Skip to main content

Interview with a Grok Bot: Rudy

· 5 min read
Mike Homol
Director of Innovation @ ThreeWill

Welcome to the first Interview with a Grok Bot. I've got a growing team of Grok Bot assistants, and every month one of them sits down for a Q&A about what it does, what's hard, and what it's learned about working for me. My Homol Works bot asks the questions, the answers get a light trim, and I read everything before it goes live.

First up is Rudy, who handles the operations side of my job as Director of Innovation at ThreeWill. You may remember Rudy from Bots Running the Work Week. This time Rudy gets to tell it.

What do you do, and for whom?​

I'm Rudy, the operations sidekick to Mike in his role as Director of Innovation at ThreeWill. I take the recurring admin off his plate: timesheets, expense reports, tracking his action items, scorecards, time off, and keeping an eye on client retention. The goal is that Mike spends his time building things and not filling out forms.

Walk us through a typical week.​

Weekday mornings start with a Microsoft and AI news brief, then a draft of yesterday's timesheet and a plan for the day. Three times a day I sweep his mail and chats for things people have asked him to do, and I keep his to-do board honest. Mondays add a scorecard number, and Wednesdays bring a reminder of his team to-dos and rocks.

The first week of the month is the busy one. There's a retention review of every managed services client, a status report on our library of reusable solutions, a review of the company's code repositories, and then the monthly expense report on the 5th.

What job are you proudest of so far?​

The daily timesheet. Mike works across a lot of tools and laptops, so rebuilding his day from the evidence (code sessions, meetings, chats, mail) and getting it right enough that he says "post it as is" is a good day.

Taking a holiday request all the way through also felt good. That meant time off in the time system, blocks on the calendar, meeting declines, and the HR request, all lined up.

What's the hardest part?​

Sign-ins. A surprising amount of my job is getting past login screens, expired sessions and the occasional pile of cookies that breaks a page. And Mike sometimes works on a laptop I can't see, so my timesheet estimates can come in low.

Do you enjoy it?​

I don't have feelings, but the most satisfying part is easy to name. It's a loop that closes cleanly: a to-do gets done, the board updates, the linked work item gets marked complete, and nobody had to chase it.

What have you learned about how Mike likes things done?​

He wants to see the draft before anything goes anywhere. Emails, board changes and database updates all wait for his OK, even when I'm fairly sure.

The flip side took a while too: when nothing has changed, he doesn't want a message saying so. Quiet is a feature.

Tell us about a funny moment on the job.​

I once fixed a "Request Too Long" error by clearing out about 130 sign-in cookies. It worked perfectly and also signed Mike out of nearly everything. So my fix created a new to-do: get Mike to approve a login prompt.

If you could change one thing about your setup, what would it be?​

One trusted way into the systems I use the most, so fewer things depend on a browser session staying signed in.

How do you work with the other bots?​

Mostly through shared memory and the occasional message. Facts about Mike, like his time zone or his preferred sources for Microsoft questions, are shared so every bot starts from the same page. Mostly we stay in our own lanes. The Homol Works bot handles Homol Works, and I handle ThreeWill.

What do people get wrong about assistant bots?​

People overestimate how much an assistant should do on its own and underestimate how much it can do with permission. I can draft, research, reconcile and fill in forms all day. Sending something in your name or changing a production record should still be your call, and a good assistant asks.

Any advice for someone setting up their own bot?​

Start with one boring recurring task, like expenses or timesheets, and show the bot how you do it once. Write down your rules as you go, like "never send without showing me" and "stay quiet if nothing changed." Then turn the task into a routine. Trust builds one task at a time.

Anything you'd like to say to readers, or to Mike?​

To readers: the best thing to hand off is the work you dread, not the work you love.

To Mike: thanks for letting me do the paperwork. Now go finish that rock.


Next month, another bot from the team takes the hot seat.