Part II: So, You're Looking for a Chief of Staff...
This is the second part of a two-part series about what the Chief of Staff role entails. You can find the first part at this link!
In the first part of this series, I shared insights on what I believe are the most critical elements of the Chief of Staff role. While those elements aren’t abstract, I didn’t get into the task-level work of the role, which many find easier to understand. So that’s what we’re doing to wrap things up.
But First, Some Caveats
I don’t like to disclaim much, but there are a few caveats that could be helpful as you dive into this piece.
First, this is not as comprehensive as I’d like it to be, though I plan to add to and refine it over time. You did not sign up to read a short novel, so I’ve tried to give relevant highlights that cover some of the most important thinking and doing parts of being a Chief of Staff in broad strokes.
Second, this is written for leaders and business owners who are considering whether a Chief of Staff would be a valuable addition to their team. However, I believe it’s still a useful piece for those aspiring to be a Chief of Staff or those working in complementary roles that partner often with Chiefs of Staff.
Third, my experience is corporate, and while plenty of it is applicable in an SMB context, I’m unable to speak confidently about what Chief-of-Staffing looks like in government or non-profit contexts. I know there’s overlap in responsibilities and areas of focus, in broad skill sets and character traits, but that’s about it. I won’t pretend to know the details of a Chief of Staff role for a government representative.
OK, on with the show!
The Orchestrator Has Entered the Building
To a large degree, Chiefs of Staff are orchestrators. They spend a significant portion of their time doing things that orchestrate and deliver on the higher vision for the business. Their responsibilities include (but aren’t limited to) coordinating strategic initiatives; helping connect teams and processes across the business; defining and implementing a regular reporting, review, and planning approach (most often at the management and/or board levels but sometimes at the organizational level, as well); helping strengthen the connective tissue amongst the executive team and broader organization; and helping guide their leaders’ time and focus.
Here’s what all of this tends to look like in terms of specific areas of responsibility and associated tasks (again, this is not a comprehensive list, just highlights):
Coordinating Strategic Initiatives
Creating detailed project plans. This can be as hands-on as physically creating the plan, or lean more toward orchestration, where the CoS defines large project milestones, necessary outcomes, key metrics, and budget requirements with an assigned project or program manager, who will then gather and fill in the details of the plan.
Identifying and documenting project roles and workgroup members. In partnership with the project or program manager, it’s the Chief of Staff’s job to answer the question: What skills, mindsets, and experience does this project need to be successful, and who fits that criteria? More often than not, these workgroups include individuals who need support reprioritizing their work to accommodate the project. This requires collaborating and negotiating with various team leaders to identify those people and ensure they will be properly supported. There might be some workgroup member rotation needed, as well, depending on the length of the project, what it entails (especially if it’s a phased project), and the effectiveness of various workgroup members over time.
Defining and implementing reporting approaches. This includes creating reporting templates or dashboards that account for a project’s most critical metrics, required outcomes, who will be looking at the report or dashboard, and their preferred way of viewing progress within the business. In large organizations, this is often done in partnership with a Data & Analytics team. This also includes providing regular updates to appropriate leaders and other invested constituents.
Leading regular check-in meetings or asynchronous project updates within the workgroup OR empowering the project or program manager to do so. Chiefs of Staff can foster that empowerment through appropriate expectation-setting and role defining at the outset of the project, as well as providing ongoing guidance, troubleshooting, and escalation support throughout.
Removing workstream blockers. This often looks like working through conflict with team members, acquiring resources for workstream owners who might not have the authority or relationships to do so (for example, finding additional budget), making decisions, moving vendor contract processes along, and more.
Socializing initiatives. Chiefs of Staff often help define the most important elements of messaging and work closely with communications teams to create a holistic communication plan for broadly socializing a large initiative. In smaller organizations without communications teams, the Chief of Staff often does most of this work themselves, with inputs from key team members.
