My two most recent hires were generalists, not specialists. Here’s why I think t
By Allie K. Miller · February 14, 2026 · Curated by George's Blog
My two most recent hires were generalists, not specialists.
Here’s why I think that matters in the AI age and the most important skill they can have.
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1. stuff moves quickly, a generalist presumably is more able to adapt because they can see the patterns/connections and abstract a helpful framework faster (example: in their first couple weeks, both hires were building with Claude Code in the loop. That “AI is part of the job” default is exactly what I’m optimizing for)
2. related but perhaps more important, they are also more willing to adapt. Their identity is not overly defined by tasks. The switch from task to management has low friction. They more easily move with the tide. There’s no “that’s not my job” mentality
3. we’re a small team so we were already more likely to hire a generalist than a specialist
4. they immediately understand the expansion power of AI and desperately want to take advantage of it. There’s no “stay in your lane”, it’s more “stay on your highway” with many options and opportunities
Generalists with curiosity, goal-orientedness, good pattern matching, taste and judgement, intentionality, management, and strong communication skills (to both humans and AI) are well positioned for the AI age.
But the BIGGEST advantage to have…
The MOST important skill I want them to have right now…
It’s the opposite of Imposter Syndrome…
I’m calling it Pro-poster Syndrome.
It’s a semi-delusional optimism that every wall, every blocker, every obstacle is one prompt away. Or at least worth a try.
It’s going from “I can’t” to “hmmm maybe I can” to “Hell yeah! Why not me with some help from Claude, huh? Stand back and watch!”
It’s bias for action and bias for capacity.
Unfortunately, this still isn’t how people look for jobs. And it’s also not really how people refer friends for jobs.
Everyone is still in a 6-word long job title mindset (“senior industry SMB sales for herpetologists”) and less zone-of-influence oriented (“sales” or “field”).
I absolutely think we will see more enterprises hire generalists to be Swiss Army knives with AI across a function or department. It’ll just be interesting to see how they actually recruit for that.