The startup world, specifically in tech, is often represented as a place where the money is never ending, the ideas are abundant, and there is always a chance to be part of the next big thing.
As an organized do-er in a sea of visionaries, real and self-imagined, I struggled with identity through most of the first 10 years of my career in the startup community as I never held the same title twice. I was the definition of a generalist (before the role of generalist existed).
I want to help those surviving and thriving in a “what have you done for me lately” startup culture to articulate their value and professional worth as a do-er of all things and master of none.
Embrace yourself for your excellence in chaos
The chaos of unknown outcomes is where I find the most professional (and arguable personal) comfort. I have been a Chief of Staff or generalist in industries ranging from cannabis to fintech to SaaS to, most recently, a non-profit tech bootcamp - chaos is the common denominator.
At this stage of a startup, expertise is desired but often hard to find, nonexistent, or unaffordable. At this stage, chaos is what a company has in abundance and it is what I do incredibly well. Chaos for me has shown up in many forms such as missing or unknown processes, unproven sales or marketing focuses, a lack of human resources or hiring support, and a changing product/company vision as extreme growth provides more insight into the customer’s needs - and those are just a few examples.
Communicate Your Value - Chaos in Practice. When I sit for job interviews, which I have done roughly annually for 10 years, I can say with 100% confidence that I can get your task/company/department/team/project to iteration #1. It will not be perfect. But I know how to ask questions, go find experts, request support, pull in team members, communicate next steps, and give the true experts on your team a jumping off place for building the next (and better) iteration. Perfect is an enemy of good and chaos rarely allows space for more than good enough. As a generalist, you know how to take the victories and the losses, learn, and try again. That is invaluable.
What I hope for you fellow generalist: Thriving in chaos isn’t a universal talent. The ability to see the company for what it is currently AND what it could be AND the path of how to get there is so unique. Visionaries see what the company can be, those that keep us grounded see the company for what it is, and those very experienced in their skill can see their path. You bridge them all. You are the do-er of all things and the master of none. I hope for you that you embrace your ability to embrace the chaos and the full picture.
Know yourself and your patterns. Your patterns are your superpowers.
I THRIVE in companies 0 - 100 employees. Not everyone is built for every stage of a startup lifecycle and the workplace would be a better place if more of us admitted that to ourselves. The moment I embraced that I was most successful working directly with founders in small companies, building and proving concepts, my story both for myself and others became clear. I may never take a company to IPO, but I will be the one who helped to build the foundations and was happy to hand off my role and start again when the company outgrew me.
Communicating the Value - Know Your Patterns and Know What They Are Worth. Being a generalist doesn’t mean you have to be great at all things at all stages of all companies. Being a generalist means you are great at a variety of things and you know how to identify when a company needs you before the company itself knows.
What I hope for you fellow generalists: That you find and not fight your patterns. Trying to be everything to everybody can lead to imposter syndrome, exhaustion, and discontent. Embracing who you are and what you’re great at makes you best in class and focused on roles that will empower you to learn and grow.
Know When to Say No - To Yourself and to Others
Saying No to Yourself - Never compromise your values. In a world where your superpowers can build anything, build something you would never be ashamed to discuss with a group of people you didn’t know.
Saying No to Others - Tell your boss and leaders, no, and do it as often as they need to hear it. You may be the only one with the view and access to give them that information and it’s critical.
Communicating the Value - The Art of Saying No. Executives at all sizes of organizations are surrounded by cheerleaders and “yes” people. That is somewhat by design. As a Chief of Staff or generalist, you don’t have an allegiance to any specific department, project, or task. There is extreme value to any leader in having someone they trust that will disagree, present an alternative point, or tell them no. This doesn’t mean you are destined for constant confrontation - it means the Executive you work for just made their most important hire in someone that isn’t afraid to voice the blindspots and be honest, compassionate, and direct.
What I hope for you fellow generalists: That saying no is what will define your path. Your skill set is so diverse, you don’t have to stay anywhere that doesn’t align with what you want to build in the world. Additionally, you have the influence to help an organization hold itself accountable which is invaluable to the right leader.
In conclusion, what I hope for you fellow generalists (and managers of generalists) is that you take the time to make a list of your superpowers and give yourself the time and grace to find a role that fits. Know your worth. Know that saying “no” at the right time to the right executive can save a company or company culture and that is a very powerful influence. Most of all, I hope that your list of superpowers helps you understand the value you bring personally and professionally to the organization lucky enough to have you.