Tricky Situations and What You Can Do to Overcome Them

The People Side of Prioritization – Where the PoR Framework Meets Human Nature

As a Chief Product Officer, CTO, or CPTO, you will inevitably encounter tricky situations that make it difficult to get your R&D team aligned and functioning at a high level. These situations often have less to do with technology, roadmap or operations, and more to do with the human realities of leadership, communication, and power.

I’m an optimist, and I believe that the Plan of Record (PoR) prioritization process can help resolve most of these challenges. But it doesn’t happen automatically. It takes a concerted effort, persistence, and a willingness to work through short-term setbacks and frustrations. These moments often become the crucibles in which your leadership is tested — and strengthened. Sometimes, they even lead to the kinds of wins that put a smile on your face and make you remember why you love the job.

In the next five posts of the PoR series, we’ll go through the most common tricky situations that I’ve encountered — and offer concrete guidance on what you can do about them.

The Tricky Situations We’ll Cover:

• Hidden Assumptions about the Goals
  When the stated company goals aren’t the real drivers of executive behavior, prioritization becomes reactive and confusing.

• Pitfalls of ROI Analysis
  When decision-makers over-rely on ROI to evaluate technical investments, critical long-term needs like platform modernization get shortchanged.

• History of Top-Down Engineering or Product Management
  When your predecessor made all the calls, it takes work to rebuild a culture of trust, ownership, and distributed decision-making.

• Struggling with the Detail
  When executive stakeholders don’t understand — or don’t want to understand — the trade-offs, your PoR must become the translation layer.

• Ego and Power: Why the PoR May Seem Threatening
  When your PoR gains traction, not everyone may be happy about it. Some may view it as a power grab. This is where transparency and humility matter.

Up Next - We’ll help you identify situations where hidden assumptions might create conflicting priorities. If you can diagnose the problem, you’ll be in a better position to manage the conflict.