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Did you know that millennials will make up 75% of the workforce in 2025? With whole new generation of employees as well as a shift in workplace dynamics, it’s more important than ever to have a strong entrepreneurial leader at the top.

Your ability to lead is always being put to the test, even if you’re a newly-minted entrepreneur with no employees. The success of  your day-to-day interactions depends on it – from your dealings with contractors, customers, clients to navigating the general marketplace.

But how exactly do you qualify good leadership? Most people realize that leadership qualities are important but can’t quite figure out how to measure it.

Having run several successful ventures over the last 20 years, including the Wish Group, I’ve had more than a few opportunities to learn and observe the keys to good entrepreneurial leadership. In my experience, when it’s missing at the top, the organization is not destined for long-term success. The leadership vacuum drives away quality talent and wastes the efforts of those who do work for the business, as they won’t be motivated to achieve your goals.

What exactly is entrepreneurial leadership?

Before we dive deeper into what makes a good entrepreneurial leader, we should lay out a definition for entrepreneurial leadership. It is a mindset that focuses organizations towards turning problems into opportunities that create economic and social value. It very often goes hand in hand with a relentless optimism about the world.

Psychological testing also indicates that this type of leader is able to thrive in uncertainty, exhibits a passion for ownership and is able to persuade others towards their purpose. They are nimble, decisive, agile and embody the entrepreneurial spirit.

As an intangible quality, there are no concrete metrics or data to measure the effectiveness of entrepreneurial leadership. But it is easy enough to tell when it is missing, as it impacts every other aspect of a business that we can and do measure, such as employee productivity.

The good news is, if you don’t consider yourself an entrepreneurial leader right now, it is learnable.

Different entrepreneurial leaders have different styles

When it comes to being a great entrepreneurial leader, there is no one perfect way of doing things. Everyone has their own style, and each employee responds differently to it, depending which part of the world they’re from – we’re all unique and work at our own rhythms.  Some might respond better to a boss who’s more demanding while others prefer a laid-back approach.

As an entrepreneur, you tend to have a singular vision and a certain way of doing things that gets you where you need to be. This is how I got to where I am today. I always kept the big picture in mind – what direction I wanted to take my business in any given moment and any potential opportunities for growth.

Employees don’t have access to this information. As an entrepreneurial leader, it is incumbent on you to communicate these things to them in an effective manner, so that they can understand the larger purpose of their work.

You’ll always want to be setting a positive example. The more you can inspire your employees and make them happier to be a part of your team, the more productive your workplace will be as a whole.

6 of the most important leadership skills

Here are six of the most important qualities that I believe that every entrepreneur should have to be a good leader and sustain their business success:

1)  Know yourself

One of the key characteristics of great entrepreneurial leadership is that they know themselves and what matters. A successful leader has a singular vision for the company and understands why they’re doing what they’re doing. They know their own talents and limitations. They’ve put together a concrete business plan.

Without a stable base, you can’t set expectations for others or persuade them to follow your lead. Everyone whose help you need has to believe that you are the right person for the job.

Successful leaders understand what they’re all about. They exude the necessary self-confidence, take responsibility for their decision making and are transparent in all their dealings. When they find their business in a difficult situation that could have big implications on its future, they have the confidence to take a step back and consider things before deciding. It’s what I like to call a ‘pause moment.’

The end result is that you’ll manifest a culture of trust and belonging. You see this all the time in successful companies like Adobe or Hubspot – and, dare I say, Wish Group. Employees can and will be comfortable coming to these kinds of leaders with ideas for change and innovation. This makes it that much easier to reach your business’s goals and objectives.

2)  Nurture employees

As the captain of your business, you have a responsibility to everyone that works under your stead. You want to get the best out of them. Entrepreneurial leaders that take the time to develop the talents and skills of their workforce see it paying dividends for their businesses.

Too often, this side of the business gets neglected. Did you know that 79% of employees report quitting their jobs due to a lack of appreciation? By creating a more fulfilling climate for employees, you’ll be able to acquire, develop and retain a more motivated human resource pool.

