(Almost) Everything you wanted to know about being a CTO

If you’re an ambitious developer, senior software engineer, team lead then you’re likely to be targeting a rise to the CTO role as quickly as possible.

But what it’s really like up there at the CTO summit?

What type of issues cross a CTO’s desk on any typical day?

What are the fundamental issues that change when you move from the technical to the managerial?

Actually, that is the fundamental change that takes place when you reach a senior tech role, where you have to move out of the weeds, away from the keyboard and start working strategically.

But first ….

What is a Chief Technology Officer anyway?

The CTO could be described as poster boy or girl for the technology in a company, particularly so because as disruption is automating every industry, the CTO has become one of the key roles in any modern company, often THE key role (just don’t tell the CEO).

They often take on executive responsibility for the technology, the team and the product – there is some debate about how much / little crosses over with the CIO role, but that’s a debate for another time.

With such rapid change taking place there will also be an expectation that they become the in-house futurologist with an acute understanding of technology trends and how they could impact on an organisations wider business goals.

Strong expertise and a deep understanding of tech is a given and traditionally that might have been the only expectation of a CTO, but in recent times the role has become much more outward facing creating the need for a significant transition of skills, not experienced by any other C Level Executive. 

Coming out from behind the keyboard requires parking some of your technical skills, or at least placing them on an equal footing with the leadership and management skills you will need to become an effective tech leader. 

You will certainly have to leave the code behind (though there is debate between CTOs about this issue) but certainly you will have to move away from the coding culture you’re familiar and comfortable with.

Key new skills?

Successful tech leaders master a range of the softer skills such as empathy (absolutely key according to the tech leaders we interview), emotional intelligence, continuous reasoning and a coaching mindset.

People problems are no longer ‘other peoples problems’ because if they’re in your team you need to manage them.

Communication is absolutely key in particular your ability to communicate with clarity and precision to non-technologist stakeholders, be they colleagues, investors, customers and even the CEO.

Oh yes, the CEO. The source of much happiness, trauma and miscommunication in the CTO community particularly when they limited insight about the core technology and try to make decisions and demands that don’t fit in with the technical reality.

Good luck with that one, keep on reading.

What are the common traits of a successful CTO?

As mentioned, they have to master a range of softer skills that is often primarily focused with around bridging the gap between technical and the non-technical, between the tech team and the market. 

CTO’s and the technology team are increasingly expected (and if they’re a half decent team then they should be demanding) to speak directly with customers and liaising with their own technical teams.

They have to be open minded and willing to learn about and try new ideas. They certainly shouldn’t be fixed to one particular technology. They have to create space to learn and predict market developments and absorb input from team members.

The CTO needs to mould them into a customer-centric operation, focused on what the market wants ahead of what they think is cool and fund to build. Ultimately, the customer remains the most important stakeholder and product development should always be driven by a validated, lean start up learning process, not by the CTO or star performers in the tech team.

OK so Steve Jobs could build it and they came but that’s not the norm and CTO’s must be flexible and open to new ideas, technology and customer driven product development.

The CTOs who flounder are often those who struggle to master the art of communication, who pursue their own ideas, rather than listen to the customer instead of driving their technology strategy through informed decisions, market insight and validation.

Another familiar tripwire is a struggle to delegate and to create the sufficient free time and space to read, learn and focus on areas such as strategy and tech planning where you can particular value to helping the company achieve their business goals.  

The ability to delegate is one of the core leadership skills required to give yourself sufficient head space and avoid that sinking feeling of trying to cope with too much, too often.

How would you describe an average day in the life of a CTO?

The obvious answer is ‘there’s no average day’ particularly when working (as we hope you all are) within a fast moving environment.

There is also going to be a huge difference as the CTO in a lean start up versus CTO in a large organisation so we asked CTO Academy Co-Founder Jason Noble to give us some insight about his experiences of what an average day might look like … 

[NB: When we first wrote this article we were living a normal, pre-COVID life referencing a commute into work  …. how life has changed the average routine)

1. Hop on the train into Central London and alongside my fellow start up techies, open up the latest copy of ‘Wired’ – OK, I’m not that hip and don’t view that as a priority, normally I’m catching up on relevant tech articles I’ve forwarded to the kindle! 

