The biggest fears of a CTO Vs the biggest fears of a VP Engineering


The biggest fears of a CTO Vs the biggest fears of a VP Engineering — Here’s the pattern I’ve observed:

CTO Fears:

✓ Risk of technological obsolescence

With technology advancing at a crazy rate, it can be a daunting task to stay on top of emerging trends and ensure that the company’s technology stack is up-to-date.

#Cybersecurity threats

On this one — unfortunately I see a lot of CTOs not being able to make the business case to the board about why preventing cyber attacks is much better for the company than fixing them when they happen!

In my experience the problem is not that they don’t stay ahead of the latest threats — it’s that they don’t have the budget to implement robust security measures to protect the company’s assets!!!

✓ Scaling the company’s technology infrastructure in line with a rapidly growing team they now have to manage

The bigger the engineering department, the more pressing the need for strategic planning and effective communication skills becomes, to ensure that everyone is aligned and working towards the same goals.

VP Engineering fears:

✓ The risk of technical debt

The backlog of technical debt slows down development and hinders innovation — again making the business case to start tackling the tech debt (especially if it’s gotten too big!!) is often a source of worry for VPs Engineering because the “boards don’t get it!”.

✓ Managing a high-performing team while maintaining a positive work culture

It’s important for VPs of Engineering to build a team culture that fosters collaboration, communication, and trust, while also setting high standards for performance and accountability.

People often struggle to manage tech divas — and these people can become like rotten apples to a good engineering culture (“if the tech diva is allowed to do X, why can’t we!?” type cracks appear in the culture).

Moreover a lot of VPs Engineering worry about having difficult conversations with staff while trying to be a “nice boss”.

“I don’t want to be a jerk, yet I need to give them negative feedback” said a VP to me.

✓ The potential for project delays and missed deadlines

I think unforeseen technical challenges are definitely one of the biggest fears.

Shifting priorities or a lack of resources for a project can also contribute and again, often VPs Engineering can struggle to make the business case for more resources for engineering.

✓ The potential for burnout among their team members

It’s all well and good to work through the burn down chart but if you burn your team out in the process, the whole project is screwed!

Engineers often work long hours on complex projects, which can lead to stress and fatigue. It’s important for VPs of Engineering to prioritise work-life balance and create an environment that supports employee well-being.

Do these match your fears?

What patterns do you observe?



Adelina Chalmers a.k.a The Geek Whisperer

Helps Engineers who are Leaders (CEO/ CTO/ VP) get buy-in from their peers/teams/investors by transforming Communication techniques into Algorithms