Unlocking Your Chief of Staff Story: Why It’s Harder Than You Think

By Guest Author Katie Montbriand

Whether you’re an aspiring Chief of Staff or already in the role, nailing your career story is necessary. But telling a compelling narrative about this role is not always easy. If you’re staring at a blank sheet of paper and willing a resume to appear, let’s examine why it might feel like an uphill battle. Crafting a narrative demonstrating why you’re a perfect fit for a CoS can seem daunting for the reasons listed below.

There’s no Set Career Path

Many roads can lead to the Chief of Staff role, which means there isn’t a set of previous experiences that neatly ladder up to this career. This differs from many specialist roles (first Junior Account Manager, then Senior Account Manager, then Account Director). Often, with the Chief of Staff role, the onus is on the candidate to show how the dots connect toward their desired role.

It’s Tough to Get Feedback About Your Story

Although the Chief of Staff role is getting more attention, it’s not well understood in the broader job market. So, unless your mentors or advisors have some exposure to the role, they aren’t well-equipped to help you position yourself to land in the CoS seat.

No Two Chief of Staff Roles Are the Same

While there are foundational skills and elements of the role, each organization may look for a slightly different skillset or position the role to solve a unique set of problems. No set list of skills and keywords fits into every Chief of Staff profile.

Hiring Managers Are Unfamiliar with the Role

Often, the person hiring for the role hasn’t done it before. They are skilled at whatever discipline got them to the senior executive position (sales, founding a company, product) but haven’t necessarily been in the CoS seat or worked with one. It can be challenging to connect with people who don’t have a deep understanding of what a CoS can do the way a finance executive can relate to managing finance professionals.

You Don’t Have the CoS Title on Your Resume

When you combine ‘new to the role’ with ‘no two roles are the same,’ you need to show that you’re qualified and capable by triangulating your past experiences. This double disconnect means more storytelling responsibility for you as the candidate!

Storytelling can still feel challenging even when you’re already in the Chief of Staff role.

Whether looking for a lateral move or thinking about your career steps beyond the Chief of Staff position, you have hurdles to navigate.

Your Work Isn’t as Visible

Much of what you do is in the background or unknown to anyone outside your immediate leadership team circle. While the organization knows, feels, and appreciates your presence, it can be challenging to translate that into quantifiable achievements on a resume.

Outcomes Are Unique

It’s difficult to measure things like culture shifts, how change management was less disruptive than usual, or that the leadership team was finally aligned and moving in the same direction. In a resume or profile, you have to describe these types of accomplishments for non-CoS audiences.

People Make Assumptions About the Role

Because of the range of duties and expectations, you can’t assume people know what you were accountable for based on title alone. You first need to frame up the context of YOUR role and then layer on the accomplishments and results you are proud of.

Time in Role Can Be Complex

Sometimes, Chief of Staff roles have a specific term. When framing your story, there may be initiatives that you start but don’t finish. Or projects where you helped with strategy but not execution. You have to own and celebrate the impact you made while you served.

Building a Chief of Staff career narrative can be challenging. The key to standing out in a crowded job market is to focus on your unique blend of skills, smarts, and story. To learn more about Nova’s Chief of Staff Certification course, download the Syllabus. Nova also offers career coaching packages, in conjunction with the Certification course.

About Guest Author Katie Montbriand

Katie Montbriand spent a decade driving transformation at a Fortune 500 company. As Chief of Staff, she pioneered a first-of-its-kind team of ‘Culturists’ dedicated to enhancing employee engagement and fostering authentic workplace connections.

Bringing her passion for positive disruption to her latest venture, Lived and Loved, Katie enables people to access and share their career stories in innovative and impactful ways.