In a vibrant small to medium enterprise (SME) I was working with recently, I was leading a workshop to introduce the Scaling-Up! Playing to Win™ strategy to execution framework and how it has added >$224m growth revenue to my past clients since 2018.

The room was filled with leaders eager to enhance their capabilities and drive their organisation to new heights. As they delved into discussions about leadership and development, one senior executive who is in his late 60s raised a pressing concern:

What if we invest in developing our leaders’ capabilities, and they leave us afterward?

Sensing the tension in the room, I paused for a moment, allowing the question to linger. Rather than focusing on the fear of loss, I responded thoughtfully,

What if we choose NOT to develop their capabilities, and they stay?

This question I asked, shifted the atmosphere, prompting the leaders to reflect deeply on the implications of their mindset.

I then shared a story from my experiences working with various SMEs (family owned, multi-generational and those with about 10 to 15 years into the business but stuck and not growing for more than 5 years):

One of the SMEs I spoke to, the leadership was so paralysed by the fear of losing their top talent. They hesitated to invest in their people, fearing that those they nurtured would leave for better opportunities elsewhere. They also decided NOT to change anything in the business, blamed all their employees for mistakes and continued with the current toxic culture.

They did not engage me and after spending 4+ hours together, I shared my observations and told them if they continued with this, they will have the same conversation next year with a worst business scenario: people leaving, inability to attract talent, declining revenue from $19m to less than $15m and no innovation or new products to serve existing clients.

True enough, 9 months later, they called me again for help. However, I am already engaged and do not have any capacity to serve them until 6 months later. They told me they lost 30+ people, and barely managed to hire another 10 even after 6 months. They missed the chance to cultivate a highly skilled, motivated workforce and one by one their competent employees and managers left. Revenue decline was worse than what I forecasted. From a $19m revenue, they shrank to $10m revenue.

In that SME, capable leaders ultimately sought growth and challenges elsewhere. Those who remained felt unappreciated and stagnant, leading to low morale and declining performance. I illustrated how this fear-driven approach not only stifled individual potential but also compromised the organisation’s overall opportunities and success.

Then, I contrasted this with a different SME where the leaders took a bold stance.

They embraced the philosophy of developing their teams without fear of loss. Instead of seeing the potential departure of talent as a threat, they celebrated it as a testament to their effective leadership development.

People grew over a 15-month program, innovated, and flourished within a culture of support and empowerment. From a $9m revenue company, they thrived into a $21m revenue company. This organisation became a magnet for talent, drawing in enthusiastic individuals who wanted to be part of such a dynamic environment.

That story really landed with the leaders in the room.

They started to shift their mindset – realising that growing people isn’t just a risk. It’s a huge opportunity. When we build our team’s capabilities, we’re not just helping individuals thrive – we’re creating a culture where people want to stay, contribute, and grow together.

As the workshop went on, I could feel the shift. They were leaning in. The questions they asked were deeper. They weren’t just talking about developing others anymore – they were talking about becoming the kind of leaders who make that growth possible.

By the end of the session, they left the room with a clear decision: to stop leading from fear, and start building from purpose. That’s what Playing to Win is all about – creating the kind of environment where leaders rise, teams thrive, and businesses grow.