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The Art of Working for an Entrepreneur

Working for an entrepreneur can be an incredibly fulfilling, exciting, and challenging experience. Like a rollercoaster it’s fast, surprising, and has all sorts of unexpected twists. The pace is gnarly.

An entrepreneur’s passion is what fuels their incredible drive; they move quicker, think faster, and act so swiftly that it might even feel spastic to an outsider. This spastic behaviour and gnarly pace can be daunting for employees who’ve never worked for an owner, especially those coming from corporate environments. So, before you go off and join the hottest new start up consider whether working for an entrepreneur is right for you.

Because many entrepreneurs are emotionally invested in their Company, you’ll need to tap into a different relationship tool box to make it work. Here are our top tactics to mastering the art of working for an entrepreneur:

Tactic #1: Be Patient

An entrepreneur is often someone who had a really great idea and managed to make a business out of it. They’ve got drive, spirit, and tenacity but this doesn’t mean that they’re an expert in every area of their business. From people management to marketing to sales, they’re learning, too. And, though most are willing to admit it, it doesn’t mean they’re going to hand over the reins to you (the expert they’ve hired) that easily. Be patient. Trust is a fickle thing for some entrepreneurs. They may have been burned one too many times in the past or maybe they’re in an uncharted area. What you need to know is that if you’re patient, loyal, and deliver results – they will growto trust you.

Tactic #2: Practice Empathy

Unlike your last C-level boss at ABC Corporation, when an entrepreneur is stressed out, it’s because he has the weight of his world on his shoulders. This is especially true for sole proprietors. The pressure can get to extreme levels and as a result his behaviour can get pretty emotional. Why? Because the Company is his baby and that is a very, very personal thing. Never forget this. An easy way you can practice empathy (and gain trust) is by being a confidante and listening with compassion to your owner. You can also realign your goals. Often as new employees we come into the new organization full of energy and enthusiasm to change things and make an immediate impact. While you’ve likely been hired for that same ambition, too much/too fast can be challenging for an owner to adapt to. Especially when you start changing things that have sentimental associations. Expect to raise your game when it comes to your communication skills in exercising empathy and aligning expectations. Expect to talk it out, often.

Tactic #3: Raise Your Game

Realize that stability is 2nd stage to excitement and being cutting edge. This is a huge consideration you need to make before considering working for an entrepreneur. They work all the time and they want you to mirror their level of excitement, their agility in processing new information and accepting changes. This pace can feel instable (and often it is). Bottom line: if you want to work for an owner, you need to work like an owner. Care (almost) as much as they do, don’t limit your availability to 9-5 and have a flexible interpretation of your job description. Expect to learn new skills, outside of your domain, and adjust with a smile. Being able to have a resourceful, flexible, and dependable team is to running a successful company.

Working for an entrepreneur/owner is a learning experience and in my opinion, entirely worthwhile. You can learn about agility, adapting, and innovation and experience the most authentic engagement and company cultures around. Witnessing honest passion and drive first hand and allowing you to be influenced by it is an immeasurable and special experience and I’d recommend it to anyone.

Hard work spotlights the character of people: some turn up their sleeves, some turn up their noses, and some don't turn up at all. – Sam Ewing

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