A Day in the Life of a Chief of Staff

There’s been a lot of talk lately about the chief of staff role and how it translates to multiple industries. Here’s a window-view of what a “typical” day might look like at a small startup with seven employees (and remember, there is no such thing as a “typical” day in the life of a chief of staff).


6:00 a.m.

Wake up. Check email. My executive sent me their presentation notes to review one last time. Hop onto my laptop to read through; only find one statistic slightly off. Send back so my exec has ample time to review before their 2:00 presentation.


6:30 a.m.

Shower, get dressed, eat breakfast while packing my lunch. Make sure there’s food in the cat’s bowl because I won’t be home until later tonight. Grab coffee and head out the door.


7:15 a.m.

Exec calls on my drive in, wants to brainstorm marketing strategy to a potential client. This could be a big contract for us and we want to make sure we handle it right. We strategize a few scenarios and how we can best leverage each situation to earn the client’s trust. Our call drops off in the parking garage, but I’ll be up in my exec’s office in five minutes to continue the conversation.


7:30 a.m.

We finish our conversation and her whiteboard is full of our ideas. We move on to talking points for the 8:00 team huddle. She asks me to onboard Jadyn, our newest employee. He started a couple weeks ago, in the middle of a big project, so we haven’t onboarded him properly yet. I make a mental note to grab one-on-one time with Jadyn asap.


We discuss our newest culture shift: making sure everyone understands what working as a team means--all hands on deck, no one siloed. We’ve been pushing this mantra for a few weeks now, reiterating in team huddles, on our Slack culture channel and in our weekly status communications.


7:50 a.m.

Exec takes a call from an important vendor. I head to my desk and check email. Ten new messages. Four are junk, one is from a headhunter (I’m settled in my current position...maybe in a year or two?), three are internal mini fires that need attention, one is from my exec seeking clarification on my presentation notes, and one is from a newer client.


I respond to the client first, answering their questions in detail and thanking them for reaching out. I respond to the mini-fires next.

  1. Tasha’s son is sick so she’s working remotely. She’s got a big project due this week. I ask her to spend as much time on it as she can and do a status check with me later.

  2. Clint isn’t quite jiving with his newest client. He is highly skilled in analytics, connecting dots and strategizing, but he isn’t the best people-person. Partnering Sarah with him should bring the emotional balance needed.

  3. Jadyn sent a slew of questions and is incredibly apologetic about it. This is on us. Rather than respond via email, I pull him aside before the huddle to tell him I’m his support person from here on out and apologize for our lack of clarity and proper onboarding.


8:00 a.m.

I start the huddle without my exec because she’s still on the phone. Quite often I’m the one who leads these anyway. I can always depend on Karen to bring a complicated question as we wrap up, but I tell her we need to “put a pin in it” for now. She’s a bit put off, but I remind her that we’re all busy with projects and her question isn’t relevant to those so it can wait a bit. Exec is still on the phone.


8:40 a.m.

Finally sit down at my desk for real. Scan both my calendar and my exec’s to make sure we’re aligned. Hers is missing a client meeting we’re both attending, so I add it. Answer more emails. Look at last month’s P&L statement to create an infographic and presentation charts to use in tonight’s board meeting. Email to my exec for approval. Continue prep for client meeting.


9:45 a.m.

Jadyn knocks on my door with a question, which evolves into several questions. He’s got promise to be a really good asset to the company once he learns the ropes, so I’m happy to help.



10:30 a.m.

Exec asks if I want to do a walking meeting to continue strategizing on that client. Once outside, we bounce ideas off each other like wildfire. I take notes on my phone. After just twenty minutes of circling our building, we feel ready for our meeting with the client later in the week. I make sure my notes are coherent and organized, then share them with her.


11:15 a.m.

Eat lunch at my desk while I read up on the business streams our newest client is involved in. I try to educate myself on our clients’ industries as intimately as possible so I can provide proper support to our team and my exec, as well as sound confident when talking to the board. They always have a question or two that deviates from the agenda, so I prepare myself.


12:00 p.m.

Bring Sarah and Clint into my office to tell them the plan for partnering. Clint seems a bit dejected at first, but I remind him we all bring strengths to our work and that he and Sarah will complement each other well, and we agree that the client’s project scope warrants an additional person for efficiency-sake. I leave it to them to talk more about the client.


12:20 p.m.

Tasha’s finally online because her son is napping, but she can’t access the company shared drive. I send her the docs she needs and then look into why she can’t access them. All it takes is a settings adjustment and she’s good to go.


1:30 p.m.

Exec pings me to stop by her office for a pep talk about her presentation. She’s incredibly smart, but gets major anxiety about speaking to an audience. Her presentations always earn positive feedback. I know because I usually tabulate the surveys.


2:00 p.m.

I’m co-hosting my exec’s virtual presentation from my office, ready to solve technical problems, respond to and monitor the comments string, and let in latecomers. The presentation goes perfectly, making it worth all the extra hours I put in preparing.


3:30 p.m.

Finish agenda for board meeting, adding in current budget numbers and future forecasting. Send to my exec for review, who immediately approves. Make a few personal notes and reminders on my own copy and continue preparing my presentation slides.


5:00 p.m.

Take a quick walk around the building to stretch my legs and get outside one last time before the sun goes down.


5:45 p.m.

Hop on zoom to set up for board meeting. Make my exec the co-host; she is presenting on our newest clients, using notes that I wrote for her. Everything goes as planned, thankfully. Our company is in a good place and we were able to celebrate that.


7:05 p.m.

Organize my desk so I can jump right in tomorrow. Say goodnight to my exec. She’s still working on that client strategy, making sure we’ve thought of everything before we meet with them later this week. Someday I hope to be in her position, running my own company. But for now I’m happy for the experiences I’m gaining as a chief of staff. Here’s just a short list of skills I used today:

  • Fact checking

  • Editing

  • Marketing

  • Sales

  • Business Development

  • Staff Development

  • Human Resources

  • Communication

  • Management

  • Decision-making

  • Budget analysis

  • Presenting


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