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CEO handbook

This page details processes specific to Mike McNeil, CEO of Fleet. Below are a list of processes the Executive Assistant collaborates with the CEO.

In this section

The CEO support team

EA to the CEO

Task Description Frequency
CEO e-mail management Triage inbound communications, draft responses, flag actions Daily, multiple times
General communications in #help-ceo slack channel Triage inbound communications, draft responses, flag actions Daily, multiple times
Schedule internal and external meetings for the CEO Triage inbound communications, draft responses, flag actions Daily, multiple times
Meeting requests in #-meetings and #help-ceo slack channels Triage inbound communications, draft responses, flag actions Daily, multiple times
Preparing agendas and content for CEO's meetings Create and edit agenda, provide context, and contact information PRN
Expenses for the CEO Intake expense receipts PRN
Ad-hoc requests from the CEO Triage requests, prioritize actions, flag actions for further review PRN
Total travel coordination for the CEO Triage travel request, plan and coordinate flight, stay, and conceirge arrangements PRN
Coordinate the weekly E-Group calendar events for the Executive team Triage requests, agenda prep, flag actions, follow up Weekly, PRN

CEO preferences

Scheduling with the CEO

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Reach out to the EA to the CEO in #-meetings with the required details to book a meeting with the CEO. All meetings on Mike's calendar should be scheduled and vetted by the EA to the CEO.

  • Please do not directly schedule a meeting onto Mike's calendar without confirming with the EA to the CEO in advance or unless requested directly from Mike.
  • The CEO requires meetings to originate from his calendar and on his Zoom account.

Meetings before 9 am and after 6 pm Central require Mike's approval before scheduling. Please reach out to the EA to the CEO with your rationale for an exception.

  • If Mike agrees to a meeting at 9 am or earlier, please schedule a block on his calendar on the previous day reminding him that he has a meeting before 9 am Central the following day.

Morning times should be held for team members and external folks whose timezones make it harder for them to meet later in the day.

  • The EA to the CEO will confirm that recipients have accepted invites.
  • If a recipient has not accepted, the EA to the CEO will reach out to confirm attendance at least 24 hours before the meeting is scheduled to begin.

Don't schedule over the Weekly E-group call unless approved by Mike.

  • Refer to Mike's list of priorities in the Priority calls (internal doc).

All holds on Mike's calendar need a reason so he can judge when the hold might no longer apply.

Meeting agendas should be added to the calendar invite by copying and pasting the link in the top of the calendar invite description in this format: "Agenda:link".

Sales meetings are important. If the CEO can help the process, feel free to include him in the meeting by working with the EA to CEO on this.

  • Please include the sales rep and solutions architect in this meeting.
  • The person requesting the meeting should provide an agenda document to the EA at the time of their request to schedule.

Last minute changes or cancellations should be communicated to Mike via DM rather than public Slack messages or messages in a thread.

  • If there is additional context to share, you can cross-post another Slack message as part of your DM.

CEO email management

  • Labels: /DOTO Mike, /FYI Mike, /EA is monitoring, /Signature needed
  • Emails that need the CEO's attention should be "starred"
  • EA should prepare draft responses, move drafts to the Inbox, and label

Travel preferences

Current preferences for flights are:

  • Aisle seat
  • Direct flight whenever possible
  • Check a bag for all trips longer than one night
  • Add Brex card information for pre-flight snacks and drinks forms
  • Frequent Flyer details of all (previously flown) airlines are in 1Password as well as important travel documents

#Help Mission Control slack channel

This channel is for the CEO to drop ideas and tasks for his executive leadership team. The name of this channel was carefully chosen to reflect how we'll work together to help visualize and execute the plans for Fleet.

  • Labels: TODO, DOTO, FYI
  • Mark requests with 👀 to indicate that you are working on the task
  • Mark requests with ✅ to indicate that you completed the task

Contacting the CEO

Keeping up with Slack is tough enough, even more so if you’re the CEO. That’s why Fleeties have different ways to contact Mike depending on the urgency of the request.

