How Founders Can Clock When to Level Up their Leadership

Aisha Yang is a very different leader today than she was when she started Herbaland Naturals in 2009. Back then, as she sketched out a plan for a vitamin resale company at her kitchen table with her husband and co-founder, Musharaf Syed, and started building a business around the idea, her style was plucky and resourceful. “I did everything,” she says with a laugh. “I had to learn every single detail about running the business, and I had to put out every fire.”

As the company expanded, however, Yang’s work became more complicated, involving interconnected relationships with a growing network of suppliers, employees, partners and government officials. Over time, her hands-on style started to feel awkward and — worse — ineffectual. “I realized that the business was no longer about me working with a few colleagues,” she says. “I had to become a different type of leader, and that meant I had to see myself in a different way.”

Today, at the helm of a large, multimillion-dollar business, Yang leads as a CEO. Her job is no longer to get in the weeds, but rather to see what’s coming, set the strategy and mobilize her teams to execute. Her leadership evolution has been necessary: Herbaland has become the largest manufacturer of gummy vitamins in Canada, a fully vertically integrated operation with six production lines, hundreds of employees, exponential revenue growth and sales in 45 countries.

As a leader, Yang has successfully navigated a transition that has long tripped up many entrepreneurs as their companies scale. “It’s a cliché to say that founders flounder, but unfortunately that’s usually the case,” wrote entrepreneur, investor and leadership coach John Hamm in an influential 2002 Harvard Business Review essay. “Executives who start a business or project fizzle more often than not once they’ve gotten their venture on its feet.” Those that succeed, Hamm continued, do so by taking deliberate steps to confront their skills gaps and become the leaders their growing companies need.  

But identifying the need to upgrade can be tricky — especially when you’re in the trenches of growing a business. Smith Business Insight contributor Deborah Aarts spoke to Yang and two other accomplished Canadian entrepreneurs (and Smith School of Business alumni) to get their advice on how founders can assess when it’s time to level up their leadership.

Are you learning new skills?

Yang recognized relatively early that if Herbaland was to continue to grow, she would have to as well. She understands why so many founders stagnate at the point at which they first achieve success. “It’s easy to become narrow-minded,” she says. “And it’s easy to think, ‘Well, I’m an expert in this industry, I got us here, I know everything, I don’t need advice.’” But she also knows such a mindset carries collateral damage: Employees begin to resent being ignored and start to disengage or leave. Innovative ideas aren’t given room to shine. Opportunities pass the organization by. “As a founder, you have to reflect and be very aware things may change if you are not improving yourself,” she says. 

Perhaps unsurprisingly, Yang takes professional development very seriously. She completed a Smith Executive MBA in 2024 and is currently in her second year of a doctor of business administration degree at the University of Calgary. (She’s researching the constraints faced by women entrepreneurs.) Her drive for continuous learning has helped her hone capabilities that have proven invaluable in steering Herbaland’s growth. She’s learned how to effectively communicate strategic goals to a range of stakeholders, for example — something that wasn’t needed when the company was just a few people. And she’s become adept at mobilizing the many complex, organizational variables needed to turn an idea into a sellable, scalable product.

For Yang, constant learning is part of the job — and part of what makes it fulfilling nearly 20 years in. “As a leader of an established company, you have a lot of privilege to set the tone, to shape the culture and to empower people,” Yang says. “That’s why it’s important to humble yourself, to keep learning and keep improving, so you can continue to give back. And it’s important to embrace this change as an opportunity, even if you don’t yet feel comfortable or confident about it.”

Are you doing your most valuable work?

There wasn’t a single moment that made Connie Lo realize she needed to lead Three Ships Beauty differently than she’d been doing since she and her co-founder, Laura Thompson, started the natural skincare brand in 2020. Rather, it was a gradual accumulation of indicators.

There was her habit of pushing off blocks of focused work to tackle smaller, more hands-on tasks that her team could handle on their own. There was the growing frequency of employees suggesting she delegate more work to them. There was her frustrating tendency to reach the end of each week feeling utterly exhausted, but with fewer strategic gains to show for her work. “It can be hard to take a step back and recognize how many more resources you’ve built up over the years — and how you no longer need to, or should, be doing everything anymore,” Lo says. “But once I saw the signs in myself, it was impossible to ignore.”  

Lo is currently in the midst of a leadership glow-up, adjusting her habits and behaviours to free up space for long-term strategic work. With a provocative marketing campaign set to win new customers, sales closing in on $20 million, and an ambitious goal to triple sales in the next three years, she knows she needs to lead in a way that adds real value and sets Three Ships up for further success.

“You either evolve or die; the risks are too high not to,” Lo reasons. In her view, a founder clinging to a leadership style that has outlived its purpose is akin to sticking with dated software that can no longer handle the volume of activity. “Just like your internal tools, systems and teams need to evolve as your company scales from $1 million to $5 million to $10 million to $50 million-plus, so do your leadership skills,” she says. “The company doesn’t stay the same, and neither can you.”

Is it time for a new challenge?

All this said: Leading a scale-up is not for every founder.

When serial entrepreneur Arshia Jahangiri was building his first company, a mentor told him something that stopped him in his tracks: The business would grow a lot faster if someone less creative were in charge. Why? Because Jahangiri’s passion for tinkering — his tendency to introduce new ideas and try different approaches — was getting in the way of finding and serving the customers it needed to support its core business.

It was Jahangiri’s first lesson in the value of self-awareness for entrepreneurs. “As a founder, you have to understand what you are good at,” he says. “I realized I’m very good at starting a company and getting it from zero to one. But scaling from one to 100? That’s not me. I’m not the kind of person who can sit somewhere for long.”

Jahangiri has come to realize that five years is his ideal tenure in a business: enough time to launch something valuable, get it off the ground, start a growth trajectory — and then hand it off to someone else.  He is currently three years into his current startup, Solenery, an AI-powered platform to help homeowners adopt solar power and net-zero upgrades. The company has secured pre-seed funding, found product-market fit and started gaining traction, so his role is changing. Last summer, he updated his job title from “Founder” to “CEO.” It might seem a superficial tweak, but for Jahangiri it is an important one, signalling the end of working in the business and the start of working on it. “Your mentality needs a little bit of shift,” he says. “That’s because if you don’t scale the way you’re thinking, and your processes, and the way you delegate, the business can’t evolve.” In his case, that means preparing for an exit (via merger, acquisition or leadership transfer) so he can start the process of doing what he loves best: building, all over again.

Jahangiri knows too well how hard it can be for entrepreneurs to recognize when the circumstances around them have changed, especially when they’re caught up in the adrenalized rush of growing a new business. That’s why he’s a big advocate for scheduled self-reflection. “I think every entrepreneur should regularly take a pause, zoom out and really look at what’s happening with their leadership,” he says. For him, that means doing a mini-audit of sorts every few weeks to make sure how he’s spending his time aligns with the needs of the business and his own strengths and interests as a leader. “It’s so much better than pushing myself to be something I am not,” he says. “A bit of self-awareness can make all the difference.”