2.  Once in the office I generally start my day by catching up with the operations team, check up with systems and make sure everything ticking over OK.

Find out it any releases due today and any problems which need CTO input.

3. Really important element of the modern CTO schedule is liaising with customer services. Customers are the no.1 priority – even for the tech team – so it’s important for the CTO to keep an ear to the ground with market feedback.

4. You want a close relationship with the CEO, it will make your life a lot easier.  Most days will feature some contact with the CEO and being pulled into occasional meetings where your technology insight is needed.

With more complicated technologies and or high value sales, there could be close liaison with the sales team and you might even be brought into the sales process itself.

An average day for the CTO can involve interactions with many of the other departments and executives. Alongside this you need to create sufficient slack to deal with the curve balls that often emerge, particularly with early stage companies.

Indeed, the CEO is often as much of a challenge as the customer, changes of specification, strategy, timeline being regular spanners that can impact that nice tidy schedule you started the day with.

5.  You also need to create and stick to some space for yourself and for thinking time. You will have moved up the next level of decision making and strategy, most of which needs detailed consideration, research and argument.

Good time management is critical for any successful CTO and carving out some me time is critical.

Bags of other stuff emerges but these have been the key elements in my recent CTO roles.

What is the relationship like between CEO & CTO?

We’ve already alluded to the fact that your most important relationship as CTO will often be with your CEO. It can also be the most fraught as CEO’s and CTO’s are typically very different types of character and followed very different career paths.

It’s wrong to categorise any CEO as typical because they are by their nature supremely individual, but you’ll often find that they are very creative, visionary but often unrealistic. We’re not talking Steve Jobs here but most CEO’s will want things done yesterday and probably not having a strong technology background.

It’s therefore an important relationship for the CTO to understand and manage. You need to understand the character to decipher the messaging.

If last minute curve balls are delivered then it’s important to establish turnaround compromise.

Always build in elasticity so you can take on last minute issues and absorb some of the CEO’s idiosyncratic tendencies!

What are some of the key issues that cross a CTO’s radar?

Ten years ago cyber security was some way down the list of CTO priorities but increasingly today it’s amongst the most prominent.  Security and particularly a breach, whether internal or external, is a constant source of potential disruption and worse so as CTO you need to make sure you have processes in place to be able to deal with any such breach.

That said, it’s virtually impossible to stop a breach because of the movement of technology and also that a lot of breaches are done through social engineering.

Therefore a priority for you is to educate your staff and your users on how to best protect themselves and if something does come up, to ensure you/they have the processes in place to be able to deal with it quickly?

A recent case I personally experienced, where process helped immediately shut down a problem, happened when a developer accidentally leaked an API key that gave extra access to systems that users shouldn’t have been able to.

It was picked up very quickly and everything was shut down, all the API keys were changed and it was confirmed that nobody had actually used that API key whilst it was in the wild for a few minutes. There was no panic because processes were in place.

Another issue that might cross your radar is data theft.

Data theft can be malicious with somebody hacking in a security breach, but it could be something as innocent as an API that you’ve provided to users where somebody has worked out how to get more information than they should do. Having the tracking mechanisms and automatic stops in place will prevent that.

And data loss is another important issue.

Are you regularly backing up your systems?

Are you checking that the backups are there?

It’s something that very few people actually do, though they often say they do.

Even though I’ve got a few years under my belt as CTO (maybe because I have a few years under my belt) I always want to be up to date on tech, both generically and within my immediate area of expertise. I need to understand what’s going on.

I also need to understand the latest techniques, the best frameworks, what’s happening in the cloud, what’s happening for infrastructure, the arrival of no code solutions and all the services that we can take advantage of tol make our product faster, smoother and better for customers.

Which leads me to consider on a regular basis as to whether I’m using the right tech.

Am I building a system which it is built on the correct frameworks and languages for the type of customers it is correct?

Quite often I come across projects whereby they’ve built a generic web system, let’s say in PHP, but the performance and the need of the users is significantly greater.

What’s Around The Corner?

One of the reasons you need to delegate is to create sufficient amount of time for you to understand longer terms strategies and technological innovation.

If you’re stuck behind the laptop and micro managing your team, you will struggle to get the head space and insight about what technology is around the corner and how it might impact your company and sector. You need to be up to date with the latest technology and avoid being too internal. That’s for the CIO, when you get big enough for both of you!

