If you’re an Executive Assistant, Chief of Staff, or Force Multiplier eyeing a role alongside a founder, entrepreneur, or small business owner, read this first.
I’m a huge advocate for the power of strategic right-hand partnerships in entrepreneurial businesses. When the fit is right, this kind of role can be deeply fulfilling, dynamic, and wildly impactful for both the leader and the Force Multiplier.
But make no mistake: this isn’t corporate life. The title might be familiar, but the way you operate, problem-solve, and show up each day will look radically different from what you may be used to in a traditional C-suite support role at a mature company.
Jennifer Star, strategic career consultant and owner of Star Focused Search, agrees. She says, “The amount of creativity, strategy and level of work entrepreneurial Executive Assistants do has no boundaries and often they are learning things as they are building. They not only connect the dots, but identify them, color them, and rearrange them so they meet the immediate needs, as well as the long term needs of the founder. The level of emotional intelligence and ability to pivot is also at a different level.”
Working with a self-funded, growth-minded founder is not for the faint of heart. These leaders often blur the line between personal and professional. They move fast, change direction often, and thrive on vision, not structure.
The entrepreneurs I’m referring to aren’t running massive VC-backed startups or planning their IPO exit strategy. Instead, they’re building lean, agile, purpose-driven businesses that prioritize lifestyle, legacy, and long-term autonomy. Think multi-six or seven-figure earners leading small but mighty teams where every decision counts and every team member carries real weight.
Before you say yes to a role like this, you need to know what you’re really signing up for. Because while the work can be exhilarating, it also demands an appetite for ambiguity, a high tolerance for chaos, and a willingness to grow as fast as the business does.
7 Things to Consider Before Working with a Founder/Entrepreneur
Working with an entrepreneurial leader is not easy. Before deciding to work with a founder, entrepreneur, or small business owner, there are some important things you want to think through.
1) YOU HAVE TO BE OKAY WITH UNCERTAINTY – If you like a clear job description and want to know exactly what you’ll be working on over the next six months, then working with a founder or entrepreneur may not be for you. Roles and responsibilities shift. New team members are hired and then reorganized, often with new responsibilities and job titles. Employees leave and work needs to be reallocated. Resources are scarce. Your leader doesn’t always have the answers. The company may not even be around in five years. This can be terrifying (and thrilling)!
2) YOU HAVE TO BE OKAY WITH AMBIGUITY – You and your leader are building the plane while flying it. Your entrepreneur or founder will usually know that they want to build a plane, but that’s about it. What type of plane? Where will it fly? Who will build it? Who will fly it? How many crew members do we need? The situation (i.e. vision) is generally unclear, but heck, are they passionate about it and absolutely certain that it can be done! Enter you, their Force Multiplier, who will be jumping in to help them learn how to build and fly a plane. Good news? You’ll have your wings at the end of the project!
3) YOU HAVE TO BE OKAY WITH CONSTANTLY SHIFTING PRIORITIES – Your leader wants to start a charity, open a new restaurant, run an Ironman in New Zealand, sell t-shirts online, ramp up sales, discontinue a service, or start a podcast? Most founders and entrepreneurs are big-picture thinkers, with an endless supply of ideas, who are incredible at starting, but not always great at following through. And that’s exactly why they need a Force Multiplier. But if you’re not okay with uncertainty, ambiguity, and a constant reshuffling of priorities and projects, then you will burnout in record time. On the flip side, if being able to help a leader focus, get clear on their goals and priorities, and make actual progress on their ideas sounds interesting then you may be in the right place.
4) YOU HAVE TO BE OKAY LEADING OTHER LEADERS – Why didn’t anyone tell the Emperor that he had no clothes? Because, clearly the Emperor did not have a Force Multiplier by their side. As the right-hand partner to an entrepreneurial leader, you have to be willing to tell them the hard truth, even when no one else does. You often have to reign them in, refocus their attention, tell them when they’re wrong, shine a light on their blind spots, and at the same time challenge them to level up their leadership, champion their ideas, and communicate their vision to the rest of the company. Being a leader is a must.
5) YOU HAVE TO BE OKAY WITH ABANDONING PROJECTS – That podcast that your leader was hell-bent on launching at the end of the year? That one that you have spent months researching, setting up a website for, sourcing a podcast production team, and outlining the first 30 episodes? Yeah, they decided that they would rather be a guest on other people’s podcasts than host their own. Frustrating? Disappointing? Sure. Did you have a ton of discussions upfront before moving forward with this new project? Of course. Sometimes, even your best efforts will be met with a pivot or decision to abandon a new project or initiative. And you’ll be there to roll out communication around the change, handle contract cancelation, shut down entities, and more. There is an interesting dichotomy where you have to take extreme ownership over the success of a project, and yet also be willing to let go of the outcome.
