What should you do in your first months as a CTO?

“Take some time to adjust”

One thing our respondents agreed on is that being a new CTO is certainly not a walk in the park. Some highlighted the importance of prioritizing tasks, while others pointed out that no CTO can make it alone. If you want to set yourself up for success in your new role, you need to work closely with the rest of the organization from day one.

“Starting off as a new CTO can be challenging. When taking up the position, people assume you already know everything about the tech industry. However, you often need some time to adjust.

Every company considers different technologies and trends as important to their business. Therefore, it can take some time to get up to speed. It can help to do some research about the companies’ software, for example, or the latest technological trends it used. Although you’re new to the company, don’t be afraid to share innovative ideas while also remaining flexible.

Being a CTO is all about leading a team, and inspiring them to think outside the box and use new technological trends to the company’s advantage.”

—Kenneth Weesgaard,
CEO at GoSimplo

“The most important thing is to get to form your own 360 on people, product, and customers by sitting down (virtually) with as many people as possible. Focus on getting to know your leadership team and how they work together, but also reach beyond that and meet with the informal leaders in the organization to understand how work gets done and who can help create anchor points to the strategic narrative you want to build.

It’s important to articulate where you see the organization going in the early days and speak with empathy and humility about where you see opportunities to do things better. 

Equally important in the first 90 days is to build a sense of the alignment between investments in product defined in the roadmap and internal stakeholders (such as PS, service, operations) and external customer lens.”

—Hugh Cumming,
CTO at Vena

“Let go of the urge to write code”

While it might be tempting to jump headlong into solving technical problems, especially if you’ve worked as an engineer before, make sure you’re thoroughly familiar with the company’s culture, processes, and KPIs first. The initial days and weeks should be more about learning and absorbing, rather than executing, according to some of the professionals we spoke to.

“A new CTO needs to start as a sponge: soaking up everything from technology stack to team strengths and weaknesses. While it’s tempting to focus on solving engineering challenges at first, figuring out how the technology organization contributes to the company bottom line is likely the shortest path to success. 

There’s often a web of informal stakeholders in product, design, sales, and success that all care deeply about how engineering allocates resources, and bringing them in as early as possible will build trust and enable faster and higher impact innovation.”

—Aaron Podolny,
Co-Founder and CTO at Scribe

“Many tech leaders come from technical positions. Our responsibility now is no longer to write code, however tempting that might be, but to shape visions and coordinate teams.”

 —Hendrik Wallbaum,
Head of Frontend at Taxdoo

“In the first few months of being a CTO, listening, reading, and absorbing internal strengths, gaps, as well as relevant industry trends is most important. 

While you may enter an organization with wonderful new ideas, it is important to fully understand the environment and challenges to adjust your approach to ensure success for CTO initiatives and for the organization’s technology strategy.”

—Kathleen Moriarty,
Chief Technology Officer at the Center for Internet Security

“As a tech leader, I struggled with the fact that I had less keyboard time. It took me a while to learn to balance my time and stay up to date with technology without actually taking on a lot of development assignments.”

—Dor Zilka,
Head of Digital Development at Cal
(Israel Credit Cards)

“Ditch perfectionism”

It’s going to be messy. You’re going to learn as you go along and it’s only natural that you will make mistakes. If you’re a high achiever with a perfectionist streak, the first few months of your new role could be very challenging unless you give yourself some space to experiment and grow.

If you work for a startup, you might feel that you often need to wear several hats at once. Just don’t fall into the trap of thinking that you have to excel at everything—that’s simply unrealistic. The sooner you ditch the urge to be perfect, the less likely you are to experience burnout down the road.

“What I had to do in the first 6 months was setting up the stack tech at no cost (all these AWS credits) while trying to spend the €80k as efficiently as possible on freelancers. You need to be able to do everything yourself and eventually hire a freelancer for the things that you absolutely cannot do.

