Blog on Drew Harris - Fractional CTO/CPTO

Why AI Shouldn't Answer Questions It Doesn't Fully Understand

Mon, 06 Apr 2026 08:00:00 -0500

A few weeks ago, I was coaching a founder through a difficult hiring decision. He’d already asked ChatGPT about it.

“It gave me a solid answer,” he told me. “But something felt off.”

I asked him three questions. His whole framing shifted. The answer he needed was completely different from the one he got.

The AI wasn’t wrong, exactly. It just didn’t know what it didn’t know.

The Assumption Nobody Talks About

Every time you ask an AI a question, it makes a quiet assumption before it says a single word.

The Context Problem

Wed, 03 Dec 2025 08:00:00 -0800

I was on a call yesterday with Benjamin Baxter, a content strategist who helps B2B founders with LinkedIn. We were supposed to be planning something technical, but the conversation went somewhere more interesting.

Ben mentioned that the biggest tell of AI-generated content is “vague generalities that aren’t based in any personal experience.” The classic “I was talking to a billionaire…” posts that everyone knows are made up.

It made me think about a CEO I worked with years ago.

Where I've Been: Building the Wave I've Been Waiting to Ride

Wed, 26 Nov 2025 08:00:00 -0800

You’ve probably noticed the silence. No posts since March. No weekly insights. No new stories from the fractional CTO trenches.

I didn’t disappear. I didn’t burn out. I didn’t run out of things to say.

I went deep.

The Moment You Stop Paddling

When you’re surfing, there’s this moment—right before you catch a wave—where everything goes quiet. You stop paddling. You feel the water lift beneath you. You commit.

That’s where I’ve been for the past six months.

Simple Pleasures

Wed, 12 Mar 2025 07:54:00 -0700

Some of the best things in life are the simple things:

The first steps your child takes
The smell of fresh baked goods
The warmth of the rising sun after a cold night
S’mores shared with loved ones cooked over a campfire.

A smile shared with others.

Bobby McFerrin, best known for his song “Don’t Worry, Be Happy,” has another song on that album that is one of my favorites: “Simple Pleasures. “This song inspires me to cherish the simple pleasures in life and inspired me to write this article. Give it a listen. It sure puts a smile on your face!

Engineering: Stop the Its Complicated Excuse and Start Delivering Predictable Value

Thu, 06 Mar 2025 04:00:00 -0800

We’ve all seen it. Every department has clear accountability:

Marketing owns conversion rates.
Sales own pipeline metrics.
Finance owns P&L statements.

And engineering? Too often, it’s shrouded in mystery. “It’s complicated,” we hear. Deadlines slip, priorities shift, and teams hide behind technical complexity.

But here’s the truth: engineering can and should be held accountable. Unmanaged expectations are a significant reason why so many IT initiatives fail. 70% of them, according to some studies. It’s time to bring engineering out of the black box and into the light.

Hiring Freeze? Thrive Anyway: Unlock Growth by Re-Igniting Your Existing SaaS Team

Wed, 05 Mar 2025 06:40:00 -0800

In today’s turbulent SaaS market, “growth at all costs” is out; efficient, sustainable progress is in.

With hiring freezes and budget cuts looming, many companies feel trapped. But what if your most significant growth lever isn’t a costly external hire but the untapped potential of your current team? This article challenges the scarcity mindset, revealing how investing strategically in your existing employees can yield surprisingly better ROI than chasing talent you can’t even afford to pursue.

Riding the Wave: A Surfer's Guide to Scaling SaaS Operations

Tue, 18 Feb 2025 09:30:00 -0800

In the dynamic world of SaaS operations, success often feels like catching the perfect wave. As a fractional CTO and CPO, I’ve observed striking parallels between mastering the art of surfing and navigating the challenges of scaling SaaS operations. Let me share why this analogy resonates deeply with our operational excellence approach.

Getting Past the Breakers: Building Your Foundation

As surfers must paddle past the breaking waves to reach the calm waters beyond, scaling your SaaS operations requires pushing through initial challenges. Sometimes, like skilled surfers performing a duck dive, you must dive beneath the incoming waves to make progress. In SaaS operations, this means knowing when to go under, through, or around obstacles rather than letting them knock you off course.

Leveraging AI in SaaS: From Hype to High Performance

Tue, 21 Jan 2025 15:09:00 -0800

The AI revolution isn’t just coming—it’s transforming how successful SaaS companies build, scale, and deliver value. But many aren’t telling you that the real competitive edge isn’t in having AI—it’s in knowing how to use it strategically.

