributory dissent is a skill. A culture.
And a strategic advantage that turns feedback into foresight.
You don’t need to be the loudest voice.
You just need to create space for the right voices to speak.
Want to Build a More Strategic CS Culture?
Inside my 1:1 CS Strategy Coaching, I work with CS leaders to:
✅ Move from execution to influence
✅ Build systems that drive retention and expansion
✅ Lead their teams with clarity, confidence, and cross-functional credibility
There are two coaching tracks available:
🔹 Core Track – $4,995: Bi-weekly sessions for 3 months
🔹 Intensive Track – $7,995: Weekly sessions for faster momentum
You’ll also get:
✔ A 60-min kickoff strategy session
✔ Slack/email support between sessions
✔ Session recordings and templates to continue implementing