#125 - Gregory Stoos, CEO of Planless - On freeing project teams to execute, not replan

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Previously titled “A story about how technology augments project teams to work the plan, instead of plan the work” — renamed by the publisher on Aug 12, 2026

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Recorded28 Jul 2020

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Show notes

This podcast interview focuses on product innovation that has the power to transform how we manage and deliver projects. My guest is Gregory Stoos, CEO of Planless. Gregory has over 15 years of experience in entrepreneurship and managing positions. Besides founding Planless, he also co-founded Apperativ, a new generation software development company. Prior to that he’s been responsible for building top-level and disruptive products in the technology world or the marketing and advertising space. The red-thread throughout his career has been ‘projects’. No matter if he worked for a creative agency or a technology company, managing and planning projects was front and center. And that sparked the big idea behind his latest company Planless, which he founded September 2017. Planless is on a mission to help project teams focus on working the plan, instead of planning the work. And this inspired me, and hence invited Gregory to my podcast. We explore the productivity issue so many project teams suffer from around the world and that results in not being able to deliver work on time, or not at the expected quality. We discuss what’s broken, and why rethinking how we manage projects is the only way to break free from this problem. Here are some of his quotes: The big idea is that project management tools are all more or less the same. And there is one big issue in actual solutions is that planning work, allocating resources and managing people's workloads is still done manually in all these tools and is very time consuming and very inefficient. I'd like to say that planning is humanly impossible. Basically, it is teams executing the work that self-organize themselves, and lose a lot of time doing it. And most of the time, we see that they are not capable of delivering work on time or not with the quality that was expected. In this particular industry, everybody thinks really a lot about return on investment, right? That's the main focus about hiring marketing agencies. You want to invest a dollar and get three, four or five out. The thing is, what about the ROI of people? What if you could just increase your productivity by 30, 40, or 50%? During this interview, you will learn four things: How we can deliver more transformative change by stepping away from the problem, see the big picture and then rethink the foundational concepts Why agile is both a blessing and a curse That too often it’s not the technology that’s the issue to create value and momentum, it’s mindset and behaviour of people. Why we should aim to get attention from the market before they can get the product. It validates whether you are on to something big and with that everyone benefits. See acast.com/privacy for privacy and opt-out information. Learn more about your ad choices. Visit megaphone.fm/adchoices

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