4 Reasons You Won’t Get That CTO Job …

Andrew Weaver
April 18, 2023

I’ve been involved in high level IT recruitment for more years than I want to remember (as I’m often reminded by younger colleagues).

But one thing experience helps refine is an instinct about what can open the door to that dream CTO job but also, what can quickly slam it shut. 

None of it is rocket science, for example …

– You need to understand your core motivation and what you really want from life and career. Failure to know enough about themselves is a regular reason I see people making the wrong career moves. 

– Timing you can control, Luck you can’t. Having a career roadmap and attaining the skills needed to execute it means you have more chance of creating your own luck.

– Do some research into the company you’re dealing with and the people you’re likely to need to impress.  A little research can go a very long way.

Dress appropriately.  Ripped jeans and a “Guns n Roses” t-shirt might work at home but will probably make a poor dim impression at the interview.  As I say, not rocket science but amazing how many people I’ve seen make a misjudgment here … first impressions count etc.

– And too much personal information too early, often as a result of overconfidence in the process, can kill the chance dead. I’ll save one particular example for later.

Here are 4 examples why talented candidates failed to secure a CTO role …

1. The Premature Application

Are you actually ready for a CTO role?

Too many people apply for senior roles without understanding whether they’re actually ready and skilled to make it work.

This also comes back to understanding your own motivations and what your optimal career experience looks like.

If you’re looking to fast track yourself into a CTO role then the quickest way to achieve that operational moniker is to start your own company and/or being an early hire in a fast growth startup and get promoted way ahead of schedule …  what we call The Accidental CTO.

But most advertised CTO roles are looking for the complete product and will require you to have acquired the leadership skills, knowledge and judgment to achieve a rapid impact in this business critical role.

When considering your own readiness for a senior role, you need to conduct a strengths and weaknesses audit on yourself to identify and rectify any skills gaps.

There are ways to short circuit this process …

Become a lifelong learner.

Work with a coach or mentor who can help you execute a disciplined career roadmap.

Have a clear plan that enables you to be ready for the right role.

There is often a clear disparity in the quality of applicants between those who have grown around a clear learning plan and those who have tried to “wing it”.

2. Hiding Behind The Keyboard

There might have been a time when you could hide behind the keyboard, stay in your comfort zone and make decent progress with your career.

That option is rapidly disappearing as the CTO becomes a more hybrid and commercial-centric role.

Whether we like it or not, lack of an online presence and personal brand may work against you when applying for senior roles.

You need to show prospective employers that you’re willing to put your head above the parapet,willing to show the world who you are and what you can do.

The obvious starting point is on Linkedin – the first port of call for recruiters (as we know to our cost) but also to prospective employers and those conducting some due diligence on your background.

If your profile is non-existent/dated/full of gaps* (delete as required) then you’re selling yourself short.

But raising your market profile is more than just a polished Linkedin page. It’s about showing who you are and how you think.

Writing content, Getting involved in online/offline debates, becoming a thought leader and keynote speaker.

And that dread of dread … networking. 

Lockdown might have been a dream to those who loathe networking (pretty much all of us) but being seen in the market and cultivating relationships with peers and recruiters, can have an impact further down the line
Reach out, have conversations, get on the radar … become visible.

3. Getting Ahead of The Noise

Recruiters are often overwhelmed with applications, particularly for the really attractive roles.

I’m aware that some recruiters have to manage application numbers into the 000`s and certainly it’s standard practice for most senior roles to be wading through 00`s of applications. 

It can be a daunting challenge working through this kind of volume and being confident you’ve separated the wheat from the chaff. 

You might think recruiters lack a heart (and I wouldn’t argue about some) but even those who genuinely care about the candidate experience can struggle to work their way through this kind of volume and be sure they’ve selected absolutely the right candidates – it’s our equivalent of missing out on signing the next Beatles. 

But how do you move from being cast aside with The Chaff, to being considered one of The Elite?

How do you make your CV and application stand out versus the many competing applicants, many of whom are probably equally capable of getting and doing the job?

You need to make everything clear, concise and focused on demonstrating the attributes a hiring firm is looking for – whilst acknowledging that most hiring firms and recruiters will never get the dream candidate who ticks every box.

You should focus specifically on the impact you have made for previous companies you have worked for – give examples. 

Too many candidates simply list out the roles and headline tasks, without making their key impact stand out. 

As a prospective CTO you will have worked through enough CVs yourself to know what stands out and what doesn’t but make sure the information you’re supplying is relevant to that particular role.

You know the 3 second rule with websites – apply the same philosophy to your CV.

That recruiter might spend more than 3 seconds reviewing your CV but not much more, you have to make sure the key information STANDS OUT.

Don’t be afraid to rework everything for specific roles and bring in help or guidance for an objective assessment of what you’re planning to submit.

You only submit that CV once.

4. The Over Confident

Ultimately people buy from people.

People want to work with people they Like, Know, Trust.

So when you get a foot in the door of an interview process, be natural, be yourself, build rapport but never assume anything.

Show them you’re a people person, that you care about bringing people with you and that you can demonstrate the ability to negotiate and compromise that has helped you deliver real impact in the past.  

But it’s remarkable how great preparation and even a solid presentation can be ruined by the simple truth, first impressions count and never lose sight that the whole interview is forming that first impression.

Clothes, body language, gait, arrival time etc. all have an impact and we know how judgmental people can be … but one surprising curveball I’ve seen more than one excellent candidate suffer from, is overconfidence.

Not just overconfidence about getting the job and breezing through the interview (though I’ve seen my share of candidates do that) but more specifically a growing overconfidence within the interview panel themselves, which leads me to a true story …

When asked by colleagues to look back at an interview process where a fantastic candidate managed to snatch defeat from the jaws of victory, I was immediately taken back to a specific moment.

High performing candidate.

Excellent CV.

Strong performances throughout the process and at the final interview the rapport was excellent.
I sensed an imminent offer but also a sneaking worry that the candidate was beginning to over relax.
We arrived at those end of the interview, softball personal questions.

That’s all he had to negotiate to secure the role and let’s be frank – for me to secure my fee.

And he was asked a final throwaway question about what he enjoyed doing socially.

His answer was a case study in arrogant overconfidence and momentary lack of concentration as a revelation about his private life drew a gasp from the panel and a sigh from me.

In an instant, it was all over.

CTO Academy Career Development Service

If you enjoyed this article and have ambitions for a senior role or indeed, have an interview for one coming up soon …
I offer a free discovery career call as part of our career development service at CTO Academy.

Find out more via our Careers Page or email me direct on [email protected]

I look forward to helping you avoid similar mistakes.

Richard Weaver

Head of Careers

CTO Academy

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