The career path to a Chief of Staff sometimes isn’t as clear cut as one would like but we know Administrative professionals are interested in learning how to get there. We had an extraordinary group of Admin panelists who spoke first-hand about their path to Chief of Staff while offering up useful advice and anecdotes. Topics covered included:

– How do the roles of Chief of Staff and Executive Assistant differ?
– What to expect in the Chief of Staff role – and is it the career path you really want?
– How do you make the transition internally?
– How do you prepare for the Chief of Staff role?
– Advice for those considering a Chief of Staff role
– Which three phone apps can you not live without?

Moderated by: Hallie Warner, Chief of Staff to the Founder and CEO – Adam Hergenrother Companies

– Ashley Wood, Chief of Staff of Global Shared Services, Ryan LLC
– Jaclyn Gaughan, Chief of Staff to the Chief Executive Officer, Guerrero Media
– Nev Dooley, Chief of Staff, NTT Application Security
– Yvette Pearson, Chief of Staff, ICEYE
– Allison Miller, Chief of Staff, Alliance Health Care

The Path to Chief of Staff Whitepaper

1: How do the roles of Chief of Staff and Executive Assistant differ?

Anyone who has served as an Executive Assistant knows there are nuances to the role, many of which depend on the executives you support, the industry you’re in, and the company you work for, says Hallie Warner, Chief of Staff to the founder and CEO of Adam Hergenrother Companies. “How Executive Assistants and Chiefs of Staff go about getting the job done involves both strategy and tactics — they are simply working on different parts of one big, important, high-impact job,” she says. EAs tend to be logistical thought partners who focus on details in the short term, while Chiefs of Staff are strategic thought partners who tackle the long-term goals and vision of not just their executive, but the entire company.

EXPAND YOUR FOCUS. The EA role tends to be more task-focused — an EA typically focuses on the present and the weeks ahead, says Yvette Pearson, Chief of Staff at ICEYE. But a Chief of Staff will focus on the months, quarters, and years ahead. And, Pearson adds, an EA typically compiles only the information their executive asks for, whereas a Chief of Staff “focuses on the information they know their boss needs — even if the boss doesn’t know it yet.” A Chief of Staff’s work, Warner says, is driven by the demands of the founder or CEO’s long-term vision — so expect to tackle tasks such as interviewing for future leadership positions, writing a book, creating presentations or writing speeches, meeting with potential business partners, refining recruiting and retention processes, and establishing objectives and key results.

BE A BRIDGE BUILDER. Not only are Chiefs of Staff strategic partners with their executives, but also with everyone in the company, from the receptionist to the middle managers to the CEO. Those relationships are crucial to effectively execute the goals and vision of the organization. “I get texts that say, ‘Is the counselor in?’ — basically asking if I have time to talk through issues with an executive or with salespeople to help create the best ‘move forward’ plan,” says Ashley Wood, Chief of Staff of Global Shared Services at Ryan LLC. “You have to be that ear — that solutioning partner — to whoever it is you’re dealing with on a daily basis.”

QUESTIONS TO CONSIDER …

SHOULD I EXPECT TO HAVE DIRECT REPORTS?

The number of direct reports will likely depend on the size of the organization and its structure, Wood says. Often, a Chief of Staff may have one or more EAs who report to them — but it’s important to remember that in many ways, the CEO’s direct reports also are the Chief of Staff’s direct reports, particularly when you consider the importance of building bridges.

WILL I BE IN A HYBRID ROLE?

Whether you’ll be asked to continue to perform EA duties while also serving as Chief of Staff again depends on the size and structure of your organization. “I’m currently doing both — and it’s structured that way,” says Jaclyn Gaughan, Chief of Staff at Guerrero Media. That’s also the case for Nev Dooley, Chief of Staff at NTT Application Security, who says adding an additional EA to her executive’s team would likely create more problems than it would solve. “For us, it works,” she says. “The challenge is switching my brain from EA to Chief of Staff because there are significant differences between the roles.” For Warner, it comes down to understanding very clearly what an EA role looks like in your company or industry versus what a Chief of Staff role looks like. “Do a lot of self discovery, take personality assessments, and talk to people who know you well,” she says. “Make sure you really understand which role is the one for you.”

