5 Questions Every New Chief of Staff Should Ask Their CEO

Stepping into a new Chief of Staff Role Can be Overwhelming

Stepping into a new Chief of Staff role can feel like jumping onto a moving train. Your CEO is brilliant, moves at breakneck speed, and expects you to keep up. Yet no one hands you an operating manual for how this particular leader works day-to-day. The result? Many Chiefs of Staff spend their first months reverse-engineering their CEO’s “operating system” through trial and error. Fortunately, there’s a better approach. By carving out time in Week 1 for a focused conversation, you can surface your executive’s working style and expectations upfront – saving months of guesswork and misalignment. As one experienced Chief of Staff put it, “every leader has a different operating system, decision rhythm, and energy profile… the fastest way to build trust and be effective is to make the implicit explicit early on. One honest conversation in week one can save months of second-guessing, misaligned expectations, and unnecessary friction later.” In other words, the sooner you decode how your CEO operates, the sooner you can shift from reactive survival to intentional partnership.

This article lays out five critical questions that new Chiefs of Staff should ask their CEO in the first week. These questions, originally highlighted by leadership coach Michelle DeFouw in a viral LinkedIn post, are designed to reveal the CEO’s preferences in communication, decision-making, strategic focus, personal energy management, and role expectations. We’ll expand on each question with insights from experienced Chiefs of Staff, executive assistants, and leadership coaches who commented on that post, providing practical tips and nuanced considerations. We’ll also include a quick-reference table and five additional user-suggested questions worth adding to your Week 1 agenda. The tone here is practical and executive-savvy – our goal is to equip you with a high-leverage conversation starter that drives clarity, trust, and alignment from Day 1.

Five Essential Alignment Questions for Week 1

The five questions below serve as an onboarding blueprint for understanding your executive. They cover how the CEO likes to communicate, how they make decisions, where they naturally focus attention, what drains or energizes them, and how they define the Chief of Staff partnership. In one conversation, you can map out your CEO’s working norms – instead of spending weeks or months figuring these out the hard way. Here’s a summary of the five key questions, why each matters, and a sample phrasing for each:

Question Area	Purpose	Sample Wording
Communication Cadence	Uncover how your CEO best processes information and prefers to communicate for maximum clarity.	“How do you prefer to process information – verbally in real-time, or written so you can think it through?”
Decision Architecture	Learn how your CEO wants decisions presented to them (options vs. recommendation) to align with their decision-making style.	“When you need to make a call, do you want to hear several options with my recommendation, or just my single recommended course of action?”
Strategic Orientation	Understand where your CEO naturally focuses (externally on vision/market or internally on operations/team) so you can cover the complementary ground.	“Where does your attention naturally live – external (market, customers, vision) or internal (team, operations, culture)?”
Energy Management	Identify what drains your CEO’s energy (to shield or delegate) and what recharges them (to prioritize and protect).	“What drains you that I can take off your plate? And what recharges you that I should protect?”
Partnership Expectations	Clarify how the CEO defines the Chief of Staff role and what they expect you to own independently vs. merely consult or advise on.	“What does ‘Chief of Staff’ mean to you – and what do you need me to own versus consult on?”

This table provides the big picture. Next, let’s break down each question in detail – why it’s important, how to approach it, and key insights shared by seasoned Chiefs of Staff and advisors on how to make the most of the answers.

1. Communication Cadence – Finding Your Information Flow

Communication is the lifeblood of the CEO–CoS relationship, so it’s critical to get the cadence right. The first question to ask is about communication cadence: “How do you prefer to process information – verbally in real-time, or in writing so you have time to think?” Some CEOs work through ideas by talking them out in impromptu chats or calls; others think better with written briefs, emails, or memos they can digest on their own time. By explicitly asking this, you uncover whether you should be scheduling more live touchpoints (and in what format: face-to-face, calls, Slack chats?) or sending detailed notes ahead of meetings.

