Dawn of a new leader - the flying CIO
Why do some technology leaders spend their entire careers in permanent roles, while others hop between temporary or consultancy posts, or even launch their own business? Computing speaks to CIOs on both side of the fence to hear the pros and cons
The Monday morning commute. All-day meetings. The grind of the corporate treadmill. These are just some of the reasons people across many industries prefer to work for themselves, rather than hold down permanent roles.
For some technology leaders, the answer is to become a sort of flying doctor, a flying CIO, if you will. You go independent, either as a consultant, an interim, or some combination of both. It's interesting though that commutes, meetings and even some element of grind can all still occur, even when you're your own boss.
So why do technology leaders elect to ditch the comfort of the regular paycheque, for the terra incognita of going it alone?
I love to solve problems, and working in this role allows me ample opportunity to do it without a lot of the day to day operations.
Why you should…
Mark Ridley spent 18 years as the most senior member of the technical team at reed.co.uk, then helped Accenture to build its new innovation centre in Dublin before taking a group CTO role at venture builder Blenheim Chalcot. Now he runs his own CTO advisory practise, focusing on bringing tech and strategy playbooks to scaleups and established businesses.
Mark Ridley
He cites several factors behind his decision to jump ship.
"I love to solve problems, and working in this role allows me ample opportunity to do it without a lot of the day to day operations (and emails) that confront a permanent CTO," Ridley tells Computing.
David Wilde, former CIO of Essex County Council, saw an opportunity to build a firm to enable him to share his expertise amongst a broader cohort of public sector organisations.
"I wanted to create a business that can support public sector organisations to a) get the basics right on good IT; b) understand what digital can do and pull it into their business plans; and c) start joining up public services around places and people (NOT institutions)."
Carl Stokes, former CIO of insurer NHBC felt that he was moving with the times by becoming a flying CIO.
"I'd been considering it for a couple of years after meeting some long standing interims and hearing how much they enjoyed it. This led me to speak to a few others, and also some thought leaders on the whole concept of the gig economy. This is the way the world of work is moving. I doubt my kids will have 9-5 jobs like I have for my career up to this point.
"A friend of mine has written a great book on this. I recommend reading The Interim Revolution by Pat Lynes. I found it, and his advice, very useful as I made the switch."
Ridley explains that he enjoys the diversity of serving multiple clients.
"For me, the largest benefit is that I get to collect stories. Moving between portfolio clients, I can get a much greater sense of what the common challenges and solutions are.
"By having a portfolio of clients, I increase my bandwidth for experimentation. This means that there's often quite high information asymmetry between me and the CTOs that I work with, as I've been able to see solutions tested in many different companies and industries first hand."
Wilde sounds a similar note.
"You can really focus in on challenges and opportunities to do high impact stuff and the variety is great. I really enjoy working with a number of clients with different ambitions, needs and challenges."
Stokes agrees with the others, but adds that permanent CIOs can often become tarred by anything which goes wrong - something an interim avoids.
"It's great fun and very rewarding. You are constantly making a difference, and I find the interpersonal dynamic is therefore different. You get thanked a lot more for example. Being a permanent CIO past a couple of years in a role you often start becoming the blame magnet, even though you've measurably improved things year on year."
I enjoy being part of an exec team tasked with leading and making a company successful.
However, many technology leaders find equal fulfilment in a permanent roles. One example is Christina Scott, who moved from being CIO of the Financial Times to the CTO post at News UK.
When asked if she has ever thought of taking temporary or consulting roles, she says no.
"I've never considered it as I've always enjoyed my permanent roles," she admits.
"I enjoy being part of an exec team tasked with leading and making a company successful. I feel in this role you get a broader view of what is happening across the whole business. You feel more invested in the long term success of a company," Scott adds.
She goes on to characterise the benefits of a permanent role.
"You get more stability (perhaps!), you're invested in the long-term, you get a deeper understanding of the business, leading a team you have often built and grown yourself."
Why you shouldn't…
Leaving a permanent post doesn't immediately transfer a CIO to a world of high fives and handshakes. Wilde goes on to cite reduced job security as one of the major drawbacks of leaving a settled position.
"It's an uncertain world! You don't have security, accountability can be grey and you don't have the convenience of position and authority to get things done. You also have to get out there and win business - it's a competitive market and you have to travel more."
