From Entrepreneur to Leader – My Five Key Lessons
Seven years ago, I found myself sitting across a white board and thinking about building my company from scratch. Seven years later, I am reliving the same moment, following a successful acquisition and the start of a new journey with uRoutine. Between the early stages of the next venture and reflections upon what’s been and gone so far, I realize that there are some key lessons learned. In particular, as my role evolved from entrepreneur to leader, and our first business grew at an exciting rate. There comes a point in almost every successful entrepreneur’s journey when they will, inevitably, transition from being the hands-on driver of every decision, to leading an organisation towards sustained, scalable success. This shift is neither automatic nor easy. It certainly requires a fundamental change in mindset, skills, and approach. I co-founded PushFar in 2018 and we grew quickly. With that growth, my role evolved just as quickly. Things weren’t perfect (I suspect they never are in the startup world!) and there is a lot of learning each and every day. For entrepreneurs and founders who find their role evolving into the role of a leader, as your team expands and the business grows, I have put together my five key lessons in this transition and what you might expect along the way. We’ll start with, perhaps, the most obvious one – letting go and delegating!Delegation: The Daunting, Important Art of Letting Go
One of the most difficult but crucial shifts from being an entrepreneur to an effective leader is learning how to delegate. In the early days of a business or startup environment, entrepreneurs tend to wear multiple hats: product, sales, marketing, tech, finance, and customer service. This level of involvement is certainly necessary at the start – in some cases, not only is it necessary but also extremely valuable. An entrepreneur wearing lots of hats will learn a lot and this will help the business to grow faster, better. Yet, as a business scales, this multi-hat-wearing-role quickly becomes unsustainable. Trying to do everything yourself will eventually limit your growth and can lead to burnout. Delegation is not about relinquishing control, as much as it might feel like it is. In reality, it is about empowering others to take ownership and be the support that you will probably need. It starts with hiring people you trust and clearly defining roles and expectations. More importantly, it involves letting go of the belief that no one can do things as well as you. A well-chosen colleague or hire can often do a specific task better, faster, and with more focus than an overstretched entrepreneur. Recognising that there are others who can do things better than you is important, early on. Leave your ego at the door when you’re starting your business, and this process of delegation will be far easier – no matter whether it happens 6 months or 6 years into your business. A common mistake is delegating tasks but not the authority that go with them. If team members have to check back with you on every decision, they are not truly empowered, and the bottleneck remains. True leadership involves giving people the autonomy to make decisions and trusting them to execute their responsibilities. This shift frees up time for leaders to focus on high-level strategy and vision. An additional benefit is that your employees are likely to stay with you for far longer! Nobody enjoys feeling like they are being “managed” and trusting them with responsibility will give them a greater experience. This leads me nicely onto my second lesson. How good are you doing at delegating? Check your score, with a free assessment of delegation skills from Risely.Team Empowerment: Collaboration is Strength
A business is only as strong as its team. Cliched, perhaps, but entirely accurate. As you shift gears from entrepreneurship to leadership, your role will shift from that of a doer to an enabler. Rather than being the person who solves every problem, you need to create an environment where your team can thrive and solve problems independently. And where does that start? Well, empowerment starts with trust. This means creating an open, transparent environment where team members feel valued and heard. People perform at their best when they feel a sense of purpose and ownership over their work. Giving your team clear goals, the resources they need, and the freedom to find their own solutions leads to a more engaged and productive workforce. They won’t always get it right but creating an environment where they feel able to occasionally fail and learn from that, is even more valuable. It’s how we all learn and grow. Regular communication is also important. Leaders should encourage collaboration, provide constructive feedback and always celebrate successes. A strong team culture is built through inclusivity, shared goals, and a sense of belonging. When your employees feel as though they are contributing to something meaningful, they are more likely to stay motivated and committed.Strategic Thinking: Seeing the Whole Business
