2 Simple Leadership Lessons Most Entrepreneurs Learn the Hard Way

If there’s one thing I’ve come to appreciate, it’s the absurd odds stacked against any entrepreneur succeeding; there’s just so much that you have no idea about and need to quickly learn. For everything you must get right to succeed, there are a dozen things that could undermine you and lead you to still fail.

You could spend years learning just one small subsection of your duties like SEO, analytics, customer development, copywriting, design, fundraising, product development, development architecture, or simply great coding, but the demands of startups says you need to become competent and relatively adept at all of those and more.  And amongst all those hard skills, I didn’t even mention leadership, which I think is the most underrated skill to develop as an entrepreneur.

Leadership: the Overlooked, Essential Skill of Entrepreneurs

Leadership is a bit different, because it’s a soft skill; it’s not as easy to measure as the success of your marketing campaign or the elegance and functionality of your code.  However, it’s an immensely important skill and one with more long term value than becoming an expert in any one of the aforementioned hard skill areas; if your goal is to build a company with more than yourself as an employee, then you’re going to be leading others.  As you grow, you’ll be leading more people and spending less time on any of the individual skills you used in the early days. Instead, you will spend a lot more time on communication, vision, goal setting and coordination across teams.

As I’ve learned through my own errors and in talking to other entrepreneurs, I’ve noticed there are 2 major concepts most of us don’t recognize that are absolutely critical to leading your team whether you have a few employees or a few thousand:

1) Your employees don’t work for you; You serve them.

Having employees means that you’ve been able to convince others to work with you on your idea.  Appreciate the incredible feat that it is.

However, do not think that because they work for you that they are now enlisted to your dictatorship. You need to involve them in core discussions, listen to their ideas and feedback, and cultivate a culture of appreciation. A happy, engaged employee is significantly more productive than a frustrated, stymied, or sad employee. This ebbs and flows, so you really need to watch for it on a daily basis, especially if your company is growing or changing rapidly.

Praise is your secret weapon.

Showing appreciation for those that work for with you is not optional; you cannot over-recognize their best efforts. At the same time, it is a balancing act. Each employee will respond differently, so it’s a skill that requires fine tuning for everyone you work with. Some people want to be publicly recognized. Others feel physically uncomfortable to be praised in front of others.

Unfortunately, what I, you, or anyone else prefer is completely different than the next person you hire, so taking the time to understand how people prefer to be recognized is a worthwhile investment; an hour spent developing and appreciating your employees will pay you back exponentially.

2) Uncover and fix problems when they’re small.

With all the hustle and constant activity buzzing around a growing company, it’s easy to overlook small problems. Don’t.

When problems are small, solutions are small as well. When problems grow up, then it takes big, dramatic solutions to overcome them. If it’s an interpersonal issue or a major team issue, then suddenly that small issue can lead to someone having to be let go or teams feeling deeply divided.

Catch problems when they’re small by reading your employees;  look at their face and posture, and if an employee seems down or upset…asking them if something is up and seeing if you can help has huge immediate and long term benefits. Use your 1 on 1s as a way to privately discuss the issues on their minds and work to improve them. A small investment now can save you fire fighting later and falling into reactive management.

Experience the upside of prevention.

Conflicts and small issues are often simple misunderstandings or honest mistakes. Tackling them head on breeds a culture of accountability and openness to healthy criticism. 

When you get your team in this habit, it becomes much easier to avoid major problems, because they never get that big. Having a discussion about firing someone is a much more dramatic discussion than talking to an employee about a minor issue that may have caused conflict or hurt the company.  And if you've had a series of conversations about a problem that hasn't changed, it's much less surprising to let someone go than to wait and then let them go with limited warning.

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Just like hard skills require practice and active use to become sharper, leadership skills like the concepts above require practice and reflection to become great at them. And the payoff is already in front of you; I bet there’s times you’ve noticed your team’s mood affected productivity or a problem grew larger than it should have and caused trouble. This is your opportunity to do things differently going forward.

Have you learned these lessons the hard way? What key leadership skills do you think founders need to learn most?

Want to stay on top of what matters most to your team? Looking for help following the best practices of great leaders?

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