The company changed. The pressures changed. The Office of the CEO did not. Why the OCEO should have seasons by design, and how to tell when yours has fallen behind the business it serves.
Map a public company CEO's last decade and it might look something like this:
The CEO who started that decade had one clear mandate. The CEO who ends it answers to the White House, their family, major shareholders, and a public that notices every misstep, all while coordinating a global supply chain, sitting through board meetings and earnings calls, and pushing to win an AI race. The relationships have changed too. The CEO's circle now includes fellow chief executives, major investors, and government officials, many of them supported by sophisticated OCEO functions of their own, and every interaction between those offices makes the gap visible.
It would be unwise for that CEO to run the same OCEO function they started with, unless by some miracle the team has grown alongside them. That's rare. Experience of, and exposure to, the CEO's new world count for a great deal. The people hired in the turnaround years were supporting one clear objective, where it was obvious where, why, and with whom the CEO's time was spent.
Yet walk into most companies and you'll find an Office of the CEO that was designed five years ago. The same structure, the same scopes, often the same people. That would be fine if the company were the same company it was five years ago. Very few are.
The Office of the CEO exists to multiply the CEO's time, judgment, and reach. When the function goes stale, it stops multiplying and starts leaking.
The CEO begins absorbing work the office should be absorbing. Information reaches them raw, because nobody in the office has the experience to digest and triage it first. Their calendar reflects who shouts loudest rather than where the company is going. Decisions slow at the very top, and that delay compounds through every layer beneath.
There's also a quieter cost. The CEO is being outsupported by their peers. Other CEOs, facing the same pressures, rebuilt their offices to meet them. The gap between a well-designed office and a legacy one shows up in preparation, in follow-through, and eventually in performance, even if nobody ever names the cause.
The signals arrive early, and they're easy to misread as individual performance issues.
The EA starts dropping balls they never used to drop. The Chief of Staff can't keep up with the sheer volume and weight of what's flowing through the office. Information arrives upstream thick and fast, and raw, with nobody positioned to synthesize it on the CEO's behalf.
Then there's the structural signal. As a company institutionalizes, the office needs to become sharper and more defined, with roles scoped narrow rather than wide. If a team of four is still operating on the loose, everyone-rolls-their-sleeves-up scoping that made sense five years ago, the function has fallen behind the company it serves, regardless of how hard the individuals are working.
And there's the comparative one. You quietly notice your EA doesn't operate at the level of your peers' EAs. Those CEOs hired a completely different caliber of EA, usually at a materially higher salary, because their office demanded it.
The Office of the CEO does eventually get upgraded, but rarely by design. It happens after a crisis. It happens when a long-serving EA resigns. It happens when enough balls have been dropped that people, including the CEO, finally notice.
When that trigger arrives, the response is almost always to replace the individuals involved rather than to examine the entire model from the top down. Replacing a person answers the question "who should sit in this seat?" Examining the model asks a better one: "should this seat exist at all, and what seats are missing?"
The second mistake follows the same logic. When the office is visibly straining, most leaders read it correctly as a signal to hire, and almost none read it as an opportunity to rescope the entire function. They hire an extra pair of hands, bolt it onto the existing structure, and the underlying design problem survives the fix.
Both mistakes share a root: treating the office as a collection of people rather than as a function with a design. What worked five years ago is unlikely to be what works today. Perhaps the firm wasn't public then. Perhaps the CEO didn't have children. Perhaps they're newly appointed, brought in specifically to take the company somewhere it has never been. The office was built for a person and a set of demands that no longer exist.
Reorganizing the Office of the CEO is genuinely hard, which is why so many avoid it. There's never time. Nobody wants to rock the boat. And there's a real fear underneath it: once someone has years of context built up, it stings when they leave, because they walk out the door carrying all of that accumulated knowledge with them.
There's one more reason, and it's rarely said out loud. Nobody wants to be the one to tell the CEO. The people best placed to see the office straining are the people inside it, or close to it, and raising the issue means criticizing colleagues the CEO trusts, and has often been loyal to for years. So the observation stays private, the function stays as it is, and the eventual correction arrives the hard way.
The review of the OCEO should be purposeful and always on. You never want to be in a position where the entire function needs rebuilding at once.
Companies tend to grow along a reasonably predictable curve. You know, roughly, where you're headed. The question to keep asking is whether your office is set up to support you in that direction, or in the direction you were traveling three years ago. Ask it regularly and you can tighten scopes gradually, add or replace people in step with where the business is going, and stay properly supported throughout. Reviewed continuously rather than after a resignation, the changes are small, deliberate, and unsurprising.
This is also the honest answer to the concerns above. Politics, loyalty, and the fear of moving the goalposts are all reactions to sudden change. When change is regular, incremental, and expected, it stops being a shock. Nobody experiences an abrupt restructure because there never is one.
Sometimes it means upgrading a role. The Chief of Staff hired as a generalist did exactly what generalists do well: filled the gaps between the C-suite, connected dots, wore whatever hat the business needed that week. These people thrive in ambiguity and usually love the work. As the company corporatizes through Series B, C, D, and toward IPO, the role has to change shape. The Chief of Staff becomes a sharp instrument, operating on behalf of the CEO or driving very specific, purposeful initiatives. At that stage you want an expert, aligned to today and tomorrow rather than to the scrappy years behind you.
Sometimes it means adding a role that didn't previously need to exist. When information is arriving faster than anyone can digest it, an Analyst to the Office of the CEO often earns their place, someone with the experience to understand, synthesize, and triage on the CEO's behalf.
Sometimes it means reshaping ahead of a known destination. A company two years out from IPO might deliberately rebuild its OCEO now, bringing in people who understand that world, can carry the administrative load it generates, and have the technical capability to frame the company correctly for it.
And it doesn't always mean new hires, or exits. Someone who has spent years working inside the brain of the CEO carries institutional knowledge that another executive in the business would gladly put to work. Redeploying them creates room for fresh eyes with experience matched to where the company is heading, and the knowledge stays in the building. Equally, if the current team has real capability and genuine coachability, and the CEO or those around them can accurately see what the future office needs to look like, the existing team can be rescoped and realigned to keep pace with what's coming.
The old model waits. The office is designed once, left alone, and rebuilt only after a crisis, a resignation, or enough visible damage to force the issue. The correction is large, political, and painful, and the CEO spends the intervening years undersupported without quite knowing it.
The always-on office is reviewed against where the company is going rather than where it has been. Scopes tighten gradually. Roles are added, reshaped, or redeployed in step with the business. Nobody is blindsided, and the CEO is never more than one small adjustment away from being properly supported.
A family can outgrow its home. Nobody considers moving house a betrayal of the old one. It served its season. The Office of the CEO deserves the same treatment: seasons, by design.
This is the work we do at Blackbook Associates. We're headhunters by trade, but on OCEO and OCXO functions we operate as a thought partner first, examining whether the office is designed for the company's next chapter before asking who should sit in it. Sometimes the answer is a different caliber of EA. Sometimes it's a sharper Chief of Staff, an Analyst, or a profile so specific it doesn't yet have a market name. If it supports the CEO in a meaningful way, it's worth considering.