  • Non-urgent
    • "Non-urgent" means your request can wait until the next time you and Mike are scheduled to meet in Zoom. In which case, please comment in the Hallway section of your agenda doc from the meeting you share.
    • If you don’t share a meeting with Mike, please post in the #help-ceo channel without mentioning @mikemcneil. Charlie Chance monitors this channel and will prioritize your request or add it to the 🔭🗣CEO office hours agenda.
  • Urgent
    • “Urgent” requests can’t wait until another scheduled meeting. If you have an urgent request, please mention @mikermcneil in the relevant Slack thread or channel. Please don't use group DMs.
  • Emergency
    • “Emergency” requests must be addressed the same day. If you need to contact the CEO ASAP, please post in #help-p1 Slack channel. This will send a text message to Mike’s cell phone, even if it’s in "do not disturb" mode.

OKR planning

OKRs (Objective Key Results) help to inform what to prioritize and communicate company goals while encouraging cross-team collaboration. At the end of the quarter and key points throughout the quarter (every three weeks), we review the status of each OKR (depending on the KR, either 100% or ≥70% completion is considered "success")

  • Review topdown and departmental OKRs as they are turned in.
  • OKRs are finalized one week from when topdown OKRs were initially reviewed.
  • Finalized OKRs are shared company-wide and at the "All hands" meeting and, at least to some degree, become public.
  • Throughout the quarter, Mike and Zach have OKR preplanning meetings (every three weeks) to prepare OKRs for the upcoming quarter.

Prep work

All Hands prep

Every month Charlie will do the prep work for the monthly "✌️ All hands 🖐👋🤲👏🙌🤘" call.

  1. In the "👋 All hands" folder, create a new folder using "yyyy-mm - All Hands - yyyy month name".
  2. Download a copy of the previous month's keynote file and rename the copy with the same name used to create the new folder.
  3. Update "🧑‍🚀 Welcome!" slide to reflect new hires since last month's All Hands meeting (pull this from the 🧑‍🚀 Fleeties spreadsheet using "name (pronoun), position".
  4. If applicable Update "🦉 Welcome!" slide to reflect new investors or advisors using "name (pronoun), position, company".
  5. If applicable Update "🤝 Welcome!" slide to reflect new customers.
  6. Update slides that contain dates to reflect current All Hands date.
  7. Update slides that contain metrics to reflect current information using the 🌈 Weekly updates doc.
  8. If applicable Update Quarterly OKRs to reflect current OKR goals for the quarter.
  9. Test that the transition on the last slides continue to work.
  10. If applicable Add new customer's logo to final slide.
  11. If applicable Add a "Star slide" for guest speakers.

The day before the All Hands, Mike will prepare slides that reflect the CEO vision and focus.

Calendar audit

As Fleet grows, time management for the CEO is more essential. Charlie will audit the CEOs calendar and set meeting notes for calls with external attendees. In the notes document include:

  1. LinkedIn profile link of all outside participants
  2. Company profile link
  3. Context that helps the CEO to understand the purpose of meeting at a glance
  4. Share the document with meeting participants

Additional product design review sessions are welcomed and a top priority for the CEO to get on the calendar quickly. Other internal meetings and blocked time can always be moved to make room. External meetings, travel, and personal commitments cannot be moved. To schedule, mention @Charlie in the #-meetings channel.

The CEO welcomes opportunities to support teams on customer calls. External meetings, travel, and personal commitments cannot be moved. To schedule, mention @Charlie in the #-meetings channel in Slack.

💻 Sid : Mike document preparation

Every two weeks, our CEO Mike has a 1:1 meeting with our Investor Sid. The Charlie completes four parts while constructing the associated document.

  • After the 1:1 meeting has happened, Charlie makes a copy of the original document, labels it "yyyy-mm-dd Backup copy of 💻 Sid : Mike," and moves it to a private folder.
  • Charlie will change the permissions on the new copy to share it with Mike and Zach and set Mike to be the file's owner. If there are any agenda items labeled "TODO," Charlie will comment in the backup copy to assign them to Mike.
  • Charlie prepares the original document by deleting the agenda items in the "Hallway" and "Feedback" sections, leaving only the "Vision" section.
  • Charlie will update the monthly "All Hands" link and grant Sid viewing access.
  • Charlie will send Mike links to the new document and the backup copy in a direct message in Slack.

The day before the meeting, Mike will prepare the "Vision" section of the original document. Mike will collect and update information related to annual recurring revenue, new members in the #fleet channel in the osquery Slack, the number of new customers and opportunities from Salesforce, the total number of devices using Fleet, the company's current headcount, and banking information.

