Michael O'Callaghan · Product, UX & technology
Helping teams solve the right product problem
before they build the wrong thing.
I help founders and product leaders make sense of difficult product problems — where technology, business and human behaviour collide.
Product, UX and technology leader. Founder. Builder. Operator.
Why I do this work
I've been on the other side of the table.
I'm Michael O'Callaghan. For more than 25 years, I've built and operated technology products, led product, UX and engineering work, and made the decisions that come with real platforms and real teams.
I've seen first-hand how easy it is to solve the wrong problem very efficiently. My work is to connect business outcomes, technical reality and human usability — and identify what actually needs attention.
More about Michael →Difficult product problems
You're probably here because…
- You have a product, but something isn't quite working.
- Your team is busy, but you're not sure you're solving the right problem.
- The technology is moving faster than the product thinking.
- Customers are struggling with something the roadmap doesn't explain.
- AI, automation or new technology has created more possibilities than clarity.
- You need an experienced person to look at the whole thing and tell you what they see.
This is usually where product, technology, business and human behaviour have become tangled. Bring me the difficult problem; we'll work out what is really happening.
Most products don't fail because of bad execution. They fail because the right problem was never clearly named.
Michael O'Callaghan
The place to begin
Product Reality Check
Two hours. One problem, properly named.
Bring me the product you're struggling with. In two focused hours, we'll work out what isn't working, why it isn't working, what matters most, and what you should do next — including what not to build.
You leave with
- A clearly named product problem
- A sharper understanding of what is really happening
- A prioritised direction
- The next decision to make
Method
The questions I ask
I don't arrive with answers. I arrive with questions that are hard to answer quickly — and that's usually where the clarity is hiding.
- What would have to be true for this to work?
- Who is worse off if this succeeds?
- What are you protecting that no longer needs protecting?
- If you had to cut half the roadmap tonight, what would you keep?
- What do your customers do the day before they need you?
- What's the most expensive assumption you haven't tested?
- Which part of this is the business, and which part is the habit?
- What would you build if you couldn't write any code?
How I see products
Things I notice when I look at products
Observations about human usability, overloaded products, new technology, and the gap between what a system can do and what a person can actually understand.
Fractional vs full-time: what a founder actually needs.
Fractional leadership isn't a cheaper full-time hire. It's a different instrument, and using the wrong one is what makes founders think it didn't work.
Founders don't need more information. They need permission.
By the time a founder asks me what to do, they usually already know. What's missing is someone to say it out loud with them.
Complexity is a decision you postponed.
Systems don't get complicated on their own. Every branch in the logic is a choice somebody declined to make.
Technology is not the product. Clarity is the product. Technology is just the evidence that the clarity was real.
A clear way to go deeper
Start focused. Go deeper if it helps.
A Product Reality Check is the front door. If the problem needs more continuity or leadership, the relationship can grow from there.
Product Reality Check
A focused intervention around one difficult product decision. We name what is really happening, decide what matters, and identify what not to build.
One product. One clear direction.
Ongoing Product Clarity
Regular access to me as a senior product and technology sounding board as decisions, priorities and possibilities change.
Ongoing advisory
A steady outside perspective.
Fractional Product & Technology Leadership
Deeper involvement when the problem spans product, technology, teams and execution. Senior judgement held inside the work — hands-on, and always me.
Fractional leadership
Limited capacity. Not outsourced delivery.
Build & operate
Some products I build and run myself. They're where the ideas get tested at full cost — the evidence behind everything else on this page.
50,000+ users trained · 2,500+ training companies · 98% satisfaction · 15M+ courses delivered
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Have a difficult product problem?
I'm always interested in conversations where something is complicated, unclear or not working quite as it should.
Tell me what you're seeing, what you have tried, and where the problem seems to resist a simple answer. I read every note myself.
Not ready to write a note? Start with a Product Reality Check if you would prefer a defined first step.