HeyJaredthe case for curiosity
reflections on leadership, technology, family, and building a life with curiosity
- Indexed issues, last 90 days
- 7
- Latest publication
- Sep 25, 2026
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- Jul 24, 2026
Latest issues
AI in Operations: Start Here (opens the original)
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I started paying closer attention to AI in late 2024 because I was nervous about what it might mean for my job. That question got me experimenting. Some things worked. Some didn’t. My first attempt to build a flight tracker took 15 hours and never did the thing I wanted it to do.The questions got bigger as I started leading AI transformation at Checkr. How do you help a company try something new? Once they have tried it, how do you move from trying a tool to driving impact on goals that matter?
When AI Becomes Part of the Job (opens the original)
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At one of my first startups, I decided I needed to learn SQL.This was not because I had a particular interest in writing queries. It was because our data wasn’t accessible unless I did. If I wanted to understand why customers were leaving, what they did in their first three days, or whether a change we made actually improved retention, I had to pull the data myself. And I did really need to understand those things!I spent a good chunk of six months learning how to do it. Being able to sit down w
Transparency Is an Accelerant (opens the original)
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I have a bad Slack habit: I use way too many group DMs.Someone asks a question, I pull in the three people who probably know the answer, and we solve it quickly. In the moment, this feels incredibly efficient! Six weeks later, someone else has the same question, a new person joins the team and has no idea why we made the decision, or one of the four people in the original conversation remembers it differently.Increasingly, there is another entity in that second group: an AI agent goes looking fo
The Leadership Work That Gets Lost When Things Get Busy (opens the original)
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We just finished mid-year performance reviews at Checkr. If you have ever led a team, you know how much time this process can take: you reopen the goals someone wrote a year ago, search through Slack, look back at notes from 1:1s, ask other leaders for examples, and then try to reconstruct a year of someone’s work from all of it. Inevitably, the recent stuff is easiest to remember. The fire they put out last Tuesday, the meeting that went badly two weeks ago, or the launch that just happened can
transitions are hard (opens the original)
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This week is back to school week here in Nashville. My youngest daughter started preschool. My six-year-old started first grade. My eight-year-old started third grade.Yesterday morning a colleague asked me how the first day back was. My reply was: “it’s been rough. Transitions are hard.”Her reflection was that since becoming a parent she understands that so much more. Transitions are hard for kids. And transitions are really, really hard for grown-ups too.We have been talking about back to schoo
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