Your First 30 Days on the Job as a Chief of Staff

As I passed my 30 day mark as a Chief of Staff to the CEO of Hugging Face, I looked back to see how much my role and responsibilities have changed. Because this was my first foray into the CoS role and the first time my CEO had worked with a CoS, it felt a little like finding our way in the dark. We knew where we wanted to be and a general idea of how to get there, but there was still a lot of figuring it out along the way. In this blog post, I’m going to share my first four weeks on the job as an example of how a CoS might spend their time. CoS’s can have a variety of different roles and the day to day can vary from company to company but if you’re new to the role as I was, this might help as an outline of how you may want to structure your first few weeks in the role.

Your First Week on the Job:

This first week will feel very unstructured. You haven’t built up trust with your CEO, or the team, and for me, I had started a role in a field that I was highly unfamiliar with — Natural Language Processing (NLP). In addition to your onboarding paperwork (health insurance, payroll etc.), you’ll spend a fair amount of time doing self-onboarding.

Familiarizing yourself with the space is extremely important.

‍I spent a lot of time Googling “natural language processing for dummies.” My goal for the first week was to have everything sound familiar. For example, when someone mentioned “BERT,” I didn’t immediately think of the yellow football headed Sesame Street character, but instead thought of Google’s neural network-based technique for NLP pre-training. When someone said “Transformers,” I wasn’t thinking of the Michael Bay movies, but instead knew that it was open source library by Hugging Face that had over thirty pretrained models in different languages. You should take the time to make sure you understand what your company’s product and goals are.

You’ll also begin to sit in on meetings with your CEO where you’ll be observing. There’s no expectation that you’ll need to join in on the conversation but do ask questions after each meeting. After each call, I would ask my CEO some combination of these questions:

• Why are we interested in this person?
• What would our follow here be?
• What is our relationship with this company?
• If there were any terms I didn’t understand, what did they mean?
• What are we trying to accomplish with this relationship?

The goal with many of these calls is to feel comfortable enough to lead them in the future. Take note of the questions that your CEO is asking and how he answers questions by the clients. You’ll need to be able to replicate this when the responsibilities fall on you.

Additionally, familiarize yourself with the immediate team that you’re working with.

If you’re a CoS at a larger organization, see who your CEO interacts with the most and make introductions to them.

While you’re learning about your new workplace, take time to learn about your company’s communication values and structure. At Hugging Face, I learned that email is preferred and Slack is mostly used for urgency.

Lastly, schedule a week 1 recap with your CEO at the end of the week.

In my meeting, I asked him how he spent his time during the week and how he would like to structure his time moving forward. I told him which tasks that I observed him doing that I would feel comfortable taking on and which ones I’d like to sit in on a few more times before assuming responsibility. I also gained access to his email so that I could look through past communications to gain some context about any upcoming calls. Most importantly, I detailed my strengths and weaknesses to him on the things that I felt that I could ramp up quickly on versus where I would need support to get it right.

Your first week on the job is the best time to ask as many questions as you can.

‍It’s the time where you’re expected to know the least so people are going to be much more giving in their answers. If you’re into month 6 of your job and you still don’t know what the company products are, your team is going to wholly lose trust in you.

Objective of week 1: Be a fly on the wall and observe as much as you can. You’re sitting in the trailer wagon in the back while your CEO bikes around.

Your Second Week on the Job:

Week 2 is going to involve more of the same observation tasks that you were doing before. You’re going to continue to listen in on meetings and ask questions. Your CEO might let you ask some questions at the end of the call directly to the clients so that you can start interfacing with them and building your own relationships with them.

You’re going to be assigned tasks that have finite goals.

One of my first tasks was putting together the company’s official paid holiday schedule. Along with me being hired, my hiring class was 4 people and we essentially doubled the team overnight. We had to start putting some organizational structure in place. Things like paid holidays and vacation policies had to be written out. Administrative payments like our cleaning services had to be paid and scheduled.

Your main goals here are to take the administrative tasks off your CEO’s plate so that they can free up more time to work on the big picture.

These things usually don’t take much time but 5 minutes back on a CEO’s schedule can add up quickly.