LEARN MORE …

Read The Founder & The Force Multiplier: How Entrepreneurs and Executive Assistants Achieve More Together, co-authored by Warner, and listen to her podcast Business Meets Spirituality. And read more about the difference between EAs and Chiefs of Staff in this The Founder and the Force Multiplier blog article: tinyurl.com/EACOS

2: What to expect in the Chief of Staff role — and is it the career path you really want?

The main piece of advice offered by all five panelists: Do your research. “I created the Chief of Staff role at my company,” Warner says. “I did a lot of research and said, ‘This is the job that I want.'” For Allison Miller, Chief of Staff at Access Health Care, it’s all about expecting the unexpected. “This is a fast-paced and evolving role,” Miller says. “This career path is for someone who wants to contribute to the business at a deeper level. You have to be adaptable, flexible, and able to pivot your focus to drive the team to achieve the desired results.” And seek out Chiefs of Staff for advice, especially ones who were previously EAs. “The role can sound glamorous, but it’s important to do your research,” Dooley says. “Once you get into the role, you don’t want to have to ask yourself, ‘Is this really for me?'”

UNDERSTAND THE CHALLENGES. As a Chief of Staff, it’s important to understand that your scope of practice will become much more broad. “I can touch almost any area of the business on any given day,” Wood says. “I had to invest a lot of time and energy in understanding all facets of our business from how engagements are generated, what they entail, how we are paid, what the fee structure looks like, and how we serve our clients. If you really think you want to do this role, you have to be ready to take on a number of projects and issues at any given time.”

As an EA, you may be more of a “backstage” operator, but as a Chief of Staff, you often must be prepared to take center stage. That means making tough decisions — and taking full responsibility if they go wrong. “Moving into a Chief of Staff role, you’re not supporting senior management — you are senior management,” Pearson says. “If you’re not good at making decisions, you’ll find the Chief of Staff role very tough. As an EA, you can sometimes stand behind your CEO when something goes wrong, but in a Chief of Staff role, you can’t do that — you’re front and center.”

And consider all that you may have to do — and give up — to be great in the role, Warner says. “If you are determined to move down that career path, sacrifices may have to be made,” she says. “You might have less personal time (or none at all), you will have increased pressure and responsibility, your commitment to your principal and career will be tested, you may take a pay cut, you may have to move to a different company or a new city. Be honest with yourself and what you are willing to do for your career — whether that’s an EA or Chief of Staff position — and then make peace with the answer.”

QUESTIONS TO CONSIDER …

WHAT’S AFTER CHIEF OF STAFF?

As a Chief of Staff, you learn how different departments operate, meaning you could easily step into multiple senior roles within, or outside of, your current organization. Typically, though, you don’t want to set your sights on your executive’s position. “You have to be a confidante to the person you’re supporting, meaning you aren’t after their job — that’s how they can be so open and honest with you,” Pearson says. “They need to be able to trust you and talk with you about anything.”

HOW DO I HAVE HARD CONVERSATIONS AS CHIEF OF STAFF?

First, remember that you are the second set of eyes and ears for your executive. “If he needs to hear something, he’d rather hear it from me than someone else,” Gaughan says. “Stay away from those terms like ‘Don’t shoot the messenger’ or ‘bad cop’ — if you’re relaying information to your executive, it’s because it’s something needs to be fixed or solved.” And, Pearson adds, collaboration is key. “Whatever problem you’re facing, it’s not one person versus another person,” she says. “I’m coming to you because I need you to help me face this problem. It’s you and me versus the problem, not us fighting each other.” Just don’t try to avoid those tough calls. “Part of being a leader,” Warner says, “is having tough conversations that others don’t want to have.” Another tough conversation, she says, involves compensation. If your desire to move into the Chief of Staff role is because you believe your pay will increase, that’s not always the case. “No matter the title, this is always a tough, but important, conversation,” Warner says. “If you are not being fairly compensated for the work you are doing, gather your information, data, and results, and propose a compensation adjustment.”

LEARN MORE …

Read more about transitioning from EA to Chief of Staff in this The Founder and the Force Multiplier blog article: tinyurl.com/COStransition

3: How do you make the transition internally?