That means you’ll be terrible at everything but there’s no other way around when you’re self-funded. I had to run marketing, customer support, hiring and… tech!

One important piece of advice I want to give: your time is limited, focus on testing your assumptions as fast as you can and iterate on them (product-wise).

As a CTO you need to support business and not the other way around (I see too many CTO doing great tech but disconnected from business reality—don’t fall in the trap of optimizing early).

The early days of your startup won’t be glamorous tech-wise, you’ll have to duct tape a few pieces of code together for that PoC that might last only a couple of days. No-code platforms are great for that! Even if your product will look cheap and sketchy, if someone is actually ending up using your scrappy PoC that means that you’re onto something!”

—Vincent Audoire,
Co-Founder and CTO at Feather Insurance

“If you are a perfectionist, you’ll never feel like your product is ready and, eventually, it will die as an idea. Test as early as you can with a quality—not perfect—product. Once you’re 70% to 80% completed with the minimum viable product, start to get clients on board. Incorporating their feedback will help you avoid additional reworks down the line.”

—Rohit Sinha,
CTO at SmartPM Technologies, Inc.

“In your first 3–6 months as a new CTO, make changes gradually. There’s a high likelihood that you have a vision for change and a plan in which to make that change happen.

However, you must make sure to avoid the trap of over-productivity—that is, trying to make operations perfect all at once. Rapid changes can lead to extended lulls in production as employees work to re-acclimate themselves with new software and technology. By doing this all at once, you run the risk of leaving the business at a complete standstill while employees get up to speed.

Make sure you create improvements with the guidance of your team—they could offer useful perspectives owing to their extensive experience at the company. With these considerations in mind, your first few months as a new CTO will go smoothly, and should promptly improve day-to-day operations.”

—Gregory Yong,
Chief Experience Officer at Convincely

“Books are great, but real-life advice is better”

Regardless of what it might promise, no book or course will ever prepare you for the reality of being a CTO. It will surely give you a good understanding of the essentials, but what you really need is the guidance of someone with more hands-on experience.

So, instead of burning the midnight oil poring over another handbook, reach out to potential mentors on LinkedIn or pick up the phone and schedule a coffee with the CTOs you know.

“Usually, new CTOs and tech executives are ex-engineers. Sometimes, they also get promoted from team leads. In any case, they feel comfortable with tech but do not have management experience. There are plenty of resources on management out there, ranging from topics such as motivation, team topologies, leadership to strategy, that can be useful to new CTOs.

For new CTOs, it’s good to have a mentor or at least communicate with other CTOs in a particular industry. There are many professional associations, such as CTO Craft. Conferences are also a good source of contacts and they offer space for discussions. 

It’s also helpful to pay attention to how other CTOs present themselves. The role of a CTO is not only about tech but also about tech marketing and advocacy, HR brand, product marketing, and investor relationships. Consequently, it’s important to develop public speaking skills.

Reading good quality books should be a given for any CTO. Personally, I am a big fan of Andy Grove’s High Output Management. The book just doesn’t get old.”

 —Sergey Velts,
Founder and CTO at Cybertonica

“Get to know your organization”

We also received a lot of practical, tried-and-tested advice on how new CTOs can get to know their organization better.

“If possible, a new CTO or CISO should interview the predecessor. Most CTO-led programs are tied to long-term goals with relatively long implementation cycles. The predecessor will provide some unique insight that is often left out of the documentation. If possible, have them introduce you to the other department leaders, executives, and your direct report. Their stamp of approval will make your transition much smoother!”

“Learn the culture. This requires asking a lot of questions and listening intently. I recommend mapping to the McKinsey 7S Framework, if possible. It will help you find your fit and how to best communicate across the organization.”

“I recommend performing a high-level assessment of the current IT capabilities and commitments. There won’t be enough time to get deep into the weeds, but that’s not really your focus. You need to get an understanding of your assets, how things are managed, and understand the cycles of deployment and maintenance. You might find some helpful tie-ins to ITIL or similar.”

