What to Know When Working for a ‘Quirky’ Entrepreneur

15, 2021

6 min read

Opinions expressed by Entrepreneur contributors are their own.

Working for an entrepreneur can be one of the most rewarding experiences you can have in the world, especially if you’re thinking about branching out on your own eventually. Every successful entrepreneur breaks the mold in some way, creating something exciting and innovative. 

An entrepreneur is likely to personally teach you efficient methods as well as some core basics about sales, marketing, business and project . Like any one person, the entrepreneur has both strengths and weaknesses. All entrepreneurs are different, but they do share some characteristics you should be aware of when you’re thinking about working with one.

Personal quirks become professional quirks

Most entrepreneurs are their . They do not have a separate individual and professional personality: It’s the same. While that can be a strength when it comes to branding, it also means you’re going to have to get used to a personality with some serious quirks.

No one succeeds as an entrepreneur without being unique, and sometimes that means having rough edges or singular methods.

Everything is on a rush schedule

When you’re working for an entrepreneur, you’ll quickly learn that everything needs to be done yesterday. No matter how organized entrepreneurs are, to keep up with a rapidly changing world and a competitive environment (especially if they’re in tech), they need to complete projects exceptionally quickly.

Some things might sit on the metaphorical back burner for a while, but when an entrepreneur’s focused on something, it’s a target. As an employee, you must follow suit. If this is overwhelming, do yourself a favor and communicate clearly. 

Entrepreneurs love to mentor 

Do you want a job in which you will learn things? Learning is one of the significant benefits of working for an entrepreneur. Formal is also possible when you work directly with an entrepreneur. As you discover more things you’d like to learn about, keep track of those things and ask for structured time and mentorship. Entrepreneurs love teaching and generally enjoy being very giving of their time when it comes to that.

Related: 4 Benefits of Finding a Mentor

Expect to manage your own time

While some entrepreneurs are micromanagers or paranoid due to previous negative experiences with employees, most expect you to be able to manage your own time, whether you’re hourly, salaried or on a per-project basis. Getting the work done efficiently is the most important thing for most entrepreneurs, and regardless of how they are with , they’ll expect you to be an expert at managing your own time.

Even if the entrepreneur doesn’t ask you, it’s helpful if you track your time and tasks. Using a free tool like Airtable, this takes only a few minutes per day. 

Set boundaries

You’ll have to set boundaries with the entrepreneur. Entrepreneurs have few boundaries between their personal and professional lives sometimes. After all, they’re living their passion! However, they need to be reminded that they can’t take advantage of your time. Boundary-setting rules are especially important for holidays and time you have scheduled off.

Decide what your boundaries are. 

Entrepreneurs chunk tasks — then go AWOL for a while

Chunking is a method many successful entrepreneurs employ. It means doing specific tasks in chunks to improve focus. For example, let’s say you have four blog posts to write. Instead of spreading them out between other distracting functions during the day, you sit down and plow through them all at once. This method leads to a focused mindset for many.

As an employee of an entrepreneur, this can affect you.

Related: Tips to Help You Finally Get Things Done and Stop Procrastinating

Entrepreneurs need finishers

All entrepreneurs are fantastic at generating ideas and setting up large projects. However, many aren’t good at managing all the details those projects entail — or finishing one of the many projects they start.

Their lack of ability to finish projects before starting new ones is significant for you, though — it means you’re precious to an entrepreneur so long as you can complete projects and tie up all those loose ends.

Too business-minded, or not at all

As an entrepreneur, it’s tough to focus. It can seem like an entrepreneur boss is either too focused on the business or not in a business mindset at all. Many genius entrepreneurs have been described as flighty, fleeting from one project to the next.

Be prepared to deal with a personality that sometimes seems erratic in this regard — and to retain your value, always be ready to pick up the slack.

Multi-project workload, constant starting

Most employers require you to multitask, but few require multitasking in the same way as entrepreneurs. Most entrepreneurs know that they’re best at starting projects, leaving them in capable hands and moving on to start the next best thing.

Imagine an entrepreneur like an admiral of a fleet. You, whether an assistant or project manager, are a captain. The entrepreneur jumps from boat to boat, often building new ships, expecting you to repair, maintain and finish the construction of all the other vessels. Are you ready for that challenge?

Expect lean times and feast times

Depending on the business size and the investment in it, you should expect any startup or entrepreneurial effort to have lean times and feast times. When the crunch comes, you’ll feel it. There will be fewer lunches on the company, stricter budgetary approval and more. During feast times (after a round of funding, for example), you’ll see more generosity.

This variation is a scary thing, especially if you’ve previously worked in a more corporate environment where there were never worries about a paycheck. You’ve got to trust your entrepreneur to lead you successfully through those lean times.

Related: 5 Rules of Salary Negotiation

Entrepreneurs are particular about their brands

Especially in a small business, entrepreneurs tend to be more hands-on with their brands than those working in corporate America. They’ve birthed this brand, product and service, and they’re still involved in its success. They may eventually decide to sell the company and move on to another thing (many serial entrepreneurs do this), but while they’re still involved, they’ll be meddling in every bit of media about their brand.

If you’re managing social media, expect your entrepreneur to demand approval of every tweet. It’s about the brand more than distrust, but it can be an annoying detail of working with an entrepreneur.

With these factors in mind, you’ll be able to amaze any enterpreneur — and even pave the way to become one yourself. 

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