Roadmap Malpractice

Roadmap Malpractice is about a specific pattern in enterprise software: product decisions get committed before anyone asks whether the organization can actually carry them into the market. By the time go-to-market teams see what's coming, the window for meaningful input has usually closed. What remains is execution.

Most companies are doing a lot right. They capture customer feedback, track the metrics that matter, and invest heavily in their go-to-market teams. And yet releases overpromise and underdeliver, priorities shift, announcements outrun what's actually ready, and positioning has to keep getting rewritten to hold the line. The data isn't the problem. What's often missing is the step between having that signal and making a roadmap commitment, the step where a decision gets tested against how it's going to land when it meets the market, and where the people who are in the market every day get a real voice. They see more than the risks. They see the opportunities others can't.

The cost of that gap isn't visible in engineering metrics. It shows up in longer sales cycles, positioning that gets rewritten three times, adoption patterns that don't match what was promised, and the slow erosion of conviction among the people who have to carry each release into the market.

This book isn't written against product or engineering teams. The work they do is some of the hardest in enterprise software. Roadmap Malpractice is a different lens on the same work, from the go-to-market side. It's written for anyone who has sat in a room, heard a plan announced, and thought: this is going to be harder than they think.

Sixteen chapters, built from patterns observed across multiple B2B enterprise SaaS companies.