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Points to Keep in Mind as You Look for a Chief of Staff

To drive the success of your company, your chief of staff should have these critical skills

Key takeaways

  • Critical features for an effective chief of staff
    • Broad knowledge
    • Diverse experience
    • Collaborative
    • Strong communicator
    • Empathetic
    • Pragmatic

When your business is rapidly expanding, you can easily get stuck in an administrative loop. Founders/CEOs often find themselves mired in administrative work and distracted from their long-term business goals. This is not sustainable, and it can threaten the success of your organization. 

As a founder/CEO, you need to be focused on the vision of your company. You must spend your time on actions that support your long-term goals — not juggling payroll or managing the marketing department. Unfortunately, you cannot make the day longer, but a chief of staff (CoS) can help you utilize your time better. 

An effective CoS can help you strategically allocate your resources and ensure you carve out time for the things that are truly important. That includes your business, but it also includes your personal time. They help you take a holistic look at your life and your business. 

The CoS role varies based on you and your company’s needs, and it will change as your needs change. This dynamic role requires the right skill set — here is what to look for as you search for a CoS. 

Broad knowledge and diverse experience

An effective CoS should have expertise in the areas where you need the most support, but they should also be broad generalists. You want a professional who has diverse experience in the business world. That creates a foundation for critical thinking and creative problem-solving. 

Your CoS should be able to spot problems and look for solutions that improve the company across the board, rather than hyper-focusing on a single area. They should be able to implement processes across all of the major departments in your organization including sales and marketing, administration, human resources, technology, and finance. 

This requires hands-on experience in the business world. You want someone who has extensive and diverse business experiences, not just a piece of paper that says “MBA”. 


Your CoS will work with nearly everyone in your organization. They will liaison between you and your leadership team. They will bring together leaders from different departments to ensure their processes complement and support each other. They may also take your place in meetings. 

This requires the CoS to have strong collaborative skills. They need the ability to work well with others, but even more importantly, they need the ability to bring professionals with different goals together. To assess this element, ask prospective candidates how they’ve engendered collaboration with past clients, and reach out to references to get a sense of their work in action. 

Strong communicator

Communication goes hand-in-hand with collaboration, but you don’t just need a CoS who can bring others together and facilitate group problem-solving. You also need a strong communicator who isn’t afraid to delegate tasks to employees and speak truth to power. 

When you’re building or scaling your company, it can be hard to see the forest for the trees. You can often get so entrenched in the day-to-day details that you miss overarching elements. An effective CoS manages your schedule and delegates tasks to employees so that you can free yourself from the mire of daily tasks, but they also help you see the big picture.   

They help you spot gaps between your goals and your reality. They tell you when you need to adjust your tactics or explore other approaches. They ask probing questions and aren’t afraid to offer unpopular opinions. To be effective, your CoS needs the ability to communicate with people from all levels of your organization, and they should also be able to communicate with other stakeholders about the company’s vision when you’re not around.


This soft skill is critical for an effective CoS. Their role is to support you, and they need to be able to shift their approach based on how you operate. They need a high level of empathy to pre-empt your needs and identify when they should jump in. At the same time, they should know when to fade into the background and let you shine. 

Because they work so closely with multiple people in your organization, your CoS also needs the ability to read rooms and understand group dynamics. They should be able to imagine others’ perspectives and respond accordingly. 


Pragmatists focus on the potential success of practical applications. They think about outcomes. They don’t take actions just for the sake of taking a certain action or propping up a tradition. 

This is one of the reasons that promoting a CoS from within can backfire. Although internal promotion is generally advantageous, in the CoS role, internal hires may be accustomed to traditional practices. They may be stymied by their loyalties to other employees or clients. A pragmatic CoS can take a step back and ensure that your actions align with your goals and vision. 

The CoS is a unique position. They have a lot of influence, without necessarily having any power. They need to command the respect of your leadership team, even if they have less experience with specific departments. This requires the CoS to have a broad knowledge base, a commitment to collaboration, and strong communication skills. They also need to be empathetic and pragmatic. 

Chiefly Consultants provides businesses in all stages of growth with outsourced, fractional CoS services

Hiring a CoS can be a complicated process, and in a lot of cases, you don’t need a full-time person. Instead, you need a fractional CoS who can provide you with all of the benefits of a full-time CoS without forcing you to create a full-time role. That is where we come in. 

At Chiefly Consultants, we provide start-ups with CoS Services that help them take their business to the next level. Are you stuck in an administrative loop? Are you so focused on the day-to-day that you aren’t working toward long-term goals? Then, you need the help and clarity that you can only get from a CoS. To learn more, contact us today.