I love working with start-ups.  

I had my own for ten years and so, for me, coaching founders feels like my way of giving back to a world that was such a pivotal and unforgettable time in my own career. 

Aside from working with founders, I often find myself coaching other senior leaders within start-ups, which is how I ended up being introduced to Alyssa – an experienced COO currently working for a recently well-funded start-up in the EdTech space. 

We met up for our third coaching session a few days ago and as soon as Alyssa appeared in the Zoom room, I could sense that she was more than frustrated. 

“I’m practically old enough to be their mother”, she said, before I could even ask her how things had been going since our last catch up. “I know the Board hired me to bring some maturity and leadership experience into the business, but I’m honestly trying to lead a business that is run by toddlers”! 

To give you some context, Alyssa was initially brought on board to lead a team of 15. As a result of a recent round of (very nice) funding, she was then given a mandate to grow the team to 50 employees over the next 9 – 12 months. One of the founders is 33 years old and the other is 29. They are both super smart, with a vision that has clearly impressed enough investors with deep pockets. But, according to Alyssa, they have absolutely no idea how to run a company.

“I’m not saying they’re being unethical”, she continued. “But they’re on a slippery slope”. 

I waited for her to continue. 

“I know exactly what needs to be done to create best practices for this business and to implement some kind of strategy, particularly while we are going through this hyper growth phase. But they’re not listening to a word I say”. 

I knew she wasn’t done. 

“I’m seriously tempted to tell them to shove it. I’m more than capable of taking this business places, but not if a bunch of cowboys flying by the seat of their pants ignores every suggestion I make”. 

In my opinion Alyssa is super smart, too. She has been around the start-up ecosystem long enough to have seen several bright and innovative minds create companies with ground-breaking ideas.  

I reminded her, though, that not every brilliant entrepreneur is a capable leader, and that reality can lead to some truly unique challenges for senior leaders – particularly when such senior leaders have been appointed by a Board, and not the founders themselves. 

This wasn’t the first time I had been exposed to the struggles of a senior leader in a well-funded start-up where the founders are incredibly intelligent but lack the essential skills to lead and grow a company.  

Following my session with Alyssa, I thought it might be appropriate to delve more into the challenges, strategies, and potential options for experienced leaders who might find themselves in such a “toddler-founder” scenario. 

It's important to acknowledge the brilliance of many start-up founders. Many start-ups begin with a compelling idea, a visionary concept that captures the imagination of investors and the public alike. These brilliant minds have the creative spark, the innovative thinking, the persistence, and the technical prowess to develop incredible products or services. Their visionary ideas are the driving force behind the company’s success. 

That is, at least in the early days of the start-up’s journey. 

However, the brilliance of these founders often comes with a significant blind spot – they might not have the practical knowledge, experience, or skills required to lead and scale a business effectively.

Many founders struggle to navigate the complexities of running a company. 

When founders lack a clear plan or vision, senior leaders (like Alyssa) are left managing chaos. They must therefore create structure and order, ensuring that the company stays on track. What can make matters worse is when the founders are constantly pivoting. It can then feel like the company is veering in different directions every week, making it challenging to establish and maintain a consistent strategy.  

In such situations when the founders themselves lack clarity, senior leaders find it difficult to communicate the company’s direction to their teams, resulting in confusion, demotivation, and inefficiency among employees. This then makes hiring and retaining talent difficult when existing (and new) employees can sense instability and uncertainty in the company’s leadership. 

The constant need to adapt and the pressure to deliver results in the face of a chaotic environment can lead to burnout (or abandonment) among senior leaders.

If the founders lack a vision (or fail to stick to it), senior leaders need to step in to clearly define and communicate a clear company vision to the team. As I explained to Alyssa, given that she was brought in to stabilise the company’s operations, it’s her role to also ensure that the constant pivoting (not to mention the founders’ erratic behaviour which could potentially become unethical) doesn’t lead to disaster. 

Communication is paramount. Senior leaders need to create channels for regular, open, and honest dialogue with the founders to ensure everyone is on the same page.

Given the ever-changing nature of start-ups, implementing agile principles can also help in making swift, informed decisions in the absence of clarity from the founding team. This involves placing an emphasis on adaptability, collaboration, customer focus, and a willingness to embrace change. 

With guidance from experienced senior leaders, some founders may eventually appreciate the skills needed to lead effectively. This outcome is the ideal scenario, ‘where brilliance aligns with commercial acumen’. In some cases, founders may realise their limitations and trust their senior leaders implicitly to steer the company toward stability and growth. However, if the founders resist the advice from their more experienced leadership team, the company may stagnate, or the senior leaders may simply choose to tap out. After all, in some cases, leaving the business may be the best option to maintain your integrity and well-being. 

As a senior leader, you want your contribution to be a catalyst for positive change and transformation within the company, even in the absence of clear direction from the top.

Leading a start-up run by ‘toddler-CEOs’ can be an intricate dance between brilliance and practicality. The challenges may be many, but the opportunity for transformation and growth can also be substantial. It’s a unique journey that demands resilience, adaptability, and a constant commitment to learning. Ultimately, the outcome will reflect how well the brilliance of the founders can harmonise with the practicality of experienced leadership. 

Remember,  Hellomonday can provide support to every leader, reinforcing habits through curated learning and impactful coaching, helping senior leaders navigate the complexities of working for ‘genius founders’, stabilising start-up operations, and communicating a clear vision to drive the company forward.