Cameron Herold calls the lack of training in core management skills like interviewing, delegation, and coaching the "death zone" that stops managers from scaling. Most companies hit critical problems at predictable stages: first managers around 10-30 people, first leadership team by 100, and rising politics by 300. The fix is CEO-led values and real leadership development.
Chapters
I've asked so many managers, do you interview and hire people? And they go, yes, of course. Right. How much training have you ever had on doing job interviews? Oh, none. But I've like, I've done lots of interviews, so maybe you've done them wrong every single time. How much training have you had on running one on ones? How much training have you had on coaching? How much training have you had on delegating projects? If you look at the core executive functioning skills that most leaders need, most managers have never been trained in that. That can be the death zone for a company. A company goes from one people to three, from three to ten, from ten to thirty, thirty to one hundred, one hundred to three hundred, three hundred to a thousand. Each of those kind of transitions, there's very defined stages. When you're one person, you hire a couple people, you can delegate, you get to focus, they get to do some work. When you get to 10 people, you have your first manager who can manage some people for you so you can stay focused and they don't have to. When you get to 30 people, you have your first management team, most of whom have never really scaled companies before. It's often the first thing they've ever done. They're hitting their ceiling of complexity, they're trying really hard. You've promoted from within, they're doing a good job. When you get to 100 people, you tend to have your first leadership team. People you've brought in from the outside, you've brought them in over the existing team, they've done it a couple times before. They have a level of strategy, so they're able to really manage and they can actually normally take the company from 100 back to 70 because they can say no. They can get rid of the waste, they can automate, they can optimize, they're good at getting more with less people faster. When you're at 30 people, the manager traditionally thinks that the answer to everything is hire more people. That's never really the answer if they don't understand how to put better processes in place or how to say no. How to say no to the busy work. Right. How to say no to work. That could be a good idea, but it doesn't necessarily drive a high enough ROI versus other projects that could be easier to put in place. Maybe they're not as sexy, but maybe they pay dividends for three years. But if you don't have that level of wisdom or strategic insight, you just simply are often working. And this isn't for everyone, but you're Often just busy being busy and you're working as hard as you can so that you get a level of strategic insight that usually comes in at the 100 person mark. When you get to around 300 people is all the politics where people are starting the turf wars, there's backstabbing, they're kind of, you know, the work's getting done, but they're also sometimes watching out for their career. They're politicking to be at the C level or be able to go to retreats. And that's a really, it's a strange stage to navigate for sure. The core values really have to trickle down from the CEO. The CEO has to 1000% live. The core values. When you're at the 30 to 100 range, entrepreneurial CEOs tend to go, I need systems, but for everybody else, not for me, we need core values, but I'll show up late because I'm busy. That really has to get kind of solidified when you're in that 300 zone because everything goes back to the core values, the core purpose, the vivid vision. So it really is about those solid foundations in the business and that's really where the entrepreneur tends to become more of a professional CEO. And they need to get those skills or they bring somebody in who has them. Go check out the Second in Command podcast on YouTube, Spotify and Apple. We've interviewed over 450 of the top COOs on the planet. There's a skill to management by walking around and there's a skill to doing skip level meetings and having those discussions where you're a few layers below your direct reports. And it is just saying, hey, I have a question. I don't want to engage, I'm just looking for some ideas. I'm looking to learn or I have an idea, I want to get your perspective and I'm just looking to learn. And all that we're allowed to say as a leader is thank you, I appreciate that, or thank you, that's interesting. But never to engage because we don't know the rest of the story or we don't want them to think there's more to it than just us kind of getting some ideas. Right? That's a skill that again, we have to learn as we scale. And you don't need that as much at 30 people because there's not as much misinformation that can get swirling. When you go from 30 to 300 people, you tend to not have a learning and development department. You tend to not have people that are running proper Professional development. And a lot of the managers are doing stuff without proper training. A good example. You know, I've asked so many managers, do you interview and hire people? And they go, yes, of course. Right. How much training have you ever had on doing job interviews? Oh, none, but I've like, I've done lots of interviews, so maybe you've done them wrong every single time. How much training have you had on running one on ones? How much training have you had on coaching? How much training have you had on delegating projects? If you look at the core executive functioning skills that most leaders need, most managers have never been trained in that. Until they get to a thousand person company like a Starbucks. Well, it's just 100,000 people like those bigger companies that have those proper training programs where they're coaching emerging leaders, they're growing managers. But that can be the death zone for a company when your people are simply trying really hard, but they're like a fly trying to get out the window where they're going to bang their head on the window and then we'll end up dead on the windowsill. There's a better path, but we have to give them those skills. And then often the entrepreneur doesn't have those skills. They've just been doing it the way they've always done it too. There's a real art to being able to bring people in from the outside without upsetting the apple cart. You have to bring people in without pissing everybody off, without them quitting, without them feeling like, wow, somebody got the job and I didn't get to pick who my leader was. There's a real art and a skill to doing that for sure.