In some cases, the Chief of Staff role may already exist within your company. In other cases, it may be up to you to create. Either way, you must decide if it’s a role you’re truly interested in and suited for — and let that be known.

CASE STUDY: JACLYN GAUGHAN

“After one particularly nightmarish project that I was left to do on my own, I stumbled across the Chief of Staff role and what it required. There was an article I read titled, Do you need a Chief of Staff? I put the five questions in the article into an email to my executive and asked, ‘Can you answer yes or no to these?’:

1: Are you implementing a new strategic plan?

2: Does your organization need more effective systems and processes?

3: Is your Leadership Team not operating at peak performance?

4: Are you not satisfied with how your time is being spent?

5: Do you not have enough time in your day?

He answered yes to all of them. I was like, ‘I’m going to hold this in my back pocket if I decide to bring up this title change.’ During my annual review, I brought it up. And he was like, ‘That makes sense. That’s what you’re doing, you’re more than an EA.'”

LET YOUR VOICE BE HEARD. You don’t have to wait to be a Chief of Staff to share your opinions and strategic vision. In fact, the panelists say, you should consider it your responsibility. “A rule in our executive meetings is: ‘If you know something, you have to say something,'” Gaughan says. “If you have a good relationship with your executive, that’s a great rule to live by in meetings. It gives you a voice and people start to take you a little more seriously.” Once you transition into the Chief of Staff role, it’s important for people to know that your voice is here to stay. “It was shocking for people when I first spoke up in a Leadership Team meeting about my opinion,” Dooley says. “I wasn’t just taking notes anymore — I was there as another leader in the company.” And don’t forget that Chiefs of Staff who previously served as EAs have already built important relationships across the organization and can further build on those relationships in their new role. “The interactions will quickly evolve from taking instruction relative to tasks to giving guidance on strategic initiatives,” Miller says.

PROVE YOU CAN HANDLE THE ROLE. If Chief of Staff is the role you want, then show that you can ask tough questions, make difficult decisions, manage projects, and lead others, even before you receive the promotion, Warner says. If you are already showing up as an influential leader, regardless of your title, the transition into a formal leadership role should be seamless.

4: How do you prepare for the Chief of Staff role?

When it comes to stepping into the Chief of Staff position, what education, skills, or industry knowledge should you be prepared to expand upon? While the panelists drew upon different combinations of the three to arrive at their current role, they all agreed that the skills learned in the workplace are the most crucial. “In preparing for this role, what helped me was being an EA first,” says Gaughan, who holds a bachelor’s degree in sports management. “You learn so much about the company as you’re working with different parts of the organization, and that’s more beneficial than anything a class can teach you.” Pearson agrees. “I was working as an EA in investment banking when I was 18,” she says. “There’s nothing I could have learned in a classroom that would have been as beneficial as that.”

KNOW THE PREREQUISITES. While nothing beats experience, many Chief of Staff positions require a certain level of education, such as a bachelor’s or master’s degree. The key, Dooley says, is to look at the job you want — and what kind of degree or overall experience it requires. But even if a job requires a degree, and you don’t have one, that doesn’t mean you can’t apply. “You can sell yourself and your abilities in your cover letter even if you don’t have a degree,” Gaughan says.

BE A ‘SPONGE.’ If you truly want to be successful as a Chief of Staff, absorb as much information as possible from those around you. “When my COO speaks, I listen,” Wood says. “There’s always nuggets in what she says.” And that’s equally true when it comes to the organization itself. “What does the company do? Who are your competitors? Who are the customers? What are they looking for?” Dooley say. “Connect with each and every leader (not just your CEO).” If your CEO or Leadership Team has executive coaches, she recommends seeing if you can get 45-60 minutes each week with them. “Executive coaches often have a better idea of what the company’s vision is than even its leaders do,” Dooley says. And you don’t have to wait until you become a Chief of Staff to make those connections. Reach out to executive coaches now and say, “This is what I aspire to be — how can you help me?”

QUESTIONS TO CONSIDER …

IS EA TO CHIEF OF STAFF THE LOGICAL CAREER PROGRESSION?