Equally important is understanding frequency and timing – do they want a morning update every day, or a weekly deep-dive? While the sample question focuses on format, use the discussion to also clarify what “cadence” means to them (e.g. quick daily sync vs. longer weekly strategy sessions). Setting these norms early prevents misfires like inundating a thinking-oriented CEO with chat pings, or conversely, leaving a talk-it-out leader feeling out of the loop.

One experienced Chief of Staff cautioned: “Once they tell you the answers, you should observe to be sure that’s true. This is especially true on how one processes information.” In other words, don’t just take the CEO’s word – validate it. If they say, for example, “I prefer written updates,” pay attention to whether they actually read and respond to memos promptly or if they end up calling you to talk through issues anyway. If there’s a mismatch between stated preference and behavior, gently adjust your approach or clarify (“I’ve noticed you seem to prefer discussing on the fly despite our written reports – should we switch to more live updates?”). The key is to establish a mutually effective communication rhythm so nothing important falls through the cracks.

2. Decision Architecture – How Your Executive Makes Calls

The second question is about decision architecture: “When you need to make a call, do you want options with my recommendation, or just my recommendation?” This gets at how your CEO prefers to receive input for decisions. Some leaders are options-oriented – they like to see a few paths on the table, debate trade-offs, and then choose. Others are decisive simplifiers – they hired you to filter the noise and come with a clear recommendation, not a multiple-choice quiz. If you assume the wrong approach, you can inadvertently frustrate your executive: offering a single recommendation when they wanted to explore alternatives, or drowning them in options when they really just wanted your expert take.

Seasoned Chiefs of Staff stress how quickly misalignment here can cause friction. As one commenter noted, “Misaligning on whether a CEO wants options vs. a clear recommendation creates silent friction fast. Clarifying that early saves weeks of rework and second-guessing.” In practice, if your CEO says they prefer options, you might present three viable approaches on a big decision (with pros/cons) and then give your pick. If they just want the answer, you lead with your recommendation and only elaborate on alternatives if asked. Also clarify how much context they want: a Visionary CEO might only care about high-level implications, whereas an operator CEO might want to see some data or analysis behind the recommendation. By understanding your executive’s decision-making style, you can architect your deliverables (memos, decks, discussions) to match their appetite – enabling faster, more confident decisions with less back-and-forth.

3. Strategic Orientation – External vs. Internal Focus

Every leader has a natural orientation on the spectrum from external (market-facing, visionary, growth-focused) to internal (execution-focused, team and process-oriented). Neither is good or bad, but knowing where your CEO leans helps you calibrate your support. The third question digs into this: “Where does your attention naturally live – external (market, customers, vision) or internal (team, operations, culture)?”

This question’s purpose is twofold. First, it tells you what information to prioritize in updates and discussions. For instance, if the CEO is highly external-facing, they’ll be keen on competitor news, customer feedback, industry trends, and high-level strategy – and they might lose patience spending too much time in the weeds of internal issues. On the other hand, if they’re internally focused, they’ll care deeply about team dynamics, project execution status, and operational metrics, and they might undervalue market chatter if it’s not tied to immediate execution. Knowing their bias helps you filter and frame information in the way that resonates.

Second, it highlights gaps you may need to fill. A CEO obsessed with vision and market ideas might inadvertently neglect internal team morale or process discipline – that’s where you as CoS step in to keep the house in order. Conversely, an operations-focused CEO might benefit from you keeping an eye on external disruptions or big-picture strategy so they don’t get blindsided. As one leadership coach pointed out, the power of these questions is making the leader’s implicit operating style explicit, so you can actively counterbalance where needed rather than assume “they’ve got it all covered.” Ultimately, understanding your executive’s orientation ensures you become a complementary force – if they look outward, you monitor the inside (and vice versa) – thereby covering the full field between you.

(Tip: Some Chiefs of Staff even ask a follow-up like, “What aspect of the business do you find yourself not paying much attention to lately?” to pinpoint blind spots where you might focus more.)

