Why a Chief of Staff is Important
This past year I embarked on a new aspect of my consulting career: a fractional Chief of Staff. It was like blasting off into outer space: both exhilarating and unnerving. I possessed a robust toolkit: 20+ years of business consulting comprised of finance, technology, project management, mentoring, and leadership. My past F500 clients resided in C-Suite roles, and as an early member of a start-up consulting firm, I worked for the CEO.
Why fractional Chief of Staff?
I did some market research — and plowed through scores of LinkedIn job postings for Chief of Staff (CoS). I scraped data on geography, industry verticals, company size, company maturity (start-up, how long in business), and critical job requirements. I took a peek at the current staff, looking at their background and expertise.
Here is what I uncovered.
- Program / Project Management: Must be able to manage multiple cross-functional projects. Heavier emphasis on strategic vs. operational projects. Must be “roll up sleeves” and take a “big picture” view. Understand and assess project risks and collaborate on a mitigation approach. Communicate project status — succinctly to the exec team. A PMO (project management office) or IMO (integration management office) spin to the project management requirement, especially if M&A is in the firm’s game plan. Take on specially assigned projects on behalf of the CEO. Be the project “fixer” for troubled projects.
- Strategic Initiatives / OKR / Balanced Scorecard: Own and run the OKR (Objectives and Key Results) or Balanced Scorecard definition workstream — establish, align, monitor, and report the company objectives, outcomes, and progress for each initiative. Where needed, cascade the OKRs down the organization hierarchy. OKR is the most popular accountability framework. In conjunction with the project management skills, track the strategic projects.
- Communications: The communications and presentation requirements ranged from running weekly status meetings and exec team meetings to all-hands company presentations to supporting board meetings. Also, consider the Chief of Staff a proxy communicator for the CEO participating in functional department meetings. A few CoS roles called for supporting external investor meetings. A tactical element was creating exec presentations — almost an exec-only communications point person.
- Data-Driven / Reporting & Analytics / Financial Plans: The CoS will own the strategic initiative reporting; expected to have hands-on data analytics and reporting skills. Dashboards were often cited. Analytics and reporting extended to researching market conditions. Additionally, the CoS in smaller firms (based on employee count), usually less than 200 employees, was cited for facilitating the annual plan and tracking key spend items. A strong working knowledge of financial (and cost) accounting is vital.
There are more, but these are the big, common themes that bubbled up.
Some additional anecdotal observations:
- The firms clustered around technology-centric products or services verticals
- The distribution of firms based on employee count (as reported)
- Look at the distribution, 50% of the observed firms had 200 or fewer employees.
- A few more prominent firms, based on employee count, posted for narrowly defined Chief of Staff roles, e.g., a CoS reporting to the CIO/CFO or a CoS/Spl Advisor for Division-X
My expertise and experience mapped neatly with the market need.
With the fortune on my side, I took on a fractional Special Assistant/CoS to the CEO (a start-up firm) and some one-to-one listening sessions with CEOs of modest-sized firms.
Inside Perspective
Here is a graphic of how I viewed the CEO’s world. The CEO’s challenge, especially in start-up and modest-sized firms, is transitioning from entrepreneur and expert to manager and finally to executive.
The CEO faces six big themes tugging between running the company and growing the company. While the CEO and entrepreneur cohorts are the initial experts, they must build a larger team, impart their “secret sauce” to the team and ask them to embrace the entrepreneur’s vision. Additionally, the CEO (and cohorts) must raise capital, spend the investment responsibly and demonstrate positive results.
If you ask me to describe the Chief of Staff’s value to the CEO, my reply is, “I return time to the CEO. Free space to allow the senior executives time to focus on what is most important to the company.”
Here are some of the challenges that I observed.
I know where the company is heading, and you should know too. There is a communications gap, a missing signal, between C-Suite leadership describing the firm’s vision, ambitions, and strategy and front-line employees’ understanding of the strategy. Reenforcing the concept is applauded, but unnecessary repetition when the message is unclear is not valuable. Uncertainty leads managers and teams to interpret the strategy for themselves. The impact is too many projects in-flight. People are busy, but not accomplishing activities that move the firm forward. Busy, not productive.
The CEO / Leadership Team is the “Fix It” Team. The CEO and leadership team are consistently drawn into tactical problem-solving. The front-line managers and teams are missing critical institutional knowledge defining how processes function. In rapid growth or fight fire mode, the CEO / Leadership team sees solving the problem themselves as the most expedient approach. Growth is built upon an unsustainable foundation.
