Why being a self-doubting CTO means you are a good CTO

I see so many first time CTOs and VPs Engineering:

✓ feeling so doubtful of their abilities,
✓ second guessing themselves and
✓ feeling like they’re not contributing to the company’s success.

These are usually the best CTOs and VPs Engineering!!!!

In my experience, the CTOs and VPs Engineering who:

✓ don’t self analyse,
✓ don’t question their own impact in the business and on people,
✓ are usually confident, arrogant and completely detached from their teams…

Those are the worst CTOs and VPs Engineering!

Confidence has a lot to answer for because unfortunately a lot of these types of CTOs and VPs Engineering are perceived by the CEO and investors as great assets!


Because they come across as confident and in the board’s mind, unconsciously, that equates to “competent”. But they’re usually arrogant because they’re insecure.

I have great news for the self doubting CTO and VP Engineering!!!

If you question yourself:

✓ where am I adding value in this company
✓ how do my engineers feel about the way I manage them
✓ how engaging and enjoyable are the engineers finding this work
✓ how can I be a better leader and strategic thinker
✓ am I an engineer with a glorified job title such as CTO, VPE, DOE, etc
✓ am I filling up my diary with one to one as I’m trying to avoid doing strategic work, whatever that may mean
✓ how can I improve my leadership skills
✓ what does great leadership look like
✓ what do good metrics for my team look like
✓ are the metrics we use for measuring my performance adequate for the stage our company is at
✓ what makes me feel like I’m not adding value
✓ how can I help my leader to carve out metrics, targets and set direction
✓ what opportunities for managing upwards am I missing
✓ am I still acting like an individual contributor (IC)?
✓ what does a good strategic contributor (SC) look like
✓ am I just waiting for the CEO to tell me what to do or am I proactive in co-creating the direction of this company with the CEO and the rest of the C Suite
✓ do I work well across departments
✓ have I spoken to other departments about the way they would like engineering to respond to their requests
✓ how well do non technical departments understand my communication of the engineering work… and so on.

If you ask yourself ANY of the questions above, you’re probably a much better CTO or VPE than you might think!!!

You might not be experienced yet, but you are open to learning and that’s hugely important.

You are interested and open to improve and that is worth your weight in gold!

You can always become a better CTO or VPE if you want to, but if you are arrogant you will be left behind and people will start leaving in droves.

Have you been fooled into thinking a confident CTO was a competent CTO?

Which of these questions resonated with you?

#cto #ceo #vpe



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