One week ago, 220 Chiefs of Staff from around the country attended the first-ever Chief of Staff Summit in Washington D.C.

New and seasoned Chiefs of Staff gathered together for a unique opportunity to connect with one another and learn from incredible keynote speakers like philanthropist Jean Case, Professor Adam Grant, and Brian Rumao, the Vice President & Chief of Staff at LinkedIn.

In this special episode of Chief of Staff Collective, Catherine and Caroline debrief the Summit and the main takeaways from the event, especially the importance of focusing on self-care so that Chiefs can execute effectively on the job.

Stay tuned for more content and takeaways through our blog, podcasts, and more.

In This Episode, You Will Learn:

• Who attended the 2019 Chief of Staff Summit. (1:14)
• Highlights from the Summit. (3:56)
• Why it’s so important for Chiefs of Staff to focus on self-care. (10:59)
• What the future looks like for Chief of Staff summits. (16:55)

Resources:

2019 Chief of Staff Summit

Jean Case’s LinkedIn

Be Fearless by Jean Case

Adam Grant’s LinkedIn

Give and Take by Adam Grant

Brian Rumao’s LinkedIn

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Stay tuned for a special episode of the Chief Of Staff Collective Podcast dropping at a special time later this week to recap our first ever 2019 Chief Of Staff Summit in Washington DC.

Hear from:

• Philanthropist, Jean Case
• Wharton Top Rated Professor, Adam Grant
• Vice President & Chief Of Staff at LinkedIn, Brian Rumao

And much, much more.

Stay tuned to your favorite podcast player for this special episode!

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Are you listening?

As Chiefs of Staff, one of our main job requirements is our ability to communicate with others effectively. This skill includes truly listening, absorbing, and understanding what people are trying to communicate with us.

In this episode, KM Zouhary talks all about the importance of developing communication skills as a Chief of Staff, putting significant emphasis on the importance of listening, and how foundational that skill si to cultivating human connection. Katie’s career led her to take on several different roles so far – including attorney, professor, improvisor, and former Chief of Staff – all of which have communication and human connection at the core of those roles.

So, get ready to learn all about Katie’s unique journey, along with her insights into the power and cruciality of communication.

Some Questions I Ask:

• Tell us about your Chief of Staff role. (4:52)
• When you jumped into your Chief of Staff role, were you familiar with what it would entail? (6:54)
• How did your Chief of Staff experience enhance your law school experience? (7:52)
• In your own words, how do you define communication? (13:09)
• How do you prioritize listening while still ensuring that you get your point across? (34:21)
• How do you use communication to demonstrate additional traits and qualities? (38:15)

In This Episode, You Will Learn:

• How the Chief of Staff role changed KM’s career and life. (4:59)
• How connection became the common thread throughout KM’s life and career. (10:54)
• Why the Chief of Staff should really be called the Chief Engagement Officer. (16:47)
• Why it’s important to understand the potential discrepancies between how communications are delivered versus how it’s received. (23:59)
• Why non-verbal communication is the most important part of communication. (31:08)
• How to create connection as the Chief of Staff. (42:53)
• How physical appearance plays a role in being authentic and still communicating effectively. (49:14)

Connect with KM Zouhary:

Cadenza Communications

LinkedIn

Resources:

Executive Presence by Sylvia Ann Hewlett

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What do you want to be when you grow up? 

That’s supposed to be a question asked by adults to children, but so many of us find ourselves asking that every day. Sometimes the question goes a little deeper than just a job. 

When you grow up, the “What do you want to be” question turns into, “Where do you belong?” The truth is, you don’t just find this place where you belong in the world; you have to create that space for yourself. For Megan Grocutt, she took a winding road through a few different roles, leading to the place she was meant to be. From an aspiring actress to Chief of Staff, Megan finally had that “coming home” feeling.

Some Questions I Ask: 

• How did you start working for Tracy Anderson? (2:17)
• Do you look back at your time working for Tracy Anderson and see that role as a Chief of Staff role? (24:26)
• How is the Chief of Staff role similar to acting? (31:36)
• Where are you on the path to self-discovery? (33:54)

In This Episode, You Will Learn: 

• What it looks like to pursue your passion. (8:30)
• How the line between personal and professional life got blurred for Megan. (10:59)
• How the need for instant gratification affects your outlook on life.  (13:22)
• How Megan built up her confidence to seek the role that was right for her. (16:30)
• What it was like for Megan to finally find her “home” as Chief of Staff. (26:41)
• How Megan approaches the role of communication as Chief of Staff. (31:52)

Connect with Megan Grocutt: 

LinkedIn

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The time is getting closer. 

The office is a little quieter than usual. Casual chit-chat has subsided, and everyone is abnormally consumed by their work. Everything is tense. 

It’s time for annual performance reviews. Heading into your boss’s office to discuss the ins-and-outs of how you’ve done in your job over the last year can be an intimidating experience, even if people are doing their jobs well. The issue is that these feedback sessions are so formal, and happen so seldom, that they’re ineffective. 

