Working Through the Executive Assistant, Not Around Them

Thursday, 14:10, at Acme. The desk phone rings and it is Grace, assistant to Martin, the chief executive. "Martin's in the airport lounge and his laptop won't get on the wireless. He boards in twenty minutes and he needs to send the term sheet before he does." Sofia, who has been on the desk of four for two years, asks the questions she would ask anyone. She asks which network, what the screen says, and whether the phone has signal. Grace does not know, because Grace is at her desk on the fifth floor. Martin is six hundred miles away in a lounge with a coffee and a deadline. Sofia asks whether she can call Martin directly. Grace says, "He won't pick up a number he doesn't know. Tell me what to tell him." For the next twelve minutes Sofia talks to Grace, and Grace messages Martin. Martin tries things, and Grace relays what happened. The term sheet goes from Martin's phone at 14:23 using the phone's own connection. That was the second thing Sofia suggested and the first thing Grace could get him to try.

The executive assistant is the person who manages an executive's calendar, correspondence, travel and, in practice, their technology. For the help desk the assistant is the real requester: the person who raises the ticket, answers the questions, schedules the fix, tests the result and says when it is done. The executive is the subject of the ticket and only occasionally a participant in it. A desk that treats the assistant as a messenger to be got past on the way to the executive has misunderstood the arrangement. It will spend its time trying to reach a person who does not answer unknown numbers. A desk that treats the assistant as the requester, with a standing arrangement and a regular check-in, gets the executive's problems solved. The assistant can actually get the executive to try things. This article is part of our VIP & Executive Support series. It is about that working relationship.

It covers the assistant as the real requester, then the standing arrangement and the proactive check-in. Next come the escalation path that goes through the assistant and the one that must not. Then come the assistant's own access and what happens when the assistant changes, followed by the assistant's own tickets. The courtesies and the traps follow, with a table of who may ask for what. A short war story and the assistant arrangement note to copy finish the article, in that order.

The Assistant Is the Real Requester

Put the assistant on the ticket as the requester, with the executive copied or not according to the arrangement. Send every reply, question and confirmation to the assistant. This is the opposite of the desk's usual instinct, which is to find the person with the problem and talk to them. The instinct is wrong here for a plain reason. The executive is not available, does not read tickets, and did not raise this one. The assistant did, will read the reply within minutes, and knows whether Martin can take a call at three or is in a meeting until five. Every message the desk sends to the executive directly is a message the assistant will have to find, interpret and relay. They will do this with less context than if it had come to them first.

The assistant also knows things the executive does not. They know that the laptop has been "a bit slow" for a fortnight. They know that the phone was replaced in the spring and the mail was never quite right afterwards. They know that the executive is travelling next week and the week after. The fix must happen on Thursday or not until the month's end. They know which of the executive's complaints are real and which are impatience. They will tell the desk, in confidence, if the desk has earned it. A technician who takes the assistant's account of a fault seriously gets a better description than the executive would give. That is because the executive saw the symptom once and the assistant has heard about it four times.

The confirmation goes to the assistant too, and the assistant tests. "Can you check that Martin's calendar shows the Tuesday meeting on his phone?" The assistant can answer this in a minute by looking at the shared calendar or asking. The same question to the executive is a message that may be read on Friday. In QuerySolv and most tools, the assistant's reply to a resolved ticket reopens it. Where this happens, the assistant saying "it's back" a day later lands on the record with its history rather than in a technician's own inbox. That inbox is where executive tickets have traditionally gone to be forgotten.

The Standing Arrangement

The standing arrangement is a short written note, agreed between the desk and each assistant, that answers the questions the desk would otherwise ask at the start of every ticket. It covers how to reach the assistant and how they reach the desk. It lists which devices the executive has and which matter most. It says when the executive can and cannot be interrupted. It records what the assistant may ask for on the executive's behalf, and the dates the desk needs to know about. It is one page and takes twenty minutes to agree. It saves that twenty minutes on every ticket afterwards. The technician picking up the ticket reads the note instead of asking Grace, again, whether Martin prefers a call or a message.

