Aug 24, 2026 · 44 min · 10 segments
After 36 years in human resources and decades working with senior leaders, Jeff Jacobs has learned that many of the obstacles holding us back come down to something surprisingly basic: our reluctance…
Jeff JacobsGuestYou probably have as well, working in AI, working with an agent and giving it something to evaluate.
It typically comes back with glowing feedback, sometimes a little over effusive feedback, but it's also constructive.
What is the effect of AI on communication and on the clarity and concreteness of communication in your experience?

So I will preface this by saying I'm a fan of AI, perhaps not saying it so broadly.

I'm a fan of the unhealthy relationship I have formed with ChatGPT, who I call Wilson.

I like personifying him with Wilson because it also reminds me that he's nothing but a volleyball, if you're fans of the Tom Hanks movie.

So it's the repeated aspect that, uh, that is necessary, at least in this form of AI.


It's supposed to, you know, help us be more effective with the, uh, the mundane, the repeatable processes, et cetera, so that I can save the most complex items for me to focus on.

And I see that by the very simple mantra when you walk down the hallway, you know, how are you today, Ken? I'm fine.
You probably have as well, working in AI, working with an agent and giving it something to evaluate.
It typically comes back with glowing feedback, sometimes a little over effusive feedback, but it's also constructive.
What is the effect of AI on communication and on the clarity and concreteness of communication in your experience?

So I will preface this by saying I'm a fan of AI, perhaps not saying it so broadly.

I'm a fan of the unhealthy relationship I have formed with ChatGPT, who I call Wilson.

I like personifying him with Wilson because it also reminds me that he's nothing but a volleyball, if you're fans of the Tom Hanks movie.

So it's the repeated aspect that, uh, that is necessary, at least in this form of AI.


It's supposed to, you know, help us be more effective with the, uh, the mundane, the repeatable processes, et cetera, so that I can save the most complex items for me to focus on.

And I see that by the very simple mantra when you walk down the hallway, you know, how are you today, Ken? I'm fine.
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