From the Archives · Oct 1, 2026
Enough Challenge to Grow
With Adrienne Cooper
Founder, GLADsome Work Inc.

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How do you help someone stretch without pushing them past what they can handle? In this six-and-a-half-minute excerpt, Adrienne Cooper and I talk about flow, the stages of learning, and what managers can do in the small moments of a working day to support both the person and the team.
From the Archives brings you short highlights from past Escape Velocity conversations. This excerpt is from episode 28, originally released March 25, 2026.
Listen to the full conversation with Adrienne Cooper →
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Transcribed from the recording and lightly edited for readability. Some overlapping speech and repeated words have been omitted. Timestamps refer to this excerpt; small transcription errors may remain.
You talk a lot about flow and flow state. Can you talk a little bit more about that, how you incorporate it, what it means to you, and what role that has inside of an organization?
Yes. Flow state, obviously there are books about this and I've read them, and that's really where it came from for me. It was kind of like an aggregation of being introduced to Agile, like the capital-A Agile. And that was really the juxtaposition between how we had worked at Allstate. It did not feel like capital-A Agile. It felt a little bit more like command-and-control, waterfall. And I think the thing that wasn't as diverse at Allstate was it was just so risk-averse. Less about the humans and their lived experience, but there was just this really tight cultural belief. Obviously it's an insurance company, right? So they were highly risk-averse.
So moving into worlds in engineering and product, being introduced to Agile and understanding contracts are meant as backups. When you have the culture on the team that really understands each other, gets into flow, you don't have to be so contractually bound in the work that you do. And you can iterate based upon what you learn as you go. So that's an element of flow.
But I think another part of flow is when you move through these stages of: I don't know what I don't know. Then, oh, I know what I don't know, and now I'm a little freaked out. And then you learn about the thing that you don't know, and you get better at doing it. So you're competent, but you're so conscious of the learning, to get into a place of maturity in that discipline where it's coming second nature to you. And that's a different type of flow.
So when you have a team that has found both group flow state, where they're familiar with one another, there's a shared purpose, the communication frameworks are there. And then you have the people who are able to move from that unconscious incompetence to unconscious competence, and they're flowing in their natural state. That's where you kind of get the meeting of the two.
And then having a system that allows people to go through those stages. When they find something new, they are able to talk about it, share it, figure it out, and flow through the different stages that way too. So that's that continuous improvement, continuous development idea that was really an aha for me when working in product and engineering.
How do you help organizations systemize that? If you've got a junior designer, developer, strategist, product manager, or aspiring product manager, somebody who's coming in who does think, I need to stay inside my lane and do the tasks that I'm told to do, how do you encourage that? Because someone needs to be wanting to stretch themselves, right? And then having the work there to challenge them, but not so much that they can't rise to the occasion.
Right. But they get outside of that flow zone comfort, where the anxiety and challenge are out of balance. They're feeling too anxious with the challenge at hand, to where they just shut down.
Because we know you don't want people to become bored and just kind of complacent, and that can lead to burnout. So I think that flow state is in that sweet spot where the work doesn't feel like work, but it's not easy. But the challenges are aligned to kind of where you're at.
Right, you get that just right amount of stretch. And I think that's where it's in the micro moments every day with teams. Often it's classically set up as managers and people. And so the way you help the managers and people set themselves up for success with the micro moments, then that's the systems question, right?
And so the systems question then becomes: what's the purpose of this group or organization? How does that translate into what we want to do or what problems we want to solve, for whom, and in what time frame? So that's what you translate into a written mission. And then your vision is that longer-term aspirational idea connected to that core purpose.
And then the behavior system, whether it's written as values or core principles, these are the daily expectations and behavior that we want to see from people. And then those get translated into the other operating documents. This is our expectation of people managers. This is our expectation of people at certain levels of maturity in their career, or role level is often how it gets described in HR, your skills matrix and job families.
So that's where you take these classic operational systems, but you insert the combo of creativity and structure. And then your learning and development systems tie into that as well. Who needs the right information at the right moment to help them level up along the way, both individual and then the managers leading those teams?
It's true that managers create a lot of the climate that employees experience. So the better a manager is at recognizing where their individuals are on their own different flow journeys, the better each person does. The better that all levels up for the team, which levels up for the company, which levels up for whatever problem they're trying to solve for the market.