The devices line is the one most desks skip and most regret. An executive typically has a laptop, a phone, sometimes a tablet, sometimes a second laptop at home, and often a personal phone with work mail on it. The assistant knows the full list while the desk knows the ones that have had tickets. Write them all down, with which one the executive actually works from, because "Martin's laptop" in a ticket may mean either of two. The technician who prepares the wrong one has wasted the visit. The line also records which devices the desk supports and which it does not, so that the personal tablet question is answered before it is asked.

The interruption line is the assistant's gift to the desk. "Never before nine; never during the Monday leadership meeting; messages are read between meetings; a visit is possible most days between two and three if booked the day before" turns a technician's guess into a plan. It also makes the proactive check-in possible, because the desk knows when the executive will not be at the desk. An empty desk is when the laptop can be taken, patched, restarted and returned without anyone losing an hour. The patch window for an executive's laptop is wherever the assistant says it is. The desk's own maintenance schedule has never once consulted a travel calendar.

The Proactive Check-In

The proactive check-in is a five-minute conversation with the assistant, every two to four weeks and always before travel or an event. In it, the desk asks what is brewing before it becomes a ticket. "Anything not quite right with Martin's kit? Anything coming up that we should know about?" The answers include the fortnight-old slowness and the phone that needs its storage cleared. Other answers are the conference next month in a venue with bad wireless, the new assistant starting in three weeks, and the board date that moved. Each is a ticket avoided, or a ticket raised early, at a time the desk chose rather than the morning the executive boards a plane.

The check-in is also when the desk does its own maintenance. Updates that would otherwise interrupt the executive at an airport are done in the window the assistant names. The laptop's pending restart is cleared. The loaner is confirmed as still prepared. The phone's management profile is checked for anything expiring. The desk comes to the executive floor on its own schedule, at a time nobody minds. The executive's devices are the best-maintained in the building, which is roughly the opposite of the usual state of affairs. Before travel, the check-in has a fixed shape. The devices are patched and restarted, and the remote-access client and the second-factor method are tested. The phone has the conferencing client signed in, and the assistant has the desk's out-of-hours number. Before an event, the check-in is the week-before step of the prep in Board Days and Big Events.

The check-in has a cost, which is a few hours a month across the list. It is the best-spent few hours in VIP support, because it converts the unpredictable executive emergency into predictable maintenance. Count the hours and report them with the rest; the last article in this series says how. In my experience, a desk that runs check-ins for six months finds that its executive tickets have halved. It also finds that the ones remaining are genuine faults rather than neglect caught at the worst moment. The executives notice nothing, which is correct. The assistants notice everything, and they are the ones who will say so to the chief operating officer.

The Escalation Path That Goes Through Them, and the One That Must Not

Nearly everything goes through the assistant. That includes timing, preferences, the executive's calendar and devices, and questions about what the executive meant. It includes confirmation that a fix worked and the scheduling of any visit. The desk that wants an answer from the executive asks the assistant to get it, and the assistant decides whether to interrupt. This is the normal path and it should be used even when the executive is sitting at the next desk. That is because the assistant is keeping a picture of the executive's day that the desk cannot see. A technician who walks past the assistant to ask the executive a question has just told the assistant something. The message is that the arrangement does not apply when the desk is in a hurry.

Three things must not go through the assistant, and the arrangement note says so plainly so that nobody is offended when the desk declines. The first is identity verification before a reset or an access change. The executive proves who they are, by the desk's standard, in person or by the agreed method. The assistant cannot do it for them, however well the desk knows the assistant's voice. The standard is in Verifying Identity Before a Reset. For the executive-specific reason, consider a call claiming to be from the assistant and asking for the chief executive's password reset. That is precisely the shape of the attack the standard exists to stop. The assistant will understand this, because the assistant is the person who would be impersonated.

The second is a security matter on the executive's accounts. A suspected compromise, a phishing click, a lost device: the desk contains it at once. It tells the executive directly by a channel the desk trusts, and tells the security function. The assistant is told what has been done rather than asked to relay the decision, because minutes matter. The assistant's own access to the executive's mailbox may also be part of what is being looked at. The third is any exception to a policy. The assistant may ask on the executive's behalf, but the assistant cannot authorise. Neither can the executive if the policy is not theirs to change. The request goes to the policy's owner by the route in Saying No Upward. The assistant is told who decides and when. "Martin says it's fine" is a message, not a decision, and the technician who treats it as a decision has just made it their own.