During this week, I also took time to start building out my own CoS network. I started with a straight forward search on LinkedIn, looking for people with a CoS title who had been in the role for over a year. If I ever find myself with some downtime, I’ll turn to the Cos Tech blog or Slack channel to see what other CoS’s are doing and seeing if we can implement any of those practices in our company.

At the end of this week I put a recurring weekly meeting on my CEO’s calendar and laid out an agenda with what I would want to cover:

• General temperature check of what went well in the last week and what didn’t [I use this section to document what my accomplishments were for the week and what I specifically want feedback on]
• Discussion topics that I wanted to talk about [I use this section as a running list during the week where I throw in things that aren’t urgent but need to be followed up with]
• The CEO’s priorities [This is the section that my CEO will fill out before our meetings and we’ll take time in the meeting to talk about how I can best provide support in each of these areas. He’ll usually narrow the priorities down to 3 so that we can take impactful measures towards each item.]

Objective of week 2: Instead of just watching your CEO bike around, you’re now on a bike with training wheels.

Your Third Week on the Job:

This is where things start to pick up from a task standpoint. Your CEO should start to trust you with more responsibilities. In my experience, this is where I started to become his stand in for more low stakes meetings: intro calls, information gathering sessions, insurance approvals, new office negotiations. I also prepped his meetings with background information and followed up with the stakeholders afterwards.

You’re the main point of contact on a lot more tasks, but you need to keep your CEO informed.

Remember, your job is to support your CEO and they can only do their best work if they’re informed. Just because you’re running email threads and communication doesn’t mean they should be left in the dark. My CEO asks to be cc’ed on almost every email so depending on your communication style with your CEO, do what’s appropriate here.

Continue to build out your CoS network

‍This task never really ends. You can ask your CEO for feedback as often as you like but in order to take new initiative and bring positive impact to the table, there’s a certain sense of proactivity that you will need to develop. While a lot of the CoS role can be reactive in nature due to your CEO’s needs and asks, where you’ll really be able to build your sense of career and direction post this role will come from what you are inquisitive and curious about. Other CoS’s will be your best resource for this as you see where their careers have taken them and what paths are open and available for you to explore. You don’t need to know where you’re headed now, but you can start to get a sense of what your options are so you can ask to be more involved in those aspects of the business if something strikes your fancy.

Objective of week 3: You’re able to balance on your own. The training wheels are still there but you’re getting more accustomed to handling things on your own.

Your Fourth Week on the Job:

This is the week where my calendar blew up. Not only was I still sitting in on meetings with my CEO, I was also having meetings scheduled with many of the relationships that I was now responsible for. You’re essentially taking on the day of your CEO as a shadow and a standin. It might even feel like you don’t have down time to do anything but jump from meeting to meeting.

The best thing for you to do at the end of this week is to reevaluate how you’re scheduling your time.

While it might be exciting to feel like you have a completely full week of meetings, that leaves you with very little time to be reactive. This was feedback that my CEO gave me: leave time in your schedule to pursue non definitive tasks. Not everything you work on needs to have a deadline. That latter piece of feedback resonated with me resoundingly. As a CoS, it may feel good to have a running checklist of things that you can cross off but remember that you’re not here to be an admin and mark things as done. You’re here to support your CEO and become a resource for him in how to best spend his time and energy. While you’re not managing his every minute, you are becoming more of a gatekeeper to his decision making so as to reduce decision fatigue. Oftentimes I’m the first one to read an email and I’ll follow up on whatever I can respond to and leave my CEO with a singular decision that only he can make.

Make sure you leave time in your schedule to be reactive and also time to reflect on what tactically can be done next so that you can start to prep for the future.

Objective of week 4: The training wheels come off! You’re riding on your own with projects for you to handle from start to finish, but don’t forget to take breaks and stop pedaling every once in a while to observe your surroundings and plot where to go next.

Given the variable nature of the CoS role, not everyone’s first 30 days will look exactly the same, but if you’re looking for a way to get started, hopefully this article gives you a sense of where you can spend your time and how to allot your schedule accordingly.