First-time CTO? Here are 10 tips from an experienced Chief Technology Officer

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Congratulations! Years of hard work finally paid off, and you’re a new, first-time CTO now. It’s probably the scariest experience in your IT career – suddenly you transformed from a great developer into a businessman and you’re having a hard time adjusting to new responsibilities with no one to help you. I know it all – because I’ve been there myself. With the trial and error method, I’ve learnt some hard lessons, mistakes were made and battles were won. Now, I’m here to help you and pass some wisdom and practical tips about the CTO’s role. 

I’m not gonna lie, if you have no business or management background, your beginnings as CTO are going to be bumpy and challenging. After all, your main task is to make sure that the technology side matches the company’s business strategy. That demands not only technical proficiency (which of course you have mastered, otherwise you wouldn’t be here). CTO job description includes also team/project management capabilities, strategy, leadership, etc. I know that’s a lot to take in.

You’ve probably seen thick encyclopaedias for beginner managers that could kill a person with their volume but not necessarily provide with practical advise. I prefer a human-friendly approach.

Below, you will find ten tips that I wish I’d have known when I was a newly appointed CTO years ago.

 

1. Specify the requirements and the CTO’s role with the board and confirm them with your own words

Responsibilities of a CTO vary in every company – so the first thing you need to do is to establish what’s going to be expected of you.  The easiest way to do it is to directly ask the management how they see the role of a chief technology officer.

Set up a meeting as soon as possible, write down responsibilities and requirements together in a guideline document and finally, sum up everything at loud, with your own words to get a confirmation that everybody understands each other clearly.

It’s advisable to set a time frame (e.g. three months) and determine what needs to be done during that period. When the deadline comes, just discuss progress on a separate meeting. That will keep the whole management up-to-date and you’ll get the opportunity to discuss problematic issues and receive feedback.

Remember that company’s board/management is your new team now. So you’ll have to please and directly cooperate with them. This will give you a clean start, show your initiative and introduce you to the new role better.

2. If you have too many CTO responsibilities, say that you need more people straight away

Very soon an avalanche of things will be thrown at you – do this, advise on that. If at some point you realise that there’s just too much to do (even after settling the guidelines), you need to be assertive and simply ask the board to:

  • Postpone some tasks – unfortunately, that might cause delays and sometimes it won’t be an option, so make sure to prepare a timeline with deadlines to support your claim.
  • Hire more people – from the boards’ perspective, the tasks you’ve been trusted with are just supposed to be done. That doesn’t mean you have to do them yourself. Hire either a direct assistant for you or additional staff if you’re lacking skills in certain areas. For example, if you have too much management duties – hire someone for the human resources department. Do you check and approve salaries? Maybe you need someone with financial background. Depending on the situation, these people can be found (and promoted) internally or externally after additional recruitment process. Lacking developers? You can create an in-house team, use services of freelancers or even hire a software house. Possibilities are endless. 
we need more man, game of thrones quote sansa talking to jon snow
Feel you, Sansa.

3. You must have the courage to say that something won’t work. In case of conflict, suggest sleeping on it

You need to learn to speak up. Maybe you don’t have enough experience nor competences, but if you know that something just won’t work, say it clearly. The people you work with now are (nearly always) strong characters and will have their own narrative. If you don’t interfere and say what you think during important meetings, they will decide for you. And you will end up doing things against your better judgement.

Research is your best friend here. When you try to get people on board with your vision, prepare data to support your opinions, answers to potential counterarguments and possible outcomes/profits. Sometimes it takes more than five minutes to convince business people to your ideas.

In case of an absolute crisis, suggest a break or postpone the meeting to another day, so everybody involved has enough time to think the problem through. From my experience, it works miracles.

4. Learn to prioritise your tasks

Be prepared to be a busy bee. You will get a lot of different tasks and you will never have enough time for all of them. That’s why you need to understand what’s important and what can wait.

Remember not to bury yourself in something that takes ages to complete but is not so urgent. Don’t let one small topic steal all your attention for half a day.

CTO’s job is to know everything about the company’s technologies, tools and services, and to set directions for future development. That means no more micromanagement – you’re here to solve the big-picture problems, so leave little tasks to somebody else. 

a person swamped with two thumbs up sticking up

5. You need to leave some free time to… think

This is going to be a shocker – doing nothing is important! Your high position requires a lot of strategic thinking so you need some time to release your inner Alexander the Great and just think the problem through with no pressure. Your calendar cannot be booked from sunrise to sunset. When you need to decide the fate of the project and find the right direction, you just need some you-time. It will also be useful because:

  • You’re not a developer anymore, so don’t be shy and plan your week around your duties.
  • The company needs someone who can immediately react when something urgent is going on in the project – meaning you. Free time gives you the opportunity to move things around and plan accordingly to emergencies.
  • Keeping up-to-date with technology needs time, and there’s no one who can do your research for you. Lack of knowledge may lead to serious consequences for the entire company, including technical debt. Believe me, you probably don’t want to tell your developers they need to start over and re-write the whole product because you neglected to do your research before. Nobody’s that brave…
sculpture the thinker with caption: not now, I am busy
Stay away, CTO at work.

6. Define the ideal vision of the company, break it down step-by-step and consult it with the board

You’re sitting there and thinking, so let’s put this time to good use. Hold your horses and don’t start a revolution straight away – imagine how your ideal company would look like and prepare steps to get there. Be patient because it can take up to several years, including a few huge stages and million baby steps. After all, we’re talking about technology scope, tools, methodologies, market requirements, competition, etc.

When you sort the details out – you’ve guessed it right – you’ll need an okay from the management board. Just to make sure that your plan brings profits, street credit among IT community and falls with the company’s business strategy. 

