Blog Img

How to go from Developer to CTO – Simon Dowling

Back to Blogs

So you want the top spot, but when are you ready?

When starting a career some people have a clear target. For some developers, that may be to lead a team or maybe create their own superstar product. For others, it’s the idea of eventually becoming a CTO.

It’s an odd title CTO; Chief Technology Officer. It’s changing all the time and depending on the industry, the size of the company and its maturity, it can encompass a grab bag of different responsibilities.

I didn’t always have a goal for my career. At one point I was just happy to be making a living in a role that fed my technical interests. However, that soon changed after my first few years of delivering projects and developing solutions directly for clients.

What is a CTO anyway?

Essentially, a CTO is charged with leading a company’s focus on technical or technological issues; that’s a broad definition, but also the truest.

Generally speaking, there are two main types of CTO:

Technical Lead

The Technical Lead CTO is what you may come across in a small start-up or software focused company in its earlier stages. A person able to balance the right amount of lead architect, developer, solution architect, engineering lead, team lead, and business driver.

The weighting on responsibilities is heavily focused on the actual technical output of the company and making decisions in the best interests of the company on technical matters.

Operational Lead

The Operational Lead is less focused on purely technical concerns and more on taking a holistic lead of the companies overall technological strategy and direction.

The Operational Lead is the type of CTO you would see at a large corporate organisation. These roles are more business focused in the sense that they require strong business acumen. In some cases, Operational Leads don’t come from a technical background at all.

The type of CTO a company needs changes over time, the same way the type of CEO a company needs changes over time as it steps through various maturity and growth models.

These changes in requirements may mean a different person must be brought in to take on the role. In other cases it allows for the same person to grow with the company and build their own experience.

Personally, I come from a strong technical background. I am a Software Engineer first and foremost and (at least for the time being) I still enjoy being able to lead technical discussions, debate technical issues with the engineering team, and get my hands a little dirty cutting code.

I enjoy those technical aspects, but have also had the opportunity to expand and fill out my business understanding. I’m not sure my own progression is typical. People land in the CTO role from countless different avenues. However, what I lay out below are the things that have helped me build a better understanding of the overall functions of a company, preparing me for a position that is firmly in the Technical Lead camp.

So you want to be a CTO?

Once I realised I wanted to be in the driving seat of a company, leading the technical aspects and being able to make key technical decisions, I knew I needed more than my previous software development experience.

Although I studied Software Engineering, my history shows that I was never a core development team member. The closest I came was applying my technical ability to speed the time-to-solution.

I initially started working in a technical consultancy role within a data migration team for a large Telecommunications software vendor. This was my first role and also my first customer-facing role.

Get in front of the customer

It doesn’t matter how, or as what, but until you have seen the other side of the request chain, you will never truly appreciate the work that teams do from a Professional Services perspective to:

  • Manage customer expectations

  • Deal with immediate issues that can’t wait

  • Find the best solution for right now (regardless of whether it’s best long-term or not)

  • Get shouted at

The last point is only partially tongue-in-cheek. Not in a ‘raised voice unhappy’ manner (that easily counts in to the 100s), but in a ‘fit of rage’ manner. When somebody’s job is on the line at a customer, they have no control over the outcome of a project, and they start to realise that there is no clean way out of a problem, some resort to lashing out. But it’s a great learning experience.

Why are they so upset?

What could you have done better?

Why do they feel you’ve let them down?

Generally, it comes down to to a failure in communication:

  • You failed to communicate an issue soon enough

  • You failed to appropriately communicate the risks upfront

  • You failed to understand their real problem and instead were driven by assumptions

In your future CTO role communication skills are vitally important; to deliver direction, understand real problems, and identify solutions with a clear understanding of the risks attached. Such things may need to be communicated to the internal engineering teams, to a board, or your other fellow executives.

Be accountable

Independent from the size of the company and depending on the type of CTO role, the idea of leading from the front is common regardless.

As a CTO you are not there just to further your own agenda, not to just ‘look good’, but to drive the company forward as a whole. You are the single person others look to for decisions on short-term, tactical matters as well as plans for long-term, strategic goals.

Nobody is perfect. And trying to be perfect is not your job. Your job is to make informed decisions using the information at hand. Or in cases where there isn’t enough information, to set about collecting more so that a decision can be made.

If you can undermine your own decisions, you’ve immediately proven they’re potentially flawed. You need to strike a balance. You must be able to gather enough convincing information, use it to formulate a direction, and commit to it without succumbing to paralysis-by-analysis.  

Again, the easiest way to train this skill is to be forced to make these kinds of decisions in front of others. Lead a project that has plenty of eyes on it. Drive a project as a solution architect or lead architect. Have people expecting your decision, waiting on it and having to follow it wholeheartedly.

There will be naysayers. But that’s the whole point. If you can defend, justify, and continue to drive your vision, you’ve proven yourself able to make those high-stakes executive decisions.

Some of your decisions will inevitably go wrong (oh boy can they go wrong), but there is real value to be extracted from such errors. Mistakes like these will quickly teach you to be accountable and take fair criticism. You should listen to that criticism, feed it back into further refinements, and understand that as time marches on, your decisions and solutions will evolve.