What if there was a way to make sure these conversations have a real, positive impact on the staff? 

In this episode, Margaret Richardson shares her professional experiences around measuring performance, success, and overall accountability. As the Chief of Staff to the CEO at Devex, her story is one that exemplifies how essential her role is, even when most of the work happens behind-the-scenes to ensure all staff members are performing at their best all the time. 

Some Questions I Ask: 

• Did you feel like you were the one for the Chief of Staff role at Devex? (4:53)
• How did you bring yourself up to speed in your early days as the Chief of Staff? (9:55)
• How do you measure performance, success, and overall accountability? (13:35)
• What would be your advice to a Chief of Staff who wants to implement the tools that Devex uses? (20:30)
• If you could talk to your past self, what would you tell them about the Chief of Staff journey? (24:17)

In This Episode, You Will Learn: 

• How Margaret ended up as the Chief of Staff at Devex. (2:30)
• How Devex contributes to the global development industry. (6:47)
• What tool Devex uses to track performance and goals. (14:12)
• How performance reviews every two months positively impacts the culture of the company. (16:53) 
• How Devex’s performance review system improves company efficiency. (21:23)

Connect with Margaret Richardson: 

LinkedIn

Devex

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How does it feel to be the Chief of Staff of an organization? 

Does it ever feel a little…lonely? 

The Chief of Staff position is so complex and jam-packed with responsibilities that sometimes the job description itself seems, well, vague. 

In this episode, I speak with Ted Riter, an incredible coach who has worked with executives around the globe. Recently, he published an article depicting some of the struggles that come with being the Chief of Staff of an organization, including understanding the work itself, what obstacles everyone has to uniquely overcome, and what mental makeup the Chief of Staff must have to survive on the job. 

Ted Riter shares his insights into the life of the Chief of Staff, how to avoid burnout, and why trust is so essential to the success of someone in this position. 

So, get ready to learn about Ted Riter’s take on the mental makeup of a successful Chief of Staff, and how to get in that space yourself. 

Some Questions I Ask: 

• How did you start digging into the current challenges Chiefs of Staff face? (1:46)
• Why is the Chief of Staff role so lonely? (3:25)
• What advice do you have for someone struggling in the social limbo of the Chief of Staff position? (7:45)
• How does someone build trust once they step into the Chief of Staff role? (10:46)
• What do you say to those that feel anxiety around the uncertainty of their own future? (23:57)

In This Episode, You Will Learn: 

• Why Chiefs of Staff so often long to be understood in their job. (4:17)
• What crucial qualities are required to be a successful Chief of Staff. (7:51)
• How a curious mind results in earning authority. (10:54)
• How to hold a grounded place during a time of chaos. (12:54)
• How to build trust with people who expect you to have all the answers. (20:54)

Connect with Ted Riter: 

LinkedIn

Resources: 

“It’s Lonely Near the Top: Challenges for Chiefs of Staff” by Ted Riter

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Where’s the line? 

How do you know what constitutes as too much feedback, or not enough? As the Chief of Staff, you might be the only person in a place to provide genuine feedback to the President. 

For Amber Daniels Fogelman, finding the right balance for providing feedback for the President at OneGoal has been one of the key traits that makes her an effective Chief of Staff, coach, and friend. Receiving feedback puts one in a vulnerable position. When done well, a sense of closeness is created between the President and the Chief of Staff. 

Get ready to learn about how to navigate the feedback cycle within the Chief of Staff and President relationship, and mutually creating space for growth in the process. 

Some Questions I Ask: 

• Tell us more about your role at OneGoal as Chief of Staff to Kwame. (1:41)
• Tell me about your relationship with Kwame at OneGoal. (4:16)
• How do you think about your role as advisor or coach to Kwame? (12:29)
• What is the best method to provide feedback? (21:48)
• How did you find the right balance to providing feedback to direct reports? (35:38)
• What key traits make you a great coach? (40:38)

In This Episode, You Will Learn: 

• What makes a great working relationship between a Chief of Staff and President. (4:32)
• What helped craft a trusting partnership between Amber and Kwame. (9:02)
• How Amber and Kwame function as accountability partners. (14:45)
• Why it’s important to give executives feedback. (18:08)
• How Amber helps expand Kwame’s capacity to make an impact. (34:48)
• Why having an internal coach is beneficial to the organization overall. (41:38)

Connect with Amber: 

LinkedIn

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When the CEO looks to hire their Chief of Staff, they have to ask themselves a crucial question: Who is it exactly that you need? 

Once the CEO makes that decision to hire, they commit to giving up control—which is a hurdle in itself—and giving it to the new Chief of Staff. The relationship that forms as a result between a CEO and a Chief of Staff is unique, yet crucial to achieving success.

This was a lesson that Adam Hergenrother learned when he hired his Chief of Staff: Hallie Warner. Together, they wrote the book on establishing, maintaining, and enhancing the relationship between the CEO and Chief of Staff. 

