The most compelling reason to bring in a Chief of Staff is that organizations have become increasingly complex. The leadership team members each focus on their own horizontal or vertical domain. Only the CEO oversees the entire system that spans all business units and functions. However, CEOs typically aren’t hired for their capability in managing an organizational ecosystem and they hit a plateau at some organizational size or complexity.

A Chief of Staff, on the other hand IS great at building, running and optimizing these systems.They will make sure the organization runs like a well-oiled machine and that the operating model gets the maintenance and upgrades it needs.

This frees the CEO’s time for high-leverage strategic work, (aka the things that they are actually amazing at).

Pros:

• A Chief of Staff is a force multiplier who creates leverage for an executive so they can do their highest impact work.

• A CoS is an extra thinker with broad context to deploy against tough strategic questions.

• Most executives aren’t getting honest feedback from their team or board. A CoS offers feedback to help the leader grow and raise awareness of blind spots.

• The entire leadership team benefits from having someone steering strategic planning and execution. This process creates transparency around expected outcomes and how to communicate progress.

Cons:

• As a leader, it can be difficult to let go of the things that made you successful in the past. You have to rewrite your own operating processes to get leverage from a CoS.

• Bringing in a CoS and gatekeeper changes the leadership team dynamic. The process must be managed to ensure the group continues to operate well.

• Hiring the wrong CoS can be disruptive to the team and a distraction for an already-busy leader.

• Hire someone you trust across the dimensions of judgment, analysis, and interpersonal relationships. You will get the most benefit by deploying them as an independent resource that doesn’t require your ongoing input for every decision.

• First, ask your Chief of Staff to conduct an assessment of the organization, leadership team, and processes. They will offer a fresh perspective on the areas of highest leverage and make recommendations.

• Then, choose one or two priorities per quarter and resource them appropriately (staff hours, leadership team attention, outside consultants). These priorities are things that will require change from your leadership team or broader organization, limiting the volume of change increases the likelihood it will stick.

• Your CoS will oversee initiatives including all hands, strategic planning, and operating rhythm. Ask them to review the current practices and ensure they reinforce the organization’s objectives. Give them broad authority to adjust and experiment with new practices.

• Hiring someone too junior for the role. If they don’t inspire trust and respect from the leadership team, they will be ineffective.

• Undermining the outcomes that you asked them to drive. This will happen if an initiative is under-resourced or a side project for everyone else. The work won’t succeed if the whole group does not see it as essential.

• Changing course too often. Culture, organizational and strategic initiatives take time and commitment to come to fruition. If you change the direction each quarter, you will never experience the benefits of these projects.

• Not trusting them or ignoring their advice. Your Chief of Staff is the one person who is there to give the CEO straight talk all the time. That includes uncomfortable truths. Don’t shy away from listening to this valuable expertise.

The basic qualifications for a Chief of Staff include executive presence, communication skills, strategic thinking, and the ability to execute.

There are also more nuanced attributes that make someone successful in this role.

What to look for:

• Confident enough to sit at the executive table, and humble enough that the leadership team wants to partner with them.

• Willing to play behind the scenes most of the time, and able to execute an agenda

• Can fluctuate between operating at the strategic level and in the details

• Builds relationships quickly throughout the organization and is trusted to challenge leaders constructively

• Does not get flustered. Ever. A frantic Chief of Staff can trigger fear in the broader organization

• Willing to commit to the change curve for new processes, and open to adjustments along the way

• Incredibly discreet regarding sensitive information, while also serving as the inviting face of the organization

Things that are not needed:

• Industry or company expertise - a Chief of Staff needs to be a quick learner who can go broad or deep as needed.

• Someone similar to the CEO. You want to find a Chief of Staff different enough to notice blind spots but aligned in values.

• An administrator. If you already have an Executive Assistant, don’t expect your Chief of Staff to do that job. If you don’t have an EA, consider hiring one.