Find mentorship

What’s easier than doing something for the first time?

Finding and talking to people who have overcome the same problem or difficulty.

Mentorship isn’t necessarily a structured, buddy system. Nor is mentorship just finding somebody who does the exact same job as you and copying them.

It’s about finding a set of diverse set of sources that provide you with a well-rounded view of the areas you need to understand. Some of the people I count as mentors include:

  • Sales people

  • Project Managers

  • Solutions Architects

  • Lead Developers

  • Business Executives

  • Lead/Senior Consultants

Understand that what you need to learn isn’t how to mimic somebody else’s experience-level, but drive your own goals. Finding a mentor doesn’t even mean they need to realise they’re your mentor (although they would probably appreciate knowing that you find their opinion and way of working valuable).

I don’t subscribe to a formal mentorship programme structure. There’s plenty to learn by building relationships with people without the overhead of some sense of dependency or buddy-system.

Round out your knowledge so that you can understand key business areas such as:

  • How do companies best make money and what do clients buy?

  • What makes customers feel like they are being listened to?

  • How do people react to bad news? What makes that bad news more palatable?

  • In a tight spot, what is the cleanest, fastest method out of a problem?

  • What is considered a good tactical and strategic approach?

  • How do you communicate and deliver criticism and thought leadership?

Also understand that as you progress in your own career, you may be somebody else's mentor for a period of time. They may come to you with direct questions, or may pay more attention to how you handle situations.

You don’t need to make a fuss, but do share your time willingly. There’s value in continuing the cycle. Sharing your unique experiences and viewpoint will help others reach decisions on how best to overcome challenges and obstacles.

Learn the business of business

The value of having mentors outside your own competency and being customer-facing is that they build your knowledge of what business actually is.

A lot of people still hold the opinion that building a successful product or company is the result of a bit of hard graft and dedication. Sorry to disappoint, but it’s a bit more complicated than that.

As you progress in your career and explore other roles on the way to your ideal position (CTO, right?), paying close attention to your mentors should expose you to the realities of business.

Selling to customers, negotiating, understanding when to back off, understanding when to push an opinion, and understanding the nuances of what makes ‘good business’

This falls more on the soft end of the skills spectrum, but generally focuses on some basic understanding of business workings (legal, monetary, contractual, product-based) and then refining your ability to read a room and read people.

There are some boilerplate parts to business that just have to happen. There are also some parts that are purely based on basic human interaction and communication. These are where experience and sitting in on the right meetings come in to play.

Hear the higher-ups promote your company, hear how customers respond, and understand what motivates customers at an executive, VP or director level.

Understand the value of teams

Being able to deliver and consistently hit deadlines (apart from being almost impossible long-term), doesn’t prepare you for understanding the role teams play on large projects.

It goes without saying that there are a broad range of people and personalities. As a result, managing individual reactions and needs often becomes a job in and of itself. It’s wise not to brush off this responsibility. You’ll realise the value when deadlines are looming and you need people to band together.

Teams exist for a reason. Regardless of what judgements are made about certain individuals and whether they are pulling their weight, a team is required to balance tasks, spread workload, and introduce diverse opinion and thought into processes. Without understanding the value of what it takes to direct and help a team succeed, you won’t be prepared for any further people management responsibilities.

This is also an ideal opportunity to learn stepping back. Delegate tasks, ask for input, ask for their commitment to an idea, and then see how it gets handled. Your communication skills will be tested (as you try to share your vision), your patience will be tried (you no longer are in full control of all outcomes) and it will be a chance to learn that when it works, a team can be an amazingly productive, welcoming and valuable space for people to work in.

Peek behind the operational curtain

You’ve seen the customer-facing side of the business, you’ve dealt with accountability and you’ve handled teams (either directly leading or indirectly inspiring and driving). But what makes a business run day-to-day?

Here is where an executive mentor can help. A senior member of staff can answer questions on what happens with company policy, how are staff hired, and in some cases, allow you to get up close and personal with some of those policies.

To understand a company you need to understand how they manage people, organise their workforce, and ensure that their needs are met to enable them to perform at the top of their game.

Being involved in the hiring process is a good introduction to what companies have to deal with when managing the softer operational-side of running things. Become one of the interviewers. Help identify people who would strengthen the team and the company as a whole. Understand what goes into onboarding a new member of staff and the lengths companies go to to ensure a smooth transition from interview to team member.

Decide your path

However you decide to get there, the CTO role requires a well-rounded individual who has seen not only their day-to-day team focus, but also the holistic view of the company.

As you make a journey through building the experiences above, it may require changing your daily role, changing your job, or even changing companies. It’s rare nowadays to have the opportunity to explore the full extent of your potential all within one organisation. But if you are lucky enough to be afforded that opportunity, then take it. The comfort of understanding the overall team and the company as a whole will only strengthen your ability to pick up these experiences at a faster rate.

However, don’t be afraid to explore. Setting yourself apart from others often requires a breadth of experience that gives you insight into the diversity of activity and people that make up a business. This demands a willingness to branch out and explore various industries and company sizes.