“Look for quick wins for your first 90 days. This will create positive synergy in the team, as well as get momentum going.”

“Build your initiatives for the first year but be mindful of requesting too much money or resources. Most organizations have an undefined appetite for change, but when you push too much change in, you will know when you exceeded that appetite.”

“Review all of your 3rd Party Vendor Agreements, along with the MSAs and SLAs. In the post-pandemic world, much of what you are responsible for will not live inside your ecosystem. You need to know what expectations have been set with your vendors. Their breach is your breach.”

—Patrick Kelley,
Founder and CEO at Critical Path Security

“Understand the mapping of resources to priorities. For example, is money being spent well? Are people working on what matters? If not, why?”

“Drive focus in the organization, initiate a reorganization or reallocation. Shake up the status quo.”

“Dive deeply into quality. How is testing being performed? Whose job is quality—just the QA team’s or everyone’s? What’s the level of automation? How often do issues affect customers?”

“Set metrics around bug fix priority, set code coverage (80%) and automation (100%) goals.”

“Understand cycle times. How quickly can we deliver for our customers and our business? How frequently do we push changes? Can I push a small change in less than a day?”

“Simplify the process, invest in VSDP, set goals around delivery time (>50% of changes < 1 week).”

—Eric Billingsley,
CEO at Guide-Rails

“Focus on learning the new company, industry (if applicable) and day-to-day responsibilities specific to the CTO at this company.”

“Evaluate how the company is performing in relation to their KPIs, how to use your current technology infrastructure or new options to increase performance.”

“Identify any knowledge and/or skills gaps within your internal IT.”

“Develop a vision and strategy for the company based on your findings and communicate that to the executive team.”

—Matthew Shiner,
CTO at Meta Technologies 

What should you focus on as a new CTO or tech executive?

“Build good relationships”

Although the specific areas of focus will depend on the type of company you work for and your industry, there is some general advice that could be applied across the board.

Building relationships, letting people get to know you as a person, building a strong team—this is something you can’t go wrong with, according to the experts we spoke to.

“The focus may depend on the industry of the organization and the maturity level of the technology strategy. In addition to gaining an understanding of the organization as well as operational practices, relationship building will be essential to success. Relationship building is essential not only with peers, but also other influencers in the organization who may be at varying levels of management or individual tracks.”

—Kathleen Moriarty,
Chief Technology Officer at the Center for Internet Security

“Make sure people get to know you as a person, especially the way you think and make decisions and how you lead others. You won’t have all the answers and will need the team to be super engaged to help you be successful. Great companies and products are built bottom-up and not top-down. Cover off the basics around security and risk early to avoid any surprises later on.”

—Hugh Cumming,
CTO at Vena

“You need to trust your team, but don’t take trust for granted. It takes time and it’s very expensive to build up. It’s also very easy to break it.

Obviously, you have to rely on psychological safety and an open environment, but once you build that trust you don’t need to worry about micromanaging people. They know what to do and you are confident they will achieve the results. So, focus on trust and you’ll get all the rest as a bonus.”

—Junior Godoi,
Software Engineering Manager at Scurri 

“Focus on growing your team, finalizing your goals and developing a collaborative environment across the organization. This will deliver higher value relationships internally and externally.”

—Matthew Shiner,
CTO at Meta Technologies

“Facilitate decisions, rather than make them”

Setting a clear process for decision-making will reduce friction in the team, free up your time, and make your life easier overall.

“For leaders, the task is to facilitate decisions rather than make them. As a result, looking into how decisions can be made and consciously giving concrete decision-making processes a frame is super helpful.

When deciding on a component library, I communicated that this would be a process where we don’t look for consensus but consent in the sense that not everyone has to agree but strong opposition would halt the process.

Making this clear upfront was very helpful in reducing friction related to the process and kept discussions focused on the topic at hand.”

