How to Find a Great Chief of Staff

Written by vChief

September 28, 2021

At some point in your business, you may determine you are ready to hire a chief of staff. Of course, at that point in your business you’re probably already feeling a bit overwhelmed with everything you have stacking up on your plate, and so adding one more thing to your to-do list might feel impossible. Trust me, while it will take a little extra work up front to get the right person by your side, once you have the ideal candidate in a chief of staff role, you will realize it was totally worth it.

Here are my top tips to help you find a great chief of staff who will fit right into your business (and add value) from day one.

Organize and prioritize

Before you do anything, you will want to make a list that includes:

  • Tasks that keep bogging you down which aren’t appropriate to hand off to your executive assistant or anyone else on your team
  • Any “big rocks” that you need support on
  • Areas where the team is feeling overwhelmed
  • Goals for future development that you just haven’t been able to accomplish

Go over this list and prioritize the importance of each of these tasks, ranking them from most critical to least pressing. Get feedback from your team in this process. This is the rough draft of your chief of staff job description. Also spend some time looking for themes across that list – what relevant skills and responsibilities will be critical to achieve them? Now you know why you need a chief of staff and what skill set you’ll be looking for. We give more detailed steps and examples for writing the chief of staff job description in an earlier post.

Should I promote from within or hire an external candidate?

Now that you have a clear idea of what you’re looking for, think about your team. Is there anyone already within your organization that might be a good fit for the chief of staff role? Would they be willing to transition, and are you willing to move them out of their current role? Give this some careful consideration.

You’ll want to really zone in on the expectations you’ll have for the chief of staff role. Are these tasks better served by someone who is already familiar with your organization (i.e. business development, networking, communications, operations management)? Or do you need someone who can handle multiple projects that don’t always require intimate knowledge of the organization, just the ability to be analytical, strategic and strong at executing?

If you’re in a large enough organization, a rotational program may make sense, where you pull rising leaders into the chief of staff role for 18-24 months, which will give them deeper insights into the overall business, and then shift them into functional leadership roles once they finish their stint. This is common in corporations but could also be put to great use in mid-size companies.

Whether you use someone internally or not will depend on how you’ll be utilizing your chief of staff. In some cases, it may be the obvious answer. Other times, having an outside person enter into the role is the most strategic move to grow your business. They may bring with them a fresh perspective on the challenges you face and be able to identify gaps in your operational processes or bring new ways to mobilize growth.

The hiring process

While the hiring process should look similar to any other position you would hire for (and involve HR and your team just the same), you’ll also want to be extremely hands-on in the process as you’ll be looking for someone who you can establish a good rapport with and can think like you–even think for you at times.

This particular quality may be hard to determine from a conference room, Q&A style interview. Perhaps top candidates can come in for a second round of interviews that involve shadowing you for part of your day. Make sure they get to see key aspects like board meetings, customer calls, brainstorming sessions–anything sheds light on what the day-to-day operations look like, how they’re managed, and how the personalities all fit together. Afterwards, sit down one on one and ask for their observations and feedback. You’re going to need a person who can relate to you easily and adeptly, and is also quick to understand the pulse of the organization, so putting them in everyday situations will be more telling than sitting face to face asking staged questions. It’s also a good starting point for building a strong relationship with your chief of staff, which is a critical element for success in the role.

Key attributes

While you already have your job description in place, giving you a relatively good idea of the skills and knowledge you’ll be requiring of the ideal candidate, here are some key attributes that definitely contribute to the success of a chief of staff:

  • Adaptability: This is probably the most important trait of any chief of staff. They must be able to go with the flow and catch whatever it is that you throw at them on any given day, and do it with a smile!
  • High EQ: Even if you’re having your chief of staff complete mostly analytical tasks, a high EQ is key in their ability to be your second set of eyes and ears within the organization. They’ll be able to get a good read of what’s working and what isn’t, and can help you adapt a plan.
  • Analytical: Of course, you’ll want them to be able to see business metrics in black and white in order to make sound decisions about business growth.
  • Effective communicator: In addition to understanding what needs to change and how to change it, they also need to be able to follow through with communicating those ideas effectively, both with you as well as other team members.
  • Ability to influence and motivate others: The chief of staff often needs to get people who they don’t manage — team members, board members, partners, or other stakeholders — to do things on behalf of the leader or organization. It’s critical that the chief of staff is able to build and leverage relationships to accomplish this.
  • Proactive nature: You want a chief of staff who will anticipate your needs, raise issues before you do, and who generally has an ear on the pulse of the organization to flag potential concerns before they become problems.
  • Balance of loyal and questioning: While you definitely want your chief of staff to be supportive and loyal, and back you up when you plan out and execute new initiatives, they also should be willing to question why you do things the way you do. It’s beneficial if they have a different perspective than you to ensure that the decisions you are making are truly for the good of the organization. The chief of staff sees things from your perspective but, because they’ve been channeling that high EQ, they also see the myriad of perspectives within the organization and can use that information to make strategic decisions

Where do I find my chief of staff?

If you’ve decided that you’re best off hiring from outside your organization, you may be wondering how to find a good chief of staff. We can certainly help–that is our bread and butter!

We’ll get to know you and your organization, find out your pain points, and then look to our talent pool to find the right match. We have been doing this for five years and we have a 97% approval rating, so we’ve got a good track record for finding “the one” for the organizations that we work with.

If you lead the search on your own, it is important to cast a wide net and get the word out, posting the role online. What you’ll often find, however, is that your network is a really great place to look for talent. Let your friends and colleagues know what you’re looking for and ask who they know who could be a great fit for both the tasks and for your working style and organizational culture.

Fostering career development

Most often, the chief of staff role is meant to be somewhat interim and does not usually become a permanent part of your roster. They will be integral during those high growth periods within your organization, supporting you in new projects and initiatives. Once you get to a place of stability, you’ll need to decide if you want to promote your chief of staff to a more senior position at your company, like COO, or if it’s time for them to move on to a new adventure. Have honest and open communication about this with each other, and find out what their ideal career development looks like so that you can support them in taking that next step.

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