Beyond the AI Buzzwords: What Moves the Needle

Let’s cut through the noise. While competitors chase the latest AI headlines, forward-thinking SaaS leaders quietly revolutionize their operations by treating AI as what it truly is: a powerful force multiplier for human expertise. The question isn’t whether to adopt AI but how to deploy it for maximum impact.

Leave Behind to Move Ahead: A Different Approach to New Year's Growth

Tue, 31 Dec 2024 09:59:00 -0800

Today, we leave 2024 behind us and bring our memories into 2025. Many people focus their new year on resolutions, asking themselves how they will be better at this or that in a new year. A friend of mine recently spoke at church, and regarding resolutions, he encouraged people to also think about what they will leave behind in 2024. This challenge got me thinking about those things that hold us back from our true potential and how we can leave those things behind as we begin a new year.

Automation at its worst!

Fri, 06 Dec 2024 11:11:00 -0800

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Today, I turned 50 years old. When I came out of my house this morning, my trees were toilet papered, and signs about my 50th birthday were put up in my yard. My wife (who is older than me) reminded me that I am now an old man. My phone and LinkedIn have been blowing up with “Happy Birthday” messages. Here are a few observations from a grumpy old wise* man…

Building High-Quality Teams: The Key to Success

Tue, 03 Dec 2024 06:00:00 -0800

“It is not good for man to be alone.” - Genesis 2:18

From the dawn of humanity, cooperation has been a cornerstone of our success. Throughout history, we’ve witnessed countless examples of what can be achieved when individuals unite for a common purpose. Consider the pyramids of Egypt, the Great Wall of China, or the Apollo 11 moon landing. These monumental feats were not accomplished by lone individuals but by teams of dedicated people working together.

The Future of SaaS: Five Emerging Trends and Innovations

Tue, 22 Oct 2024 11:24:00 -0700

The SaaS (Software as a Service) industry has experienced unprecedented growth in recent years, revolutionizing how businesses operate. As technology continues to advance rapidly, new trends and innovations are emerging that will shape the future of SaaS. In this article, we will explore some key developments poised to redefine the SaaS landscape.

Artificial Intelligence (AI) and Machine Learning (ML)

AI and ML are rapidly becoming integral components of SaaS solutions. By leveraging these technologies, businesses can:

The SaaS Leadership Toolbox: Empowering Teams with the Right Tools, Including AI

Mon, 07 Oct 2024 05:00:00 -0700

In the rapidly evolving software development landscape, the right tools drive innovation, improve efficiency, and deliver high-quality products. While specific tools may come and go, the importance of leadership and culture in supporting teams with access to the necessary resources remains paramount.

Leadership’s Role in Tooling

SaaS leaders are crucial in creating an environment where teams can thrive. By providing access to the right tools, leaders can:

Empower teams: The right tools can empower teams to work more efficiently, collaborate effectively, and deliver high-quality results.

The Blueprint & Route for Software Success

Thu, 03 Oct 2024 09:51:00 -0700

Imagine building a house. You start with a solid foundation, ensuring it can support the structure. Similarly, a solid product-centric mindset is the foundation for success when creating software.

Software as your business’s product can take many forms, including SaaS (Software as a Service), on-premise solutions, or embedded software. Regardless of the delivery model, the core principles of product-centricity remain the same.

Why is a product mindset crucial? Viewing software as a product means focusing on its lifecycle, value proposition, and target market. Just like a house needs a blueprint and a target audience, software requires a clear vision and understanding of who it’s designed for.

The Power of Values: Guiding Your SaaS Leadership

Tue, 17 Sep 2024 13:11:00 -0700

In the fast-paced world of SaaS, leadership isn’t just about driving results; it’s about being intentional with how and why you lead. The personal and professional values that guide your decisions profoundly impact your team, your product, and your customers.1. Start with Clarity: Define Your Personal Mission

As a leader, it’s essential to develop a personal mission statement. Understanding your core values not only defines who you are but also sets the tone for the culture within your organization. Reflecting on virtues like honesty, courage, and respect can ground you in your leadership role and inspire those around you.

From Side Streets to Superhighways: Fostering Growth in Software Teams

Mon, 16 Sep 2024 12:43:00 -0700

As a fractional software leader, I’ve often pondered how to create an environment where software engineers can thrive and reach their full potential. This morning’s bike ride provided a striking analogy that sheds light on this topic.

A Lesson from the Road

While cycling through a rural area, I encountered a student driver. The presence of a driving instructor in the passenger seat was a reminder of the importance of a supportive mentor. In a controlled environment, the student driver can learn from mistakes without fear of severe consequences.