Look Before You Leap: The Benefits of a Job Shadow


The Chief of Staff role is dependent on an organization and its leader, but there is a very useful exercise to learn more of the ins and outs of the actual position. One of the strategies we recommend for an organization and its prospective Chief of Staff before starting a partnership is conducting a job shadow. Job shadowing can be an ideal way for a new Chief of Staff to gain insight into the daily operations and understand the day-to-day challenges of the position, while also building rapport with people and understanding how the various job functions fit into a larger context of the organization. In turn, the executive gets more applicable one-on-one time with their future Chief of Staff to also gain rapport and feel more confident and comfortable with the new partnership.

Here are a few of the key benefits of job shadowing for a new Chief of Staff, the executive, and the organization:

Gain an Authentic View

We know the title “Chief of Staff” is an adaptable, sometimes hard-to-define and frequently misunderstood job title; different organizations need different strengths and skills from their Chiefs of Staff. Hiring a new Chief of Staff can create uncertainty or ambiguity about what exactly is expected from the new hire, and sometimes both the new hire and the executive don’t know exactly how the relationship will work until it begins.  

This is why job shadowing is so valuable: it gives the new Chief of Staff the ability to form a more realistic opinion about the position, the executive, and the organization by better understanding the scope and nature of the job’s challenges.

With job shadowing, the future COS gets an immediate, real-time education on the company – both good and bad. There are many aspects of an organization’s operations that have to be experienced in-person to truly understand. Job shadowing is a great way to know more at the outset.

Build Relationships and Rapport

The job interview process has certain limitations, and one is that it can be hard to truly get to know people; ideally, everyone spends the interview process being professional and courteous, but many organizations struggle to be candid in this kind of atmosphere. For a new Chief of Staff, the best chance to build relationships and establish rapport with the executive and other employees often comes from job shadowing. The COS gets to be a “fly on the wall” for conversations, meeting people where they work, and seeing how they go through their day without a lot of pressure and scrutiny. Job shadowing gives the COS a chance to collaborate and bond with colleagues in an educational, low-key setting. They get to know the COS’ personality, too.

Get “Under the Hood” of the Organization

Job shadowing allows the new Chief of Staff to familiarize themselves with the technical and practical aspects of the organization. They can quickly learn the nuts and bolts of the company by job shadowing with various key roles and departments to understand work processes, meet key stakeholders, map out the interrelated structures of the organization, and otherwise figure out “what makes this organization tick.”

Learn the Personality and Culture of the Company

The new Chief of Staff needs to quickly become conversant in the intangibles of the company – the overall personality and culture, the shared assumptions, and ways of working that define the company and bind it together as a coherent organization. Managing a new company’s personality and cultural “fit” can be some of the most complex and daunting challenges for any new Chief of Staff. This is where job shadowing can be essential – the COS can meet the many different personalities and get up to speed on the shared “lingo” and corporate cultural patterns even before they begin the role.

This shadowing process only continues once the COS begins the job. As they adapt to their new role, they learn even more about the organization’s cultural fault lines. Understanding the new company’s sense of itself, and how people find meaning from their roles within the larger team, is essential to being an effective Chief of Staff.

One of the best ways to make a great first impression as Chief of Staff is to conduct an earnest effort to meet and learn from as many people as possible. Job shadowing is a great way to accomplish this. The job shadowing experience provides a precious education that can be used to get the most out of your new Chief of Staff role, while maximizing the Chief of Staff’s value for the company.

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