People And Projects Podcast: Project Management Podcast

Summary In this episode, Andy talks with Olivia Montgomery, Associate Principal Analyst at Capterra and a PMP. They discuss how artificial intelligence is reshaping project management tools, skills, and expectations. Olivia brings a rare perspective, combining hands-on experience leading a PMO with years of research into how organizations evaluate, adopt, and struggle with project management software. Olivia and Andy explore why buying AI-powered tools is often easy, but realizing real value from them is much harder. Olivia explains the shift from buying software based on seat count to buying based on capability, why security is both the top source of satisfaction and frustration, and how unclear success metrics can quietly derail adoption. They also dig into the hidden risks of delegating too much to AI, including data governance blind spots and misplaced trust in tools that feel intuitive but have real limitations. You'll also hear why emotional intelligence is becoming more important as technology advances