Are you in a Chief of Staff role looking for a coach? With my own experience as a Chief of Staff and executive leadership coach, I’ve got more and more people looking to better understand this role - and how to do it well. I think the Chief of Staff is one of the most exciting roles in business. So much so, that I wrote a book on it. Check out An Insider’s Perspective on the Chief of Staff here.

Whether I’m helping someone transition into a COS role, working with senior leadership to understand how the role might add value to their particular organization, or working with an established COS to hone their game, these have been some of my most rewarding coaching engagements. 

As I mention in my What is a Chief of Staff? blog, the role can be an incredibly valuable, high-impact position. Yet, it is often misunderstood and underutilized. The COS is far more than an executive assistant. Given adequate insight, trust, access, and authority, the COS is a strategic partner and trusted advisor to the CEO and executive leadership team.

Read on for three recurring themes I’ve seen in my coaching relationships with Chiefs of Staff - and a few insights for each.

Establishing a Relationship with the Principal

This is by far the most common hurdle I see new Chiefs of Staff face. Whether they’re working with the Chief Executive Officer, President, or Chief Operating Officer, the COS role is most effective when they’re in lockstep with their principal.

The two should almost be able to anticipate each other’s words, thoughts, and actions. This doesn’t mean the COS has to agree with the CEO on everything. In fact, the COS should be able to disagree and speak candidly with the CEO when needed. 

More and more CEOs looking to make a change in their business or leadership team are implementing a COS. Perhaps the CEO wants to step back from the business, focus more of their time on product development, or needs someone to handle day-to-day operations as the company grows so they can focus on the more strategic decisions.

These are great goals that the COS can help with, but they require big adjustments in reality. Especially for founders, leaders with long tenure, or anyone used to calling the shots, change can be difficult.

Usually, there’s multiple layers of change occurring. For one, there’s a new leader coming into the business. If it’s the first COS a company has had, a new role needs to be established. Secondly, it’s not just any role. A COS role is dynamic and not always straight-forward or black-and-white. A COS is a high-level, high-stakes, and high-impact player establishing relationships with key stakeholders such as the CEO, C-suite, executive leadership team, and/or board of directors.

On top of all this, the COS is being asked to facilitate change within the org - not just at the top, but throughout. They need to be willing to examine and change internal processes, team structures, and/or the mindsets of the staff.

With so many moving pieces, it’s critical for the COS to be on the same page as their principal.

How can an executive coach help?

Building Relationships

A coach can help a COS understand how to foster those critically important relationships with the CEO. Building those relationships takes time, effort, dialogue, and a little bit of trial and error. 

A coach can help you think about how to have these conversations, what topics to bring up and when, and whether you might be missing a certain angle or consideration. 

Establishing Value

A coach can work with a COS to better understand how value is added in two ways. One is helping the CEO understand the way they add value may be different than before. The other is helping the COS through that realization and transition themselves (for their role). 

Commonly, organizations bringing on a Chief of Staff are going through big changes. The CEO might be used to “doing it all themselves” and just working longer hours to get it done. A COS can help the CEO by making sure they’re spending their time and energy in the right places - helping them work smarter.

Sometimes a CEO adds more value by not stepping in, and therefore, empowering the team to find a solution on their own. On the other hand, the COS can help the CEO see when it’s time to make a decision only they can make. We won’t allocate additional budget to that area of the business next year, we are going to merge with that other company. Additionally, the CEO may need to be the one to step in to resolve a logjam between senior executives when no one else can. 

For a COS, the way they best contribute to the team may be new too. A COS can come from a myriad of backgrounds - they can be coming from operations, they may have led client facing or customer service teams, or be trained as a project manager or a consultant. Most of the time, there was a tangible or empirical measure that told them if they were performing their job well.  A coach can help the COS (and their CEO) understand one of their main roles is designing the company’s culture. 

• Are processes clear? 

• What red tape is keeping those in the know from making the right decisions? 

• Do people operate out of a sense of fear or empowerment? 

• Is micromanagement rampant or are people making decisions quickly and being proactive?

• Do staff understand how their day-to-day work ties into the business’s overall success?

• Do people know what other teams actually do? 

• Is information shared, or are teams siloed? 

The COS can dig into these questions through conversations and observation. The COS and teams can then work together to shape the business for the better. 

Motivating and Supporting

“It’s lonely at the top” is a cliche for a reason. CEOs are human too. They have down days. They doubt themselves. Part of the trusted relationships between COS and CEO is your ability to read the CEO, and know when and how to step in, especially in ways that other leaders cannot. You might need to deliver a little pep talk. You might need to get the CEO to shut their laptop and get some fresh air. You will need to know when they just need to vent.

Building Bridges With  the Leadership Team 

While that relationship with your principal is…(sorry for this folks)...the principal one, a good COS will work with all members of the leadership team, from the C-suite, Vice Presidents, to directors, or other managers or key personnel within the organization. 