• You likely have limited direct experience with the role. As a CEO you have exposure to most functions within an organization, but the Chief of Staff role doesn’t fit into any of the traditional buckets. You may not know how to direct or coach this person as well as your other team members.

• There is a power differential. This person will be your advisor, confidante and challenger. Yet, they are still (in most cases) far more junior than you and the rest of the executive team. Make sure your CoS has a support structure in place beyond you.

• An inverse model is at play. The CoS is there to support you. They manage you as much as you manage them. You have to be comfortable with your report telling you what you should do vs. the other way around.

A fractional executive is someone who supports your business in a less than full-time capacity - typically ¼ or ½ time.

Usually, these are seasoned professionals in their domain who can jump in quickly and leverage their experience to solve problems. Fractional leaders are often brought in when a company needs high-level expertise but doesn’t have a full-time role (yet).

Similarly, a fractional Chief of Staff works side-by-side with you and your team to provide the same guidance and support a full-time hire would, but for part of the week.

They can be an incredibly effective tool when you need an operating system reboot or when your company is reaching a new level of growth and requires a fresh perspective.

As an added bonus, fractional executives have experience across multiple companies and industries and can bring new ideas to your organization.

Pros of the fractional model:

• Speed: the hiring cycle is much faster

• Flexibility: hire for what you need today and scale up or down as needed

• Lower total cost: compared to full time hire

The main drawback is that you don’t have access to support full-time.

Unequivocally yes, you can be an effective Chief of Staff remotely.

The key to effective remote leadership in any role is establishing and maintaining trust-based relationships. This can be achieved in many ways: video meet and greets, virtual coffee chats, text threads, Slack groups, etc.

For a remote Chief of Staff, it is essential to first build relationships and then have ongoing check-in mechanisms. This requires extra effort and attention in a remote environment.

The goals is to ensure crucial information passes through the CoS desk, without disrupting the regular flow of work.

As long as a remote CoS has access to people and information, they can do the job well.

Note - for certain things, in-person truly is the most effective format: examples team offsites, facilitated workshops, etc. If possible, a remote CoS should make an effort to be in person when it matters most and take full advantage of opportunities to connect live.

Chief of Staff roles vary, and the job descriptions reflect the unique nature of the role from team to team.

Before you start the hiring process, get clear on these key questions.

Critical responsibilities:

• What are the specific domains of ownership (vision setting, corporate comms, budgeting) ?

• What degree of administrative work is expected (if any) ?

• Is there a direct team or reports to manage?

• Are there any incumbent team members that will feel an overlap with the CoS role? Where are the boundaries?

Objectives:

• What special projects you expect the CoS to oversee?

• Which strategic initiatives or transformations you want the CoS to lead?

• What does success look like for this role, what metrics will you measure?

Skills & qualifications:

• If there are any gaps on the LT you are looking to augment, be explicit about the skillsets.

• What qualifications will make this person trusted and credible (education background, previous roles, etc) – you want to limit time spent ‘proving themselves’?

• What are the must-haves for any candidate (typically great communication, influence, strategic thinking, execution, etc)?

You may not list each of these elements explicitly in the JD, but having an answer will help you craft the role expectations.

Once you answer these questions, translate them into a job description that covers: objectives, responsibilities, and qualifications.

There is definitely a surge in interest on both sides of the equation - companies that want to hire a Chief of Staff and people who want to do the role.

My three-prong answer to why more companies are identifying a need in this space:

• Businesses and teams have gotten more complex. More stakeholders, more systems, more coordination needed. As the network expands, there is a greater need to bring in someone who can oversee and manage how everything works together to produce business results.

• Leadership is getting lonelier. In the old world, a leader might have a trusted confidante or two within the leadership team. As execs move around more frequently, this is no longer the case. Leaders still need a sounding board and advisor, and look to a Chief of Staff to fill that void

• The work used to be hidden. Today’s leaders have more time and attention demands than ever before. There is less capacity for team leaders to raise their hand and help with ‘extra’ things like strategic planning or designing an operating system on behalf of the broader organization because they are at capacity with their core role