The $400,000 Chief of Staff Is CEO’s Secret Weapon in the AI Age  

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2:01Carol Massar:Bloomberg Audio Studios. Podcasts, radio, news. You're listening to Bloomberg Business Week with Carol Masser and Tim Stenevek on Bloomberg Radio. We have a great story we want to get to. We've been talking about this a lot. We haven't. It's been on the terminal. We've been like, we got to get to Matt Boyle and talk about it. It has a growing number of corporate leaders buckling under the stress and uncertainty of the AI age. I would argue that's why they get paid millions, are looking for a very human solution. And that is a chief of staff. If you want to know how hard it is to be a CEO right now, you can check out another one of Matt's recent stories as well.

2:37This one, though, is about a chief of staff. Matt Boyle, senior reporter, work in management for Bloomberg News. He joins us here in the Bloomberg Interactive Brokers Studio. What the heck does a chief of staff do? Kind of everything, I would say. Yes, it is one of the most unique roles I've ever looked at in sort of the C-suite. and I guess it is in the C-suite. It's legit. They're attached to the hip, to the CEO or the division president, whoever they're working for. But let's say a CEO, you have to be a concierge. You have to be a confidant. You have to be a consigliere. You have to be kind of everything, but it all comes down to another C word, chemistry.

3:11If you do not get along with the boss, the CEO, it's never going to work no matter how talented you are. Who are the types of people who are successful chiefs of staff? Imagine you combine, like the best executive assistant of all time with like a strategic genius from McKinsey. And you might get a great chief of staff because one day they're just sort of like answering emails or they're writing a speech for the boss. The next day, the CEO is like, oh, we got to enter, you know, the Chinese market. Go figure it out. Or, you know, or there's there's a problem on the factory floor. Go take the pulse of all our factory workers and report back to me.

3:48So like they are thrown onto these complex assignments with literally usually no notice. and they just kind of have to figure it out.

3:55Carol Massar:How often does a chief of staff grow along with an executive who ultimately becomes CEO and the CEO like tags them, takes them along as they move along? Well, yeah, I spoke to one woman who did the job for both Jeff Bezos and Eric Schmidt. So if you get a taste for it and you're in certain circles like tech and the word gets out that you are a very good chief of staff, you can do it for some time. Although the median tenure is only 2.3 years because I mean, a lot of times they might burn out or there's no chemistry with the CEO. Right. You're also at their beck and call. Exactly. It is a 24-7 job.

4:26Your time is not your own. I have been friends with some chiefs of staff, and we've been out for drinks at 11 o 'clock at night, and there's a call coming in. Oh, got to go. My boss. So, yeah, it is a tough role, but it's done by highly ambitious people who want to use that job as a springboard to something even bigger.

4:43Carol Massar:Where do they go? They often go into the C-suite proper. It's because they are roaming around the company and they know all the inner workings. The next job can be often the chief operating officer, certainly. Or you're running a business unit, a unit of the company you are at. Sometimes you just become a chief of staff again. But the real ideal is to leverage that into a C-suite role. Are men or women better chief of staff? Sorry, Tim. I'm just curious. Loaded question. Yes. I don't know if it came up at all. I wish I had some stats on it, although there's a lot of statistics out there. There's a whole chief of staff association.

5:18There are executive recruiters who just hire for this role. So I never got any sort of real, like sort of hard, like, you know, gender breakdown on it. But it's less, I think, to do with demographics and just more to do with, you know, how competent are you? How much are you able to sort of put your ego aside? Because these are all ambitious people who probably want to be CEO one day. But if you are the chief of staff, it is not about you. You know, so my experience with chiefs of staff come from my work many years ago working at the Huffington Post. And Arianna Huffington had chiefs of staff.

5:51And it's pretty remarkable to see where they went after. So one of her chiefs of staff, Dan Coe, went to go ahead and run for Congress. He ultimately lost. But then he became Marty Walsh and Boston's chief of staff when he was mayor of Boston. And then he went to work in the White House. Herbie Ziskin went to work in the White House as well for Kamala Harris for the vice president. I mean, it's really remarkable to see where these— That's pretty impressive. Look, that's an N of two. That's an N of two. But it's also a much more common rule. You mentioned White House to see this in political circles, particularly the West Wing.

