It’s Lonely Near the Top: Challenges for Chiefs of Staff

Article submitted by guest author Ted Riter.

EXECUTIVE SUMMARY

The role of Chief of Staff continues to grow in corporate and nonprofit America. While the responsibilities for this role vary from organization to organization, within organizations, and even between predecessors and successors, there are common challenges across the board for chiefs of staff. This paper presents both challenges for those in this field and recommendations for success as a Chief of Staff.

THIS STUDY

The background information for this study was gathered through interviews conducted November 2018-February 2019 with over three dozen current and former Chiefs of Staff. These Chiefs of Staff were in long-established corporations, startups, nonprofits, government agencies, and family offices[1]. They were in diverse fields, including high tech, pharmaceuticals, philanthropies, and higher education. Most Chiefs of Staff had served in their position for 12-18 months. Some had transitioned to other roles within the same organization or started their own ventures. A small number of Chiefs of Staff saw themselves as “career” Chiefs of Staff. Most Chiefs of Staff filled this role for a Chief Executive Officer. Some filled this role for other Executives or an entire C-Suite.

THE CHIEF OF STAFF ROLE

Chiefs of Staff are inspired and inspiring professionals, dedicated to the success of their Executives and their organizations They are eager learners, selfless with their time and energy, and masters of navigating sensitive situations. And, they are often placed in this role with great hopes, but little guidance or support for self-development.

Though a universal job description for Chiefs of Staff does not exist, Prime Chief of Staff, a leader in this field, breaks down the role of Chief of Staff into the following six functions: [2]

  • The Goalkeeper – Manage and triage workflow of the executive. Prioritize, delegate, and complete work on behalf of the executive.
  • The Operator – Add structure and process for better communication within the office of the executive as well as across teams. Ensure activities are running efficiently.
  • The Implementer – Drive business priorities from start to finish. Execute special projects or initiatives on behalf of the executive or the organization.
  • The Integrator – Create cohesion among teams and departments. Connect the dots across the organization for improved alignment and engagement.
  • The Proxy – Act on behalf of the executive for greater visibility and accessibility. Prevent bottle-necking and promote decision-making when the executive cannot be present.
  • The Advisor – Serve as a strategic thought partner, sounding board, and confidante. Inform organization strategy and decision-making.

These six functions are helpful when conceptualizing the role of a new Chief of Staff. Those interviewed in the field had a less nuanced view and responded:

  • I manage the staff – the CEO included.
  • My goal each day is to help connect people to people, people to ideas, and people to purpose. I spend 90% of my time helping people understand the “why.
  • I do a lot of listening and “pealing back the onion.” I’m the internal consultant/versatilist – I help every department scale.
  • I represent my CEO with special projects and make their life easier.
  • I am not chief of the staff, I am a chief connector

Chiefs of Staff routinely reported that their functions relied heavily upon both the needs of the Executive and their work and life experience. Mark Organ, Influitive CEO and thought-leader in the field of Chiefs of Staff, offers the following guidelines for hiring a Chief of Staff:[3]

  • A manager-level hire – This person would be responsible for typical administrative tasks like calendar management and booking travel, but he would also make important judgment calls on how the CEO should best spend her time and what meetings would be most valuable for her to attend.
  • A mid-career, director-level hire – This person may have 6-12 years of experience. He would be in charge of tasks like running town halls, preparing speeches and prepping the CEO for leadership meetings. He’s unlikely to take on any strategic responsibilities, however.
  • An experienced VP-level executive – This person is already an experienced executive who’s looking to become a CEO one day. She may meet with department heads to talk through goals and targets, and work on developing tactics for various parts of the business.

THE CHALLENGES

The Chief of Staff role is filled with challenges, some of which are unique to this position

Job Descriptions & Loneliness

Loneliness is not an uncommon experience for leaders. It often comes from a perception that they must “carry the burden” on their own. Chiefs of Staff report an added layer to this experience, often feeling that no one quite understands what they do in their organization.

