Category: Discussions

I keep hearing this same frustration from COOs. Different companies, same problem: “Every time we get busy, something breaks. I’m tired of fixing the same problems over and over.” That’s the most expensive way to learn about your systems. This conversation comes up constantly because honestly? Growth is supposed to be good news. But every…

I’m sitting in on a marketing-sales alignment meeting last week. About 20 minutes in, the CMO drops her frustration in: “You guys rejected about 59% of our qualified leads last month.” The sales director doesn’t even blink. “Because they weren’t actually qualified.” Now, I dealt with marketing a good part of my life. That one…

So this COO tells me about their quarterly efficiency review. He’s going through all their workflows with his team, and they get to this one approval process. He just looks at me and says: “We have a 3-day approval process for something that should take 30 minutes. I know it’s stupid, but I can’t figure…

I was talking to a CEO last week and at some point he just says: “I found out my team is putting client data into ChatGPT. I nearly had a heart attack.” That conversation stuck with me because honestly? This isn’t just happening at his company. Here’s what I’ve learned from talking to dozens of…

I was talking to a CEO last week and at some point he just says: “My best engineer spent 6 hours yesterday explaining our API to a prospect. That’s $500 of engineering time for a sales meeting.” That made me laugh, but also… ouch. I mean, we’ve all been there. You’re in a sales cycle,…