Amanda NorthcuttFounder & CEO | Keynote Speaker, LevelUp · B2B sales as a solo is HARD. I’ve got you. I help consultants & coaches sell high-ticket services comfortably & confidently, while enjoying consistent, predictable revenue | Founder & CEO | Speaker |

The Chief of Staff Challenge Every CEO Faces

24 Sept 2025 · 1 min

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In this monologue, the speaker—an experienced advisor who works closely with CEOs—highlights two persistent challenges that chiefs of staff (CoS) encounter. First, CEOs frequently ask how to quickly onboard and train their new CoS, seeking recommended resources, courses, or structured onboarding programs. Second, CoS often struggle to assess their own performance because the role lacks clear, quantifiable metrics such as sales quotas or standard KPIs, leaving them to rely on informal signals like the CEO’s satisfaction. The speaker notes that this ambiguity forces CoS to figure things out on the fly, making it difficult to gauge success despite apparent alignment with the CEO’s priorities.

Chapters

You know, it's still something that I'm very involved with today, and I love talking to CEOs, understanding what it is that they need. The kind of very natural follow-up after you place somebody is twofold. The CEO then asks you, how can I get my chief of staff, you know, up to speed? Are there any resources? Are there any onboarding? Is there something like a course that my chief of staff should go through so that I can really make sure, you know, they are getting onboarded as quickly as possible? And then the kind of unspoken part for, I think, what many chiefs of staff experience, which is something I went through as well, was like, I don't know if I'm doing a good job. This is not a typical role where you have the same kind of metrics or like sales quotas or, you know, kind of metrics that you can measure your role by. And so, there's a lot of kind of figuring it out on the fly and trying to figure out, okay, I think I'm doing a good enough job. My CEO seems happy, you know, they seem like they're working on the things that they want to work on, but it's sometimes a little bit hard to quantify.