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Paul Cheek

Paul Cheek

Senior Lecturer at MIT Sloan and Executive Director of the Martin Trust Center for MIT Entrepreneurship; bestselling author of Disciplined Entrepreneurship: Startup Tactics and founder of the AIDE Institute.

Sep 17, 2026

20:35
So dive in on those two things, because we're right, we're right on top of those two things.
20:40
Oh, I love it.
20:41
I love it.
20:41
And we got to start with ROI.
20:44
The return on investment with AI, it's something that everybody's looking at and thinking, where's the short-term ROI? We're not seeing it.
20:52
Are we looking in the wrong places? Are we doing the wrong things? And the thing that I always come back to, Willie, is the fact that when a high school student decides to go to university, they say, I'm going to go do, let's just say for sake of example, a four-year undergraduate degree.
21:09
They're making a significant investment of time, let's say four years, and money, the cost of tuition, right? And when I think about that, I think they're doing that.

7 MINS LATER

28:40
What are some of the either tactics, tricks, hacks that you've seen scaled organizations take to be able to get both the board and the C-suite on that learning curve?
0:00
Now, I know you asked about org structure and things like that.
0:03
I want to pause there just on the model.
0:05
We can go into the definition of what an organization is becoming.
0:08
We can go into the state-of-the-art org chart.
0:10
But I might pause there just for any reflections you might have on that model and how you see that manifesting for SMEs.
0:17
Because the folks you work with primarily are those SMEs.
2:02
But I haven't met anyone yet who has AI deeply embedded in their organization.
2:08
Well, this is the number one question I get from executives.
0:20
What does this look like? If you describe to our leaders the traditional org structure, just so that we're all aligned on what that looks like, and then how that differs from the AI-driven enterprise.
0:31
Yeah, and we can talk about org structure and org charts and things like that, how we organize.
0:36
But I want to maybe start with the model, the definition, and then how that manifests within a company.
0:44
Love it.
0:45
The model.
0:46
traditionally, we've looked at two primary models of business and business growth.
0:50
And one would be the SME, the small medium enterprise that scales linearly with limited upfront resource requirements, serves a local or regional market, but it hits a capped level of growth.
10:07
So what does this look like if you describe to our leaders the traditional org structure, just so that we're all aligned on what that looks like and then how that differs from the AI driven enterprise?
10:19
Yeah, and we can talk about org structure and org charts and things like that, how we organize.
10:24
But I want to maybe start with the model, the definition, and then how that manifests within a company.
10:32
Love it.
10:33
The model.
10:34
Traditionally, we've looked at two primary models of business and business growth.
10:37
And one would be the SME, the Small Medium Enterprise.

29 MINS LATER

40:02
What's your vision for the organizations of the future? What does a workplace look like and what work are people actually doing? When you're sitting back on, I see a world that looks like, what does
26:45
I love that example.
26:46
But no, like a concrete example, I want to come back to your question, but I think it's important to flag that up front.
26:51
The simplest example would be whatever KPI they have in front of them.
26:56
Now, I would also say many people jump to something that is not actually an organizational priority.
27:01
And we could talk about the four characteristics that I look at for any opportunity to use AI.
27:05
But...
27:06
I see a lot of people who look at whatever that very clear KPI is in front of them.

35 MINS LATER

62:13
And then, like, what's an example that maybe surprised you and what did you learn from it?

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