In my ten years as Chief of Staff (heck, in my 20 or so years of professional life), I’ve made plenty of mistakes. Now, many months removed from my role as Chief of Staff, I’ve had some time to reflect on some of the things I would have done differently as a leader, and more specifically, with my relationship with our Executive Assistants over the years.
I’m such a big believer in the power of partnership between a leader and their right-hand Force Multiplier. But the power of partnership doesn’t just apply to an executive and their Executive Assistant (EA) or a CEO and their Chief of Staff. It is just as important for an Executive Assistant and Chief of Staff to develop a strong working relationship founded on trust, respect, and a common goal.
Sometimes learning from someone’s mistakes is more impactful than learning about everything that went right. Here are common mistakes that Chiefs of Staff make when working with an Executive Assistant. And, in full disclosure, I got many of these wrong in my 10+ years as Chief of Staff.
By sharing these potential pitfalls, I hope to bring some awareness to the Chief of Staff and Executive Assistant partnership and what to keep an eye out for so that you can do better by learning what can go wrong.
Common Mistakes Chiefs of Staff Make with Executive Assistants
1) Lack of Communication – Not maintaining open and regular communication can lead to misunderstandings and misaligned priorities. Both roles need to be in sync to support the executive effectively. In addition, changing priorities without clear communication can cause organizational whiplash, confusion and disrupt workflows. Business moves fast – sometimes too fast. When a Chief of Staff fails to keep the Executive Assistant in the loop, everyone loses. Consistent prioritization and clarity in shifting priorities are necessary.
2) Undefined Roles & Responsibilities – Because Chiefs of Staff and Executive Assistants are working together towards the same goal – ensuring the leader’s vision is communicated, organized, and executed, the exact projects and responsibilities can get a little murky. When there is ambiguity about who is responsible for what, tasks can fall through the cracks or be duplicated. Clearly defining roles and responsibilities is crucial. And once they are defined, a commitment to staying in your respective lane is necessary. However, this is not a one-time conversation. Priorities shift. The company evolves. The responsibilities will change. Regularly reviewing roles and responsibilities between a Chief of Staff and EA is critical in order to divide and conquer and make the most impact.
3) Not Encouraging a Strong Partnership Between the EA and Leader – There is still a debate about whether an Executive Assistant should report directly to the executive they are supporting or to the Chief of Staff. I think there are pros and cons to both and it’s largely dependent on the structure of the organization and needs of the Principal. For the sake of this conversation, let’s assume the EA is reporting to the Chief of Staff. If that is true then it is imperative that the EA and leader form their own relationship and partnership too. The Chief of Staff can end up being a roadblock or bottleneck if the EA and leader don’t create a strong working partnership of their own. Work can be less efficient and the EA may have diminished impact if they aren’t also in lock-step with the leader.
4) Micromanaging & Rescuing – Just as a Chief of Staff would bristle at a micromanaging leader, so too, does an EA balk at a micromanaging Chief of Staff. Overseeing every detail of the EA’s work can lead to frustration and decreased productivity. Trust and autonomy are important for the EA to perform their best. We see micromanaging rear its ugly head in particular when the Chief of Staff was previously in the EA role. It’s hard to let go of the “way things were done”. Furthermore, Chiefs of Staff may get caught in the “rescuer” trap. Rescuer leaders just want to help their team members succeed. They don’t like to see their employees struggle or fail. So, at the first sign of an issue, they jump in to help. They want to help maintain their team member’s reputation (and their own). So, why is this a problem? The Rescuer ends up creating employees who are highly dependent on their leader, not to mention you may end up with a frustrated and disengaged EA, which is simply not good for anyone’s career or the overall business.
