Mentor Musings: entrepreneurs wear many hats, but successful ones figure out the right order to take them off.
By: Jc Garrett
Tags: Mentorship, Entrepreneurship, Startup, Strategy, Organizational Culture

You’ve no doubt heard the old trope: “entrepreneurs wear many hats.” I don't think anyone who has ever acted on an entrepreneurial impulse before expected the workload to be light. The level of effort required from a business founder is herculean, but the volume of energy you’re putting isn’t just being driven by how invested you are in the ultimate outcome of the venture — practically speaking it’s being driven by the huge number of roles you end up having to take on to see the business get off the ground.

Beginning with the earliest days of forming your business idea, you will be the primary driving force behind a ton of critical functions to bring your business to life: strategy, sales, marketing, product development, customer service, finance, operations and so on. Regardless of your aptitude or past experience with a particular function you’ll constantly find yourself picking up new jobs as your venture progresses; and most of these jobs you’ll continue adding on top of the ones you’ve already assumed, meaning you’ll need to become highly adapt at balancing each successive role with the others you already manage. So far, I’m probably not sharing anything with you right now that you didn't already know. But here is one fundamentally overlooked truth about all of these many jobs you’ll be taking on:

Being successful as an entrepreneur is less about how effective you are at the many jobs you hold and more about figuring out the right order and timing in which to move those jobs to someone else.

Note here the keyword: “successful” entrepreneurs. “Good” entrepreneurs can at least marginally perform several of the jobs they hold for a period of time. “Great” entrepreneurs can exceed at many of the jobs they hold and balance between them with a higher level of effectiveness over an even longer period of time. But “successful” entrepreneurs are the ones who put a framework together that guides them down the right timing sequence of offloading these jobs which in turn scales momentum towards truly revolutionizing how their venture grows.

Even in situations where you have a partner/co-founder(s), chances are that you are going to be directly responsible for the day-to-day execution of several critically important job functions; functions which in any established business would be overseen by at least one other person. No doubt that working hard is an admirable and necessary quality for an entrepreneur, but hard work can be somewhat of a fallacy for founders. Most feel as if they are “working hard” then success is sure to follow. And certainly doing the job of multiple people would qualify as requiring hard work. But the goal is not simply to “work hard”, the goal is to put your venture on a pathway for ultimate success. Or, as one of my favorite quotes from philosopher Henry David Thoreau eloquently illustrates:

“It’s not enough to be busy, so are the ants. The question is, what are you busy about?”

Most founders embrace the wearing of many hats as a badge of honor. And no doubt that some of the most special moments entrepreneurs tend to reflect back on are the smallest ones (usually manifested during a wild time that manifested specifically while wearing one of these many hats.) But aside from a nostalgic contribution to the heroic tale you’re on, the principle of working hard should be fairly commoditized and obvious for all serious entrepreneurs. The graveyard of startups-past are littered with tombstones from companies who were all founded by some of the most hardworking and energetic people out there. Beyond burnout, here are a few of the negatives to be mindful of that just blindly working hard can produce for your company:

Prevents discovery of critical flaws in the fundamental assumptions of your business, market, customers and model

Encourages you to try to build efficiencies around how you specifically are performing a job; which can be useful in the short-term but may not apply to that same function over the long-term

Creates operational bottlenecks that aren’t figured out until far too late in your business growth journey

All this time spent diligently executing the many jobs they are holding also draws away from time that can be invested into the most critical planning piece of a founder — knowing who/how/when to bring people into their organization based on offloading the right functional needs. A lack of a plan does not limit the founders ability to take off a hat they are wearing, nor does it prevent them from handing that hat to someone else per se, but what it does do is it forces the founder to exclusively rely upon a purely “intuitive” approach to thinking about handing over these roles. Intuition is a great skill, but without time spent planning it can be nearly impossible to make sure and hit the proper context or sequence of transitioning jobs. Some common mistakes that pop-up when using “intuitiveness” as the cornerstone of your hiring strategy:

Reactionary assignment of roles/responsibilities that the founder is just too exhausted (or not interested) in personally performing any more

Misallocation of time invested into vetting or onboarding a candidate leading to higher turnover and needing to repeat the process all over again

Misappropriation of limited funds into hiring employees who either do not fit a role or the role doesn't fit the critical/scalable needs of the organization over the long-term

In short founders have to prioritize from an early stage knowing the ifs, hows and whens of removing themselves from critical business functions and operations. That’s a challenging step for most entrepreneurs; compounded by the fact that this is somewhat of a divergent method of thinking from most “traditional” career pathways. Many of your non-entrepreneur contemporaries are literally pursuing the exact opposite goal in more traditional corporate roles. They tend to focus on making themselves an invaluable and immovable part of an organization (if nothing else to establish the permanence of importance and build trajectory for their career path.) Your mission as a founder is antithetical to this: you want to make yourself as removable and replaceable as possible without impacting the trajectory of the venture over the long-term. This doesn't mean you should seek out to accelerate your departure, this just means that most roles you take on you should adopt with a strict level of non-permanence in mind so it can scale well beyond any direct input from you. Having a functional transition plan is the first step towards seeing your venture be able to grow to amazingly new heights.

A few general tips to consider as you start thinking about or building your functional role transition plans:

Bringing on an advisor(s) early on can be a great starting point. It may not offload much of the day-to-day operational side of your roles but it will give you a counterbalance to work off of strategically and also help define your functional transition more effectively.

Think less about the crafting/scoping the job you “want” to hold for yourself at the end. Don't worry about handing things off that you want to eventually begin having more oversight on yourself. Before offloading a job consider what the removal of that function buys your organization in terms of the reinvestment of time you’ll be able to make from the savings.

Taking off hats usually requires compensating others for the taking on of those hats; consider how your sequence of handing things over fits into you financing plans (especially in cases where you are fundraising — think about the “use of funds” for a particular round and how that fits logically into a fundable narrative that investors can get behind.)

Seperate the jobs you are performing into “roles” and “non-roles.” Many of the functions you hold will need to be transitioned to someone else; others may be a temporary necessity and will not need to live on past your performance of them.

Imagine what your venture looks like at various “success” intervals in the future (funding rounds, revenue thresholds, exit etc.); then create a rubric for knowing when a particular function or role is bottlenecking growth of the business towards one of those intervals.

Understand when to insource vs outsource vs no-source human capital. The handing over of hats does not always need to be facilitated by a full-time or part-time employee. Many earlier functions can be handed over to allies you can establish outside of the organization (such as the case in say technology, accounting, executive assistants, legal etc.)

Wearing all the hats is a unique and interesting part of the entrepreneur’s journey. Be sure to avoid the “hard work” fallacy created by performing so many of these roles and be sure that you are spending more time on figuring out how to offload certain jobs versus blindly maintaining them in perpetuity. Don’t let the pursuit of becoming a “great” entrepreneur cause you to miss the chance to also being one of the “successful” ones.

Interesting supplemental article here with skills to look for when you start hiring a manager for your startup.

https://www.forbes.com/sites/forbesbusinesscouncil/2020/11/18/six-skills-to-look-for-when-hiring-a-manager-for-your-startup/?sh=7c27bfd63f05