In dozens of interviews, it was clear that day-to-day, no two Chiefs of Staff serve in the same role. Job descriptions vary greatly, and often do not even exist until long after the role is filled.

According to former Chief of Staff and author Tyler Parris, “…a chief of staff is a catch-all role, filled by someone with exceptional organizational and people skills, who handles all manner of tasks not covered by an existing member of an executive’s leadership team or administrative staff.”[4]

This difficult to define “catch-all role” can create confusion for executives, directors, and staff, especially when the role is filled for the first time.

Confusion around this role may result in pushback from those in the C-suite who see the Chief of Staff as a possible barrier to communication with the CEO. Staff might fear losing influence with the CEO and have uncertainty about their standing in the organization. This fear can easily be projected upon the Chief of Staff and lead to a creation of walls that hamper communication. Some staff members even outright express to the Chief of Staff, “I didn’t think we needed you.”

A consistent message from Chiefs of Staff, is that the most positive working relationships are based upon mutual agreements rather than expectations. One former Chief of Staff knew it was time to leave the role when it became clear that the CEO’s expectation was an 80/20 split between directly supporting the CEO and project management, while the Chief of Staff envisioned it as a 50/50 split.

Chiefs of Staff recognize that they have no real peers in their organization, unless they are in a larger setting with multiple Chiefs of Staff. The comradery that is often experienced in other positions may therefore be absent for Chiefs of Staff. A Chief of Staff for a Family Office shared that it “often feels like I’m on an island – it’s unlike any other job.” And, because of this isolation, one admitted, “I’m very frustrated. I don’t know how long I will be able to stay here.”

Even those Chiefs of Staff who excel in their position might feel unseen. One reported: “It’s very lonely. Because I’m so good at what I do, they don’t even see what I’m doing.” Another said, “I feel not seen and not appreciated.”

Many Chiefs of Staff spoke of the tremendous amount of privileged information they hold. This responsibility often makes it difficult to find colleagues and loved ones to confide in and count on for full support without breaking confidentiality. And, in fact, some Chiefs of Staff reported that their partners “know too much that is probably confidential.”

One Chief of Staff confided, “My CEO might be doing things that are unethical and I’m not sure what I can do about it.”

Social and Emotional Intelligence & Overwhelm

While the Executive might be a passionate leader with a big vision, the Chief of Staff often serves as a counter balance.

One Chief of Staff reported, “My job is to be an observer with my emotions removed, and then show what I see to the CEO, who cannot remove their emotions.”

This facility for social and emotional intelligence is critical for the success of a Chief of Staff, and yet not a skill that comes naturally to all in this role. As defined by the Institute for Social + Emotional Intelligence, “Social and emotional intelligence is the ability to be aware of our own and others’ feelings – in the moment – and use that information to lead yourself and others” [5]

Some Chiefs of Staff, lacking these skills, commented:

  • I internalized all my frustrations and then I changed the way I did things. For instance, I stopped bringing many things to the CEO.
  • I’m a people pleaser, so difficult conversations are a big challenge.
  • I have a hard time initiating the conversations and then letting them go.
  • I get frustrated because I see the change but am not able to do anything about it.
  • I’m often the least experienced person in the room and this kills my confidence.

Many of the Chiefs of Staff who struggled with social and emotional intelligence, reported feelings of overwhelm and burnout:

  • I sometimes work 90-hour weeks and rejoice when it’s down to 60.
  • I recently took my first vacation in 4 years.
  • I don’t know how long I can continue here.
  • A Chief of Staff has to thrive in chaos, and I don’t know if I can anymore.
  • I have no time for my own health and relationships, let alone personal development.

This toll of overwhelm might be a surprise for some in an organization. Some Chiefs of Staff report that others see their travel schedule with an Executive or a fancy restaurant reservation and imagine glamorous and exciting opportunities not afforded to everyone. While travel can be to exciting places and access to the Executive enviable, this is by no means vacation, and most Chiefs of Staff express a desire to curtail their travel and spend more time at home.

