Why Simplicity Wins in Software—and in Business

Early in my career, I thought complexity signaled sophistication.
Big words. Big diagrams. Fancy solutions.

But after building software for 30+ years and leading a consulting firm through market swings, tech revolutions, and team transitions, I’ve learned the opposite is true:

Simplicity wins. Every time.


In software:

  • The simple solution ships faster.
  • It’s easier to test, easier to maintain, and easier to explain.
  • Clients understand it. Developers trust it. Users prefer it.

Yes, some problems are inherently complex. But that’s all the more reason not to add layers just to look smart. Good software makes the complex feel simple—not the other way around.


In business:

  • A clear offer converts better.
  • A focused strategy beats a scattered one.
  • Teams move faster when they know exactly what matters.

We’ve said no to “opportunities” that didn’t fit our core business because we know what we’re great at—and more importantly, what we’re not. That clarity creates momentum.


The cost of complexity:

  • Confused customers
  • Overstretched teams
  • Projects that drag on
  • Decisions that never get made

Complexity creeps in when no one’s watching. It takes discipline to say, “This is enough.” Or even better: “This is too much.”


Simple isn’t easy. It’s a choice.
It requires thought, tradeoffs, and a bias for clarity over control.

But when you choose simplicity—whether in an architecture diagram, a process, or a product offering—you gain something far more valuable:

Focus. Velocity. Trust.

AI Is Great—But It Can’t Think for You

I use AI every day.
It drafts proposals, outlines blog posts, summarizes meetings, and even helps prep for client calls. It saves time, sharpens execution, and makes life easier.

But here’s the mistake I see too many people make:
They expect AI to do the thinking.

It won’t.


AI is fast, but it’s not wise
AI can generate five paragraphs in two seconds. But are they aligned with your strategy? Your client’s goals? Your voice? That still takes human judgment.

Speed without direction is just fast noise.


It doesn’t understand nuance
I’ve asked AI to write content before and thought, “Well… technically, this is fine. But it misses the point.”
Why? Because it doesn’t know what matters most. It doesn’t know your team’s dynamics, your client’s unspoken concerns, or how trust actually works in your industry.


It’s a tool, not a replacement
AI can help you do the work. It can’t decide what work is worth doing. That’s strategy. That’s context. That’s leadership.
It’s like hiring the fastest assistant on earth who still needs clear direction—every single time.


How to use AI the right way:

  • Use it to generate first drafts, not final decisions
  • Let it automate low-value tasks so you can focus on high-value thinking
  • Pair it with your judgment, not your abdication

The real risk isn’t that AI replaces us
The real risk is that we stop thinking, stop leading, and stop learning—because we assume AI will handle it.

It won’t.
It’s here to help. But it still needs you at the helm.

Why I Don’t Micromanage (And What I Watch Instead)

I used to think that being a good leader meant staying involved in every detail. Check-ins, reviews, updates, approvals—I was everywhere.

Eventually, I realized something:
Micromanagement doesn’t scale. Leadership does.

So I stopped hovering. I stopped inserting myself into every decision. And I started watching the right things instead.

Here’s what I’ve learned:


1. Results > activity
I don’t care how many hours someone worked. I care about whether they delivered what they said they would.
Micromanagers obsess over inputs. Leaders track outcomes.


2. Trends > snapshots
Anyone can have a bad week. But over time, patterns emerge—positive or not.
I look at trendlines in client satisfaction, quality of deliverables, and internal collaboration. One-off issues don’t rattle me. Repeated ones get attention.


3. Questions > instructions
Instead of giving answers, I ask questions:

  • “Are you the right person for this goal or task?”
  • “What will you do?”
  • “What are your challenges?”
    This builds ownership, not dependency. People grow faster when they think, not just follow.

4. Accountability > control
Micromanagement feels like control. Leadership builds accountability.
We use daily huddles and short check-ins to stay aligned. People say what they’re doing—and then they do it. That rhythm replaces the need to chase people down.


5. Culture > compliance
If you need to micromanage, it’s often a hiring or culture issue.
The right people, in the right system, don’t need constant supervision. They thrive with trust and clarity.


I don’t micromanage because I don’t have to.
Our team runs on trust, visibility, and accountability—not control.
That’s more sustainable, more scalable, and—frankly—more enjoyable for everyone involved.

The Most Underrated Meeting on My Calendar

Most people dread meetings. I get it.
They’re often too long, poorly run, and end without anything getting done.

But there’s one meeting I’ve kept for over two decades—rain or shine, remote or in-person. It’s quick. It’s focused. And it’s the most underrated thing on my calendar:

Our daily huddle.


What it is (and isn’t):
It’s not a status meeting. It’s not a brainstorming session. And it definitely doesn’t involve PowerPoint.
Our huddle is 15 minutes, same time every day, built to keep everyone aligned, accountable, and connected.


Here’s how it works:
Each person quickly shares:

  1. Big updates from last 24 hours
  2. Stuck items where help is needed

That’s it. No tangents. No deep dives. If something needs more discussion, we take it offline. The goal is to keep things moving—and surface blockers fast.


Why it works:

  • It creates clarity. Everyone knows what’s happening and who’s doing what. No guessing.
  • It builds trust. When people show up and consistently do what they say, credibility grows.
  • It keeps teams connected. Especially in remote settings, that daily touchpoint is a glue.

What it’s replaced:
Longer, less frequent check-ins that often felt like overkill, or came too late.
With our huddle, we solve minor problems before they snowball or “slay monsters” while they are little. We stay nimble. And we never waste time wondering what’s going on.


Final thought:
Not every meeting is worth protecting. But this one is.
The daily huddle keeps our team focused, our projects on track, and our culture strong.

If you want more on how we run it (and how you can too), I break it down further on my website and in my book The 100: Building Blocks for Business Leadership.

The AI Assistant I Use Daily (And What It’s Replaced)

I’m not interested in hype. I care about tools that save time, improve output, and help me lead better.

So when AI entered the picture, I didn’t dive in headfirst. I tested. I questioned. And now? I use it daily—not as a novelty, but as a real assistant.

Here’s what I use, what it’s replaced, and how it’s changed how I work.


1. Brainstorming and outlining
What I used to do: Stare at a blank page, jot disconnected ideas, reorganize them endlessly.
What I do now: Ask AI to generate outlines based on a topic I’m thinking through—blog posts, internal comms, training content.
Result: I start 10x faster. I still tweak and guide the structure, but I’m never starting cold.


2. First drafts of communication
What I used to do: Spend too much time rewriting emails or announcement drafts to strike the right tone.
What I do now: Feed a few bullet points to AI and ask for a clear, professional first draft.
Result: It cuts my writing time in half. I still personalize and trim—but the heavy lifting is done in seconds.


3. Meeting prep and research
What I used to do: Search LinkedIn, dig through old emails, skim websites for client or prospect info.
What I do now: Ask AI to summarize a company, recent news, or role-specific concerns for the person I’m meeting.
Result: I walk into meetings sharper—with context and talking points ready.


4. Naming and titling
What I used to do: Lose time picking a blog title or subject line.
What I do now: Ask AI for 10 options and pick one.
Result: Better titles. Faster decision-making.


5. Idea vetting
What I used to do: Bounce ideas off a colleague or let them sit for days while I thought them through.
What I do now: Use AI as a sounding board—asking “What are the downsides?” or “What would a skeptic say?”
Result: Faster clarity. Still human judgment—just faster.


What AI hasn’t replaced:

  • My judgment
  • Strategy
  • People skills
  • Trust
  • Leadership

AI doesn’t replace the hard stuff. But it helps me get to the hard stuff faster. And that’s the point.