I recently had someone reach out to me as they consider the next steps in their career after running a small business. He asked several questions about my career journey and specifically about my role as Chief of Staff.
And, instead of just sending my responses to him, I figured I would share them here in case anyone else finds them useful.
In addition, if you are trying to figure out your next career step, use this as inspiration! Don’t be afraid to reach out to someone who’s career you admire or are interested in. Ask to meet for coffee. Send them a list of questions. You won’t get what you don’t ask for. So, just ask!
Considering a Chief of Staff Career?
For some additional context, I was a Chief of Staff for about 10 years. I worked directly with the founder of the organization. He had about five core companies and a handful of additional projects that we were working on at any given time. He is what I could consider a small-business founder/entrepreneur – completely bootstrapped – as opposed to a funded start-up founder (there is a difference!). I was able to grow as the businesses grew, and have my hands in every aspect of the business along the way. And for that, I am grateful.
Now, without further ado, let’s dive into his questions.
Could you share a bit about your career journey and how you arrived at your role as Chief of Staff?
I’ve been an assistant since my career began. First, as a marketing & PR assistant at a nonprofit fresh out of college, then moving to an Executive Assistant role at a public high school. From there, I landed a role as a real estate marketing assistant, then quickly moved into an Executive Assistant position at that company and was there for the next 13 years! I moved from an Executive Assistant position to Chief of Staff role about 5 years into that role.
After about 4 or 5 years as an Executive Assistant, I began to research other roles that I might be interested in, such as COO and Chief of Staff. I quickly realized that the Chief of Staff position was what I was basically already doing and where I wanted to continue in my career. I pitched the role to my Principal and created the role at the company for myself.
To read more, as well as get some leadership, career, and entrepreneurship tips, check out The Founder & The Force Multiplier. While it’s a bit more geared towards the Executive Assistant role, so much of my experience working with an entrepreneur was on the cusp of EA and Chief of Staff (and generally leaned more towards Chief of Staff). Regardless of title, I think it’s a good behind the scenes look at the “right hand partner” (the Force Multiplier) to a founder!
What does a typical day or week look like for you in your position?
As Chief of Staff, each week is a bit different, and that’s why I loved the role so much. It played to all my strengths as a strategic generalist, an intrapreneur, and a leader.
Here’s what a typical day looked like for me as Chief of Staff.
What aspects of your role did you find most challenging?
The most challenging aspect of being a Chief of Staff was people. And by people, I mean learning to understand, navigate, and handle different people’s agendas, needs, desires, working styles, communication, goals, motivation, etc. This encompassed working with, and leading, direct reports like our Executive Assistant, operations and marketing teams, finance teams and vendors, as well as leading up to my Principal.
If you don’t want to invest into growing yourself as a leader or learning how to work better with people, then being a Chief of Staff (heck, being in any leadership position), is probably not for you.
The other most challenging part, that maybe we don’t talk about enough, is how much you have to give of yourself when you are in a Chief of Staff role (or any Force Multiplier role). Your primary responsibility is to ensure the success of another individual. In the best situations, your success is mutual. As you work to maximize the effectiveness of your Principal and ensure their agenda is executed, so too, will your career grow and success multiply. But there is a mental and emotional cost of being in a role that requires you to, in essence, become the clone of another, while ensure their goals and vision become reality. Where does that leave you (and your wants and needs) in everything?
Now, don’t get me wrong, myself, and most Chiefs of Staff I know enter into this contract with eyes wide open and understand the sacrifices associated with the role. But, it is worth mentioning that just because we have agreed to it, that doesn’t mean it’s not hard.
What did you find most rewarding or enjoyable about your work?
Being a Chief of Staff is an education in leadership, business, negotiation, and, in my case, entrepreneurship, like nothing else. The sheer variety of projects, problems, people, companies, and decisions that I got to create, lead, or be a part of over the past decade was incredible. The growth and learning opportunities were amazing.
A few projects and moments stand out:
1. Writing and publishing The Founder & The Force Multiplier was a dream come true. I have always wanted to write a book, and with the support of my Principal – we did! And it kicked off a whole movement, company, and community that I am proud to still be leading today.
2. Being a part of hosting a year-long leadership coaching program, Project | U, for five years was amazing. The people I met through that program are successful and inspiring leaders. If I was able to impact them in even just a small way during our time together, then I succeeded. They definitely impacted my life (probably more than they know).
3. I worked with my former Principal for 13 years. About two years into working together I helped him get his first real estate expansion team off the ground. From there, it was about 9 years of growth, hiring, failing, learning, leading, expanding, and finally ended in a large acquisition a couple of years ago. That was a huge business win that I was proud to be a part of.
So, yes, growth and learning are always my favorite parts of my Chief of Staff career. Being able to see a vision come to life is a close second.
What essential skills or experiences have been most crucial to your success in this role?
Being growth-minded, willing to adapt and be flexible, and being endlessly curious were instrumental in helping me succeed as a Chief of Staff.
If there was anything that I didn’t understand or thought that we might need to know in order to start a new company or continue to grow our existing team, I went and learned about it, came up with a plan for implementation, got my Principal and team’s buy-in, and then made it happen.
On a more practical level, as Chief of Staff (or any Force Multiplier) I think the most important skills are leadership, communication, project management, cognitive thinking, and strategic decision-making. Studying and practicing these skills will help make you a successful Chief of Staff.
These are all skill-sets that we will be working on in The Force Multiplier Academy.
If you could go back five years, what professional advice would you give to yourself?
I really wouldn’t change that much. Everything happens for a reason and I gave it all to my career (thankfully my relationships survived) and it paid off.
The only things I may tell myself to do differently would be:
1. Create an exercise routine and stay consistent with that (health is wealth!).
2. Start my own business sooner. Whether that was a side hustle such as content creation or affiliate marketing, creating an online course, or building a virtual assistant business – something that was completely mine. I always had multiple streams of income, but not one business per se. If I had something that I owed completely years ago, it would just mean that I’m 5 years closer to my long term goals today.
Are there any common misconceptions about your role or industry that you’d like to share?
Right now, there are so many conversions happening about the Chief of Staff role, from whether or not Executive Assistants can transition into Chief of Staff roles (not all of them should, but they absolutely can), to Chief of Staff “light” functions (how does this differ from a “traditional” Chief of Staff and what even is a traditional Chief of Staff?), to the many levels of Chiefs of Staff, the compensation ranges, and all of the confusion about what a Chief of Staff actually does.
I’m not sure there is any one glaring misconception about the role. But, there is absolutely confusion about the position. Without one universal definition or job description of the Chief of Staff position, the confusion continues and the role remains somewhat open to interpretation, as well as open to a ton of nuance depending on what size or stage the company is in, who the Chief of Staff supports, the scope of the company, the industry, the Principal’s needs, etc.
My word of advice is to read every job description carefully (ones that are labeled Chief of Staff, and ones that have Chief of Staff-like titles, such as Director of Strategic Initiatives or Founder’s Associate). Make sure what the role is asking for is in alignment with your experience and career goals.
Is there anyone else you think I should connect with to learn more about this field?
To learn more about the Chief of Staff role, check out these Chief of Staff resources:
- Chief of Staff Network
- Ask a Chief of Staff
- Emerging Chief of Staff Trends
- Which Chief of Staff is Right for You?
- How to Become a Chief of Staff
- The Right Hand Talent Blog
- Tack Advisors Webinars – What is a Chief of Staff and What Can They Do For You?
- Chief of Staff Job Description
Still have questions about the Chief of Staff role? Email me at hello@founderandforcemultiplier.com and let’s talk!
