It’s true that my work as a strategic leadership, innovation and communications consultant most often brings me to collaborate with big brands and international corporations. Tackling their challenges and scaling (or tempering 😊) ambitious visions keeps me happily busy. But one thing I absolutely never want to abandon is carving out time to work with entrepreneurs. There’s something profoundly energizing about stepping into their world—a space buzzing with ideas, risks, tears, hope, hesitation, and raw ambition.
Mentoring entrepreneurs isn’t just rewarding; it’s a rare and raw privilege. Over the years, I’ve come to recognize the patterns, pitfalls, and moments where a little nudge can and should make all the difference. There is a plethora of hurdles these entrepreneurial bright minds face, but often, I need to boot their butts with surgical precision to navigate them from being enthusiastic do-ers to becoming the visionary leaders their businesses (and their wallets) need.
The Reflection Deficit
I can’t count the number of times I’ve seen entrepreneurs sprinting at full speed… in circles. They’re brilliant, hardworking, and relentless, but they’re so caught up in the daily grind that they forget to ask, Where am I actually going? Reflection—taking a moment to pause, breathe, and evaluate—is often seen as a luxury rather than a necessity. But without it, opportunities are missed, crucial markets shift unnoticed, and tomorrow’s challenges creep up unprepared.
It’s a classic case of the hamster wheel: endless and mindless motion without progress. True leadership requires breaking free from the ‘hamster wheel’ and making thoughtful decisions, as Michael Heiberg, CEO and founder of Ocean.io, aptly puts it.
When I mentor, I have to plead them to treat reflection like a sacred appointment. No, it’s not a waste of time. It’s their strategic lifeline. Whether it’s a weekly hour or a full day every month, this is the space where clarity is born, and where the next big moves take shape. But the entrepreneurial mantra, that the agenda needs to be 100 hours full of do stuff for comfort is one that is very difficult to kill. Early on, I get it, entrepreneurs have to do everything. They’re the accountant, the marketer, the salesman, the tech support, and occasionally, the office janitor. But as their businesses grow, clinging to this mindset is like trying to steer a rocket ship with a bicycle handlebar. The constant hustle doesn’t scale, and it’s exhausting to watch—let alone live.
I gently (or not-so-gently) push them to embrace their new role: leader. It’s not about abandoning the grind but shifting focus to the tasks that only they can do. Delegation isn’t just about lightening the load; it’s about creating space to steer the company toward its vision. And yes, letting go is hard. But the reward? Liberation, innovation, and the chance to actually enjoy the journey.
The Delegation Deficit
Delegation is the Achilles’ heel of so many entrepreneurs. Either they avoid it altogether, convinced no one else can do the job, or they try… but botch it. Badly. They hand over tasks without clarity, micromanage the execution, or worse, take everything back at the first sign of imperfection. It’s a vicious cycle. When I tackle this with entrepreneurs, I emphasize the art of thoughtful delegation… and I confront them with an all time classic Disney ear-worm: “Let it gooooooo”.
Start small. Pick tasks that can realistically be handed off, should be handed off. Be clear, vocal, over-communicate if needed, and then step back. Trust, but verify. Over time, this builds a team that doesn’t just execute but thrives independently, freeing the entrepreneur to focus on growth and strategy… and that is what entrepreneurship is about.
The Loyalty Trap
Here’s a tough one: loyalty. Entrepreneurs often form deep bonds with their earliest hires. These were the people who stood by them when the coffee machine was a luxury, every brought his/her own toilet roll, and late pizza-crunching nights were a norm. But as the company evolves, not everyone keeps up with the pace. While loyalty is commendable, holding onto under-performers can drag the whole ship down. I’ve had difficult conversations about this, but they’re necessary. It’s not about discarding people; it’s about ensuring the business has the right talent to match its ambitions. Growth means making space for new skills, fresh perspectives, and sometimes, tough decisions. It’s never easy, but it’s always worth it.
The Busy Badge of Honor
Being busy is like a badge entrepreneurs wear with pride. Back-to-back meetings? A never-ending to-do list? They’re thriving! They are working so hard! Except… they’re not. Busy-ness is often a mask for inefficiency, and when you’re constantly putting out fires, you rarely have time to light new sparks.
I challenge this mindset. Effectiveness, not busyness, is the real measure of success. Prioritize what matters most, let go of what doesn’t, and learn to say no. Every “no” is a deeper “yes” for what matters more. It’s not about doing less; it’s about doing what counts. Most often, stepping away from the chaos is the most productive thing you can do. That means “letting go” -again-, but unlike in the Disney song, the control conundrum is a difficult one. Control is the entrepreneur’s security blanket. After all, they built this thing from scratch, using sweat, money, mom’s money, and their friends’ life-savings to start this thing. Letting go can feel like inviting disaster. Here’s the hard truth: trying to control everything will exhaust you, frustrate your team, and ultimately stifle growth.
I encourage entrepreneurs to start small. Delegate minor tasks, build trust incrementally, and embrace the idea that mistakes are part of the process. Leadership isn’t about perfect execution; it’s about empowering others to execute perfectly (or close enough). The freedom that comes with relinquishing control is transformative—for both the entrepreneur and their business.
The Vision Vacuum
Without a vision, even the most talented teams wander. Yet so many entrepreneurs struggle to articulate concisely where they’re going. They’re too busy navigating the now to think about the next. But a company without a clear vision is like a ship without a compass—adrift and vulnerable… and nearing the rocky shores of the island of failure.
I push entrepreneurs to craft and share their vision. It’s not a one-and-done exercise; it’s a living, breathing document that evolves with the business. And it’s not just for them—their team, investors, and even customers need to feel inspired by where they’re headed. And, that vision needs to be pushed, hit, challenged, beaten with a stick to see if it holds up to the test of reality. That feedback can feel very uncomfortable—both giving it and receiving it. But avoiding feedback is like driving blindfolded. Problems fester, opportunities are missed, and everyone ends up frustrated.
Build a culture of open, constructive feedback. It’s not about criticism; it’s about growth. When done right, feedback becomes a powerful tool for alignment, improvement, and innovation.
Mentoring entrepreneurs isn’t about handing out solutions; it’s about sparking insights and guiding growth. It’s about helping them move from reactionary doers to visionary leaders. It’s not easy, but then again, nothing worth doing ever is. Scaling a business isn’t just about markets and revenue. It’s about scaling yourself: becoming the leader your company needs and the person your team looks up to. It’s messy, exhilarating, and completely worth it.
If you ask me, it’s the best kind of adventure.