Get ready to learn about how the CEO and Chief of Staff can truly engage in fierce, strategic conversations, challenge each other’s thinking, and stay true to the vision of the company. 

Some Questions I Ask: 

• Can you tell us about your book? (0:54)
• What makes Hallie different from the other candidates for the Chief of Staff role? (4:58)
• Early on, what specific moments did you feel that you were building trust and rapport with each other? (8:03)
• Hallie, how did you push against Adam to hold him accountable? (13:03)
• What is the 0 to 10 principle? (14:55)
• How did the concept of a “user manual” come to be? (23:31)
• Where do you align? How are you complementary to one another? (26:49)

In This Episode, You Will Learn: 

• Why Adam needed a Chief of Staff. (5:31)
• How not having to follow up with a Chief of Staff builds trust. (9:35)
• Why it’s important to give up control to find success. (10:58)
• Why Adam values having someone to challenge his thinking, even when it’s frustrating. (14:29)
• Why it’s valuable to have more support staff than others in the business. (22:17)
• How to support staff help bring clarity and freedom within organizations. (30:06)

Connect with Adam Hergenrother: 

LinkedIn

Connect with Hallie Warner: 

Hallie Warner

Resources: 

The Founder & The Force Multiplier by Adam Hergenrother and Hallie Warner

Adam Hergenrother Companies

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Ever wonder what the Chief of Staff career path looks like? 

Honestly, there is no single path for it, and everyone has a very different experience landing a role like this. Most people don’t intentionally seek out a Chief of Staff role. According to Mary Ostafi, it’s a role that finds you. 

Throughout her career so far, Mary Ostafi has worked her way up, down, and around the ladder. She actually left her job as the founder and CEO of Urban Harvest SLT to becoming the Chief of Staff of Fair Trade USA. But why would she make this seemingly “backward” transition? 

For Mary, this role is a blend of everything she was looking for. It’s a challenge, provides space for continuous learning on the job, and so much more. 

Get ready to learn how Mary Ostafi found success in her Chief of Staff position and how she empowers the community around her. 

Some Questions I Ask: 

•Describe your background and early career. (0:05)

•What about the Chief of Staff position that resonated with you? (7:15)

•Which role feels more comfortable for you: CEO or Chief of Staff? (10:00)

•Why did you consider a Chief of Staff role? (15:08)

•How did you plan those early months in the position? (18:33)

•How do you measure success in your role? (21:17)

•How do you describe your role to others on the team? (25:44)

In This Episode, You Will Learn: 

•How passion helped mold Mary’s career. (3:39)

•How Mary became Chief of Staff of Fair Trade USA. (5:22)

•How Mary adjusted from holding the CEO position to the Chief of Staff position after switching organizations. (8:34)

•How Mary molded the Chief of Staff role at Fair Trade. (16:21)

•How Mary prepared for her Chief of Staff role. (20:27)

•How Mary works best practices into her organization. (23:40)

Connect with Mary Ostafi: 

LinkedIn

Resources: 

Urban Harvest STL

Fair Trade USA

Chief of Staff: The Strategic Partner Who Will Revolutionize Your Organization by Tyler Parris

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When you work toward a major goal, what do you expect from yourself? 

It’s so tempting to expect perfection out of your mind, body, and just yourself overall. But really, when you set yourself up to expect perfection, you’re truly only setting yourself up for failure. 

When Libby Moore was Oprah’s Chief of Staff, she expected perfection from herself. Every time she inevitably made a mistake or something didn’t go as planned, she would promise to herself and Oprah that will never happen again. Of course, it happened again, and more mistakes would follow from there. 

In response, Oprah told Libby, “I don’t expect you to be perfect. I expect you to do your best.” 

With that unnecessary stress and strife lifted off her shoulders, Libby continued growing and improving herself through her work. She learned that the more you are your authentic self, the more people will gravitate to you, the more your career will rise, and the happier you’ll be. 

So get ready to listen to Libby Moore’s fascinating journey to self-acceptance, personal and professional fulfillment, and how she shares this mindset with others now. 

Some Questions I Ask: 

•How did you earn Oprah’s trust: (1:03)

•How did you make sure you continued learning and growing through your work? (6:07)

•How did you handle conflicts with Oprah and how were they resolved? (11:18)

•Why did you leave your job as Oprah’s Chief of Staff? (16:12)

•What type of work are you doing now? (24:58)

•Knowing what you know now, what would you tell your 25-year-old self? (33:11)

In This Episode, You Will Learn: 

•What a Chief of Staff’s day-to-day work looks like. (7:01)

•How Libby always stands in her truth in the face of conflict. (12:07)

•How Libby knew that her work with Oprah had served its purpose. (16:38)

•Why Libby always challenges what people tell her to do. (21:46)

•How Libby reframes her mind to routinely get back to the basics. (26:42)

Connect with Libby Moore: 

Website

LinkedIn

Instagram

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