Sometimes you just know something’s not right. Like when my kids have friends over and I don’t hear anything for ten minutes – I don’t know exactly what’s going on, but I know something’s afoot.
That's exactly where I found myself recently while working with my AI co-CEO (whom I affectionately call Denise) to reimagine AgileSherpas' go-to-market strategy.
We were making great headway in exploring the market opportunity, considering positioning and value prop and key differentiators. Denise and I have only been collaborating for a couple of weeks, but we were vibing. There was give and take, lead and follow – it felt like I had found an exciting new dance partner.
After several sessions our progress reached a point where I was comfortable taking it public, so I started putting it into a Miro board to share with my team.
And then there was a different feeling. That “something’s not quite right” feeling replaced the “dancing with a great partner” feeling.
Every time I tried to turn the strategy into actionable next steps, I hit a wall. My marketing and CEO instincts were telling me that this go-to-market strategy, however objectively good it might be, wasn’t the right approach.
Eventually Denise and I returned to the dance floor and tried a different tune, and the outcome ended up quite different. I’ll walk you through exactly what happened in both the video and the article that follow, but here’s why I want to share this story:
LLMs have digested the whole internet, but they should not replace our guts.
Skilled professionals have deep-seated instincts born of decades of lived experience, and those instincts matter.
A human-AI partnership can lead to breakthrough moments when we learn to dance together effectively, but don’t let AI lead you blindly over a cliff.
The Initial Waltz: AI's First Pass
Historically AgileSherpas has focused almost exclusively on helping marketing teams translate Agile frameworks to apply to their unique context. We still do that of course, but at the heart of that work is an obsession with process improvement and waste mitigation.
In other words, we help marketers do the right work at the right time.
Right now the “right work” for just about everybody is figuring out how to incorporate AI capabilities into their daily workflows. We can totally help with that, but we aren’t known for it (yet).
As I started developing a strategic approach to this extension of our core capability, I knew AI could be a powerful ally in reshaping our market position.
Working with my co-CEO GPT (kudos to Paul Roetzer and the team at SmarterX for developing and sharing this!) I began exploring how we could innovate our go-to-market approach.
The first iteration looked promising on the surface. My AI partner produced a content-forward strategy that aligned with our organization's DNA. It suggested implementing a hero-hub-hygiene model and proposed innovative ideas like an "AI + agility in action" newsletter.
There was even a clever suggestion for a stand-up format focused on sharing trials and learnings.
As a content-driven organization led by a former content strategist, the approach was singing our song.
When Good GTM Isn't Good Enough
But here's where it gets interesting – and where the human element becomes crucial.
Despite spending a week refining the strategy, and despite nothing being obviously wrong, something felt off.
It was like trying to force a puzzle piece that looks like it should fit but doesn't quite click into place. After spending over two decades in marketing and eight years running this business, my intuition was sending clear signals that we hadn't quite found our rhythm.
Every attempt to move the strategy into our marketing team's backlog felt like dancing with two left feet.
The resistance wasn't logical or easily articulated – it was visceral.
Finding My Strategic Rhythm with AI
Sometimes the best moves come after taking a step back.
As a visionary entrepreneur, pausing isn't my natural state, but I forced myself to step away from the project for a few days. When I came back, I changed the music entirely.
Instead of asking for a strategy built on content and lead generation, I posed a different question to Denise:
"Let's imagine that AgileSherpas does not exist. What would be the perfect go-to-market strategy for a brand new company that wants to target middle-level managers thru senior leaders at larger organizations (more than 40 ppl in the marketing dept)?"
That's when the magic happened.
The shift in perspective led to a hybrid strategy that balanced immediate impact with long-term growth. We developed an approach that combined social and outbound outreach with a "build in public" approach, allowing us to share our journey transparently.
This wasn't about waiting for the content snowball to grow large enough to create momentum – it was about creating multiple paths to success simultaneously.
When I saw this new direction, the recognition was immediate. This was our song.
The Power of the AI + Human Partnership
What makes this story particularly compelling isn't just the final strategy, but the process that got us there. It demonstrates how AI can be a powerful collaborator while highlighting the irreplaceable value of human experience and intuition. The final strategy wasn't simply AI-generated or human-designed – it was a true synthesis of both.
As we continue to integrate AI into our strategic planning processes, this experience offers valuable lessons about the future of decision-making. The most effective strategies won't come from either AI or humans working in isolation – they'll emerge from thoughtful collaboration where each partner brings their unique strengths to the table.
AI can process vast amounts of information and generate innovative approaches, but it's the human ability to sense subtle misalignments and pivot approaches that brings these insights to life.
Together, we can create strategies that aren't just theoretically sound but deeply resonant with our organizational reality.
The dance continues, and I'm excited to see where this partnership leads us next.