If the COS is a new role for the organization, other leaders might naturally wonder how they’ll work together. When do I go to the executive assistant versus the Chief of Staff? When should I go straight to the CEO? Is my access to the CEO being cut off or altered? Is the COS a project manager for special projects?

Often, there are elements of coordination and project management that overlap with the COS role, but these aren’t the primary responsibilities of a COS. One of my clients moved from an executive assistant role to a COS role. Understandably, this required a lot of adjustment and clarification for everyone involved! The COS isn’t just the leadership team’s go-to for one-off tasks or nice-to-haves, but a critical member of the team with invaluable contributions. 

How can an executive coach help?

Working with a coach can help you understand the kinds of conversations you need to have and actions you need to take as you build bridges throughout the business and establish your new role. 

Aligning Leadership

A coach can help you figure out what actions you can take to coordinate changes or initiatives at a high-level across the leadership team. Part of your role is to make sure everyone is rowing in the same direction. Whether you need to step in, support, provide information, insight, or perspective, a coach can help you show the leadership team that your new role makes their own decision making better informed, quicker, and easier.

Assessing and Guiding Leadership

A coach can also help you assess how leadership is doing at their job, and what you can do to support or guide. What does success for the leadership team look like, and how does it align with business priorities? How can you make them look good, and help them be prepared for a big meeting with the CEO or the board? A coach can help you understand when to nudge the COO or VP in a certain direction - and when to forego subtlety in favor of a metaphorical 2x4 across the head...for their own good.

Backchanneling...in a Good Way

And, a coach can help you understand how to utilize backchannels in a good way. People aren’t always willing to be 100% honest with the boss. Part of your job will be to get unfiltered information from across the entire organization. This will also require building trust and good relationships, making sure people feel heard and understood. An adept COS knows what to do with that information. How and how much should you present to your principal? This requires a nuanced understanding of the dynamics and personalities involved. A coach can help you hone your own X-factor and the soft skills it takes to perform well in a COS role.

Getting Comfortable in the Chief of Staff Role

The Chief of Staff is a unique role. A good COS needs to be flexible, good with people, and able to switch gears between the big picture and the tactical reality. As a Chief of Staff, you move fluidly through the business, adjusting your communication style to your audience, knowing when to console, cajole, convince, or light a fire. You’ll need high emotional intelligence and self-awareness. You’ll stretch and grow in the best ways as you learn more about what makes people tick, including yourself! In my own experience, serving as a Chief of Staff is the most challenging — and fun — role I’ve ever had.

How can an executive coach help?

Maximize the Value of Your Position

Every COS is a little bit different. The roles and responsibilities at one company can be drastically different at another. Are you handling M&As or is that your CEO and legal team? Are you refining and standardizing recruiting and hiring processes or are you focused only on key hires? What skills of yours complement the CEO’s, and where should you step in for them? How can you best play to your strengths? Figuring out exactly what you need to dial in to truly shine in your role will take some tinkering, and working with a coach can be a good way to expedite the process.

Keep You Focused on the Right Things

Creating clarity at the organization and keeping the CEO and leadership focused is key, but you need to focus on the right things, too. You’ll need to be cognizant of the altitude of involvement. What are your best points for leverage and how can you give the leadership team the biggest bang for their buck? What can you do that no one else can? Where are the gaps that don’t fit neatly into one area of the business, but that need to be done, and done well? Having access to a coaching relationship can help you identify these opportunities and develop an action plan for taking advantage of them.

Cultivate New Skillsets and Mindsets

A COS needs to be thinking several steps ahead. You need to know what’s happening now and the potential outcomes and relevant contingencies. Look out for what others aren’t seeing, and figure out how to smooth out the road ahead. Similarly, you may need to establish new procedures or cadences for the business, and help others adapt to new ways of doing things. Learning to speak truth to power, managing egos, and managing through influence rather than authority are all key skills to have. Which skills your particular role most benefits from, and how to hone them, is something a coach can help you work out.

Need a Coach?

Hopefully, these thoughts above are helpful, and you can pick up a few tips and tricks from my experience with the COS role. If any of the above sounds familiar, you might be a great candidate for Chief of Staff coaching. If you’d like a trusted, knowledgeable, and experienced partner to take your COS skills to the next level, schedule a call with me today.

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About The Author

Emily Sander is an ICF-certified leadership coach with more than 15 years of experience in the business world and the author of Hacking Executive Leadership. She’s been featured in several print publications, online articles, and podcasts, including CEO Today Magazine, Leading to Fulfillment, and Leadership Powered by Common Sense. 

Emily has a passion for helping business leaders reach their full potential. Go here to read her story from seasoned executive to knowledgeable coach. If you want to send Emily a quick message, then visit her contact page here.