One Chief of Staff offered, “I am envied by many because it looks fun. At the end of the day, it’s not a glamorous thing. I’m one of the hardest working people in the organization.”

Chiefs of Staff leave their position for many reasons, including acceptance of a predetermined tenure end-date, and following bigger dreams. However, many are burned out with no more to give in this position and gratefully move on to other positions in the current or different organizations.

SOLUTIONS

Most of the Chiefs of Staff interviewed self-identified as “successful” in their roles:

  • They are fully supportive of their Executive.
  • They feel supported by their Executive.
  • And, they believe they are helping the overall success of their organization.

And yet, even many of the successful Chiefs of Staff expressed a need for more support. With this added support, the role of Chiefs of Staff will continue to grow and benefit organizations across the globe.

Fuzzy Job Descriptions

Creating a job description for a Chief of Staff, especially for the first person to fill this role, is both challenging and worth the effort.

In addition to the measurable responsibilities for a Chief of Staff, the hallmark of a good Chief of Staff-Executive relationship is one built on trust. A high level of trust enables the Chief of Staff to predict the Executive’s behavior, understand the decision-making process, and allow the Executive to focus on the biggest priorities.

Recommendations to Build Trust:

Create measurable outcomes and goals from the beginning: One Chief of Staff suggested making a list of the top 5 tasks for the week and delegating everything else.

Schedule private time for direct communication: One Chief of Staff recommended undisturbed meeting time one to two times per week to give the Executive peace of mind so they can focus on what is most important for them to be doing.

Practice vulnerability: Vulnerability is not typically welcomed in the workplace because it is associated with weakness. However, vulnerability is an extraordinarily powerful tool for building trust in any relationship, including between an Executive and Chief of Staff.

There are many exercises for safely expressing vulnerability. The simplest practice is to admit and own mistakes without assigning blame to others.

Loneliness

Since there is unlikely to be peer support for Chiefs of Staff within an organization, find those who “get it.”

Recommendations to Alleviate or Prevent Loneliness

Join an established Chief of Staff network: New opportunities for connection are being created through the efforts of Prime Chief of Staff and a current Chief of Staff herself, Caroline Pugh. Together, they are hosting events around the country and have created an online community of practice[6]

Create a Chief of Staff network: As the role increases in the business world, there are more and more opportunities to find or create a local network with Chiefs of Staff from all sectors of the workplace. Formality is not necessary.

Find a mentor: Chiefs of Staff are generous with their time and energy even when they have moved on to other roles, and they are often open to mentoring others.

Social and Emotional Intelligence

Daniel Goleman, a pioneer in the field of social and emotional intelligence, teaches that leadership is based primarily (85%) on emotional intelligence and (15%) on IQ. Fortunately, emotional and social intelligence are also skills that can be honed through training.

There are four areas of concentration that can be trained for Chiefs of Staff to excel in their positions:[7]

  • Self-awareness – knowing your internal states, preferences, resources and intuitions.
  • Self-management – managing one’s internal states, impulses and resources.
  • Social awareness – awareness of others’ feelings, needs and concerns.
  • Social skills / relationship management – ability to create desirable responses in others.

Many Chiefs of Staff have a very high level of social and emotional intelligence. They report:

  • I’m good at learning new skills.
  • I’m fearless when it comes to failure – I hop into the ringer.
  • I’m not afraid to put out a shitty first draft; zero to one is easy for me.
  • I am very often the youngest person in the room and try to make age irrelevant in a meeting.
  • I like to sit in the back of the room and take it all in.

Recommendations to Build Social and Emotional Intelligence

Hire a coach: The coaching industry is growing even faster than the Chiefs of Staff field. Good coaches might have good answers to a Chief of Staff’s questions. The best coaches will have good questions to a Chief of Staff’s answers.

Budget time and funding for professional development: Training pays dividends. The best professional development has a component geared for Executives as well as Chiefs of Staff.

