JooBee Yeow, a trained systems engineer with a PhD in Leadership Development.


September 18, 2023

Founders, at some point you might need to fire your friends 

You should never keep someone because you like them

JooBee Yeow

5 min read

I was recently talking to the CTO of a hyper-growth startup that will remain nameless and I asked them: What keeps you awake at night? 

They said that they felt they had kept pace with the company and grown into the role of CTO but that there would come a time when they did not have the skills and experience to take it to the next stage. Their biggest fear was that when the moment came, nobody would tell them. 

“I don’t mind stepping down and learning from someone more experienced than me. But I can’t do that if no one tells me,” they say. 


It is understandable for founders to be grateful and loyal to employees who have been with them during the tough early stages of building a company.

They may have done an amazing job in getting a business up and running. Or perhaps they took a huge risk in joining an unproven business. As a reward for their hard work, loyalty and trust, a founder might give them a team and a flashy executive job title. 

Don’t repay your employee’s hard work and loyalty with a job they can’t do

But as the business scales, so does the job — and it can get to the point where the employee just can’t handle it. Often, it isn’t a reflection on the individual, it’s just that the challenges of launching a scrappy startup and being an executive at a large company are very different, and require a different set of skills. 

The problem is that, all too often, founders don’t have that conversation — they actively avoid it. It is your responsibility to grow the business and your people to achieve the business goals. If your managers are not scaling with the business, take ownership. Talk to them. 

Don’t repay your employee’s hard work and loyalty with a job they can’t do or don’t enjoy. Reward them by being honest. 

Get on the same page and give them a chance to step up

Most of the time, employees will know when they’re struggling. What they’re afraid of is doing badly in their job and being asked to leave a company they love. So you need to be empathetic and actively work together to solve the challenge. 

From the conversations (yes, plural), both of you should be clear on three things: (1) your expectations of success in the role, (2) the plan to get on track, and (3) an agreed timeline. 

Sometimes, this is all your employee needs to step up and, as their manager, it is your job to provide that and give them a chance.

But what if it doesn’t work out? 

I see founders and managers make the mistake over and over again of avoiding conversations about the worst-case scenarios in order to spare someone’s feelings. But in sparing feelings, we are disempowering the employee by not letting them be a part of the solution.

You should never keep someone because you like them

What we might assume is a terrible outcome for others, might not be for them. So, put it all out on the table.


Option 1:  Layer above them

Allow your employee to be mentored by someone who is experienced. The new person will also take on the next level of responsibilities your employee is not able to step into now, giving them the space to grow their capabilities and set them up to take on a larger role in the future.  

The catch is, if you have already-inflated job titles, it can be hard to create new layers. If the title you have given away is a VP or C-level title when you are at 50 employees, for example. 

Option 2: Replace them

If the scope of the role has transformed (for example, VP of 50 people to VP of 500 people), or is transforming very quickly, there will be a significant impact on the experience of the people they manage and the business results if the person in the role is not able to deliver. 

In this case, you need someone with the relevant experience immediately — which means the employee in the role will need to be replaced. 

Not fired, I should add: replaced. If the employee has always been a great performer and their role outgrew them, there are still opportunities in a scaling startup in which they could thrive. 

If they were VP of engineering, they could remain in the same function: resume their previous role as head of engineering and learn from their new manager.

Or they might want to broaden their experience as a product manager. Or they might decide people management is not their cup of tea and move back into an IC (specialist) role as a principal engineer.

In the short term, this might seem like a setback, but in the grand scheme of things, they are moving forward towards a bigger goal.

Option 3: Part ways

If you’ve had honest and candid conversations, and have done everything you could together, parting ways may be the only outcome.

Sometimes having these conversations can help someone take stock of their career journey and motivation. It could be that they’ve been with you since graduating, and would like to gain new experiences in a different environment or industry. 

Or they might realise that they enjoy being part of a 50-person startup rather than a 500-person scaleup. 

You should never keep someone because you like them. Unless there is a business need for the role, the individual will struggle to have impact and make a success out of it. Eventually, they leave with their confidence knocked or worse, leaving a negative impact on the morale of other employees. 

If you truly like them, make sure their capabilities and passions are matched to the right role. If the role doesn’t exist, use your network to connect them to a role that is a better fit.

The three options above are by no means exhaustive. Depending on your startup’s capacity and capability, there will always be other solutions if you and your employee work together.

Having these types of conversations is uncomfortable, but it is an opportunity to build trust and relationships. Even if the outcome isn’t favourable, both you and your employee can look back knowing that the best efforts were made together

Avoiding the conversation is easy, but it almost always ends up with trust being broken. Once lost, trust is difficult to regain.

JooBee Yeow

JooBee Yeow is a trained systems engineer with a PhD in Leadership Development. She works with founders, CEOs, C-suite leaders and operators to break through growth barriers and accelerate performance. She is creator of the Scaling start-ups blog series and the Learngility Open Source.