Hiring or promoting your first Chief of Staff can be a game-changer—or a frustrating mismatch. It’s a powerful role, but also a misunderstood one. If you’re considering bringing someone into this seat, it’s worth pausing to assess not just whether you need one, but whether your organization is ready to make the most of them.
Here are five things to reflect on before you take the leap.
1️⃣ 𝗔𝗿𝗲 𝘆𝗼𝘂 𝗮𝗹𝗶𝗴𝗻𝗲𝗱 𝗼𝗻 𝘄𝗵𝗮𝘁 𝗿𝗲𝗮𝗹𝗹𝘆 𝗺𝗮𝘁𝘁𝗲𝗿𝘀?
A Chief of Staff can help reinforce alignment—but they can’t create it from scratch. If your leadership team isn’t crystal clear on strategic priorities, the Chief of Staff will end up chasing clarity instead of amplifying it.
Start by asking: Does everyone know what our top 3 priorities are? Are they making decisions and tradeoffs accordingly? If not, the first step may not be hiring—it may be aligning.
2️⃣ 𝗔𝗿𝗲 𝗱𝗲𝗰𝗶𝘀𝗶𝗼𝗻𝘀 𝗯𝗲𝗶𝗻𝗴 𝗺𝗮𝗱𝗲… 𝗮𝗻𝗱 𝗳𝗼𝗹𝗹𝗼𝘄𝗲𝗱 𝘁𝗵𝗿𝗼𝘂𝗴𝗵 𝗼𝗻?
Many leadership teams can talk strategy. Far fewer execute consistently. If you frequently revisit decisions, stall on implementation, or struggle to maintain momentum, a Chief of Staff can absolutely help—but only if there’s a willingness to assign ownership, hold people accountable, and follow through.
This role works best when there’s enough discipline and transparency that a Chief of Staff can serve as an execution partner, not a clean-up crew.
3️⃣ 𝗗𝗼 𝘆𝗼𝘂 𝗻𝗲𝗲𝗱 𝗹𝗲𝘃𝗲𝗿𝗮𝗴𝗲—𝗼𝗿 𝗷𝘂𝘀𝘁 𝘀𝘂𝗽𝗽𝗼𝗿𝘁?
Be honest: are you looking for a strategic partner to extend your reach—or someone to manage your calendar and inbox?
Both needs are valid, but they require very different skill sets. The most common mismatch I see is a leader who says they want a strategic Chief of Staff—but really needs an Executive Assistant. Or vice versa. The best outcomes happen when the expectations are clear, aligned, and shared from the start.
Ask yourself: Am I ready to be a little uncomfortable for the sake of multiplying my impact?
4️⃣ Are you ready to let go of some control?
This one’s tough—especially for founders, executives, and senior leaders who’ve built the organization themselves. But a Chief of Staff can’t operate effectively without trust, context, and access.
If you’re not ready to delegate key responsibilities, share sensitive information, or include someone else in high-level decision-making, the role will struggle to get traction. Ask yourself: Am I ready to be a little uncomfortable for the sake of multiplying my impact?
5️⃣ 𝗜𝘀 𝘆𝗼𝘂𝗿 𝗼𝗽𝗲𝗿𝗮𝘁𝗶𝗻𝗴 𝘀𝘆𝘀𝘁𝗲𝗺 𝘀𝘁𝗿𝗼𝗻𝗴 𝗲𝗻𝗼𝘂𝗴𝗵 𝘁𝗼 𝘀𝘂𝗽𝗽𝗼𝗿𝘁 𝘁𝗵𝗲 𝗿𝗼𝗹𝗲?
A Chief of Staff will be most effective in an environment with at least a baseline of structure: regular leadership meetings, shared goals, clear priorities, and a cadence for planning and review.
If those elements are missing, a Chief of Staff may end up having to build that infrastructure before they can actually use it. And that can lead to frustration on both sides. Before hiring, consider: do we have enough foundation for this role to thrive?
What to Do Next
If some of these questions gave you pause—you’re not alone. That’s exactly why I built the Chief of Staff Readiness Scorecard.
It’s a quick, 7-minute assessment designed to help you evaluate your leadership team’s clarity, structure, and execution discipline—and determine whether hiring (or promoting) a Chief of Staff is the right move.
You’ll walk away with:
📊 A personalized scorecard
🔍 Insights across five key categories
✅ Recommendations tailored to your results
Whether you’re a CEO, HR business partner, Board advisor, or a current Chief of Staff trying to shape the role—this tool is designed to bring clarity to a decision that’s too important to leave to guesswork.
