Leadership Development for Your High-Performing Chief of Staff


You found yourself a stellar Chief of Staff (COS). They’re a pro at getting things done, and can quickly switch gears to discuss strategic vision. At meetings they’re prepared, articulate, and ready to conquer anything. They are a high performer, and you can see their potential a mile away. Guess what? You’re not the only one. Before another organization scoops them up, develop a plan to keep your Chief of Staff growing as a leader within your organization. A Chief of Staff role isn’t stagnant, so your development efforts shouldn’t be either.


Clearly Communicate Your Plans

If you have a Chief of Staff who is a true high performer, there’s no need to keep it secret. Talk to them about their career goals and what you see as a good fit for their future with the organization. Let them know that you’ll be challenging them to grow by exposing them to new opportunities. Set up regular meetings to check-in on their integration in the role and allow them to ask questions about their experiences. These don’t have to be long meetings. Consider a 10-minute walk-and-talk once a week to get a quick, but regular, touch base.

As your Chief of Staff learns more about your organization and various functions of your organization, they will likely have ideas on continued growth opportunities. What areas do they find interesting and want more exposure to? Do they want to take on more managerial responsibilities? Having regular conversations about their own growth and development within your organization is essential to their long-term success.


Align Their Skills with Strategic Vision

Growth for the sake of growth isn’t beneficial to you, your COS, or the organization if it doesn’t directly align with the big picture.

If improved efficiency is a corporate priority, give your COS projects focused on managing budgets and operations. However, if new product launches top the organization’s strategic plan, allow them to work on cross-functional teams with research and development or marketing departments.

Your Chief of Staff comes to your organization with many strengths and talents, but that doesn’t mean they won’t learn additional skills through real-time challenges. Giving them only one-off special projects that don’t relate to the core business will not help them develop the skills they need to keep climbing your organization’s ladder.


Push Them Out of Their Comfort Zone

Resiliency and emotional intelligence are some of the best predictors of success. Take note of how they react to customer complaints, bad press, conflict between employees, or production delays. Do they stay calm under pressure? Do they suggest solutions or immediately initiate contingency plans?

While you don’t want to overwhelm them with problems, placing them in challenging situations where they have to make critical decisions will prepare them for future positions with greater scope and responsibilities. Some of the most challenging, but rewarding, moments in a Chief of Staff role have little to do with learning a new task. Instead, they come from dealing with people or tough situations where there isn’t an easy solution.


Offer Formal Coaching and Development

It is likely your Chief of Staff was hired for their breadth of skills and diversity of experience, not for the industry expertise. Therefore, help them get up to speed on your industry or sector by sending them to tradeshows or conferences. Allow them time to learn about your business through their colleagues or graduate-level classes.

Closer to home, encourage them to join peer networks for Chiefs of Staff or suggest a Chief of Staff coach. Networking with their peers is a great way for them to learn from others and bring new ideas into the organization. The role of Chief of Staff can feel isolating, but with the right support network, your Chief of Staff can gain objective advice and tips for lasting success.


Provide Frequent Feedback

Let them know where they excelled and where they still have room to grow. Patrick Mork wrote for The Startup, “High performers are always looking to improve. Getting constant, constructive feedback is a key part of this process. Rather than hearing what they do well, they’re usually much more focused on getting actionable feedback on where they can improve and what they don’t do so well.”

In addition to feedback, this development plan requires a little flexibility. Since it’s highly customized to your Chief of Staff, you can both contribute ideas as to what is working and what isn’t working so well. If there’s an area that piques their interest, allow them to explore it further.

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