The Challenges of Being a New CTO: 10 Issues and How to Handle Them

We’re not here to talk about tech. Chances are you’ve risen through the engineering ranks and tech is already your strong suit. So this isn't about repeating what you already know.

This article is about the real challenges that come when you shift from doing the work to setting the direction.

When you leave behind the comfort zone of architecture, infrastructure, and code, and enter the zone of people, politics, and competing priorities, the problems you’re solving become very different. Let's get into them.

Challenge #1 – Stepping into someone else’s shoes

It’s not easy to step into a new role. As a newly minted CTO, you’ll inherit your predecessor’s roadmap and technology strategy, as well as their problems and technical debt. Some of which – if we’re honest – they’re happy to have in their rear view mirror. 

One of the first priorities in post as a new CTO will be to review the existing roadmap and decide what to continue, pause, or sunset. (Check out this summary of The First 90 Days for more digestible tips for new leaders). 

For example, you might inherit a client-facing platform rebuild that is over schedule, over budget, and draining time from your most senior engineers. The roadmap says to push ever onward. But is it still serving business needs? If not, it might be time to sunset it. 

What to do: 

• Create a backlog audit of inherited projects to understand what they are, why they were initiated, and how they’re progressing.
• Assess their ongoing relevance to current business strategy and decide whether they’re still needed.
• Prioritize remaining projects based on business impact vs risk, cost, and effort.

Challenge #2 – Escaping gravitational operational pull

Stepping up from an operational background, it’s natural to feel more comfortable in a hands-on role. But if you’re constantly getting drawn into day-to-day delivery, you’ll have no space to think strategically about how tech and talent can best support business objectives.

Yes, people might like seeing you in the daily stand-up, reviewing the new sprint plan, or solving production incidents. You’re the CTO after all – the company’s top-tier tech expert. But if you keep hold of the reins, no one else can grow confidence and learn, and that can keep you trapped in operational mode.

What to do: 

• Develop an escalation framework for which operational issues require your input and which can be resolved by others, then delegate relevant operational decision-making to senior staff.
• Set guidelines and guardrails for work, but resist the urge to micromanage or ‘just do it yourself because it’s quicker’ – this short-term fix will become a rod for your own back in the long-term.

Challenge #3 – Setting strategic direction 

It’s a big change from management to leadership. Your main role as a newly minted CTO is to ensure all technology initiatives directly support the overall business strategy and contribute to the bottom line.

Whether your firm is targeting revenue growth, increased efficiency, or longer customer lifetimes, you decide how tech and talent will help achieve it. But where do you start? 

What to do: 

• Go on a listening tour (👈 this article is for resource managers, but the practice still applies) with execs, product owners, and team leads.
• Understand their objectives, painpoints, and what success looks like to them.
• Map out the initiatives that are going to move the needle most for overarching business priorities vs those that are just nice to have.

Challenge #4 – Becoming a Babel Fish 

In a technical role, you and your colleagues spoke the same language. But in the C-suite, you’re probably the only one who speaks fluent tech.

As a result, you’ll become a human Babel Fish, converting complex technical ideas into business terms for execs, and translating strategic goals into actionable instructions for tech teams.

This is essential for keeping everyone aligned and pulling in the same direction.

What to do: ‍

• Aim to lift up comprehension rather than dumb down explanations, to build mutual respect and understanding between teams.
• Consider workshops, shadowing, or cross-team demos to help stakeholders increase their fluency in other ‘languages’.

Challenge #5 – Prioritizing initiatives and managing expectations

As a CTO, you will find everyone has a problem for you to solve (perhaps even some that the previous CTO already rejected!)

But not all projects are created equally in IT or software businesses. Some drive higher strategic value than others, like achieving high profit margins, securing the goodwill of a major customer, or transforming business efficiency.

And since you only have a set budget and resource capacity for work, you need to decide which ones to take forward.

Remember, you’re not there to be popular. Your role as CTO is to deliver the highest business impact and value with limited resources available. That means fairness, transparency, and rigor in decision-making. 

What to do: 

• Ensure each initiative is tied to a clear business goal that stakeholders understand and agree on.
• Establish a clear criteria for ranking initiatives – such as business impact, risk of inaction, and resource requirements – to ensure decisions are transparent.
• Use capacity planning techniques to understand how different initiatives will impact overall business capacity, to avoid creating downstream delivery issues.
• Be clear and diplomatic – if the answer is no, explain why: costs, risks, trade-offs (if X, then not Y). If the answer is not now, be clear on timelines and when you’ll review the decision.

Challenge #6 – Getting stakeholder buy-in

Securing stakeholder buy-in is tricky but essential. Your role is to envision the future – not only defining what you plan to achieve and creating a roadmap to get there, but articulating that in a way that rallies everyone around the same goals.

Otherwise, you risk resistance and low adoption that can undermine desired business impact.

This is especially true for delivery-heavy internal initiatives like standardising development frameworks or introducing new project management tooling.