Overwhelm

Overwhelm can be a result of fuzzy job descriptions, loneliness, and poor social and emotional intelligence skills. And, there are practices to prevent overwhelm on and off the job.

Recommendations to Alleviate or Prevent Overwhelm:

Practice self-care: Physical exercise, meditation, healthy eating, and time off might sound trite. However, they are recommended by every successful Chief of Staff interviewed for this report.

Practice embodied leadership: Our bodies are excellent teachers if we are attuned to them. However, we spend most of our day in our heads. Through training in embodied practices that stretch our nervous system, Chiefs of Staff can better hold the disruption and stress of the day.

Train for clear communication: Difficult conversations are inevitable in any leadership position. Learning clear communication skills is an art form that will be of benefit both inside and outside the organization.

RESOURCES

 Books Recommended by Chiefs of Staff (with some surprises in the mix):

  • Being You, Changing the World by Dain Heer
  • Chief of Staff: The Strategic Partner Who Will Revolutionize Your Organizationby Tyler Parris
  • Daring Greatly and Dare to Lead by Brené Brown
  • Difficult Conversations by Bruce Patton, Douglas Stone, and Sheila Heen
  • Discover Your True North by Bill George
  • Man’s Search for Meaning by Viktor Frankl
  • Playing Big: Find Your Voice, Your Mission, Your Message by Tara Mohr
  • Powerful: Building a Culture of Freedom and Responsibility by Patty McCord
  • Principles: Life and Work by Ray Dalio
  • Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity by Kim Scott
  • Resilient: How to Grow an Unshakable Core of Calm, Strength, and Happinessby Forrest Hanson and Rick Hanson
  • The 7 Habits of Highly Effective People by Stephen Covey
  • Thinking in Bets: Making Smarter Decisions When You Don’t Have All the Factsby Annie Duke
  • Tiny Beautiful Things: Advice on Love and Life from Dear Sugar by Cheryl Strayed
  • The Undoing Project by Michael Lewis
  • Your Oxygen Mask First: 17 Habits to Help High Achievers Survive & Thrive by Kevin N. Lawrence

Books Not Yet In Print

In addition to recommending books, some Chiefs of Staff envision writing the following:

  • How To Do It All – Including taking care of yourself
  • I’m A Chief of Staff…Now What?
  • Paving the Way for Process
  • The Story of Creating This Place: Things that seemed so big, but in the end are pretty small
  • Things That Make Sense But Don’t Make Sense

 

FOR FUTURE CONSIDERATION

An Unexpected Finding

One of the unexpected findings of this study is that many Chiefs of Staff experienced difficult childhoods or other challenges in their formative years. Though this paper cannot make a direct link between a difficult childhood and success as a Chief of Staff, it is an interesting area for further exploration. When questioned about specifics, these Chiefs of Staff confided they were often the ones who mediated family disruption: Arguments, divorce, death, illness, crisis. Perhaps, the experience navigating these challenging situations made it easier to step into the Chief of Staff role and mediate the high stakes, big egos, and charged energy of the workspace.

Transitioning Into and Out of the Chief of Staff Role

As the role of Chief of Staff grows outside of government, it is becoming seen as a stepping stone to higher leadership positions.[8] Though a great proving ground for numerous C-Suite and VP positions, the transition is often not seamless. There is a training opportunity both in the time before stepping into the Chief of Staff role and upon exiting. There is also an opportunity for addressing the emotional impact of transitions felt by Executives and Chiefs of Staff as the relationships come to an end.

CONCLUSION

Chiefs of Staff are proving to be invaluable assets for Executives in business and nonprofit organizations, just as they have been for many years in the government and military. Those who participated in this study were smart, talented, energetic, and motivated for success. They were great ambassadors for their Executives, their organizations, and their roles as Chiefs of Staff.

As this position becomes more common, it is important to address the challenges unique to Chiefs of Staff and offer appropriate training and coaching to ensure continued success for both the role and for those who serve in these positions.

 

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