Not thinking about work as a series of projects. The day-to-day, business-as-usual activities are the firm’s operations. Teams must be skilled and competent to carry out the operational processes. Talent is recruited and evaluated based on their ability to deliver the operational promise. The “attitude gap” is not viewing improvement opportunities as investments in ideas to achieve significant organizational objectives. The improvement ideas are not distilled down into expected outcome(s), timelines, and resources. Improvement ideas are not thought of as projects and treated with the needed scrutiny and accountability.
Culture really does set the tone for success. The CEO and stakeholders that regularly enforced the organization’s identity, communication style, emotional intelligence, and leadership traits developed the most lasting employee commitment. Something can be said for establishing a solid culture as it made for a team more accepting of trying new methods. A CEO that encourages and respects team input is apt to elicit more substantial ideas. Equally important, the CEO must embrace change and communicate to the organization that change is necessary. The CEO can not waiver and fall back on old habits: organizational change just won’t happen.
Tools and Methods Applied
Vision & Strategy: Diagramming the vision and business direction using a strategy map addressed the issue of consistency of communication across the organization. The drafting of the strategy map forced stakeholders to understand what was important and where change was expected to occur. Sharing a picture minimized employee uncertainty. If you can draw it, you can point and ask specific questions. The strategy map was drafted for “top of the house” only. I opted for simplicity to start the conversation.
Accountability Framework: Used the strategy map to set the overarching objectives and blended the OKR (Objectives and Key Results) framework to establish critical projects. Separated “business as usual” from “strategic projects.”
Project Roadmap: Took the collection of projects identified (current and recognized during the Accountability Framework exercise) to create a project roadmap — tagged projects with who does what and when. Now stakeholders can see the complete set of projects — current and anticipated. It also provides insight into resources and funding. New projects can be evaluated for value and effort and inserted into the overall timeline picture if accepted. While it doesn’t stop work creep — you can certainly see the impact and have the needed prioritizing conversations. It does clearly call out — how much work can realistically be accomplished by the current team. Now teams can take an objective project-centric approach to when and where improvement opportunities are launched.
Playbooks: The brass tasks work of identifying and fixing processes. And — documenting institutional knowledge needed to run operational processes. Use productivity (e.g., WorkOS) tools, like Notion, to simplify and communicate the operational process. The goal is to eliminate the C-Team as the “Fix it” or “How did you do that before” team. Playbooks support scaling the organization.
Why is the Chief of Staff important?
The CoS is not encumbered by running the operation, as is the Chief Operating Officer, Head of Marketing, or Accounting Controller. Given the degree of “independence” by reporting to the CEO, the CoS works cross-functionally and focuses on building org-wide processes and efficiencies. The CoS helps them execute critical strategic initiatives and build operational scale and efficiency by partnering with functional teams. Translates defined strategies into executable workstreams that yield the intended result of the business objectives.
The CoS functions as the CEO’s proxy in crucial meetings and becomes the CEO’s “early warning” system.
When taken in total, the CoS has shifted tactical work away from the C-Suite and to the responsible person. All projects are elevated for visibility, resource allocation, and outcomes — which should be the purview of the C-Suite.
You might think of the CoS as the “chief strategic project officer”.
With my sleeves rolled up, I can appreciate why the CoS is an essential, meaningful role, especially in the start-up to the modest-sized firm. The CEO sets the firm’s vision and operating direction. The CEO provides the nudge to get the organization moving. The CoS becomes the flywheel to create momentum. While the applied techniques are useful, e.g., solid project management or facilitating/building a financial forecast model, the CoS’ value is drilling down from the strategic topic to the operational detail. This engages the team, validates the strategy, and collaboratively creates the operational initiatives needed to achieve the CEO’s vision. The CoS can focus on building the framework to operationalize the strategy. The C-Suite now has the calendar whitespace to lead and deliver its organizational responsibilities.
If you are interested in learning more about the fractional Chief of Staff role or specific organization leverage planks, let’s talk. I started StrategyOnPurpose Consulting to focus on bringing a unique perspective blending process improvement methods, organization accountability frameworks, and technology — enabling organizations to execute their strategy and deliver on their customer and employee promises. Reach me at mhadd@strategyonpurposeconsulting.com or find me on LinkedIn
