Staying Ahead

March 4, 2024

Learn how to stay two steps ahead of your exec at all times, to keep their life on track, proactively plan, and reduce overwhelm for them and for you.

You are an indispensable operator if you are able to stay two steps ahead of your exec at all times.

Here’s how to do it.


Very simply put, you just need three things.

  1. Ask yourself what your exec needs to get done

  2. Ask yourself what they will need to get the task done

  3. Ask yourself what you can do to help them get the task done in as few steps as possible

I like using real examples to teach, so below is an example you may have to do one day.



Step One: What needs to be done?

You see that your exec has a board meeting coming up in two weeks.

Because you’ve never helped an exec with a board meeting before, you’ve just asked ChatGPT what your exec needs to get done to prepare and execute flawlessly.

During your discovery, you find your exec needs to get these things done:

  1. gather and compile reading for their board members
  2. create a presentation for them
  3. prepare an agenda for the meeting

Now, you know what needs to be done. Great job!


Step Two: What will they need?

From there, you ask yourself the second question: what information or tools will they need to get those things done?

You decide they will need:

👉 Easy access to all of the relevant documents
👉 Deep work time dedicated to working on:

  1. gathering and compiling the reading materials
  2. creating the presentation itself
  3. practicing ahead of the meeting


Step Three

Finally, you move onto the third question: where can you help them move faster?

Because you are an excellent operator:

👉 You search for and find agendas from previous board meetings. They look fairly consistent, so you decide to turn it into a template that you can use in the future to generate agendas easily. You store this template into Notion.

👉 You know your exec needs those reading materials, so you compile all the links in one place, and make sure they have access to all the documents.

👉 You put calendar holds in their schedule to ensure they have adequate preparation time prior to the meeting. You also add yourself into the deep work calendar invites, so you can be there for support and accountability if needed.

👉 You send one big Slack message to your exec in your async channel, with something like this:

Hello [exec], I know you have a board meeting coming up in two weeks, so here’s what I’ve done to help you prepare:

  1. I’ve created an agenda based on your previous board meeting agendas - all it needs is to be filled in with the proper information. The link is here.
  2. I’ve compiled all the links below that will likely be relevant for your board meeting for your review as you put together your presentation:
    -financial report for revenue and profitability
    -financial forecast for next quarter
    -company OKRs and KPIs with status updates
    -strategy document outlining our product initiatives
  3. I’ve blocked off sync time with your co-founder for x-xx-xxxx at x:xx since they’re on the board too and you might want to make sure you’re fully aligned before going into the board meeting - once you confirm with me you’d like the sync, I’ll send the invite out to them.

  4. I’ve set aside deep work time for you to work on your materials this Wednesday the 3rd, your longer deep work block on Friday the 5th, and next Wednesday the 10th. See screenshot below-
  5. I intend to email the board a reminder with all of the relevant links and agenda once you’re done with it on x-xx-xxxx, and will share a draft with you prior to sending it out.

1. Are there any links to documents or data you’re missing to create the presentation? (Y/N)
If so, I can compile it for you and put it somewhere easy for you to access. Right now, it’s all in this Notion doc
here so you can work from one central place.

2. Please confirm which date you’d like to finish the agenda, presentation, and supporting materials by. (DATE)
That way, I can send it out to the board members ahead of time for their homework.

3. Confirm that you’d like to sync with your co-founder prior to the board meeting and for how much time (I’ve blocked off an hour, but please let me know if you’d like more or less.) (Y/N, DURATION)

Thank you!


You’ve now made it much easier for your exec to prepare for their board meeting. Congratulations!

Now, ask yourself: where else can you apply this kind of "staying ahead" attitude?

💡 For a bonus reading, if Step 3 scares you, or you aren't quite there yet with your written communication, check out this write-up on effectively communicating like you're the Chief of Staff to the President.

Above is an easy checklist for you to remember how to apply this write-up to your work, courtesy of Atlas Assistants.

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Regina Gerbeaux

Who’s Regina Gerbeaux?

Regina Gerbeaux (@_rpgbx) is the executive coach to some of the fastest scaling startups in the world. She is also a founder currently interested in the food delivery and logistics space.

Regina was the first person trained by Matt Mochary (executive coach to the CEOs of Coinbase, Brex, and many more) in the Mochary Method Curriculum.

Her tactical templates and operational write-ups have been referenced and used by fast-scaling companies, including BioRender, Tembo, dYdX, and many more.

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