6:25You think of the show, the West Wing, you know, the chief of staff on that show was a hero. But it really has moved from politics—well, it started in the military, then to politics, then to big corporates. But now, like, startups have chiefs of staff. Microsoft has more than 300 chiefs of staff running around Redmond and the world. I don't know exactly why. Why do you have so many? Good question. They wouldn't talk to me. I don't know why. But there are usually more of them in tech and financial services circles. For some reason, you're going to see more of a preponderance of them. But 300 kind of blew my mind.

6:59Why does the role take on different significance in the AI era? Well, let's see. I mean, the CEO is trying to figure out AI. We all are trying to figure out AI. The role of the CEO is so much more complex. You've not only got AI, you've got geopolitical chaos going on. You need someone, let's say, with AI. Okay, how is this going to change how we work? What sort of governance do we need? What about all these tokens? How expensive are they? And I know, obviously, some of those decisions will fall under a CFO or an HR chief. But a good chief of staff can grab some of that AI adoption responsibility and just run with it.

7:32And if you're suddenly the point person on AI in a big corporate, you're looking pretty good.

7:37Carol Massar:What was the wildest thing that you, in reporting this out, that you came across? Well, I came across some old friends of mine from high school and college who have done this role and are certainly good at this role. But what got me was the professionalization of it. There are courses at Harvard Business School and Oxford about becoming a better chief of staff. McKinsey runs a forum where all chiefs of staff just show up and they kind of just trade notes and kibitz and talk about the job. Can you imagine the energy level of those people? Oh, my God. A lot of type A. A total type A. It's one of those things.

8:10Carol Massar:Do you want the wine flowing or do you not want the wine flowing? Yeah. Because you think about how much access they have and what they hear. They are in the room when things are being said. Journalists would love to be able to fly on the wall of the chief of staff forum. Right. Do you think this lasts? You know, this stuff can kind of be fads. Yes, you're right. Some C-suite roles are kind of fly by night. Not this. I mean, this role goes back to Napoleon. I don't think it's going away anytime. As long as there are CEOs, there will be chiefs of staff. $400 ,000, is that? That was a little bit of an outlier.

8:40It's more common to be like, but still, you're making six figures.

8:43Carol Massar:Yeah, I was thinking you should be paid even more. Yeah, I'm thinking more, too. Well, some of them certainly get more. Now, those are just the posted roles. Some of them are never posted because they know exactly who they want. And they might be making half a million. Who knows? But commonly median salaries, you know,$250,$300, still a nice chunk of change, certainly. But some of them could easily make far more. And then it's what they can make after that that is really impressive. I could just imagine the documents they have to sign. I mean, the documents they have to sign, they have to get the lunch order right, too.

9:13I mean, don't forget that.

9:14Carol Massar:Hey. Let me just tell you guys something. I would be the worst chief of staff. Would you? Oh, yeah. I think you'd be great. No. Why do you think so? I don't have the organizational prowess. You need to be so organized. You do need that. I mean, a lot of journalists are organized, but a lot of journalists are badly organized. So like, yeah, it goes both ways. It's also why I could never produce this show. I think I'd be great. I'm not organized enough to do that. I think I'd be fun. Go for it. Go for it. No, no. I'm really happy. I'm really happy here. Matt Boyer, we love you. Senior reporter, work and management for Bloomberg News.

9:48When you're running a business, the best days are the ones where priorities stay on track. For midsize and large companies, risk can affect multiple parts of the organization at once, from property and liability to cyber and regulatory challenges. At that level, managing risk becomes an ongoing discipline. At the Hartford, the focus is on helping businesses manage risk before it turns into something more disruptive. And when losses do happen, that work is paired with insurance coverage shaped by years of underwriting, risk engineering, and claims experience. Learn more at the Hartford.com slash risk mitigation.

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