fleet/handbook/business-operations/ceo-handbook.md

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.

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 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.

1:1 Mike:Sid document preparation

Every two weeks, our CEO Mike has a 1:1 meeting with our Investor Sid. The Digital Experience Team 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 Mike from Fleet & Sid," 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, Charlie will prepare the "Vision" section of the original document. Charlie 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.

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 purpose of meeting at a glance
4. Share 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 Chance in the #meetings channel.

Gong

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:"

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).

All Hands prep

Every month Charlie will create do the prep work for the month "✌️ 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 spreasheet 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.
8. If applicable Update Quarterly OKRs to reflect current OKR goals for the current quarter.
9. Test that the transition on the last slides continue to work.
10. If applicable Add new customer's logo to final slide.

Participation in the CEO shadow program

This section explains more about the CEO shadow program.

In this section

• Eligibility
• How to apply
• Parental participation
• Rotation rhythm
• Preparing for the program
• Important things to note
• What to wear
• Pre-program tasks
• What to expect during the program
• Preparing for meetings and events
• CEO's Calendar
• Responsibilities
• Considerations for other companies starting CEO shadow programs
• Alumni

Eligibility

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.

• KPI (Key Performance Indicator)
• OKRs (Objectives and Key Results)
• Revenue definitions such as ARR (Annual Recurring Revenue)
• Keep a finance dictionary handy

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.

Responsibilities

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

Alumni

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.