 —Hendrik Wallbaum,
Head of Frontend at Taxdoo

“Get all stakeholders on the same page”

Creating agreement between all stakeholders is always important, especially if you’re a new CTO who has just joined the company. To do so, it might be helpful to focus on clear communication and transparent processes.

“What I would advise new CTOs is to always think about stakeholders, the market, and the competition. At the end of the day, it’s their job to win against competitors using given time and resources, be aware of risks, including risks of overengineering, underengineering, and managing people.”

—Sergey Velts,
Founder and CTO at Cybertonica 

“As a new CTO, it’s essential to understand what stage the product is at and the short-term and long-term vision for the company from the perspective of all stakeholders. All of them have to be on the same page.”

—Rohit Sinha,
CTO at SmartPM Technologies, Inc.

“Even if the workplace does need a serious overhaul, you need to make sure that your changes are well understood and properly executed by the team. Consider crafting an operations handbook outlining the provisional changes you plan to make within the organization. This helps to standardize communications and ensure that all stakeholders are on the same page. 

After all, the number one thing you must avoid is a communication breakdown. It can leave employees feeling deflated, disengaged with their work, and potentially resistant to your leadership.”

—Gregory Yong,
Chief Experience Officer at Convincely

What are some of the traps you should avoid as a new CTO or tech executive?

From overthinking to trying to do it all at once, there are many pitfalls awaiting new CTOs. Our experts shared their advice on how to avoid some of the common mistakes when you’re just starting out.

“Maintain a level of flexibility”

“It is important to maintain a level of flexibility so that as a new CTO you might adjust your approach or even strategy based on the new information gained as you learn more about this organization, its culture, as well as industry trends and inflection points.”

—Kathleen Moriarty,
Chief Technology Officer at the Center for Internet Security

“Be prepared to learn and adapt. Flexibility, in the world we are living in, is the most valuable skill you can develop. So say yes to everything, take everything as an opportunity and as a challenge to learn.”

—Alvaro Moya,
Founder at Lidr.co

“Don’t do all the technical work yourself”

“As a CTO, you should avoid the ‘technology only’ trap. Focus on driving conversations to better enable decision makers to make informed, data-driven decisions. 

CTOs do more than just managing the technology, they play a critical role in following the organization’s strategic path. It’s important to communicate this to the wider organization.

Similarly, don’t do all the technical work yourself. You need to have time to focus on bridging skills and knowledge gaps by hiring qualified staff and leadership.”

—Matthew Shiner,
CTO at Meta Technologies

“Don’t be swayed by the promise of a sale”

“Don’t chase a sale. The CTO owns the product, the road map and the implementation of the vision. There are times where a customer will ‘promise’ to buy the product once specific changes are made. My advice is not to be swayed by that. Ensure the changes will apply to your broader set of customers, the core fundamentals stay the same and the product vision is maintained. Don’t spread yourself too thin; otherwise, things will be buggy and clients won’t be pleased.”

—Rohit Sinha,
CTO at SmartPM Technologies, Inc.

“Don’t compare your new company to the previous one”

“Avoid over-using references to past experiences to highlight better practices. We’ve all said, ‘We used to do this at…’ and remember people may have thoughtfully put in certain processes without the same experiences. It’s important to create a metaphor for the changes you want to see without trying to inject another company’s practices directly.

Don’t overthink it and try to change the world all at once. Make a series of small changes and learn and adjust and work towards the larger changes as the organization gets to know you.

Focus forward and don’t get overly distracted by history—you weren’t there when any of the past decisions were made, so best not to try to adjudicate them differently. That can disengage folks that you will need on your journey.”

—Hugh Cumming,
CTO at Vena

“Make compliance and security part of your processes”

“Stop doing as much as you can—create space to do what you need to do next.

Agility is the cure for most issues in a technology org. If you have fast cycle times you can create or fix anything that comes your way.