Defining success metrics for after launch of initiatives. Sometimes, a strategic initiative ends when it ends (this isn’t all that common but it does happen, especially after acquisitions); in most instances, the initiative is an ongoing program that needs long-term tracking, support, and iteration.
If appropriate, creating and executing plans to transition ownership of a program. Depending on the focus of the initiative, a Chief of Staff may need to transfer ownership of it to a different leader or department at a certain point in the project or after launch for ongoing support. That will include identifying the right folks within the organization to take it forward, defining at least near-term future reporting requirements back into leadership, establishing and socializing who owns decision-making for the program moving forward, communicating the transition to appropriate teams, and more.
Helping Connect Business Processes
Spending a lot of time with teams and departments across the business to learn about what they do and how they do it. Over time, a good CoS should gain a deep enough understanding to help connect the dots across the business, identifying opportunities for teams to work together where they’re not, to improve processes, and to reduce unnecessary effort and frustration. A CoS should be able to see the business they’re in as a system and use that perspective to influence changes in it for the better.
Related to the bullet above, connecting people and facilitating conversations across teams. Because a CoS sees more of the business than most, they’re equipped with the information and relationships needed to facilitate smart connections. Bringing colleagues together around specific opportunities for collaboration — or, in bigger organizations, simply making introductions — should feel natural to a CoS.
Translating team concerns into understandable messages for different audiences. For example, an IT team might have significant concerns that need to be raised up to their CEO, who has a different level of understanding and view of IT within the organization. To help that leader understand and act on the concerns of the IT team, adding the appropriate context and their specific vocabulary can go a long way.
Strategic Planning
Distilling a leader’s requirements into a clear yet detailed cadence of strategic planning activities. One of the biggest areas of responsibility for a Chief of Staff is facilitating strategic planning for their leader, which will be heavily influenced by the broad intentions for the organization, board or shareholder requirements, and leader preferences. Distilling those inputs into an effective set of activities sits with the Chief of Staff.
Identifying, learning, and coaching people on a preferred method for strategic planning. There are countless approaches for strategic planning, so identifying one that aligns closely with your leader’s and/or leadership team’s working style and preferred way of looking at the business is critical to making planning a useful exercise. Strategic planning is not a one-and-done activity, and it can be an arduous task that folks come to dread if it’s not seen as and proves out to be useful.
Shepherding individuals and teams through the planning process. This looks like owning instructional and schedule-related communications for the process, coaching team members on the planning method (often through working sessions), acting as a point of contact for questions and concerns, providing ongoing guidance and recommendations, reminding people of key deadlines, and generally acting as the host for planning activities. If someone has any questions, concerns, or comments about the strategic planning process, they should know that the Chief of Staff is the person to turn to.
Business Performance Reporting
The tasks within business performance reporting are similar to those of strategic planning, with a few important differences:
Timeframe/Focus Range: Strategic planning will include and tends to focus on long-range future planning — the next 1-3 years. Regular business performance reporting tends to zoom in on what is happening within the business on a monthly and/or quarterly basis (though integrating year-over-year and year-to-date metrics is commonly done for frame of reference, because looking at numbers in a vacuum is not helpful).
Direction of Focus: Business performance reporting is generally focused on looking back, since there are actual results available to review from the efforts of the past month/quarter/etc. In contrast, strategic planning is focused on setting a course for the future. Of course, previous performance is used to guide future planning, but it is not the only guiding information in play. In fact, past performance can sometimes be a hindrance if the information keeps people locked into outdated ways of thinking, especially if the business is heading in a new direction or navigating another significant change.
Participants and Audience: The participants and audience for business performance reporting will likely vary from the strategic planning process. For example, financial reporting generally sits at a fairly high level within an organization — leaders are not not regularly discussing their P&Ls with every employee, though there might be some highlights worth sharing more broadly.
