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4 Habits for Entrepreneurial Success: Advice From a CEO Leading the Ed-Tech Industry

Rob Waldron November 7, 2019

Leading a company is filled with the highest of highs, the lowest of lows, and everything in between. Over the past two decades of leadership, I’ve encountered thrilling wins — and I’ve also spent many a sleepless night worrying. I know how heavy a weight the pressure of leadership can be to a new CEO or entrepreneur.

Through it all, I’ve learned a tremendous amount about leadership habits that support personal and professional happiness and fulfillment. Below are a few tips which, if applied to your own leadership strategy, will lead to a path filled with more exhilarating peaks than sleepless-night valleys.

1. Go to battle — with your pride.

As a freshly-minted MBA early in my career, I thought I had it all figured out. Boy, how wrong I was!

In my first management position at a test prep center, I was assigned the task of improving margins, but I had no idea where to start. Thankfully, my employees were bastions of knowledge and had plenty of ideas for improvement based on their first-hand knowledge of the center. By simply shutting up, listening, and implementing their suggestions, we doubled sales.

None of this would have been possible if I’d let my ego win out. I quickly learned that the best managers are only as good as their employees. A good leader knows that their ideas aren’t always going to be the strongest in the room, and that’s a good thing. Surround yourself with the best team you can and be open to their unique perspectives. Open-mindedness will make a massive difference in your business and will serve you well down the road.

2. Surround yourself with teammates who inspire you, and treat them like gold.

Your employees are the backbone of your company. Just as a talented employee can elevate an entire team, one mushy apple can quickly rot the whole bunch. That’s why I view talent management as my most important role as CEO and dedicate more than half of my time to recruiting top talent to our organization — this is no small feat, as we’ve already hired nearly 300 new team members this year, but it is worth every minute I’ve invested!

When interviewing new employees, you want to find people who not only have the right skill set but who also fit in with your culture and believe in your company’s mission. This can be tough to suss if you don’t make the effort to get involved in recruiting, and nailing culture and mission-alignment ensures your team is filled with inspired, driven individuals who will stick with you for the long haul.

And once you find that team, treat them right! That means paying them a living wage, creating an inclusive culture, and providing flexible working arrangements so that your employees don’t have to choose between working hard and making memories with their families. A happy, purpose-filled workforce is good not just for your employees but also for your company’s bottom line.

3. View negative feedback as an opportunity for growth.

Ever receive a less-than-stellar performance review? Still stings a little, right? As CEO, it’s easy to remove yourself from the feedback loop of performance reviews, but it’s not advisable.

In my years as a leader, I’ve learned to embrace — and even solicit — negative feedback as an incredible opportunity for growth and improvement. Each year, I invite all 1400+ of my employees to rate my job performance in an anonymous, company-wide survey. In the spirit of transparency and self-improvement, I report my scores and the unfiltered employee comments out to the entire company.

This holds me accountable and is not always easy, but it has opened my eyes many times to glaring blind spots, allowing me to continue to grow and become a more effective leader each year.

4. Don’t get mired in the now.

It’s so easy to zero in on immediate goals like next quarter’s earnings, but this myopic approach can be disastrous in the long term. Take a step back, zoom out your focus, and take a long-term view if you want to help your company weather the next storm. Focus on sustainable planning, long-term talent investment, and thoughtful research and development spending, and you’ll be uniquely prepared to withstand challenges that will topple more short-sighted companies.

By implementing these habits, I hope you’ll be able to avoid some of the pitfalls leaders commonly face in their careers. With a strong sense of purpose and a network of consciously minded peers and team members around you, you’ll be better prepared for the curveballs that come your way.

Social Entrepreneurship / Stakeholder Capitalism
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