It can be — but it doesn’t have to be, and the role isn’t necessarily for everyone. As an EA, you see so many sides of your organization — so your next move could be into an HR or event management role. “Before moving into a Chief of Staff position, I did extensive research about various C-Suite career opportunities, coaching and consulting roles, and other leadership positions,” says Warner, who eventually narrowed her goals to COO or Chief of Staff before ultimately deciding Chief of Staff was the right fit. “Perhaps your next move is COO or VP of Business Development or Director of Public Relations or Executive Director of a nonprofit. Consider all of your options and choose accordingly.” And, she says, don’t forget that EA is an incredible career in its own right.

READ …

RADICAL CANDOR: HOW TO GET WHAT YOU WANT BY SAYING WHAT YOU MEAN

If you’re wondering how to approach tough conversations, this book (written by Kim Scott) offers some fantastic suggestions, Wood says. “You want to always have confidence that whatever message you are delivering is important and that you’re doing it in a concise, transparent way that doesn’t lose the message,” she says.

FIERCE CONVERSATIONS

This book, written by Susan Scott, offers some additional frameworks for how to draft and start uncomfortable conversations. In the book, Scott advocates for “interrogating reality” and moving forward to find solutions. “As Chiefs of Staff, we need to be able to have conversations that other people in the company may not be comfortable having with each other or their executive,” Warner says.

LEARN MORE …

Read more about the education, skills, and industry knowledge you should be prepared to expand upon in the Chief of Staff role in this The Founder and the Force Multiplier blog article: tinyurl.com/COShowto

5: Advice for those considering a Chief of Staff role

Buckle your seatbelt, Miller says. If you believe this is the right step for you, make sure you are ready for the maturity and self-awareness that is required. “The time commitment is significantly more, and the safety net is smaller,” Miller says. “The risk is greater, as is the reward for a job well done.”

BE CLEAR-EYED ABOUT HOW MUCH SUPPORT YOU WILL HAVE. “I thought when I became Chief of Staff that I would have more support in getting projects done, and that wasn’t the case,” Gaughan says, noting that depending on the organization you work for, you may not have an EA team supporting you. “Sometimes you still have to do it yourself. The biggest thing I had to wrap my head around is that I was still siloed.”

LET YOUR ASPIRATIONS BE KNOWN. Do you think Chief of Staff is the perfect role for you? Then tell your executive. After all, Dooley says, no one is going to read your mind. “Don’t wait for someone come to you with that opportunity,” she says. “Even if the role doesn’t exist, let your leader know you’re interested in creating it. Take on more strategic projects and own them.”

BUILD RELATIONSHIPS (AND KNOWLEDGE) ACROSS THE COMPANY. As Chief of Staff, you are the proxy for the person you support, meaning you must take time to learn the people and responsibilities that comprise the multiple departments within your organization. “I might get one little sentence from our COO, and I have to connect the dots — what does that mean and how we are going to execute on it?” Wood says. “Then I have to pull in people from other departments to develop the team that’s actually going to get it done. A skill I lean into often is being relational and people-oriented. I build relationships around the firm so I can call up our CFO or SVP of Sales and say, ‘I need you on this.'”

QUESTIONS TO CONSIDER …

WHAT ARE THE MOST IMPORTANT QUALITIES OF BECOMING A HIGH-PERFORMING CHIEF OF STAFF?

Maturity, sustainability, and creativity are crucial, Miller says. “Career maturity is needed to navigate complex issues, assignments, and teams. Sustainability is needed for this intense and demanding role. And creativity is necessary, as you are often the first line of solutioning when it comes to problem solving or creating a path to achieve a goal.”

For Gaughan, the most essential skills include communication and being a “utility player” — someone who can jump right in to almost any situation or position and be able to provide value.

And for Warner, there are several important qualities that serve as the ingredients for success, including the ability to thrive in a leadership role; being a big-picture thinker who is organized and operationally minded; the ability to make tough decisions and connect the dots across an organization, as well as adaptability and flexibility to fill the gaps of a growing company; the confidence to tell hard truths, especially to your principal; natural curiosity and a growth mindset; the enjoyment of variety, challenges, and change, as well as working to solve problems and move projects forward; and a wide range of education and experiences, with communication, project management, and leadership serving as underlying skills.