Charles Blain

Leadership

The Power of Not Knowing

"Let's workshop it." When I say these words, I watch shoulders relax. The pressure of having to figure it out alone lifts. No one person has to have all the answers. They bring their context: * The daily challenges * The technical constraints  * The team dynamics I bring

Leadership

The Power of Tactical Empathy

The armed man paced back and forth, weapon aimed at the hostages. He shouted at the negotiator outside, "I'm in control here!" But the veteran FBI negotiator didn't respond with threats or demands. Instead, he quietly said: "This seems stressful. Help me understand

Dancing With Machines

A Teams message blinked on my screen: "How do I use AI with all these meeting notes?" "A vision," I replied. One word. Short answer but here’s the longer one. Most people dive straight into the tools. They see others using AI and jump in

Marketing

Features Don't Matter

We like to think we're rational decision-makers. That we carefully weigh features, compare benefits, and make thoughtful choices about what to buy, wear, and use. The truth? We're still operating on the same basic software as a three-year-old at the playground. They don't analyze

Innovation

The 40 Ideas Trap

I have forty+ ideas in my innovation pipeline. That's the issue. Each sparkles with possibility. Each could work. Each deserves attention. That's why I'm stuck. We celebrate ideation and brainstorming as the core of innovation. But here's what nobody tells you: having

Mindset

The Stone Age Software Bug

For 300,000 years, human energy followed the sun. Hunt, gather, rest. The pattern was clear. Then, in just 200 years, we changed everything. Now we sit in climate-controlled rooms, staring at artificial lights, doing work our ancestors couldn't have imagined. But our bodies? They're still

Leadership

Who Owns the Answer?

I sat in the meeting room corner, resisting the urge to jump in. Two teams were stuck. Typically, leaders would come in with solutions. But today was different. Instead, we gathered the people who felt these challenges in their bones — the ones who faced these problems daily, felt the friction

AI

The Understanding Gap

Last week, I lost a whole day of coding not due to a computer crash or forgetting to save, but because I trusted AI too much. Here's what happened: I used an AI coding assistant to build a complex feature. Initially, it felt remarkable. The AI understood my

AI

Three Minds, One Caution

Last week, I faced a decision that split my thoughts three ways: My instincts warned, "Don't trust this prospect." My documented past experiences suggested they were appropriate. My AI analysis of their public data revealed surprising issues. All three were right. All three were wrong. The

Marketing

Why Memes Outperform Targeting

Watch a schoolyard during recess when a new game sweeps through. One day it's handball. The next it's elaborate clapping sequences. Then something entirely new. Marketing executives spend millions trying to create this effect, yet these playground trends spread without a single advertising dollar. Why? Because

Innovation

What Data Can't See

You're in a meeting. Something doesn't fit. While others see the data and nod, you sense a missed pattern. How do you explain a feeling? Most of us learned two ways of thinking: * Deductive logic (if A=B and B=C, then A=C) * Inductive logic

Mindset

The Airfoil Workday

The most valuable insights come from unexpected places. I watched my colleague draw a simple wing on the whiteboard. "Here's something interesting about air," he said. "When it moves fast over the top of a wing and slow underneath, it creates lift. That's

The Walking Mind

Steve Jobs would hit a wall. A product decision, a design choice, something that wouldn't resolve through more thinking. So, he walked. Ten minutes through Apple's campus, no phone, no agenda. Just movement and space.  The answer would surface not through force, but through release. We

Mindset

Invisible Norms

Groups don't see their own norms. Fish don't notice water. Teams don't feel their culture. Organizations can't spot their assumptions. We only see our patterns when we step outside them. The question isn't "What are we missing?" It&

Leadership

Our People Know What to Do

Watch what happens when a manager steps away. The team doesn't collapse. They don't stop. They start talking to each other. Start solving problems. Start building something better. Our people always knew what to do. We just had to let them be.

Strategy

Strategy Lives

Strategies don't fail because they're wrong. They fail because we treat them like monuments instead of gardens. We carve them in stone, present them in decks, print them in manuals. Perfect plans waiting for a perfect world. But look at how real progress happens: Small shifts

Analytics

We Measure Our Mysteries

Watch what a company measures. Not for the numbers. But for the questions that keep their leaders awake at night. When Superhuman obsesses over NPS instead of feature velocity, they're asking a deeper question: "How do we transform email from obligation to joy?" When Medium prioritizes

Mindset

When Roles Dissolve

This morning, in another client call, I notice something. Some meetings feel like coffee with an old friend. Others like stepping into a ring. Until now, I thought this was about personalities or stakes or pressure. But watching this client ask about project timelines, I see it differently. The meetings

Innovation

The Human Layer

I'm sitting down drafting an invitation letter to a few team members to join me on a journey that I don't even know if they'll survive. I'm not sure if I'll survive. The cursor blinks. Each word feels like a

Marketing

Love's Analytics

In a bullpen filled with SEO specialists and CRO experts, where conversations usually flow through conversion funnels and search rankings, someone drops a question that halts every keyboard mid-type: "Is love a feeling or a decision?" The irony sits heavy. Here we are — professionals who optimize for human

Mindset

When We Become They

Individual clarity dissolves into collective maybe. Not because we care less. But because we think more about what others might do. And thinking about others potential actions becomes waiting for others. Until the possibility freezes.

Leadership

The Handoff Moment

In the conference room this morning, I watched faces tighten as we discussed a client relationship at risk. The instinct was immediate — add more processes, create more checkpoints, layer on more reviews. But something wasn't quite right about that response. What if the answer wasn't more

Mindset

The Wrong Kind of Right

I'm watching her face tighten as we scroll through the campaign data. The conference room feels smaller with each passing minute. We've found the issue — basic data reading mistakes, budget allocations that worked against her goals. A fixable puzzle, really. But she's not looking

Leadership

Your Tribe is the Strategy

The spreadsheet on my desk showed everything that should have mattered in my daughter's college choice — rankings, financials, programs, outcomes. But she was lost in Instagram, studying something else entirely. That's when I saw it: the pattern that changes everything about how we drive transformation. While

Innovation

The Assembly Line Lesson

Henry Ford watched his skilled workers repeatedly walk back and forth, gathering parts for assembly. Everyone said faster workers were the key to better production. But Ford saw something different. The best worker in the world can't outperform a poor parts delivery system. The workers weren't