• You've talked about the difference between being busy and being effective. What do you actually see when someone on your team is online at 10pm on a Sunday, is that a green flag or a red flag for you?

• What does "working for results" actually look like in how you set expectations at Chaser? Is it built into how you hire, how you review performance, how you run meetings?

• What's the most uncomfortable piece of feedback you've given someone that you think genuinely helped them? What made you deliver it instead of staying quiet?

• How does your team know you see them? Their work, their growth, their effort?

• What is the most humane way to fire someone, and what makes most companies get it completely wrong?

• How much of your own day have you actually automated, and what do you refuse to automate? Where's your personal line?

• AI can now write empathetic emails, personalize payment reminders, mimic human tone. Is that good for business relationships, or are we building something we'll regret? Why?

• The "always on" CEO is still glorified in a lot of startup culture. What do you think it actually signals about a leader who can't switch off, and is it ever a green flag?

• Tell me about a moment where your marketing instinct told you something completely different from what the data said, and you had to choose. What happened?

News and Updates

• What book(s) or article(s) did you read this past month that stayed with you? What takeaways do you have?

• What event(s), talks or experiences did you attend this past month that stayed with you? What takeaways do you have?

• What podcast(s) did you listen to this past month that stayed with you?