Make the Pitch: Consider Me Your Chief of Staff

One of the most successful ways to land a Chief of Staff role is by having a conversation directly with the leader about how you can be an effective Chief of Staff. That’s right. Many great Chiefs of Staff today made a strong case and it worked. They took the initiative to identify a need and filled it. They solved a problem. That’s what Chiefs of Staff do! So, how do you go about pitching a role to an executive?

Step #1: Know Thyself

Before you pitch yourself, you have to know yourself. As (aspiring) Chiefs of Staff, we are good at many things as generalists. However, that doesn’t mean you don’t have 3-5 key skills that really distinguish you. Know those 3-5 skills and know them well. If you aren’t sure, ask people who have worked directly with you. Sometimes they can be our best sources for learning more about ourselves. You can also take the StrengthsFinder assessment. For $20, you will learn your top 5 skills and how you can best utilize them.

Next, use our Chief of Staff archetypes to understand where you can be most effective in the Chief of Staff role using your key strengths. Using the archetypes helps translate your key skills to actual functions of a Chief of Staff position.

Step #2: Learn the Leader’s Pain Points

Executives don’t love when a job candidate walks into their office and says, “Here’s where you need help.” Instead, you want them to tell you where they need help. Therefore, you have to ask questions. Before going into the conversation, do your homework on the leader and the organization. Understand their strategic priorities and any big projects or interesting news. For example, if the CEO is new, they are likely undergoing change and potentially a new strategic direction. Ask about it.

Sample questions to consider:

  • Are you satisfied with the amount of time you spend on your company’s highest-level business priorities?

  • In what areas can you use additional leverage to get more done?

  • What initiatives or ideas do you have that you haven’t been able to implement because you don’t have the resources?

  • Do you feel like too much minutia ends up on your plate?

  • Do you want to bolster your leadership team in any way?

  • Do you feel like you have a strong finger on the pulse of the organization?

When meeting with the executive, asking questions will expose where challenges lie. Leaders typically enjoy discussing where things can improve and their visions for the future. Be sure to listen intently to their responses. Your goal is to learn, not simply set yourself up for your case.

Once you understand more about the challenges that exist, you are ready to make your case for how you can be most effective in alleviating their pain points as a Chief of Staff. The key here is to be realistic, not idealistic.

Step #3: Discuss the Benefits of a Chief of Staff

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It is important for a leader to understand how the Chief of Staff role benefits them and the organization. Therefore, be sure to draw the lines for them to make it very clear. You are not making a case for why they need any Chief of Staff, but why you specifically should assume the position. Therefore, be sure to note your key skills and how they will help you be most effective.

Step #4: Address Any Concerns

If the leader doesn’t bring it up, ask what concerns might exist around having a Chief of Staff. You want them to get to “Yes!” and that means addressing any potential areas of apprehension they have first.

It is important to understand any underlying concerns the leader may have beyond what they are telling you. For example, they may tell you they are worried about ruffling feathers on the leadership team, but it is important to understand why this is a worry. Try to probe, where necessary, to understand the root of the issue.

Step #5: Have a Next Step

Do not leave the conversation without having a way of following up with the leader. Oftentimes, the best plan of action is saying you will take the initiative to create a position description for the role based on the conversation. This way, there is a tangible next step and it involves putting what you know in writing. You are also taking a step out of the process for the executive and/or HR team.

If the leader would like to have another conversation first, let them know you will follow up directly with their Executive Assistant to schedule it (then do it immediately). It is important to keep the momentum going from the conversation.

If you wish to further discuss making the case to a current or prospective leader about the Chief of Staff role, schedule an advisory session with us!