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Why do good CTOs fail?

Author: Jon Holt

Why Do Good Ctos Fail?
  • Service Technology and engineering
  • Date 10 November 2021

The Chief Technology Officer is one of the most sought after roles in business. But are CTOs really set up for success in organisations today?

TPXimpact CTO, Stuart Arthur, and I thought it might be worth looking at the forces that play upon leaders in our industry — and why even the best and the bravest can be brought down before their time.

At an average tenure of under four years, the CTO role is typically short lived compared to other senior management roles. Whilst the job has grown in status — as the perception of technology has moved from cost centre to value add — it is often a thankless and lonely position.

But why is that? Why do good CTOs either fail outright, or get driven to disillusionment and early departure?

This list is not definitive, but these are the common factors our CTO clients, colleagues and friends call out as harmful or dispiriting.

1) The perpetual apprehensiveness

A CTO wakes daily to the tyranny of expectation: what has gone wrong overnight? A dashboard in red is no way to start the day.

Our tips:

  • Delegate responsibility to teams, empower your leaders and protect your free time
  • Only be ‘always on’ at key times in the year, and be strict about this

2) The relentless pace of change in the technology market

Even the smartest leaders — running teams of dynamic, gifted people — cannot possibly keep up with the progress of technology available to them.

Our tips:

  • Give each team member an area of the market to cover - and ensure they have two hours a week dedicated to learning and listening

  • Insist that insights are summarised for you in bite-size chunks, with potential relevance to the organisation clearly laid out

3) The 2% fallacy

Too many CEOs and CFOs are still working off a playbook that suggests ‘technology’ should cost a single digit percentage of turnover. But even the least digital sectors should now be spending way more (and expecting great returns).

Our tips:

  • Benchmark your spending against peers, and argue your place in the top quartile - with business arguments

  • Master the two page business case, and learn the language triggers of your board (competitiveness, efficiency, innovation, etc) that will help you make your case

4) Multi-year ‘transformation programmes’

When something difficult is perceived as essential for a business (centralising data, swapping ERP, digitising sales channels, etc) - too often an epic mission is planned.

These programmes tend to (a) take so long that the leaders who set them up have left the business; (b) cost more than they yield; and (c) fail, with the CTO left picking up the pieces or getting the blame when things go wrong.

Our tips:

  • Avoid seismic programmes at all costs, sticking instead to long term goals and agile practices

  • If a programme is inevitable, break it into chunks - accounting for periodic changes in leadership so that the work doesn’t outlast the tenure of the people running it

5) Technically illiterate boards

Too often a lonely CTO is flanked by good, but non technical people on the management team who just don’t get it.

Technology is now integral to strategy, and the happiest CTOs tend to be the ones whose board colleagues are excited enough — and educated enough - to lead and support.

Our tips:

  • Argue hard for technology being a top five business priority, with benchmarked data - especially from competitor companies leading your sector

  • Insist that at least one person on the board covers your brief, and understands it. This will be enough to ensure you can join the debate at board meetings — rather than just providing token updates to bemused silence

6) One foot in the past

Ambitious CTOs forging ahead to digitalise their companies also have to oversee security, data management, email, and phone systems… These might be more dull elements of the job, but they are intrinsic to all organisations.

However, we commonly see technology reporting in to operations. This can spell trouble for CTOs when the business still sees their role as only about the basics. (And too many CEOs still treat their CTOs as a personal IT support resource!)

Our tips:

  • Argue for technology to report in to the CEO or CFO; it’s a more relevant fit

  • Speak to the board in terms of value creation, not service delivery, wherever possible

  • Appoint a member of your team to be the leaders’ emergency problem solvers and password-resetters - and hang up if the CEO phones to say their Bluetooth mouse needs new batteries...

7) The noise from suppliers

Anybody who puts the title CTO in their LinkedIn profile becomes devastatingly attractive overnight. The phone rings, the invites to Las Vegas arrive, and the diary clogs up. Our technology services market is mature and well served; big accounts attract a feeding frenzy.

Our tips:

  • Be nice, be firm — and be impossible to reach only if a hint isn’t taken

  • Set aside a week per quarter for market engagement, where you will talk to and meet suppliers outside your roster that may have something interesting to offer. Make these dates known to suppliers who have caught your interest

8) ‘Air traffic control syndrome’

Unfortunately, this is self explanatory — a CTO is blamed when things go wrong, and invisible when things go right. But people always need recognition for good work.

Our tips:

  • Work in the open; show off your success via internal comms

  • When something interesting is happening, invite people in for ‘show and tells,’ and follow up with them when they express interest

9) Loss of authority

Whilst the CTO role has rightly risen to the top table in many large organisations, control has also been devolved to some extent. Often business units want to be left to make decisions in online services, and run the environments themselves.

This can lead to a tense stand-off in balancing the need for central controls with the business’s desire to innovate at pace.

Our tips:

  • Set central standards, explained in plain English - but allow business units to select and procure if the standards are maintained. [Perhaps ironically, the government’s Service Standard is an excellent starting point for this]

  • Establish warm peer relations with business units intent on going it alone in digital: you need each other on side

10) Mission uncertainty

Does your organisation know what it wants to become?

Ambitious CTOs can select which services they home-grow, and which they buy in from specialist suppliers. There is no right and wrong, but arguably there is too much pressure on CTOs to turn the organisation (regardless of the sector) into a ‘technology company’ regardless of whether or not that is strategic or sensible.

Our tips:

  • Understand how important technology is to the business, and pick a suitable path

  • Always consider the global marketplace: you might want your software team close to you - but that will cost you a premium if your HQ is in an expensive place

  • Your team cannot excel at everything you need, nor scale to it; so be intelligent customers first, and stick to resourcing only appropriate disciplines in-house

Today's technology leadership

That concludes our list of 10 things that can negatively affect the performance, effectiveness, and wellbeing of CTOs today.

The role of the Chief Technology Officer is challenging but is only set to grow in status as more organisations recognise the importance of technology. It's not always easy, but with the right team around them, and consistent backing from the business, CTOs can achieve incredible things.


Jon Holt's avatar

Jon Holt

MD Cloud & Data


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