Investor and advisor updates

We like to regularly share updates about how Fleet is growing with our investors and advisors.

  • Charlie tracks the most recent updates with investors and advisors and coordinates emails, zoom calls, or the investor or advisor's preferred method of communication with @mikermcneil and preps materials as needed.

Document preparation

At Fleet, document prep steps are determined by the type of meeting.

Meeting type Description Automation enabled? Meeting note preference
"One-off" A non-recurring meeting that has a separate doc per meeting. Most likely Zapier Note template
External call A recurring meeting that is with a customer, coach, or advisor. No, unless rescheduled using Calendly link Journal template
1:1 A recurring meeting that direct managers and direct reports use for performance management and is emptied after every call. Most likely Reclaim Agenda template
Office hours A recurring meeting that is emptied after call used for group meetings of Fleet team members. Google calendar Office hour agenda template
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Journals are good when the primary goal is understanding status, asking questions. (e.g. a key review, a demo session, customer voice, prospect voice, community voice) There might be action items that come out of it, but they aren't the goal of the meeting. TODOs in journals are suspect and often overlooked. Whereas agendas are good when it's all about action items / decisions / discussing a topic. Like the whole reason a bullet is there is to make someone aware, to get feedback, to make a decision, or because it's an important TODO for someone on that call. TODOs in agendas are very easy to keep track of and can be trusted more.

Tasks as assigned

Private whiteboard

From time to time the CEO will ask Charlie to unroll a Slack thread into a well-named whiteboard google doc for safekeeping and future searching.

  1. Start with a new doc.
  2. Name the file with "yyyy-mm-dd - topic" (something empathetic and easy to find).
  3. Use CMD+SHFT+V to paste the Slack convo into the doc.
  4. Reapply formatting manually (be mindful of quotes, links, and images).
    • To copy images right-click+copy and then paste in the doc (some resizing may be necessary to fit the page).


How to file videos from Gong recordings (marking as "private" in gong is not appropriate. Never use it- instead, use this process):

  1. Move to ¶¶ recording in google drive.
  2. Download video from Gong, then delete it from Gong (promptly) and instead upload mp4 to appropriate ¶¶ folder in google drive.
  3. Move generated transcript doc in google drive (promptly) instead into appropriate ¶¶ folder in google drive.
  4. For both video and transcript: Double-checked permissions to make sure they are only ¶¶ viewers.
  5. Include the links to ¶¶ video and transcript here in this doc: - If appropriate, make this doc "¶¶," plus fleeties who were on the call. - Include in the doc "link to video:" - Include in the doc "link to transcript:"

Participation in the CEO shadow program

This section explains more about the CEO shadow program.

In this section


All Fleet team members are eligibile to apply for the CEO Shadow Program. Eligibility starts after you've been at Fleet for at least 6 months.

How to apply

  1. Create a pull request to add yourself to the rotation schedule.
  2. Assign your manager and ask them to approve (but not merge) the pull request.
  3. Once your manager approves the pull request, assign the pull request to CharlotteChance, link to the pull request in the #help-ceo-shadow channel, and tag @Charlie.

Parental participation

To allow flexibility for parents to participate, there will be some rotations identified as "parent-friendly" weeks. These are weeks when Mike doesn't need a shadow for the full 5 workdays or where the program is split so the weeks are not consecutive.

Rotation rhythm

  1. See one, you are trained by the outgoing person.
  2. Teach one, you train the incoming person. The shadow should be available for the full two weeks.

Preparing for the program

Important things to note

  1. This is not a performance evaluation.
  2. Plan to observe and ask questions.
  3. Don't plan to do any of your usual work.
  4. Be ready to add a number of handbook updates during your shadow period.
  5. Participating in the shadow program is a privilege that will expose you to confidential information.

What to wear

Casual. You do not need to dress formally; business casual clothes are also appropriate.

Pre-program tasks

  1. Create an onboarding issue. Outgoing shadows are responsible for training incoming shadows. We currently track onboarding and offboarding in the ceo-shadow project.
  2. Consider creating goals. For inspiration, here is an example of a CEO Shadow who added goals to their onboarding issue.
  3. Practice your introduction. See CEO Shadow Introductions for specifics.
  4. Coffee chat with co-shadow. Try to schedule coffee chats with your co-shadow before you start the program.
  5. Coffee Chat with CEO shadow alumni. Feel free to schedule a coffee chat with any of the CEO Shadow Alumni.
  6. Explore the CEO shadow project
  7. Review the CEO's calendar. Anticipate your week. Look ahead in the schedule and plan accordingly.
  8. Review the CEO handbook (TODO: insert link here)
  9. Review acronyms If you're not familiar with some of the business acronyms, take a bit of time to review them.

