Sample 30-60-90 for your Chief of Staff or EA

July 6, 2023

Congrats! You just hired a Chief of Staff or EA. If onboarded quickly, this person can start to make a high impact and save you time in the first 30 days.

Congrats! You just hired a Chief of Staff or EA. If onboarded quickly, this person can start to make a high impact and save you time in the first 30 days.

I’ve had the honor of supporting many CEOs as their onboarded their Chief of Staff and their executive assistants. Though the scope of these two roles is different, both work extremely closely with the CEO and therefore need a lot of context as well as relationship building. Since this is such an intimate working relationship with the CEO, the preparation and ownership that goes into onboarding heavily determine the success of this role. This is why I think the onboarding of a CoS and EA could look very similar, with the differences that lie in the scope and ownership of the projects assigned.

Get access now

Sample 30-60-90

Here is my template of 30-60-90 with great ideas from other clients. Please take the below as a reference and adjust it for your hire and company. Note that you’ll have to add in your specific projects that apply to the timeframes.

30 days

Step 1 — Get access to CEO’s personal and work accounts that you’ll need to take over.

  • Calendar management (if applicable) — Start to jot down how the CEO prefers to spend their time. Learn their routines and recurring appointments.
  • Inbox management (if applicable) — Shadow and observe how the CEO currently processes inbox and learn how they write. Here’s a very effective and detailed guide on how to help exec achieve inbox zero written by Regina Gerbeaux.

Step 2 — Observe and shadow as many meetings as possible with the CEO. You will need to learn the company culture, relevant leaders, how the CEO speaks, and how the CEO makes decisions.

Step 3 — CEO will have the “how we work together” conversation with you to establish working agreements and psychological safety during the first week.

💡Why? — Many 30-60-90s are heavy on “what” to accomplish, while alignment on the “how” is key to building trust and providing comfort in the relationship. This is one of the most powerful trust-building containers. It will likely take an hour or more. When I had conversations like this with my directs, they comment that no one has ever done that before, and I observed them to be more willing to share their feedback with me honestly right away.

Here are some starting points of discussion:

  1. As the CEO, write down scenarios you are fearful of happening, and with each scenario, pair it with a request. For example, if you’re ever feeling overwhelmed and over 90% of the bandwidth, please ping me right away. Ask your hire to do the same.
  2. Define what both of you will do when there’s conflict or tension.
  3. Define what both of you will do when each party observes a change in priorities.
  4. Define what both of you will do when there are big misses on deadline or deliverables.
  5. Talk about the behaviors, energy, and attitude that motivate each other.
  6. Talk about the behaviors, energy, and attitude that annoy or trigger each other. When one gets triggered, what would you like the other to do?
  7. Talk about both of your dreams and your ideas of growth.
  8. Talk about how you will be using your 1-1 times.

Step 4 — Learn the CEO’s and the company’s top priorities, OKRs, as well as how the company is currently tracking toward those goals

Step 5 — Learn the org chart and schedule meetings with key stockholders

Step 6 — Document processes and learnings as much as possible

Step 7 — Ask lots of questions

I recommend that the CoS or EA keep a running list of questions. Once a day or every other day, they will sync with their CEO and ask those questions.

Step 8 — Exchange mutual feedback

The CoS/EA and CEO are going to be meeting a lot in the first 30 days. In addition to tactical meetings, I recommend making time in their weekly 1-1 to exchange direct feedback on how it’s been working with each other. The faster you two can exchange feedback and hear each other, the stronger the bond will be.

Step 9 — Take over specific tasks and projects determined by the CEO. These should be easy tasks that can be taught in a few hours or a day.

Step 10 — Learn more about the CEO’s personal life if the CoS/EA is going to be managing a lot of personal life tasks

60 days

  • Continue to shadow meetings. At this point, the CoS/EA can start to bring up constructive feedback to the company or process since they will have a good understanding of the business.
  • Take on a few more difficult projects that will take a few days to a week to learn. This will be a great opportunity for the CoS and the CEO to pair and test out how they work with each other.
  • Continue to give each other positive and constructive feedback. At the end of the 60 days, give each other formal performance review feedback based on the first 2 months.
  • Start to enforce accountability with your exec. Ask them about unclosed loops. Ask them about their committed actions and how you can help them get there.
  • The hire has established good relationships with key stakeholders at the company

90 days

  • At this point, ideas, improvements, and feedback should feel like table stakes to a recurring conversation.
  • Start to drive or facilitate key meetings
  • Start to take over projects from the first 2 months with little involvement from the CEO
  • Start to spearhead new projects that are ambiguous by proposing solutions and next steps so that the CEO can provide feedback
  • At the end of the 90 days, give each other another round of formal performance review feedback based on the first 3 months.

What 5 out of 5 looks like

In addition to a 30-60-90, I also write down a definition of excellence as I often hear high performers in a new role asking “But how do I know I’m exceeding expectations?”

Here is my sample excellence definition for an EA. I call it what 5 out of 5 looks like, because if we use a numerical rating to look at one’s performance, 3 is meeting expectation, and 5 is can’t be any better.

  • You proactively communicate if things aren’t going to get done and why. You also let me know when high-priority things are done. I can trust that when I tell you something, it’ll get done or else, you’ll let me know. This is the most important thing in working with me.
  • You proactively letting me know if you’re plate is getting too full (>90%) or getting too idle (<50%)
  • You don’t let things slide and you’re willing to challenge me when I do
  • You communicate professionally and authentically. My clients love you and praise you.
  • You take initiative in revamping the areas you own. If you have a better idea, bring it up and I’ll support you.
  • Ask me questions right away when things don’t make sense.
  • Help me maintain a good personal life: paying pills, seeing friends regularly, going to my appointments, scheduling cleanings, etc. You can suggest I implement something before I even think of it.
  • You own and complete ABC projects with little of my supervision.

I’m grateful to have been a manager of exceedingly high performers who helped me iterate how I onboard. I am also thankful to my clients who trust me with their key hires, so that we can workshop onboarding together in session. If you have a key success tactic for a CoS/EA’s onboarding, please let me know at!

Explore Evergrowth Coaching with Sabrina Wang

Evergrowth serves fast-growing leaders to become better coaches and managers to unlock their team’s highest potential.

Oops! Something went wrong while submitting the form.

About Sabrina Wang

Sabrina is the CEO of Evergrowth Coaching for extraordinary leaders of Series A to Unicorn companies. She has quickly grown Evergrowth to over $500K ARR in sales in under 6 months of conception. Evergrowth partners with CEOs, founders, and C-suite execs of best-in-class tech companies. Her clients include CEOs and co-founders of Wayflyer, Synchron, Opswerks, Code States,, Tribe, RevenueCat, and more. Sabrina has also coached partners of YC Continuity, General Catalyst, Left Lane Capital, and Innovation Endeavors.

Before starting Evergrowth, Sabrina was the Head of Coaching at Mochary Method, started by Matt Mochary (top CEO coach for Reddit, OpenAI, Coinbase....). She hired, trained, and managed a team that sold 0 to 3m ARR in under a year. Sabrina is well-versed in the engineering, product, and design side of building a tech company. At Headspace for Work, she worked in product management building B2B SaaS products that reached 1 million users.

Sabrina is driven by her mission to help people achieve high performance and find greater impact. Her coaching is heavily influenced by her mindfulness meditation journey, studying Reiki, energy work, and other spiritual modalities.

Follow her on social

Get in touch

If working together feels like a full-bodied yes, please fill out this form to work with Sabrina.

Thanks for getting reaching out, your submission has been received. I will be in touch!
Oops! Something went wrong while submitting the form.