Is there a technology out there that could make your systems faster to deliver, or make things easier for your developers, or your customers, or your business? If so, how quickly can you integrate it into your business?

You need to set aside some time to understand the latest trends in technology and be able to drill down and see the wood for the trees. What is hype, what is the likely?  This enables you to make an educated selection and decision on whether to incorporate new technologies, rather than jumping on a headline or bandwagon.

Are you using the right technology? You need to make sure whatever is required for the business that you’re using the right frameworks and the right backend servers to support that.

So as a database grows you may find that relational databases isn’t the right architecture to use. And you may want to move up from that to data warehouse, or maybe an OLAP cube, to Elastic search.

There are always too many options, increasing choice. You may not be an expert in it, but you need the space to understand what benefits they can provide.

In addition, keep focused on your own professional development in terms of your leadership and management skills. Here at CTO Academy we recommend carving out time for online short coaches and 1:1 coaching … well, we would say that wouldn’t we!

Don’t Talk To Me About Missed Deadlines

Another common area which gets blamed on the technology team are missed deadlines, even though they happen for a myriad of often reasons.

Missed deadlines can be because the specifications were incomplete, and you started a build before you really understood as a business what it is that you wanted to build.

It also may be down to the fact that you need other people to be part of the development process. And their availability isn’t quite as easy as it is for your own team.

But, you need to communicate very clearly the deadlines that you believe you can achieve. So that the rest of the business can make decisions on that and in particular, that the sales and marketing team aren’t over promising on specification and timeline.

It’s especially the case if you use third party suppliers. That maybe suppliers who are reliant on your software, or who give you software. For those suppliers that give you software or software that you use you need to understand their road map and their development processes and their reliability. 

I’ve had dealings with data suppliers where the quality of the data was subjective at best but what was far worse was their delivery was intermittent. Made it very difficult for us as business to build and grow with it.

Definitely Don’t Talk To Me About Sales Team Deadlines

An area that I’ve known to cause significant conflict is when dealing with sales team deadlines, often driven by difficult targets and attached bonuses. It’s not uncommon that they make promises to clients that are unattainable or put a huge strain on the technology team and other tasks.

The sales team want to close the deal so they might say that certain functionality is going to be available immediately or ahead of what is realistic. You need to have regular conversations with the sales team to make sure they’re not over committing your team and the customer isn’t going to be disappointed.

What you don’t want to be is the naysayer and the person that always says, No, it can’t be done. What you need to be is flexible and build that in because ultimately the business needs customers, it needs to bring them on board.

Over Reliance On Individuals

A very common problem in businesses large and small is a reliance on one or two individuals who dominate stand ups and retain key elements of knowledge about the software being built.

Because of this imbalance of power those individuals might also become difficult and disruptive but, you can’t get rid of them because they have the knowledge and we have the dependency.

This is one of the trickier management tasks you can face so you need to employ a strategy that counters this risk and the best way to do that is double up. Try to make sure that knowledge is shared and that nobody becomes too important and has too much power or influence.

The way you manage disruptive team members will define your success as CTO.

Ultimately …

Become an effective CTO is probably the number one target for most CTO Academy members – whether en route to the top or already there.

We’ve created a slightly light hearted look at CTO life but tried to focus on the key changes that take place when arriving in a senior role and what should and shouldn’t be part of your workload.

It’s often a high pressure role and the technology almost always stops with the CTO, a level of responsibility that some thrive on whilst others prefer to keep a lower profile.

What is crucial is you understand the leadership skills needed to be effective, work towards improving those and discarding outsourcing the rest.

More About CTO Academy

Join CTO Academy for you and your team to build their leadership and softer skills with online management skills training, 1:1 coaching and professional development advice.

We were recently Ranked #2 Best Chief Technology Officer course in the world – just behind the Berkeley CTO Program with their $33,000 price tag (last time we checked, membership of CTO Academy starts from $39 per month).

Did we mention, CTO Academy membership starts from just $39 per month 

“The skill set CTOs and IT Managers now require are a world away from what was needed in the past. I find the CTO Academy training modules to be highly valuable resources, providing broad-based business skills and awareness essential for success in the modern workplace” – Eli Oshorov, Shearwater Solutions, Sydney

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