How to Know If Your Team’s Ready for AI in PM Software

The Digital Project Manager

The AI hype in project management software is real—but is everyone ready for it? In this episode, Galen sits down with returning guest Olivia Montgomery, Associate Principal Analyst at Capterra, to explore the findings from her 2025 Project Management Software Trends Survey. They unpack the real reasons behind the surge in demand for AI-enhanced PM tools and the foundational work teams need to do before expecting AI to deliver real ROI.

Together, Galen and Olivia dig into what "AI readiness" actually looks like—technically and culturally. They discuss how competitive FOMO, billion-dollar marketing campaigns, and shifting economic investments are driving decision-making at the executive level, while the realities of adoption, data governance, and employee empowerment are playing out on the ground. They also take a thoughtful look at how PMs can avoid common pitfalls (like AI hallucinations) and begin to build workflows that align with both human and machine strengths.

Resources from this episode:

• Join DPM Membership
• Subscribe to the newsletter to get our latest articles and podcasts
• Connect with Olivia on LinkedIn
• Check out Capterra
• Olivia’s report, AI & Security Are Top Concerns in Capterra’s 2025 Project Management Software Trends Survey

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1. Setting The Big Question (00:00:00)

2. Intros & Today’s Roadmap (00:01:20)

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