Episode Details

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, how PMs can stress-test AI tools before committing, and which skills will separate the next generation of project leaders from the rest.

If you're trying to prepare for the future of AI, tools, and skills in project management, this episode is for you!

• "Buying tools is very easy. Realizing the value is extremely difficult."
• "Security is not IT's job. It's the whole company's job."
• "If your main metric is just 'use AI,' that's a red flag."
• "AI is very good at predicting what is most likely to happen next, and terrible at predicting black swan events."
• "Emotional intelligence is what helps you move forward when technology can't."
• "Use AI to generate a first draft. That's the safest place to start."
• "If you don't know the topic well yourself, you won't spot when AI gets it wrong."
• "Confidence in AI can grow faster than readiness, and that's where problems start."
• "AI can flag a risk, but it cannot tell you why people are stuck."
• "Data governance is going to set project managers apart in the future."
• "No matter what job you have in ten years, emotional intelligence will still matter."

• 00:00 Introduction
• 02:00 Start of Interview
• 02:10 Olivia's Role and Career Path
• 06:53 Shifts in How Organizations Choose PM Software
• 08:23 The Security Satisfaction and Frustration Paradox
• 11:25 Why AI Tools Are Easy to Buy but Hard to Use Well
• 20:18 Warning Signs of Overconfidence in AI
• 24:03 How to Stress-Test AI Tools Before Buying
• 27:50 Why Emotional Intelligence Matters More with AI
• 34:28 The Future of Project Management Software
• 40:08 Skills That Will Define the Next Generation of PMs
• 45:20 Where to Follow Olivia's Work
• 46:20 End of Interview
• 46:40 Andy Comments After the Interview
• 49:15 Outtakes

You can follow Olivia Montgomery and her research on LinkedIn at linkedin.com/in/olivia-montgomery.

For more learning on this topic, check out:

• Episode 479 with Matt Mong, about the AI skills you need to stay relevant in the years ahead
• Episode 463 with Faisal Hoque, on how to transcend the fear and hype around AI
• Episode 384 with PMeLa, the first-ever interview with an AI on a leadership or project management podcast

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