5) Unrealistic and Unclear Expectations – Are you expecting your Executive Assistant to be up to speed in 10 weeks what took you 10 years to learn and master? Unrealistic expectations kill morale and confidence. Similarly, unclear expectations lessons productivity and impact. Chiefs of Staff would benefit from creating clear 90 day onboarding and ramp-up plans with their Executive Assistant. From there, regular meetings to discuss expectations about the role, communication, and how they succeed is important. Set your Executive Assistant up for success with clear (and realistic) expectations so you can grow and succeed – together.
6) Poor Delegation – Not delegating tasks appropriately can either overburden the EA or leave them underutilized. Effective delegation ensures that tasks are handled efficiently and the EA’s skills are maximized. Executive Assistants have demanding workloads of their own. Overloading them without considering their capacity can lead to burnout and decreased efficiency. This is one more reason why consistent communication is so important between a Chief of Staff and EA. In order for both parties to do their jobs well, understanding current workload, shifting priorities, bandwidth, and capacity for additional projects is imperative. And consistent communication mitigates making assumptions.
7) Making Assumptions – You know what they say about assumptions… Chiefs of Staff that make assumptions about your Executive Assistant’s preferred workstyle, how they like to communicate and receive feedback, what motivates them, etc. can be setting you both up for failure. Not everyone is going to work at the same intensity and pace as a Chief of Staff, and not every role in the company has to. Then again, you also don’t want to assume that your EA doesn’t bring that same level of intensity. An EA brings unique insights and skills to the organization. Chiefs of Staff should recognize and utilize these strengths instead of making assumptions or undervaluing the EA’s contributions. The Office of the CEO needed a Chief of Staff and an EA for a reason. Understand what makes your EA thrive and then use that competitive edge for everyone’s advantage.
8) Not Investing Time Into Building a Personal Relationship – A strong, trust-based relationship between the Chief of Staff and the EA is essential. Neglecting to build this relationship can lead to a lack of cohesion and teamwork. A Chief of Staff and EA may end up working together even more than either of them do with the leader. And, in positions where loneliness and isolation is common, sometimes the only person (aside from the Principal) that you can confide in and who will “get it” is each other. Not investing time into building this critical relationship, beyond just the work, is a missed opportunity for connection, more workplace satisfaction, and improved teamwork.
9) Failure to Provide (and Receive) Feedback: Constructive feedback helps Executive Assistants improve and feel valued. Neglecting to provide feedback can result in stagnant performance and dissatisfaction. Providing feedback is also an opportunity to acknowledge and celebrate the EA’s successes which boosts morale and motivation. Failing to do so can result in a lack of engagement and enthusiasm. While Chiefs of Staff may be quick to give praise or constructive feedback, are they also providing an opportunity for their EA to give them feedback? Feedback is a two-way street. Chiefs of Staff can improve their relationship with their EA and their leadership in general by asking for feedback and listening, really listening, to what is shared.
10) Ignoring Professional Development: Executive Assistants, like all professionals, benefit from opportunities for growth and development. Chiefs of Staff should support and encourage their continuous learning and career advancement. Chiefs of Staff often have opportunities to learn alongside their Principal. Include Executive Assistants in these meetings, conferences, and classes as much as possible. The Weekly Execution Plan is a great tool to use in weekly conversations to keep career goals and professional development opportunities top of mind.
11) Not Including Them in the Conversation – Having a “seat at the table” is a frequent request for Executive Assistants, and usually a given for a Chief of Staff. Chiefs of Staff should be bringing EAs into the conversation as often as possible, and not just to take notes. Context is key for EAs to perform at their best. Not to mention, they bring their unique insights to the conversation and may see a challenge or idea from a different perspective that opens new pathways for understanding or problem solving. Not including EAs in the conversation may unwittingly hinder the team’s effectiveness and company’s growth.
At the end of the day, the most effective Executive Assistants and Chief of Staff partnerships are the ones who are committed to developing their partnership, helping each other succeed, and who communicate, communicate, communicate! And avoiding these common mistakes can lead to a more effective and harmonious working relationship between Chiefs of Staff and Executive Assistants, ultimately benefiting the entire executive team and organization.
