Building a Strong Chief of Staff-Executive Relationship

At Prime we talk a lot to clients and candidates about the importance of a strong relationship between a Chief of Staff (COS) and an executive. The reason is, without it, the relationship is a bust. The COS can’t fully do their job and the executive is left doing work they shouldn’t be. Building a strong relationship takes effort, on both sides, and is important to establish early. Below are ways COSs can begin building a strong, trusting relationship with their boss.

Get to know each other

It seems obvious, but sometimes goes overlooked. As professionals, we tend not to get into our personal lives, interests, and activities with our bosses. However, this intimate relationship in many ways blurs the line between personal and professional life—for both the COS and the executive. Therefore, it is important to build a relationship on personality first. Spend time learning about each other—backgrounds, upbringings, food, sports, fashion, whatever—during commutes, down time, or over a meal. Find commonalities where you click and also where you differ. A strong relationship begins with liking and respecting each other.

Take a listening tour

This is what we call it when a Chief of Staff begins their new post—it’s observation mode. When starting a COS role, the first few weeks and even months should be spent listening and observing. This “tour” demonstrates your natural curiosity and humility. It also helps you gain a solid understanding of how things operate—including how your executive works and how they like things. Getting this baseline prevents errors, stepping over lines, or rubbing your executive the wrong way by initiating change too early.

Focus on small wins

Small wins are a great way to develop a relationship when working for someone new. We all like to prove ourselves by jumping into a big project to show our chops, but it's simple tasks that we do (and do well) that show an executive we are versatile and competent. These small, simple tasks—like writing a good thank you note or creating detailed meeting briefs—are quick to accomplish and demonstrate your ability to take direction and execute on it. When you fail to do the small things right, executives are not comfortable handing off bigger responsibilities.

Take good notes

Yes, we are talking about actual notes on a notepad. Executives are usually spouting off thoughts and directives regularly, and while you think you have everything understood, you go back to your desk and realize you aren’t sure if they said this or that. Don’t let that happen to you. Bring a notepad and pen to every single meeting and interaction and take copious notes. Even with a steel trap mind, it provides assurance to your executive that everything is being captured and taken care of.

Be candid about mistakes

With all the finger pointing and blame passing people do in an office, there is little more refreshing to an executive than hearing, “That mistake was mine. It won’t happen again.” (Obviously, that doesn’t work for catastrophic errors, but they rarely are.) You will make mistakes in this position. You will. The best Chiefs of Staff understand this fact, take accountability for their errors, and prevent them from occurring again. You build a lot of trust with your boss when you do things well, but also when you take responsibility if you don’t.