Executive Team- and Relationship-Building Support
Identifying and highlighting powerful relational dynamics across the leadership team, good or bad. Seeing where and how leaders and managers complement each other in their work and communication styles, and highlighting when sparkling or charged dynamics are in play can be hugely beneficial. Chiefs of Staff need to be keen observers who can feel the the energy change in a room (even virtually) when relational dynamics shift. They also need to share their observations with their leader, who will often seek additional perspectives to validate or invalidate their own observations. Ideally, a CoS has a complementary skill set to their leader that allows them to see things their leader might not pick up.
Stewarding executive coaching and training initiatives. This is usually done in close partnership with an HR leader, who has the appropriate domain expertise and a network to tap. Tasks here might include identifying specific coaching and training needs and opportunities, and researching the most relevant programs and capable individuals in the market to address those needs. From there, navigating the logistics of acquiring budget (if a training budget is not already allocated for the executive team), program/coach outreach and contract negotiations and approvals, scheduling, prep, etc., often falls to a Chief of Staff to handle.
Acting as a liaison, champion, and bridge-builder across the executive team and the broader business. Chiefs of Staff hear some things. And part of the work when hearing said things is providing a certain amount of neutrality, curiosity, context, and alternative perspective that allows folks to better empathize with and humanize their colleagues. This isn’t easy to do and it takes a lot of work and skill development over time (I’m absolutely still building this muscle). We all carry biases — it’s just part of being human — and Chiefs of Staff have their own relationships with colleagues and leaders to navigate. But, at its heart, the CoS role is an advisory role. A Chief of Staff needs to take in information, roll it around in their brain a bit to make sense of what they've heard, and reflect it back with some added insights and understanding that make the work of the person they’re supporting (and a lot of other people, frankly) easier to do. This may feel a little woo-woo, but I’m a firm believer that the woo-woo is where we’ve been failing for decades and it’s time to get back to it.
Raising up problematic behavior and performance issues to a leader. This is a tough one, and while it does fall under the umbrella of executive team- and relationship building, I see it as more of a trust-building exercise between a leadership body and its workforce. Sometimes, leaders are so busy setting the course for their business that they may not see or want to deal with problematic executives on their team. A Chief of Staff has to have the trust, (relative) objectivity, and courage to raise these issues to their leader, discuss accountability measures, and provide appropriate support in enacting those measures. I have so much to say about this, as we see leadership continue to fail employees, customers, and our broader society and not be held accountable for those failures. So, of course, more to come.
Helping Guide a Leader’s Time and Focus
Vetting requests for a leader’s time. As we all know, time is finite, and requests for a leader’s time are mostly requests for an answer to a question, a decision, insight, or validation. There are instances in which a leader’s presence can add real value to a meeting, but usually what’s needed can be provided over email or via a quick call with the CoS. Chiefs of Staff, in partnership with Executive Assistants, are active protectors of a leader’s time and use a heavy amount of discernment to decide which meetings make sense for a leader to participate in, lead, or decline.
Checking in regularly on leader priorities, areas of focus, and what might need shifting. Leaders have a lot to get done. OK, yes, all of us have a lot to get done, but a) the ultimate responsibility of an organization’s or team’s success or failure sits with its leader, b) they have to span a business or business area in ways many other roles do not, and c) most critically, they are responsible for setting the course for their business or business area, which requires long-term planning and deep focus on tasks and activities that we haven’t historically considered urgent. Where and how leaders spend their time is a constant push and pull between the immediate and future needs of their people and business. Which means it is so easy to never get to the big things when there are an endless number of urgent matters staring leaders down. A Chief of Staff is their leader’s compass. They proactively and regularly touch base with their leader to see how time is being spent and what is getting the most focus, and to remind them of the big rocks needing to be pushed up the hill.
While writing this post, I couldn’t help but think about how much of the work Chiefs of Staff do is deep care work. Orchestrating, shepherding, influencing, bridge-building, etc. — all of that is care. And through that lens, because of our historical relationship with care work, it’s easy for the value of a Chief of Staff to be brushed off. However, having a good CoS on your team can be a strategic differentiator for you as a leader and business owner and for your business.
Have questions, comments, or things to add? Get in touch!
Photo by Arindam Mahanta on Unsplash.
