Jonathan Simmons
You Learned by Building. What Needs to Change Now?
A working product teaches you things planning cannot. Use that learning to decide what to keep, what to change, and which early assumptions now deserve another look.
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Real talk about the problems that keep product teams stuck.
Insights on product leadership, strategy, and execution. And how to fix what's broken.
Jonathan Simmons
Can I Sell This?
Your thing works and someone offered to pay for it. Selling is a different act than building, with obligations nobody mentioned. Here are the questions to ask before you charge.
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When Building Gets Cheaper, Check What Is Still Expensive
AI can make a project possible and expose the next thing holding it back. Here is how to tell whether you need more capacity, better evidence, or a decision.
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Why "Starting with the Problem" Isn't What You Think
Everyone says they start with the problem. But most teams are actually starting with the solution and calling it problem-solving. Here's the difference.
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Focus, Execution, or Clarity: Which One Is Actually Broken
A team that's busy and still not moving could have a focus problem, an execution problem, or a clarity problem. They look identical from the inside. The fixes are not.
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Design That Has Purpose vs. Design That Has a Portfolio
Beautiful design that doesn't solve problems is just decoration. Here's how to tell the difference and keep design focused on user outcomes.
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The Collaboration Trap: When More Voices Make Things Worse
Collaboration is supposed to make products better. But too often, it creates chaos. Here's how to know when collaboration helps (and when it hurts).
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Why Most Product Roadmaps Are Fiction (And How to Fix Yours)
When a roadmap treats assumptions as commitments, dates slip and trust erodes. Here's how to build one that accounts for evidence, tradeoffs, and uncertainty.
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You Don't Need a Full-Time CPO. You Need Product Leadership.
Hiring a full-time CPO is expensive, slow, and often the wrong move. What you actually need is product leadership. It doesn't require a full-time hire.
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Staff Aug vs. Product Pods: What's Actually Different?
Staff augmentation and product pods assign direction and delivery differently. Choose based on the capabilities and ownership your team needs.
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The Art of Listening to What Clients Don't Say
A feature request can reveal a deeper problem or a solution the client has already thought through. Good listening helps you tell which.
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Product Audits That Actually Find the Root Cause
Most product audits tell you what you already know. The valuable ones dig deeper, examining products at the molecular level to find what's really broken.
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When Hiring More People Makes Your Product Problems Worse
Your team is overwhelmed, deadlines are slipping, and the obvious answer seems to be: hire more people. But what if adding headcount is exactly the wrong move?
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