In the short-term it is going to slow people down, reduce capacity, and cause stress. But it will also lay the foundation for faster and more scalable work in the future. 

What to do: 

• ‘Sell the sizzle, not the steak’. Get people excited about the big picture benefits of proposed initiatives, rather than minutae of what’s actually going to happen.
• Make sure technical details are translated into desirable team or business outcomes for each stakeholder. ‘Updating our authentication system’, no. ‘Making it faster and easier to log-in securely’, yes. 

Challenge #7 – Leading change 

Everyone wants transformation, but nobody likes change. Implementing new processes and tools is draining – it depresses actual capacity as resources are pulled into internal projects, and it drains mental capacity as employees adapt to yet another new way of doing things.

That’s why successful change management is super important, and supporting staff through change is one of the most important leadership skills you can develop. 

What to do:   As CTO, you can make transformations easier to manage by giving people:

• Clarity  – this is what’s going to happen (and why). 
• Confidence – this is going to be great (and why).
• Capacity – this is how we’ll cope with extra demand on teams and time. 
• Capabilities – this is how we’ll do things going forward.

This means engaging your communications team early, working with sales and operations to adjust capacity and ensure people aren’t overwhelmed during periods of change, and providing adequate training. We’ve got lots more to read here on change management ➡️

Challenge #8 – Aligning tech talent to business goals  

Your (human) resources are your most valuable business asset, as well as one of the biggest cost drivers. How you deploy them directly impacts speed, quality, project profitability, and business outcomes. But many tech and IT firms fail to do this effectively. 

Common challenges include: 

• Knowing which programmers are available to be allocated to projects, due to decentralized or outdated information.
• Poor skills management resulting in under- or over-qualified resources assigned to tasks, which can push quality down or costs up.
• Poor visibility into capacity – meaning you might struggle to match capacity to demand, taking on more projects than you can deliver well, or missing opportunities you could have seized.
• Failure to track utilization, which means you might be overworking staff and impacting quality, or under-using them and undermining productivity and profit. 
• Unstrategic allocations, squandering your most capable people on low-impact initiatives (see below).

All of these issues slow down an SDLC even if staff are equipped with the best tools for the work they actually deliver. To align your people to project and profit goals, you need a fit-for-purpose resource management system – one that delivers immediate visibility, actionable insights, and reliable data for decision-making.   

What to do: 

• Work with the leadership team or resource managers to assess your resource management maturity ➡️
• Identify quick wins and long-term initiatives to improve RM performance ➡️
• Discover tech to support your talent goals with our buyer’s guide to resource management software ➡️

Challenge #9 – Protecting profitably 

As CTO, you’re going to become more aware of the business’s bottom line. Don’t be fooled by busy teams and happy clients. These might suggest the business is productive and successful, but that doesn’t mean it’s profitable or sustainable. 

Success isn’t just shipping projects; it’s shipping them profitably. And project margins can suffer death by a thousand cuts; small, seemingly innocuous nicks that rapidly drain profit. Like:

• Schedule overruns that demand more staff time 
• Overservicing by going above and beyond client needs
• Misaligned staff and skills leading to rework
• Last-minute hires to plug project gaps 

As CTO, you can provide tools and systems to protect profit margins at every stage of the project lifecycle, from the proposal stage, to delivery and retrospectives.

What to do:

• Implement tools and systems for better project forecasting, so profit margins can be accurately built into proposals and quotes (remember to review forecast accuracy as part of project retrospectives).
• Improve project accounting abilities, so staff can monitor projected vs actual spend and schedule in real-time, and take corrective action to control costs.
• Capture utilization data – and match to capacity demand data – to give your HR team plenty of notice for timely recruitment to avoid unnecessary costs.

Challenge #10 – Shaping culture

Some IT and software firms have a reputation for long hours, crunching, bro culture, and burnout. This sort of work environment deters qualified candidates from applying and drives good people out of the company.

As the CTO, you’re perfectly positioned to shape the culture of your organization, creating people-positive, inclusive practices that boost employee engagement, retention, and productivity. 

What to do:

• ‍‍The saying is that a new brush sweeps clean, so you’re perfectly placed to challenge the status quo.
• Remember that your behaviour sets the tone for the teams below you, so model respect, accountability, psychological safety, work-life boundaries, and any other trait you want to take root in the business. 

Optimize your tech talent with Runn

Runn can’t magically fix the technical debt slowing your SDLC. But it can: 

• Help you make the very best use of the time and tech talent you have at your disposal – for higher productivity, faster development, and better client outcomes.
• Provide instant visibility into utilization, capacity, availability, and skills – for accurate resource allocations, confident capacity planning, and timely recruitment. 
• Improve project forecasting and accounting capabilities – for proposals and projects that protect profitability.

Discover how IT and custom software firms use Runn to optimize resource allocations, protect delivery margins, and plan confidently for future success.