The gestures don’t have to be grandiose. Good leaders start by sharing tidbits about the company culture, achievements and where appropriate, shortcomings (although not absolute ones) across the internal network and social media.

It is equally important to provide support on projects without taking over. If you’ve brought on the right people, you should feel confident enough that they can find a good solution for your business. You should create a culture with diverse skillsets, with various strengths and specialities.

Pass on your knowledge through mentorship, so that they can develop their own leadership skills. (This has been a cornerstone philosophy for all my businesses right from the beginning.) As employees develop, they’ll pay it forward to others in the organization. Push everyone up to the limits of their abilities. Successful leadership teams understand that they don’t need to take on everything on their own.

Empower your team to be better – this is one of the earliest lessons I learned as an entrepreneurial leader.

3)  Know when to listen

Great leaders in any field, no matter if it’s sports or business, know that it’s not always about what you say but how you listen. This means actively listening and making decisions based on not only your own interpretations but what others tell you. If you’re running a business, this is one of the best ways to provide everyone with what they need and demand.

This is a necessary but underdeveloped aspect of people’s communication skills. People will often say they are listening but in reality, they are focusing on what they want to say, instead of actually hearing the other person. Don’t fall into this trap!

Take the time to connect with others throughout your organization in a genuine fashion. A stronger connection leads to a stronger company, which can better cope with any difficult situations (i.e., a global pandemic).

Don’t be afraid to ask for and listen to advice when you need it. There is no shame! It helps you come across as a more empathetic leader, one that employees can trust and be inspired to put more into their work.

4)  Be malleable

The business landscape is always changing, especially now in the “new normal.” There is also no shortage of unforeseen developments (such as the shift words remote work) and market changes that can compromise your chances of success.

The only way to keep up with it all is to be a malleable leader, taking calculated risks and innovating where possible. This could mean launching a new initiative, strategy or even a service that opens up another avenue of growth for your business.

Entrepreneurial leaders thrive in uncertainty and always open to new experiences and ways of doing things. They are not limited by convention and comfortable with calculated risk – heck they took one by starting their own business! They’re not frightened by them or take unnecessary ones but use them as a source of motivation and minimize it as much as possible as they strive towards the goal.

The worst thing you can do is to search for instant gratification – make the necessary sacrifices and avoid taking the easier, shorter route. When facing an issue, a good leader will develop a long-term fix instead of relying on a series of patchwork fixes that can reopen and cause your business lots of headaches.

5)  Lifelong commitment to learning & wellness

Just like your employees, an entrepreneurial leader is never a finished product. He/she is a lifelong learner and is committed to keeping themselves healthy. They take a healthy interest in the world around them.

An effective leader has a life outside of work. They spend time away from the business to think things through as well as take time for themselves with vacations, hobbies and personal interests. Over the years, I’ve found that the best ideas usually come when you’re not actively thinking about them (and shooting a few rounds on the golf course).

Running a business is a marathon not a sprint. If you don’t pace yourself and equip yourself properly, you’ll never make it to the finish line! An entrepreneurial leader never gets too high on success and never too low when faced with obstacles. You can’t have poor sleeping and eating habits and expect to be your best self. Whenever possible, set routines for yourself so you can get into the right mindset.

6)  Maintaining your integrity

An entrepreneurial leader always safeguards his reputation and the reputation of his business. You always want to make sure your brand is known for the right reasons.

If you do find yourself in a sticky situation, honesty is usually the best policy. According to an Edelman study, 56 per cent of people don’t trust those who stay silent on important issues.

To avoid any confusion, as the leader, it is imperative that you make it clear from the outset what you stand for. Outline your personal and company values. Put together a code conduct for everyone to follow – live this code and make sure to include it in performance evaluations. You’ll find that if you keep things consistent, you’ll receive better employee performance and retention.


Need more? If you’re an entrepreneur with questions about getting started, how to lead effectively or any other topic for that matter, I want to hear from you. Get in touch with me at

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