4. Energy Management – Optimize Drains and Boosts

Even the most capable CEOs have limited time and energy. Question four, about energy management, helps you learn how to protect that energy. Ask: “What drains you that I can take off your plate? And what recharges you that I should protect?” This goes beyond a normal task delegation discussion – it’s about identifying personal energy sinks and sources for your executive.

Drains might include certain meeting types, recurring fire-drills, detailed admin work, or specific activities that sap their enthusiasm. If you learn, for example, that budgeting reviews exhaust your CEO, you might take the lead in pre-review prep and only involve them for high-level decisions, thus sparing them the fatigue. On the flip side, rechargers might be things like thinking time, industry conferences, customer visits, or even personal routines like a morning workout or family dinner. Knowing what re-energizes your CEO lets you fiercely guard that time – whether it’s blocking out an hour daily for them to brainstorm, or ensuring no one schedules over their weekly lunch with a mentor. Small adjustments here can have outsized impact on their sustained performance.

Commenters noted that this question is often the hardest to figure out organically and the most underrated. One Chief of Staff reflected: “I can usually learn how a leader thinks and how decisions get made. What takes longer is understanding what quietly drains them and what truly restores them. That insight changes everything about where effort actually matters. Once you get that right, the partnership stops feeling reactive and starts feeling powerful.” In practice, proactively taking on the draining tasks (before they burn your CEO out) and amplifying the energizing ones is a high-leverage move. It not only improves your executive’s effectiveness but also shows that you’re attuned to their well-being – a hallmark of a trusted strategic partner, not just an “assistant.”

5. Partnership Expectations – Defining the Chief of Staff Role in Their Terms

The final critical question is arguably the most foundational: “What does ‘Chief of Staff’ mean to you – and what do you need me to own versus consult on?” The Chief of Staff role can vary dramatically from one organization (or one leader) to the next. Some CEOs view their CoS as an operational executor and project manager, others as a strategic thought partner, others as a communications and PR handler, and so on. Many times it’s a mix of hats. This question forces your executive to articulate their vision of the role and clarify the level of authority and ownership they expect you to take on.

Getting this on the table in Week 1 prevents painful misunderstandings down the road. For example, if your CEO says, “I need you to own internal meetings and only loop me in on critical decisions,” that’s very different from “I see you as an advisor who will help prep me but I’ll make the calls.” In one case, you are empowered to act as an operator on their behalf; in the other, you’re more of a consigliere. Neither is wrong, but not knowing which game you’re playing is. As one comment put it, much friction arises when “cadence, authority, and ownership aren’t explicit”, causing Chiefs of Staff to waste time reverse-engineering what decisions they are allowed to make. By explicitly asking what you should own versus where you should just consult or inform, you establish clear guardrails. This not only speeds up execution (you know where you have a green light) but also honors the CEO’s comfort level, avoiding overstep or underperformance.

Furthermore, the discussion of “what Chief of Staff means to you” can surface any differing assumptions about the role. It’s an opportunity to align on how you’ll work together as a partnership. Will you serve as a proxy in certain meetings? Are you the first draft writer and the CEO the editor, or vice versa? How do you divide and conquer priorities? By the end of this conversation, both of you should have a shared understanding of the partnership model. This forms the basis of trust – your CEO knows they can rely on you in the ways they need, and you know exactly where to focus your efforts for maximum impact.

As one seasoned Chief of Staff noted, bringing these fuzzy expectations to light transforms the early dynamic “from survival to design.” It turns a reactive support role into an intentional partnership built on upfront clarity. “By naming communication, decision-making, and energy [preferences] up front, you shift the work from reactive translation to intentional partnership… These questions surface assumptions before they calcify into tension. That kind of front-loaded clarity saves months of quiet strain and misalignment. It’s a disciplined way to honor both the role and the relationship from the start.” In short, explicit expectations are the foundation of a high-functioning CEO–CoS duo.