This list is not meant to be exhaustive and should not become a glossary. While we strive to be handbook first, you may find that we are using acronyms without a clear handbook definition. If you can't find it in the handbook or find a standard definition on Google, ask someone what the acronym means. Not being able to find it could be a sign that we need to do a better job with documentation.

What to expect during the program

The value of the CEO Shadow Program comes from the broader context you'll gain and the interesting conversations you'll witness. Since your rotation is over a short period of time, there are no long-term tasks you can take on. However, there are many short-term administrative tasks you'll be asked to perform as a shadow.

Here are some examples:

  1. Make handbook updates.
  2. Solve urgent issues. For example, help solve a complaint from a customer or coordinate the response to a technical issue.
  3. Go through open pull requests and work towards merging or closing any that have not been merged.
  4. Go through open issues in the CEO shadow project and work towards closing or creating a subsequent merge request to close out.
  5. Iterate and complete small tasks as they come up. Clear them out immediately to allow for rapid iteration on more crucial tasks.
  6. Provide training to the incoming CEO Shadow(s).

Here are some examples for meetings:

  1. Prepare for, take notes during, and follow up on meetings. See more details below about your meeting responsibilities as a shadow.
  2. Share thanks in the #thanks channel in Slack when it comes from a customer or wider community member in a meeting.

Preparing for meetings and events

CEO's calendar

  1. Review the CEO's calendar.
  2. As a reminder, you should have your title updated within your last name on zoom. During the Shadow rotation update your title to "CEO Shadow".
  3. Add the CEO's calendar to your Google Calendar by clicking the + next to "Other Calendars". Then click Subscribe to Calendar, search for the CEO's name, and click enter.
  4. Some meetings you will not be required to shadow, those are indicated with "[no shadows]" in the event title.
  5. Meetings with those outside of Fleet may not be on Zoom. Prior to the call, check the CEO's calendar and load any other conferencing programs that may be needed. It may be necessary to dial in via phone for audio conferences.

Zoom information

You'll have an opportunity to join many calls and meet new people along the way. Fleet asks that you change your Zoom name to reflect "[CEO shadow - your name]" so that everyone on the call knows who you are and why you are participating.


Meetings come in many different formats. Your responsibilities may change slightly based on the kind of meeting. Here are the responsibilities shadows have during meetings:

Meeting type Notes? Timekeeping?
Key Reviews No notes Timekeeping in chat
Internal meeting (CEO not host) Notes optional Timekeeping
Customer Meeting Yes, please use the externally-shared collaboration doc Timekeeping
Anything else (unless specified) Yes, take notes Timekeeping

After the CEO shadow program


CEO Shadow program alumni are welcome to join the #ceo-shadow-alumni Slack channel to stay in touch after the program.

Start date End date Name Title Takeaways
date date name title takeaways

Considerations for other companies starting CEO shadow programs

GitLab co-founder and CEO Sid Sijbrandij answered questions in a YouTube livestream from Sam Altman, as the two discussed considerations for implementing a CEO Shadow program in other organizations. Key takeaways are documented below.

  1. CEOs should not optimize meetings for Shadows. They learn by being in the room, either in-person or virtual, and it's OK if the Shadow doesn't fully understand everything.
  2. A well-designed CEO Shadow program shouldn't burden a CEO; in fact, Shadows should actively make a CEO's day easier by assisting with notes and changing relevant portions of the company handbook upon request.
  3. Non-obvious benefits for a CEO (and their organization) include CEO empathy and humanizing a CEO, such that team members are more comfortable contributing input to an executive. Shadow alumni can translate real-world examples of assuming positive intent from their time in the program to their direct reports, further fortifying company culture.
  4. Make certain that CEO Shadows do not plan to do any of their usual work. Shadows should prepare their team as if they were on vacation. Attempting to shadow the CEO while also maintaining a full workload creates undue stress for the CEO Shadow.