Hiring a Chief of Staff (CoS) is becoming increasingly common across organizations of all sizes. From early-stage startups to established enterprises, many founders, CEOs, and business leaders are eyeing the role as their next essential hire.
A quick search online will reveal countless resources and thought pieces about the benefits and ideal timing for bringing a CoS onboard. Less attention is given to the pitfalls and misconceptions surrounding the decision to add one to your team.
Let’s explore some common but flawed reasons for deciding to hire a CoS and why these mistakes could lead to an ineffective investment.
1. Hiring out of exhaustion
A frequent misstep is hiring a Chief of Staff because you’re burned out and need relief. While a CoS can help with managing operations and streamlining internal communication, they are not a quick fix for personal burnout. If you’re bringing someone on to take over your workload—rather than delegating relevant tasks—you’re likely missing the point.
Address the root cause of your overwhelm before deciding to bring on a CoS. A clearer head will ensure you make a strategic, not reactionary, hire.
2. Bringing on a CoS as a permanent fix to a leadership gap
While a CoS can step in temporarily to provide support during leadership transitions or to address emerging business needs, they should not be used as a permanent solution to fill key executive roles like CFO, COO, or VP of Sales. A Chief of Staff can successfully launch initiatives or assume interim responsibilities, but their focus should be on ensuring a smooth handover to a dedicated expert who will take full ownership of the function.
Relying on a CoS as a permanent fix for leadership gaps not only dilutes their strategic focus on internal operations, alignment, and long-term initiatives but also risks inefficiencies in areas that require specialized expertise.
It’s important to address leadership vacancies by hiring qualified executives, while allowing the CoS to operate in their intended role.
3. Patching over management issues
Another red flag is hiring a Chief of Staff with the expectation that they will resolve underlying issues in your management team or corporate culture. While a CoS can support efforts to improve these areas, their primary role is not to serve as a mediator for internal conflicts or a catch-all solution for cultural problems.
Building a healthy corporate culture is a major undertaking that requires dedicated focus and careful planning. For example, if your leadership team is dealing with internal conflicts, these should be addressed directly with clear, intentional strategies. A CoS can certainly assist with these efforts as part of a larger strategic push, but they should not be burdened with managing deep-seated organizational problems in addition to their core responsibilities
4. Hiring before reaching significant business milestones
If your company hasn’t yet achieved product-market fit, it may be too soon to bring on a CoS. The true value of a Chief of Staff is realized when your internal operations become complex enough to demand dedicated oversight and strategic coordination.
Before hiring a CoS, evaluate whether your company has reached the scale where a CoS can add meaningful value. If your startup is still trying to find its footing, it might be wise to wait until your operational complexity justifies the need for a right hand.
5. Misallocating responsibilities
If you expect a CoS to become a “Chief of Stuff,” managing every task that doesn’t fit elsewhere, you’re underestimating the complexity of their role and mismanaging their talents. This not only limits their ability to focus on the big picture but also hampers the value they can bring to long-term strategic initiatives.
6. Confusing the role with an Executive Assistant
Similarly, if you mainly need someone to handle day-to-day tasks like managing your calendar or sorting requests, an Executive Assistant (EA) might be a better choice than a CoS. While a CoS focuses on long-term planning and strategic support, an EA handles immediate needs. Confusing these roles can lead to hiring the wrong person and missing out on the real benefits a CoS can bring.
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Hiring a Chief of Staff can be transformative for your company—when done for the right reasons. This decision should be guided by strategic needs rather than convenience or current trends.
Take the time to assess whether your company’s stage, needs, and challenges warrant the addition of a CoS, or whether addressing deeper issues in your management approach or hiring an Executive Assistant would be a more effective route.