Read more: Is software development like construction? I’ve done both and here’s the whole truth

7. Stop coding as soon as possible to avoid putting your people in a very uncomfortable position

Programming was your bread and butter for ages, you’ve worked so hard and learned everything there was to learn. You can code in your sleep, underwater and in space. Finally, your skills got you to the top. 

It’s cruel and heart-breaking but you have to part your ways with coding.

I know you love writing code (business might even expect you to do so at the beginning), but the sooner you give it up, the sooner you can start growing your business. Coding will suck you into something I like to call “the current mentality” – you don’t think about business as a whole, instead you just go deep in the code trying to solve microscale problems.

There’s also the other side of the coin – you put your developers in a very uncomfortable position. You are their boss now and it drastically changes the interactions. Programmers are generally afraid to point out mistakes of their bosses. Imagine, if you throw them fragments of code that is inconsistent, or includes an error – who will dare to do a code review and tell you to correct your mistakes? Cringy, right?

And, most importantly, the hard truth is that developers will cope without you.

Patronising them, hanging over their shoulders and dumping your vanity-code on them is anti-educational. If you still want to see code from time to time, encourage people to visit you for consultation or randomly check the progress once in a while for good time’s sake.

If you’re still code-hungry, change programming into proper technology research (see: point number 5).

Man crying on the bed with caption: worst breakup ever
There, there. It gets better…

8. Keep the information flowing

I can’t stress this one enough – make sure that everybody knows all the hows, whys, wheres, whens and whats. And I’m not talking about developers only. The whole company must know (more or less) what’s going on in different projects technology-wise. You probably have a lot of non-technical people (graphic designers, marketing, sales, and so on) who work towards the success of the company as well. Their ignorance may affect the company in many different ways: from giving wrong information to potential clients (not so potential anymore, eh?), to technical errors in marketing materials.

Communication between tech and non-tech people can be organised easily. Here are some ideas:

  • Regular project presentations with Q&A sessions where developers explain in details what’s been done
  • Technical training to explain difficult things without IT jargon to people who are not tech-savvy
  • Feedback from commercial departments (sales and marketing) explaining their perspective to developers – what they need to promote the company and bring new customers in
  • Project database with all the necessary information that can be accessed freely by anyone in the company

I understand there will be times when you’ll be trusted with confidential stuff. Of course, don’t go around with a loudspeaker to announce it to everybody because you want to be so transparent. But if there’s no reason to withhold something from your people – just don’t. 

9. Remember that you are being watched and from now on your moods will affect others. So, take good care of yourself

Movie reference time! Have you ever seen “Devil Wears Prada”? Meryl Streep plays a perfectionist editor-in-chief of “Runway” magazine (a clear reference to Anna Wintour and “Vouge”). In one scene, she attends a fashion show preview, and in her colleague’s words: “Miranda [tells them what she thinks] in her own way. There’s a scale. One nod is good. Two nods is very good. There’s only been one actual smile on record, and that was Tom Ford in 2001. She doesn’t like it, she shakes her head. Then, of course, there’s the pursing of the lips. Which means catastrophe. Her opinion is the only one that matters.”

Meryl Streep as Miranda in Devil Wears Prada, pursuing her lips
And the verdict is…

Why am I using this example? It doesn’t matter if it’s fashion, IT or RPG figurines industry. Once you’re a boss, you become a public figure – everybody watches how you handle things, listens to what (and how) you talk, senses your moods, waits for your reactions (also nonverbal ones) and adjusts themselves accordingly. 

A simple “Will you meet the deadline?” question during a meeting can be read in many different ways, from confirmation (“I like the idea, so go for it but remember about the deadline”), to a negation (“With this idea we will surely miss the deadline”). You don’t even have to say anything – raising an eyebrow (or pursuing the lips ☝) can be “symbolic” for your team. Unknowingly you can undermine somebody’s confidence or make their day.

To make sure that you don’t do this whole eyebrow-raising/lips-pursuing business doesn’t happen, you should simply take good care of yourself. Think about what you really like to do, what makes you excited and take good care of yourself. Your (un)happiness translates to others now. Do whatever you enjoy because your people will feel your discouragement. There’s no shame in delegating things you don’t want or can’t do. Someone will certainly be very enthusiastic about taking on more responsible tasks if you ask them to.

10. Get a management course. It will be beneficial for everybody

Soft business skills are something that first-time CTOs really struggle with (I know, I was there too!). Don’t be ashamed to organise management courses for you and your workmates. Hire a consultant to visit your company and plan detailed training for everybody who needs to be involved. Those can last a few days even, but if you find a trustworthy mentor, you should spare no expenses. 

It integrates the management board, gives you the opportunity to establish a common vision, and gives you feedback on where you should improve. It’s much faster and easier to be guided by someone who knows what they’re talking about, rather than figuring it out yourself. 

Just think about the times when you’ve been a developer yourself and you were managed by many different CTOs. Some of those you loved, the others you hated. When did they make you grow as a developer and when they failed to help you? Your experiences are no different from what your programmers go through. Now, they look up to you for proper guidance and it’s your responsibility to deliver and keep your developers content. And if you need external help – so be it! 

Steve Buscemi dressed like a teenager with caption: how do you do, fellow developers
Management lessons needed immediately.

Becoming a new CTO is not easy – it’s a long and tiring process but eventually, it will be very rewarding. You already speak technology, now you need to think business too. Create a great environment for you, your developers and your company to grow, and you will start seeing effects in the long run. Good luck!

At The Software House, we specialize in long-term cooperation with software companies, so if you feel that an external company could help you with software development, let us know – we’ve already successfully supported dozens of CTOs

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