The Chief of Staff role: a case for not overthinking it
Think of the role differently.
For aspiring and current Chiefs of Staff, there is one piece of advice that stands above all others: stop overthinking the role.
The position will almost certainly differ from your expectations. Quantifying your achievements will prove difficult. This has been my experience, and it resonates consistently with clients and colleagues across my network.
This challenge is not a flaw. It is a feature of the role itself.
The wrong role for traditional metrics
If you seek a position with clear key performance indicators and measurable targets, the Chief of Staff role is not the right choice. Numerous other positions offer that clarity. Your next role after serving as Chief of Staff will likely provide exactly that structure.
The Chief of Staff position offers something different and more valuable: the opportunity to understand and trust the value you add when it cannot be easily defined or measured. Your contribution emerges not from what you deliver in tangible outputs, but through your intellectual depth, your capacity for influence, and your diplomatic skills. The value lies in your service to the organisation and its leadership.
The privilege and the discomfort
This work represents a genuine privilege. It also creates persistent discomfort, which explains why most people occupy the role for a relatively brief period.
The ambiguity inherent in the position can be unsettling. You may find yourself questioning your impact. You may struggle to articulate your achievements to others. You may feel uncertain about whether you are making a meaningful difference.
These feelings are normal. They are also largely irrelevant to your success.
What actually matters
Three questions determine whether you are succeeding as a Chief of Staff. Everything else is simply detail.
Do you enjoy the work?
This might seem like an indulgent question, but it is fundamental. The role demands significant emotional labour, political navigation, and intellectual flexibility. If you do not derive satisfaction from the work itself, you will struggle to sustain the energy required. More importantly, your lack of engagement will show in your performance.
Is your boss satisfied with your contributions?
This is the most direct measure of success available to you. Your primary stakeholder is the executive you support. If they value your work, trust your judgement, and rely on your input, you are succeeding. Their assessment matters far more than any performance framework or external validation.
You need not agree with every piece of feedback they offer. However, you must maintain an honest understanding of their perspective on your performance. Regular communication about expectations and satisfaction is essential.
Are you developing capabilities for your next role?
The Chief of Staff position should not be a career endpoint. It is a developmental opportunity that prepares you for senior leadership. Therefore, you must ensure that at least some of your work allows you to demonstrate the competencies your next role will require.
This might mean leading strategic initiatives, managing cross-functional teams, or representing the executive in important forums. The specific activities will vary based on your career trajectory. The principle remains constant: you should be growing skills that translate beyond this role.
Measuring success
If you answered yes to all three questions, you are experiencing a successful Chief of Staff appointment. Congratulations.
If you answered yes to two of the three, you are still in reasonably good shape. The role rarely offers perfect conditions, and two out of three represents a solid foundation.
If you answered yes to only one question, you face a more serious challenge. This situation warrants immediate attention and possibly external perspective. The role should not feel like an extended struggle with minimal reward.
The real work happens in the margins
Much of the anxiety around the Chief of Staff role stems from attempting to impose traditional career frameworks onto fundamentally different work. You cannot measure this role the way you measured your previous positions. You cannot demonstrate impact through the same metrics that defined your success as a functional leader.
The actual work of being a Chief of Staff occurs in the spaces between formal responsibilities. It happens in the conversation that prevents a damaging decision. It emerges in the relationship you cultivate that unlocks a strategic partnership. It appears in the meeting you facilitate that finally drives alignment across competing priorities.
These contributions resist quantification. They do not appear neatly in performance reviews. They cannot be captured in project management software or status reports.
This does not make them less valuable. It makes them more difficult to communicate, which is an entirely different problem.
Trust the process
The discomfort you feel when you cannot precisely articulate your impact is not evidence of failure. It is evidence that you are operating at a level where traditional measures no longer apply.
Senior leadership rarely offers the clarity and structure that characterised earlier career stages. The Chief of Staff role serves as preparation for this reality. You are learning to trust your judgement, to recognise value that cannot be measured, and to derive confidence from outcomes rather than outputs.
This represents significant professional growth, even when it feels uncertain.
Conclusion
The value you create as a Chief of Staff materialises while you are occupied with the day-to-day demands of the role. It emerges through your accumulated decisions, relationships, and interventions rather than through any single measurable achievement.
I recommend that you not attempt to force the role into frameworks designed for different kinds of work. Trust that if you enjoy the position, your executive values your contribution, and you are developing relevant capabilities, you are succeeding.
The rest is noise.
Focus on the work itself. The impact will follow, whether or not you can measure it precisely. That is the nature of the role, and learning to accept this ambiguity is one of its most valuable lessons.
