How to Know if You’re Doing a Good Job as a CTO

Answering a Deceptively Simple Question

Photo by Frédéric Perez on Unsplash

A CTO recently asked me a deceptively simple question:

“How do I know if I’m doing a good job?”

It’s a tough one. In a fast-growing startup—or any high-pressure environment—expectations can vary wildly. Trying to meet everyone’s demands is a surefire path to burnout. Instead, the key is to define success on your own terms and hold yourself accountable.

Three Dimensions of Success

I like to evaluate my performance across three core dimensions:

• Product Health

• Technical Health

• Organizational Health

1. Product Health

• Did we deliver what we promised?
  Delivering on commitments builds trust with customers and internal stakeholders.

• Is the customer experience improving?
  Enhancing the experience drives advocacy and organic growth.

• Is our competitive positioning improving?
  Are we keeping pace with—or outpacing—our competitors?

2. Technical Health

• Is the service reliable?
  Frequent downtime erodes trust and revenue.

• Are customers complaining about bugs or quality issues?
  Fewer complaints indicate you’re on the right track.

• Do we have a good developer experience?
  Happy developers are more productive and innovative.

3. Organizational Health

• Am I able to hire great people quickly enough?
  Fast-growing teams need a steady pipeline of top talent.

• Are great people happy and staying?
  Retention and engagement reflect a healthy culture.

• Are teams empowered to deliver and collaborate?
  Clear communication, ownership, and alignment are as important as the code itself.

Prioritizing Across These Dimensions

When everything feels urgent, it’s hard to decide what to tackle first. Here’s a simple roadmap:

1. Fix what’s causing you to lose deals

Analyze every deal lost in the last three months and map each loss to one of the three dimensions. You’ll likely uncover a few key issues that weaken your product compared to competitors. Addressing these will have an immediate impact on sales.

2. Fix what’s causing customer churn

Review every churned customer from the past few months and map their reasons for leaving to one of the three areas. Churn is often tied to reliability or quality issues—resolving these will improve retention.

3. Fix what’s limiting revenue growth

This usually ties back to competitive positioning and a strong product roadmap. Focus on delivering improvements quickly to stay ahead.

4. Prioritize organizational health last

I know I’ll get flak for putting organizational health last, but in my experience, fixing the above issues often leads to a stronger organization naturally. Most CTOs I’ve advised tend to overemphasize organizational health while neglecting the factors that drive revenue and prevent churn. No organization can truly thrive if it’s not growing.

Three Questions to Guide You

As you prepare for your next planning session or leadership meeting, ask yourself:

1. Product Health: How can I rapidly improve the customer experience relative to competitors?

2. Technical Health: How can I make it easier to deliver new innovations?

3. Organizational Health: How can I enhance the capabilities of my people and teams?

These questions will help you stay focused on what truly matters. As a CTO—or a CTO-like leader—your job is to balance these three dimensions so your company can innovate quickly, delight customers, and build a scalable, sustainable organization.