The 3 Biggest Problems Every COO Faces (And How to Escape the COO Trap)

Cameron Herold identifies three problems COOs face: CEOs who break the systems they demand others follow, teams drowning in busy work instead of ROI-driven tasks, and CEOs meddling in areas out of boredom. He offers concrete fixes: hold CEOs accountable, delegate with explicit time constraints like 60 minutes, and teach CEOs to run structured skip-level meetings.
Chapters
What's the biggest challenge that you're having as a coo? Let me guess. I'm going to walk you through what tend to be a few core problems that most COOs struggle with. Number one is their CEO wants the company to have systems, but not for the entrepreneur. The entrepreneur shows up late for meetings. The entrepreneur doesn't follow any of the systems. The entrepreneur breaks the rules, but wants everyone to follow the rules. That's a problem that many organizations have. Your job as the COO is is to ensure that the CEO is following the systems and they understand that concept of what's good for the goose is good for the gander. Right, that they have to follow the system so that other people in the organization will follow the systems. They have to understand that when they show up late for a meeting, what they're really saying is not, sorry, I'm late, but f you, I'm disrespectful. My time's more valuable than yours. So your job as the COO is to show them that. Another problem that often COs have is that people are busy working on busy work, but not necessarily productive and getting enough work out the door. Well, our job as a leader is to ensure that when we delegate projects to people, we show them how little money we want them to spend on the project and how little time we want them to spend on that actual project. And here's what I mean. When you delegate a project to somebody, you can say something like, it'll only take you an hour to do the project, but they're going to debate you, they're going to give you all the reasons why it's going to take more than an hour. So. So flip the script a little bit on that. Instead of saying, this project will only take you an hour, try saying, this project is something I only want you to spend an hour on. Don't spend any more than 60 minutes doing this project. Whatever you get done in 60 minutes is good enough because at the end of the day, I want you to spend the critical few hours and the critical limited amount of money to get the result or the ROI off that project. But if you spend five hours on the project, you it's costing us too much time vis a vis all the other things that we could be working on. So that's a big problem that often COOs have is that their team aren't necessarily focused on those kind of core areas. The third thing is the CEO ends up meddling in different business areas, often because they're bored, because they don't know what else to focus on or they've done it before and they see a problem and they don't know how to stop themselves by jumping into that area. So your job as the CEO is to teach the CEO how to do a proper skip level meeting. A skip level meeting is how they skip over one of the direct reports. Maybe they don't talk to the VP of marketing and they go meet with the people in marketing, but there's an actual elegant way to do that. The CEO can go and skip over the VP of marketing and talk to the people in marketing by saying, here's some things I'm noticing. What do you think? Here's some things I'm noticing. What are we doing about that? Here's some things I'm noticing. What are your thoughts around that? Tell me what you're thinking. Tell me what you're seeing. And then the CEO's job is just to say, thank you for those ideas, thank you for what you're sharing. And then bring those ideas back to the VP of Marketing or bring those ideas back to the coo. But the CEO can't engage. Yes, we have to do that. Yes, we should do that. That idea is amazing because you never know the rest of the story. So COO's often bump into the CEO that is meddling in parts of the organization without understanding the rest of what's really going on. And then when you bring it up to the CEO, you often hurt their feelings. They get their back up against the wall, they get frustrated and they point the fingers back at you. So your job is to teach them the skills of actually being good at running skip level meetings. Hope those three things help.
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