The Assistant's Access, and When the Assistant Changes

The assistant works inside the executive's mailbox and calendar. The desk sets that up as delegation under the assistant's own name, never as shared credentials, on the assistant's first day. The kinds of access and the request form are in Shared Mailboxes, Delegation and Who Can See What. The discretion reasons are in the previous article in this series. The arrangement note records what the assistant has been granted. That way, the next technician does not have to guess whether the assistant can see the executive's files as well as the mail. It also records what the assistant has not been granted. This answers the occasional "can you give me access to Martin's folder" without a debate. The request goes to the executive, who says yes or no, and the desk acts on the executive's word in the ticket.

The assistant changing is the moment the whole arrangement is at risk. The new assistant does not know the desk, the desk's standard, the executive's devices or the check-in habit. The old assistant's access is still live in the directory because nobody owned the removal. The desk's routine is three steps on the day the change is announced. Open the old assistant's leaver tasks with the delegation removal as a named line. Set up the new assistant's delegated access on their first morning. Book twenty minutes with the new assistant in their first week to re-agree the arrangement note from scratch. Do not hand the new assistant the old note; walk through it, because half of it will have changed and the new assistant will not know which half.

An assistant who covers for another, during leave, gets the same treatment in miniature. They get temporary delegated access with an end date in the ticket. A one-line addition to the arrangement note says who is covering until when. The commonest access leak on an executive floor is the covering assistant whose temporary access was granted on a Friday and reviewed never. Write the end date in the ticket, set a reminder for it, and remove the access on the day, with a line in the ticket saying so.

The Assistant's Own Tickets

The assistant's own laptop failing is the executive's problem in a different seat. An assistant who cannot reach the calendar cannot schedule the executive, cannot answer the board's queries, and cannot book the travel. The executive's day begins to fail in ways the executive will feel by lunchtime without knowing why. The charter in the first article of this series includes assistants for tickets raised on the executive's behalf. In practice their own tickets deserve the same handling. It is more honest to write that down than to let the technicians work it out, which they will, in the shadow way. The assistant's ticket gets a fast human reply, a named technician and a visit at a time they choose. It gets its priority from impact and urgency like anyone's, which for an assistant's dead laptop on a board week is genuinely high.

The courtesy cuts the other way too. The assistant's own tickets are the assistant's. The desk does not report their contents to the executive, mention them at the check-in or treat the assistant's device with less discretion than the executive's. The assistant's laptop holds the executive's calendar, correspondence and travel, and often the assistant's own personal life besides. The discretion standard does not have a junior version.

The Courtesies and the Traps

The courtesies are simple and the desk should do all of them. Use the assistant's name and learn how they prefer to be reached. Tell them what has been done before they have to ask. Give a time and keep it, or say before the time that it has moved. Never let them find out from the executive that the desk visited. Thank them when they get the executive to try the thing the desk suggested. Getting an executive to restart a laptop is a skill the desk does not have and the assistant does. And never, in any message to anyone, refer to the assistant as a gatekeeper, a go-between or an obstacle. They are the person who makes it possible to support someone who is never at their desk.

The traps are two. The first is the assistant becoming a shadow channel, a route to help that bypasses the queue. The assistant has Sofia's mobile number and texts her directly. The executive's tickets stop existing as tickets. It happens because the assistant is efficient and Sofia is kind. The cure is the one from The Seven Ways Support Quietly Fails. Sofia answers the text, says "logging this so it's not lost", and opens the ticket with the assistant as requester. Whatever door the assistant uses, phone, chat, mail or a message to a technician, the request becomes a ticket in the same queue. The arrangement note says that it will, so that the assistant is not surprised to receive a ticket number in reply to a text. The second trap is the assistant speaking for the executive on things the executive has not said. The table below is the desk's answer to it. It says who may ask for what, so that the technician does not have to decide at the phone.