You need to leave about 20-30 per cent of your time free for sales and networking
Ridley expands on this point, stating that flying CIOs effectively become their own sales department.
"I don't work as an interim - I rarely spend more than three days a week with a client, and generally for no more than six months. Many of my engagements then transition to advisory roles. This means I can't work with interim agencies and I'm responsible for my own sales pipeline.
"You need to leave about 20-30 per cent of your time free for sales and networking, and be disciplined about the process. Sales is not a natural skill for CTOs, and finding a sales mentor has been invaluable for me."
He also misses the feeling of being part of a wider team.
"You also lose that incredible sense of building a team. My team at Reed was a family and I will always miss being part of that team, and the satisfaction of seeing them grow and succeed together."
On the flip side, Scott also recognises the downsides of permanent posts.
"There can be a certain amount of bureaucracy, cultural quirks and office politics. You can find yourself stuck in roles as you are seen as purely 'technology', and if you are at the top of that discipline you might have nowhere else to go. You also get less experience in difference companies/industries, and you can't blame issues on others!"
It's all in the timing
It seems like a good option when you have done a few CIO/CTO roles and don't wish to broaden beyond tech, but would like to change
Some technology leaders will find that their minds are made up, with a firm decision to plough their own furrow. But which point in your career journey is the optimal time to break out?
For Wilde, it's when that CIO has a few successes under the belt.
"Once you've done a few CIO gigs well and you want to focus more on transformation and innovation whilst enjoying some more variety, then it's probably time!"
Scott adds that a consulting role can start to look appealing when you simply want a change.
"It seems like a good option when you have done a few CIO/CTO roles and don't wish to broaden beyond tech, but would like to change."
Stokes adds that it's not just about having had some successes, the failures count too - referring to them as ‘stripes and scars'.
"You need the stripes and the scars. As an interim you need to make a mark quickly. You need to assess situations and make recommendations and improvements in a matter of days. You have a 10 day plan, not 100. To do that well you need experience. I don't think it's enough to be smart, you need both."
Ridley refers back to the need to sell.
"Sometimes it will never be the right switch. It's not all rosy working in a portfolio role. While you are rarely responsible for 24x7 support, security incidents or data protection, you do have to manage your own sales pipeline. It's a completely different job, not a change of company."
If you had your time over…
I love what I do, and it suits my curiosity and preference for new and transformational challenges
Perhaps the acid test for whether the move has worked for these three technology leaders is to ask if they would follow the same path if they had their time again. And on this point, they are unequivocal.
Both Wilde and Stokes answered with a definitive ‘yes', with the former only wishing he'd made the switch a year earlier, growing to two years for Stokes.
Ridley however feels that he jumped at the right time, warning that you can't go into this world half-baked.
"Absolutely. I love what I do, and it suits my curiosity and preference for new and transformational challenges.
"However, I needed to learn a lot from my time in 'real' jobs to be ready for this role. It's not something you want to blag, as people rely on you for good advice."
And being happy with their decisions means that they'd be extremely unlikely to take another full-time position, though they didn't all rule that possibility out.
"It would have to be something really exceptional, and I now have responsibility for the people who work for us," says Wilde. "I certainly don't feel the need to go back to being an employee (although I do miss paid leave!)"
Ridley agrees with the idea of only returning for something exceptional.
"I'd take a permanent position, but it would have to be a very special role. I love what I do, and I love working with the clients that I have. I see myself as building my own consulting business and leaving a legacy of the playbooks I've spent years creating. It feels like this is how I can be the most useful in my career.
"However, working in sales teaches you never to squander an opportunity, so I'll always take the call and hear out the offer."
Stokes however rules the possibility out, at least for now.
"Never say never - but as things stand I much prefer interim. Most interims I know would say the same."
What's most striking is that all three technology leaders to have left permanent roles remain very positive about the decision, despite having made it at different times over the last three years. Whilst there are benefits and drawbacks, the former seem to significantly outweigh the latter in all cases.
But that doesn't mean that it's right for every CIO. Some people will struggle with a less structured role with a looser career path, some will baulk at the loss of the monthly paycheque, and others will run a mile at the thought of selling.
Technology leadership is a diverse field with a variety of options to suit every aspiration and personality type, whether within an organisation or without.
For everything CIO-related check out our IT Leaders Festival, held at The Brewery in Central London on October 21st. Early bird discounts are live now.
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Stuart Sumner
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