One of the biggest shifts in moving from entrepreneur to leader is stepping away from the day-to-day operations to focus on long-term vision and strategy. People talk about not being able to see the forest through the trees, and this is no more relevant than when you are running a business and you, as an entrepreneur, are caught up in the minutiae of running a business. From solving immediate problems, and responding to emails, to managing the day-to-day, there will be little time to think bigger and see the business as a whole. While, of course, tasks like responding to emails and immediate problem-solving are important, a leader’s role is to ensure the business is moving in the right direction. Strategic thinking should involve understanding market trends, identifying new opportunities, and making informed decisions which will ultimately position your company for future success. Asking blue-sky-thinking and big-picture questions like “Where is the industry heading?”, “How can our company differentiate itself from the competition?” and “Where do we need to be in 12-months’ time?”, to give but a few examples. Leaders have got to set aside dedicated time for strategic planning. This might involve regular off-site meetings, brainstorming sessions with senior team members, or working with mentors and advisors to gain fresh perspectives. Surrounding yourself with a strong leadership team and leveraging their insights can help in making more informed strategic decisions.Resilience: Dealing with The Challenge and Uncertainty
For anybody who sees themselves as an entrepreneur, you will know that the entrepreneurial journey is filled with highs and lows – trust me! From financial pressures and investment rounds to market shifts and unforeseen crises, challenges are inevitable. What separates successful leaders from the rest is resilience – the ability to adapt, learn, and push forward despite setbacks. Resilience is certainly not about ignoring difficulties or pushing through blindly. Instead, it’s about maintaining a level-headed approach, assessing situations objectively, and finding solutions. Leaders should be cultivating a mindset that embraces failure, as part of the process. Think about every setback as an opportunity to learn and refine the approach. As an entrepreneur you should learn to get good at this pretty quickly! A key aspect of resilience is maintaining emotional intelligence. Leaders set the tone for their teams, so never forget this one. If any leader reacts with panic, uncertainty will spread. This is particularly true in the case of entrepreneurs who are usually not only the leader but the owner of the business. That uncertainty is enough to cripple an otherwise empowered, exciting culture. InsteadMaintaining a Strong Company Culture
Culture is the glue that holds an organisation together. Another cliché, but it is just as true. Culture is what defines how people in your business interact, how decisions are made, and what values drive the business to success, or continued success. While culture will develop naturally in the early days of a startup, as a business grows, leaders should learn to be intentional in nurturing and maintaining it. A strong culture is built on clear values and consistent actions. You need not only articulate these values but embody them in your own behavior. One such example of this could include making sure that you are truly “offline” and taking a proper break, when you are on holiday, and in-turn ensuring you allow your team the same space, undisturbed, when they go on holiday. If transparency, innovation, and collaboration are core values, then those must be evident in daily operations, hiring decisions, and leadership style. Everybody’s watching – or at least, assume they are. One of the biggest threats to company culture is rapid scaling. I have seen this myself. As new team members join, it is easy for the original vision and ethos to become diluted. This makes it crucial to have structured onboarding processes, mentorship programmes, and regular check-ins to reinforce company values. Employee engagement initiatives, open communication channels such as Slack or WhatsApp, and fostering a sense of belonging all contribute to a strong culture. When employees feel connected to the company’s mission and values, they are more motivated, productive, and committed to its success. Side note: this is harder with remote teams, so being intentional here is even more vital.The Continuous Evolution of Leadership for an Entrepreneur
Transitioning from entrepreneur to leader is not a one-time shift; it is an ongoing process of growth and adaptation. I know, as I begin to build my next business, that I need to be intentional in this. It is going to require me to continue to learn to trust others, step back from day-to-day operations, think strategically, embrace challenges with resilience, and foster a strong, purpose-driven company culture. Don’t get me wrong, I don’t think I made too much of a mess of it when I was building my last business, but this time, having learnt what I have, along the way, I can focus on ensuring that leadership mindset is there, from day one. Remember that the best leaders are those who remain open to learning, seek mentorship, and continuously refine their approach. They understand that leadership is not about having all the answers but about empowering those around them to collectively achieve success. As I embark on my next venture, these lessons remain at the core of my approach to leadership. For any entrepreneur looking to make the transition, the key is to embrace change, invest in people, and never stop evolving.Grab free assessments to support you on the leadership journey!
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