A Short War Story: Two Calendars at Greyfell Mining

At Greyfell Mining, the desk of three decided to replace the chief executive's ageing laptop. Wanting to be efficient, they e-mailed the chief executive directly to propose Tuesday at ten. He replied "fine" from his phone without looking, as chief executives do. On the Tuesday the technician, Mateo, arrived on the executive floor at ten to find the chief executive on an investor call. The call had been in his assistant Lydia's calendar for three weeks and in nobody else's. The laptop could not be touched until it ended, which was at one. The swap was done at half past six the next morning, before the chief executive's flight, with Mateo on an early callout. The chief executive's new laptop was missing the one application he used on planes, because nobody had asked Lydia what he used on planes. The desk lead costed it afterwards at about nine hours across three people, including the second visit. Compare that with the forty minutes it would have taken on a Thursday afternoon that Lydia could have named in a single message. Lydia, asked why nobody had checked with her, said nobody had thought to. The desk wrote its first arrangement note that week. The executive's calendar lives with the assistant, and so does the executive's yes.

The Assistant Arrangement Note

The note is one page per assistant, agreed in twenty minutes, kept where the named technicians can find it, and re-agreed whenever the assistant changes or the executive's devices do. The top block is contact and reach. The second is the devices. The third is the interruption and maintenance windows. The fourth is what the assistant may ask for and what must go elsewhere. The fifth is the dates and the check-in. The last is the access the assistant has been granted, with the date it was last reviewed. The note is not a form the assistant fills in. It is a conversation the technician writes down, and the assistant reads and corrects.

THE ASSISTANT ARRANGEMENT NOTE — ONE PAGE PER ASSISTANT
Executive: ______________ (role: ______________)   Assistant: ______________
Named technicians: ______________ / ______________   Agreed on: ____________   Review: ____________

1. REACHING EACH OTHER
   Assistant prefers: [ ] phone  [ ] chat  [ ] mail  [ ] in person      Hours: ______ to ______
   Desk's route for the assistant: ______________ (every request becomes a ticket, whichever door)
   Out-of-hours number for travel and events: ______________
   The executive is reached only through the assistant, except for: identity checks, security
   matters on the executive's accounts, and anything the executive asks to hear directly.

2. THE DEVICES
   Works mainly from: ______________________   Also has: ______________________
   Phone: ______________ (work / personal with work mail)   Supported by the desk: yes / no
   Home device: ______________   Supported: yes / no          Loaner prepared: yes / no

3. INTERRUPTION AND MAINTENANCE WINDOWS
   Never interrupt: ______________________________________________
   Messages read: ______________________   Visits possible: ______________________
   Maintenance window (patch, restart, swap): ______________________
   Travel calendar shared with the desk: yes / no    Event dates shared: yes / no

4. WHO MAY ASK FOR WHAT
   The assistant asks on the executive's behalf for: faults, visits, loaners, patches,
     supported software and settings, and access for the executive to systems (owner approves).
   The executive personally: identity verification before any reset or access change;
     confirmation in the ticket of any access granted to their mailbox, calendar or files.
   The policy owner: any exception (shared credentials, unmanaged device, unattended access).
   Nothing is done without a ticket; the ticket note records the fault and the fix only.

5. THE CHECK-IN
   Every ______ weeks, and before every trip and every event:  "Anything not quite right?
   Anything coming up?"   Pre-travel: devices patched and restarted; remote access and second
   factor tested; conferencing client signed in on the phone; out-of-hours number confirmed.
   Last check-in: ____________   Next: ____________

6. THE ASSISTANT'S ACCESS
   Delegated access held (mailbox / calendar / files / send-as / on-behalf): ______________________
   Granted on: ____________   Confirmed by the executive in ticket: ________   Last reviewed: ____________
   Covering assistant (if any): ______________   Access ends: ____________   Removal ticket: ________
   On a change of assistant: old access removed on the leaver ticket; new access set up under the
   new assistant's own name; this note re-agreed from scratch within the first week.

Sofia wrote Acme's first arrangement note with Grace the following Monday, in nineteen minutes. She learned that Martin had two laptops, never answered calls from numbers he did not know, and could be interrupted on Thursdays between two and three. The next trip, his laptop was patched and restarted on the Thursday before, the phone's connection was tested, and Grace had the desk's out-of-hours number in her phone. He sent the next term sheet from the lounge without anyone at Acme knowing he had been in one. Grace sent Sofia a message afterwards that said "quiet trip", which is the whole of the feedback VIP support gets, and all of it good.

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