6) YOU HAVE TO BE OKAY WITH BLURRING THE LINES BETWEEN PERSONAL AND BUSINESS – Founders and entrepreneurs do not operate in a world of 9-5 or work-life balance. It’s all about integration. As their right-hand partner, one week you may be planning a 10-year anniversary trip to Europe for your leader, or booking speakers and developing the program for a 2-day leadership off-site. You may be recruiting and interviewing for a CFO for the company or getting a taxidermied fisher-cat delivered to the office. It’s all in a day’s work of a Force Multiplier. If you want clear lines between business and personal, it probably won’t happen with an entrepreneur or business owner. But, you’ll never be bored!
7) YOU HAVE TO BE OKAY WITH DELAYED GRATIFICATION – Working with a founder or entrepreneur means playing the long game, with many starts and stops along the way. You may spend weeks building systems no one sees, solving problems no one talks about, and making things happen behind the scenes. Being able to check everything off your to-do list by the end of the day rarely happens. Quick wins are few and far between. You may be in a hustle and grind mode for years alongside your leader before you start to build traction and momentum in the business. But when those wins come, man, does it feel good because you know just how hard you and the team fought to make it happen!
10 Skills to Develop When Working with an Entrepreneur or Small Business Owner
Okay, if I haven’t scared you away and this actually sounds exciting to you – great! This, too, is the environment I thrive in.
Here’s are the skills you’ll want to continue to develop in order to survive and thrive working alongside a founder or entrepreneur:
- Emotional intelligence (EQ) – Working with a founder or entrepreneur requires strong emotional awareness. You’ll need to navigate intense personalities, manage your own emotions, and build trust in an environment where personal and professional lines often blur.
- Adaptability quotient (AQ) – In an entrepreneurial environment or small business, change isn’t the exception, it’s the rule. Your ability to adapt quickly, reframe challenges, and stay flexible when plans (inevitably) shift will set you apart.
- Leadership – You don’t need a C-level title to lead. Whether you’re influencing without authority, mentoring teammates, or taking initiative on key projects, your ability to step up and guide others will be essential in a lean organization. And don’t forget, you have to lead yourself first!
- Communication – Clear, timely, and proactive communication is non-negotiable. You’ll often be the translator between vision and execution, so it’s critical that you can share updates, ask the right questions, and keep everyone aligned.
- Resilience – You’ll face setbacks, scrapped projects, and moments of chaos. Resilience doesn’t just mean bouncing back quickly, it means bouncing beyond. You need resilience to stay focused under pressure, and stay optimistic even when things don’t go as planned (which will happen often!).
- Resourcefulness – You won’t always have clear instructions, a big budget, or a team of specialists. Your ability to figure things out fast and find scrappy solutions without hand-holding is one of the most valuable traits you can bring to the table.
- Prioritization – You’re not going to be able to do it all, even if you or your leader think you can! You’ll need to constantly assess what matters most right now, often with limited information. Honing your judgement in order to filter through the noise is key. As is the ability to lead up to your founder/entrepreneur when they are getting distracted by another shiny object.
- Strategic thinking – Understanding how your work supports the broader business strategy allows you to anticipate needs and take initiative instead of waiting for direction. You will have to balance rolling up your sleeves and getting tasks done, with picking your head up and paying attention to the big picture.
- Change management – Shifts in direction, staffing, or business models are common. Being able to guide yourself, and others, through change with calm and clarity makes you invaluable in an uncertain and rapidly changing environment.
- Systems competency – Whether it’s a CRM, automation platform, AI tools, or basic no-code apps that streamline operations, you need to be able to learn and leverage systems quickly.
Final Thoughts
Working alongside a founder, entrepreneur, or small business owner demands a rare mix of creativity and execution, flexibility and tenacity, and the ability to know when to lead and when to follow. You’ll need to embrace chaos, thrive on uncertainty, and show up with both a compassionate heart and a strategic mind every single day. But for those willing to do the deep work (on themselves and within the business) the reward is enormous: meaningful impact, accelerated growth, and a front-row seat to building a business.
If this path resonates with you, you’re not alone. There’s a growing group of high-performing Force Multipliers reshaping what leadership support looks like in the entrepreneurial space. It’s not for everyone, but if it’s for you, then you’re in the right place!
Ready to put your knowledge into action? Consider joining The Force Multiplier Academy! The Force Multiplier Academy provides leadership training for right-hand partners. Through over 40 hours of on-demand course content, live group coaching calls, guided strategic exercises, and 25+ tools and resources you can implement immediately to get results, you’ll leave the Academy ready to increase the effectiveness of your Principal, impact the bottom line, land that promotion or next job, confidently navigate your career, and more. Click here to learn more.