Top 5 Additional Questions Suggested by Seasoned Chiefs of Staff and EAs

The five core questions above emerged from one highly shared post, but the discussion didn’t stop there. Experienced Chiefs of Staff, executive assistants, and leadership coaches chimed in with their own “must-ask” questions for new leaders. Here are the top five additional questions worth considering in your Week 1 conversation (or in the weeks shortly after). These came directly from community comments and reflect hard-won wisdom from the field:

“How do I effectively tell you no?”

Every Chief of Staff eventually faces a moment where they need to push back on their boss – whether it’s to flag a risky decision or to call out that the team can’t deliver on a promise. It’s critical to know upfront how your CEO prefers you raise disagreements or bad news. One commenter pointed out this question is more than just a communication tweak – “‘No’ isn’t a communication skill – it’s a psychological safety test. The real issue isn’t whether you push back, it’s whether the system rewards truth or punishes it. The fastest way to learn that is to ask not just how to say no, but what happens after you do.” In other words, does your executive truly welcome dissent, and what process do they find constructive for handling it? Michelle D. herself acknowledged a version of this should have been Question 1, because the first five questions tell you how your CEO operates; this sixth question tells you if the relationship is safe. Depending on your CEO’s style, you might phrase it in a tactful way – e.g. “If I see a significant risk or disagree with a direction, how would you like me to bring it up?” The answer will reveal a lot. (Do they say “please speak up immediately” or do they get uneasy?). Leaders who value a true thought partner will explicitly encourage thoughtful pushback. Those who bristle at dissent might require a more subtle approach or may not be the empowering mentor you hoped for. Better to know in week one than in month six.

“What are the key dates and milestones I should be aware of, and how do you (and the organization) typically prepare for them?”

This question, suggested by a Chief of Staff in the thread, is about calendaring and cultural cadence. Every organization has critical dates that dominate leadership attention – whether it’s quarterly board meetings, annual planning offsites, major product launches, or industry conferences. By asking this, you’ll learn not only what those events are but how the CEO likes to handle them. For example, if the CEO mentions a board meeting in March, you can ask what prep usually looks like – do they want a deck a week prior or a rehearsal session? Are there internal deadlines leading up to it? As the commenter noted, understanding these key dates and the “internal culture on how these are prepared for” is huge for a new CoS. It lets you orient your early work around supporting those milestones and not get caught off guard. It also shows your boss that you’re already thinking ahead about how to make them (and the company) successful at the big moments.

“What is the organizational structure that’s not on paper – the unofficial org chart or key relationships I should know about?”

Beyond the formal org chart and titles, every company has an informal structure of influence and information flow. In the LinkedIn discussion, this came up as a highly-recommended question: “Which relationships do I need to be mindful of and how does information flow [here]?” Early on, map out the power centers and trusted lieutenants in your CEO’s world. Who are the five or ten people whose opinions carry the most weight with the CEO? (They might be direct reports, but sometimes also mentors, board members, or unofficial advisors.) Who runs the whisper network internally? Who are the blockers vs enablers for getting things done? By asking your CEO about the “hidden” org dynamics, you signal that you plan to navigate relationships thoughtfully, not bulldozing in blindly. It will help you avoid stepping on political landmines. It also identifies key people for you to build rapport with early. For instance, if the CEO says, “Our CFO and COO are my two key confidants” or “Make friends with Sarah in Product – she’s been here 10 years and knows where everything is,” that’s pure gold. Don’t limit this question to just people, either – ask about information flow: Does the real news travel through hallway conversations, formal reports, Slack channels, skip-level meetings? Knowing this lets you set up your own intelligence-gathering accordingly.

“Are there any major pet peeves or no-go areas I should be aware of?”

