How I Learned to Prioritize Risk (Without Treating Everything Like an Emergency)

Prioritizing risk took me a long time to figure out.

Early in my career, I treated every issue like it was urgent. Every problem felt like the problem. I wanted to fix everything, immediately. On the surface, that sounds noble. Responsible, even.

In reality, it was exhausting and ineffective.

Not everything can be a priority. And when everything is a priority, nothing actually is.

What finally changed things for me was getting far more disciplined about business impact. Instead of reacting to noise, I started slowing down just enough to ask myself one simple question:

What actually matters most if this goes wrong?

The Framework That Changed Everything

Over time, I boiled my thinking down to three core criteria. Three things that, if impacted, deserved immediate attention.

I call them the 3 R’s:

Revenue

Relationships

Reputation

If a risk had meaningful impact on any one of these, it moved to the top of my list.

That meant asking more intentional questions:

1. Would this hurt retention or growth in the short term?

2. Would it damage trust or strain an important relationship?

3. Would it hurt our brand or credibility in the market?

If the answer was yes, it wasn’t optional. It had to be prioritized.

Context Matters: Timing and Scale

Of course, prioritization isn’t static.

Timing plays a role. A short-term risk can outweigh a longer-term one, and vice versa. The scale of revenue at risk can also influence urgency.

That doesn’t mean smaller customers don’t matter. They absolutely do.

It simply means prioritization has to be grounded in business impact, not emotion or volume. Leadership requires making decisions that may feel uncomfortable in the moment but are right for the business overall.

Why Reputation Carries Extra Weight in B2B SaaS

One area I’ve learned to never underestimate is brand reputation, especially in B2B SaaS.

These communities are smaller than we think. Word travels fast. A situation that damages your name doesn’t just affect current customers, it impacts prospects, partners, and future opportunities.

Reputation risk compounds quietly and lingers long after the initial issue is resolved. That’s why it often deserves faster action than teams expect.

The Hard Part of Leadership

One of the hardest lessons I learned as a leader was how to truly prioritize risk.

Yes, pressure is a privilege. But that doesn’t make the decisions easier.

You still have to slow down.

Weigh the tradeoffs.

Make the call.

Not forever, but long enough to choose wisely.

The 3 R’s have helped me manage the big R: risk.

They don’t remove pressure, but they bring clarity when everything feels urgent.

So I’ll leave you with this:

What have you built your priority framework on?