Want to develop closeness with your executive? Do this.

The Chief of Staff and executive partnership is often the closest relationship in an office. As we know, this partnership is extremely critical to the success of the Chief of Staff, the leader, and the organization. So, how do you begin building closeness with an executive you barely know?

Take the lead

Don’t wait for your executive to initiate relationship building. Make the first move. Your busy executive will unlikely come into your office at the end of the day just to get to know you. Take the first steps yourself. Taking initiative will be a constant throughout your tenure in the Chief of Staff role, so get comfortable with it early on. In addition to showing initiative, it confirms your commitment to the partnership.

Learn about each other as people

When first beginning a Chief of Staff role, you barely know your boss as a professional let alone as a person. Therefore, make sure you spend time in the beginning of the relationship learning more about who your leader is as a person, not just a professional. Does s/he have kids? Where did they grow up? What was their upbringing like? Where did they attend college? What were their extracurricular activities in high school or college?

When asking questions of your boss, it’s important to be open to sharing information about yourself as well. Learning more about each other on a personal level will help you both better understand the ways in which you think and operate.

As always, use your EQ to understand the appropriate amount and intensity of your questioning. The best time we’ve found to have these personal conversations are during down times between meetings or “after hours” when the office is quiet.

Be patient

Building trust in a relationship takes time, and it certainly doesn’t happen overnight. This can be particularly true for executives. Therefore, understand that building a close relationship will take time—not days, but months. Do not expect to jive on your first day. And do not be discouraged if in month 3 when you still feel like you don’t know him/her.

Nevertheless, if you do not feel like you are making progress within 6 months of your start, there may be reason to evaluate why.

Ask rapport building questions

Once you feel like you’ve established a better working relationship, we encourage asking rapport building questions with your boss. This sounds strange, but it actually works. These questions are designed to foster vulnerability, which is essential for creating a close relationship. Try these sample questions to get started:

  • Given the choice of anyone in the world, whom would you want as a dinner guest?
  • What would constitute a “perfect” day for you?
  • For what in your life do you feel most grateful?
  • If you could change anything about the way you were raised, what would it be?
  • Take four minutes and tell your partner your life story in as much detail as possible.
  • If you could wake up tomorrow having gained any one quality or ability, what would it be?
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It all starts with a conversation.

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