– Great executive assistants often ask this question on day one, and Chiefs of Staff can benefit from it too. Every leader has quirks and boundaries. Some examples: “I hate surprise drop-ins on my calendar,” or “I never check texts after 8pm,” or “I have a rule that we don’t use slides in internal meetings,” or “Don’t bring me problems without suggestions.” These might sound small, but violating an executive’s pet peeves can unintentionally strain trust. Showing the self-awareness to ask proactively demonstrates emotional intelligence and a desire to adapt to their style. It might feel a bit direct to ask (“What drives you nuts that I should avoid?”), so you can soften it: “I want to make sure I work effectively with you – are there any work habits or approaches that you particularly dislike or love?” This gives them room to share positives too (e.g. “I really appreciate when someone sends me an agenda beforehand”). Knowing these unwritten rules helps you avoid unforced errors and accelerates the comfort in your partnership. It’s far better to learn on Day 5 that your CEO hates long emails than to find out after you’ve sent a 2,000-word manifesto and got no reply.

“How will we measure success for my role in the first 90 days (and beyond)?”

This question elevates the conversation from immediate tactics to expectations and outcomes. It’s one thing to know what the CEO wants you to do; it’s another to know how they’ll judge if you’re doing it well. Asking how they’ll measure success prompts your executive to define what a “win” looks like for the Chief of Staff function. Maybe it’s quantitative (e.g. “freeing 10 hours of my week by Q2” or “completing X project by March”). It could be qualitative (e.g. “improve leadership team communication” or simply “if I’m less stressed and more prepared, that’s success”). It might even be cultural (e.g. “become a trusted go-to for the team”). Whatever the answer, it gives you a clear target to work toward and a basis for ongoing check-ins. It also opens a dialogue about priorities: if the CEO lists five big outcomes, you can clarify which are top priority. Seasoned leadership coaches often recommend this kind of question because it forces clarity on expectations and avoids the scenario of “I thought I was doing well, but the CEO was disappointed in something I wasn’t even focused on.” Set the success metrics together, then you can periodically review progress against them. This turns your Week 1 conversation into a living plan for your own effectiveness.

Feel free to adapt these questions to your own style and your executive’s personality. Not every question must be asked in the first formal meeting, but all are valuable within the early ramp-up period. The common theme is proactively surfacing expectations, preferences, and potential friction points before they become problems. As one commenter noted, these kinds of questions “make the implicit explicit” and set the stage for trust. By combining the core five with a few of these additional ones, you’ll arm yourself with a rich understanding of your new boss and organization.

From One-Time Conversation to Ongoing “Operating System” Resets

As critical as the Week 1 conversation is, it should be seen as the beginning of an ongoing alignment process, not a one-and-done event. Think of it as drafting the first version of your CEO–Chief of Staff operating manual. Like any operating system, it needs updates. Here’s how to turn that initial discussion into a sustainable cadence of communication and calibration:

Document and observe.

After your Week 1 Q&A, jot down the key takeaways – your CEO’s preferences, the do’s and don’ts, the definitions you’ve agreed on. Then, as you start working together, observe how reality aligns with those answers. People may say one thing and do another unintentionally. For example, if the CEO said they prefer written comms but rarely responds to your memos, take note of that behavior. If they defined your role one way but keep pulling you in a different direction, note that too. These observations aren’t “gotchas,” they’re inputs for your next conversation.

Follow up and recalibrate.

Seasoned Chiefs of Staff and leaders suggest scheduling a check-in after the first 30 or 60 days to revisit these questions. Treat it as an operating system update. Share what you’ve observed: “You mentioned X was your priority; I’ve noticed Y has been taking a lot of your time. Should we adjust our approach?” or “We said I would own A and consult on B; I want to ensure that still feels right as things have evolved.” This shows proactivity and keeps the alignment tight. One leader in the discussion emphasized that once a CEO tells you their preferences, “you should observe to be sure that’s true” – and then tactfully discuss any discrepancies. By doing so, you keep the relationship honest and effective.

Embed alignment into regular 1:1s.

Rather than only having these conversations at the start or when something is wrong, build a habit of brief alignment checks in your regular meetings. For instance, every quarter (or at the end of major projects), take a moment to ask: “Is there anything about how we’re working together that we should tweak?” or “Are there new priorities or strains on your time that we should account for in our operating rhythm?” This continuous improvement mindset turns alignment into a routine practice. It’s much easier to address minor course corrections proactively than to fix a major breakdown caused by months of assumption drift.