Shift left to find and solve problems as quickly as possible to drive faster cycle times. Issues found later in the process take more time and resources to resolve than those caught early.

Building your own tools is a huge trap—your team will end up automating existing broken processes. Buy a product instead.

Don’t let compliance and security become reasons to go slow. Make them part of your process and drive them as early as possible.”

—Eric Billingsley,
CTO at Guide-Rails

Number-one tips for new CTOs and tech executives

Here’s what the experts said when asked to narrow down their advice to one crucial tip.

“Be prepared to pivot fast”

“What’s important for new CTOs, especially early on, is the ability to iterate quickly and pivot. You won’t have the right product/market fit from the beginning, and that’s OK—it doesn’t have to be perfect. But you do need to be flexible so things can be adjusted as you progress and continue to build out.

It’s impossible to anticipate all your clients’ needs, and you’ll only figure that out once clients are using the product and provide feedback. Ensure that whatever you’re building has the capability to pivot fast. If it’s too hard to make quick, necessary changes without months of rework, you may have already lost that client.

Also, you’ll want to do an incremental delivery where you have small features that make use of larger features along the way, so look at the big picture and plan accordingly.”

—Rohit Sinha,
CTO at SmartPM Technologies, Inc.

“Give it 5”

“A concept that helped me a lot when my authority increased was to ‘give it 5.’ Most things people come running with don’t require immediate action and are not as bad as they seem after you have given them 5 minutes to reflect on what is actually happening. This applies to many aspects of our work, including ideas you disagree with at first.

As a leader, your own opinion is often not what’s important. The important thing is to unleash the group, and that might require you to change your perspective. ‘Give it 5’ is a great trick that works here as well. If you want to dismiss an idea outright, give it 5 and challenge yourself to find something positive in it.”

—Hendrik Wallbaum,
Head of Frontend at Taxdoo

As part of our Tech Leaders Hub series, we also ask our guests to share with us their insights on getting things right. Here’s what some of them told us.

“Build your personal brand”

“For me, it’s around making sure that as a tech leader you build your own personal brand and you’re putting yourself out there on various social platforms so that people get to know you and understand what you’re doing.

It’s really good personally—you get invited to talks and webinars, for example. It’s also good for the company you work for as it’s bringing attention to it.

The other thing you attract thanks to your personal brand is talent. Recruitment is one of the hardest things these days, especially in tech. Getting a personal brand and being out there is one way that people actually come to find you.”

—Andrew Beacock,
Head of Engineering at Canopy

“Bring your team into alignment”

“My number one tip is to bring your team into alignment. What does that look like? You can imagine a team that is not aligned as two people holding a tug-of-war rope. The two people on either end are pulling it against each other, causing stress and getting nowhere.

An aligned team is two people holding a rope on either end and walking in the same direction. Sure, they will occasionally get hit by an obstacle—they might get wrapped around a tree or they might want to go off in a slightly different direction—but they’re always going for the same goal. That’s what an aligned team is about. It’s happier, and it produces more code.”

—Adam Craven,
CTO and Founder at principles.dev

Final thoughts on being a new CTO or tech executive

Becoming a CTO or a tech executive, especially if you don’t have previous leadership experience, can be daunting. We hope that our guide, packed with advice from seasoned professionals, will help make the transition to your new role a little easier.

If you share our respondents’ insatiable hunger for knowledge, you’re in the right place. We’ve written extensively about different aspects of being a tech executive on our blog. Here’s a selection of our recent articles and resources:

                     
• The Global CTO Survey 2021 Report
                     
• Tech Leaders Hub: Management & Growth
                     
• 10+ Must-Read Books for CTOs
                   

If you’re more into podcasts, be sure to check out our Tech Leaders Hub series—we’re pretty sure you’ll find it inspiring.

In case you need more practical support to develop your product, feel free to reach out to us. With over 18 years of experience and 800+ projects delivered, we’re ready to meet your unique software development needs and support you on your path to success.