Leverage trust to broaden honesty. If you asked “How do I tell you no?” and got a candid answer in Week 1, by Week 12 you should have some sense of whether that answer held true. Use that as a gauge of trust. If the CEO has proven open to pushback, you can be even more candid going forward (and you’ve likely earned reciprocal honesty from them). If not, you’ll have to navigate that carefully or clarify expectations again. The ultimate goal is to reach a point where difficult conversations are routine and safe – where raising a concern isn’t a drama, it’s just part of the dialogue. Many executives say their most valued Chiefs of Staff are those who can deliver the uncomfortable truths early, saving them from bigger issues later. Cultivating that dynamic is an ongoing effort.

Onboarding alignment is about creating a shared language and set of norms between you and your CEO. By asking these pointed questions in Week 1, you accelerate that understanding dramatically. You’ll still learn about each other over time – no single meeting reveals all the nuances of working with a leader – but you’ll have a framework to make sense of new situations as they arise. Instead of reacting blindly, you can say “Ah, this situation touches on their decision style or energy drain we discussed” and adjust accordingly.

Finally, keep in mind that asking the questions is only step one; true alignment comes from the dialogue and follow-through. One honest conversation can open the door, but it’s the continued practice of honesty and adjustment that keeps the operating system of your partnership running smoothly. Done right, this approach transforms the Chief of Staff role from a mere survival game of “figure out the boss” into a deliberate design of a powerhouse partnership – one built on clarity, trust, and strategic focus from the very start. As you embark on your new role, remember: the quality of your questions will define the quality of your outcomes. Week 1 is the time to ask them. Good luck, and go make that conversation count!

From Conversation to Continuous Alignment with Axell

As critical as the Week 1 conversation is, it should be seen as the beginning of an ongoing alignment process, not a one-and-done event. To truly transform your dynamic from “survival to design,” a modern, skills-first performance platform can be the essential tool. This is where a solution like Axell can turn your initial alignment conversation into a sustainable operating system for your partnership.

Axell is designed to embed the principles of the high-leverage Chief of Staff conversation into your daily and weekly workflow, helping you maintain a high-functioning CEO–CoS duo built on clarity, trust, and strategic focus.

Here are two key solutions that fit very nicely with the challenges outlined in this article:

Structured 1:1s and Continuous Feedback

The article stresses the need for a mutually effective communication rhythm and the caution to “observe to be sure that’s true.” Axell’s structured 1:1 feature and continuous feedback capabilities formalize this process. It helps you shift from relying on ad-hoc check-ins to a disciplined system where you can document key takeaways, track discussion points, and share and request feedback in real-time. This helps both you and your executive ensure that the stated preferences on Communication Cadence and Energy Management align with reality, and it provides a safe, documented space to raise difficult questions like “How do I effectively tell you no?” By leveraging continuous feedback systems, you keep the “operating system” running smoothly with constant, minor course corrections rather than waiting for a major breakdown.

Goal Alignment and Success Measurement

The question, “How will we measure success for my role in the first 90 days (and beyond)?” is about translating expectations into tangible outcomes. Axell’s goals and OKR framework connects your individual CoS priorities directly to the CEO’s Strategic Orientation and the company’s overall vision. It moves the conversation beyond mere delegation by ensuring every project you “own” or “consult on” is explicitly linked to measurable strategic objectives. This practice gives you a clear target to work toward and simplifies your periodic check-ins—progress against shared goals becomes the natural basis for discussion, providing a powerful, objective foundation for your partnership model.

Ultimately, the goal of the Week 1 conversation is to make the implicit explicit. Technology like Axell helps you maintain that hard-won clarity over time, ensuring your partnership evolves intentionally rather than just reactively. As you embark on your new role, remember: the quality of your initial questions will define the quality of your outcomes, and the quality of your systems will determine how long that alignment lasts. Good luck, and go make that conversation count!

Frequently Asked Questions