Untangling your technology spaghetti
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The internet-era CTO: What is the role, why do you need one, and how to hire for it.
A lot of our work at Public Digital is about helping our clients understand what an internet-era CTO is, what skills and experience they should have, and how to hire one.
Why hire an internet-era CTO
Internet-era organisations need to be in control of their own technology destinies.
Everyone in a leadership position needs to have a sense of what should be easy and what should be hard. No-one should automatically switch off when technology becomes part of the conversation. But you also need strong technology leaders who can make sure the whole organisation is good at technology.
These are not just people who lead siloed functions. They understand the organisation’s purpose and direction and contribute to shaping both, but in that context they also make sure that technology can help move the organisation forward, rather than hold it back as is too often the case.
Their job is to create an environment where Internet-era ways of working are possible and sustainable, to make sure that’s done efficiently, and to make sure the organisation keeps building its technology awareness and skills. That’s particularly hard to do. They will need to manage the existing IT, keeping things running while simplifying them.
Three big things to do
It’s likely that this person will have three big things to do:
- Get everything under control.
- Create the environment to demonstrate a new way of delivering.
- Continually seek out and bring to the table new ideas and opportunities.
They will take the lead on big parts of this list, but they won’t do any of it on their own. Solving technology problems usually means changing how you build teams, what your supply chain looks like, how services are designed, and how organisations are structured.
An internet-era CTO will be able to identify what good looks like, where to start, and whose help will be needed along the way.
They’ll own their biases
Internet-era technology leaders will have a bias for internet-era technologies and ways of working. They usually have scars earned from trying to work from closed, proprietary technologies and large, inflexible systems.
Like Mark Schwartz, who was the technology leader at the US Citizenship and Immigration Service, they know that “risk is lack of agility,” and that you need to optimise for being able to change your technology quickly and effectively.
They’ll lean toward open source tools with strong communities, and do the hard work to help their organisations get comfortable with that (as Anna Shipman, now of the Financial Times, did in the UK government). They will understand the clear division of responsibilities that comes when you adopt good cloud tools. And their focus will be on users above all else, like the technical directors at the UK’s National Cyber Security Centre who often repeat their mantra that “user experience should be fantastic – security should be good enough.”
Most importantly, they’ll know that change is constant and will spend time preparing for it. That means drawing on techniques like Wardley mapping to understand how tools and techniques are moving from novelties to commodities. It also means investing in building curious, learning teams who will understand all this together, and investing in architectures that evolve as Rebecca Parsons of Thoughtworks has often discussed.
The unit of delivery is the team
A new technology leader won’t be able to do all this without help from their peers. The rest of the leadership team need to work together to create an environment where they can succeed.
That means being ready to clarify your outcomes, and work in partnership to achieve them. Even if that means re-allocating budgets to achieve results. Lack of shared outcomes, and power plays over budgets will undermine new leaders on day one.
Most new leaders come in to an overflowing pile of work to do. It can take months to find out what really needs to be done, and it’s not uncommon to never find your way out. To help a new technology leader be successful you need to be ready to prioritise, sometimes ruthlessly. Chances are your organisation has a lot to do, but you need to let this person help you find the right priorities. That may mean stopping work in progress, or even letting fires rage on out-of-control projects while you shore up the foundations, consolidate your capability and reset how you work.
Too many organisations are mired not just in old technology, but in old contracts and vendor relationships. Unless you’re willing to do the hard work to change that, this new hire won’t have any room to manoeuvre. Your whole leadership team needs to be ready to let go of any expectations around sunk costs and sweating assets, and to work together to increase your agility.
How to hire an internet-era CTO
It’s no secret that technology skills are in high demand around the world, and particularly the combination of leadership, management and technological expertise that you need in this role. You’ve also got more constraints than you might have when building other parts (this isn’t the role to use when you want to start building a culture of remote working, because a big part of it is going to be building trusting relationships).
Know what you're looking for
The exact profile of person you need will depend to an extent on the main challenges you face, but generally you’ll be looking for someone with:
- several years’ experience in creating and scaling digital services to very large numbers (that might mean millions of users, or a large and distributed workforce; they shouldn’t be phased by your scale)
- demonstrable knowledge of, and experience of working with, a range of internet-era technologies and approaches. That means they’ve run systems using public cloud services (such as AWS, Azure, etc); they know what “continuous delivery” and “devops” mean and the value they provide; and they have experience working with open source tools and communities. Ideally they’ll also have introduced them in places where they were unfamiliar, and know how to sell their benefits.
- a proven ability to recruit and lead teams of developers, architects, engineers and agile, multidisciplinary teams
- really strong communication skills, both for talking to their technical peers at conferences, but also helping their fellow leaders and colleagues across the organisation understand what’s going on
- experience of migrating data and applications from legacy, proprietary technology environments, including the resultant commercial negotiation with large tech vendors
- a solid grasp of different ways of managing commercial relationships and the ability to bring the right approach to both buying commodity services and building partnerships
That’s a lot to look for in one person (that’s why the team building part is so important). But you want people who are able to embody all of these things, and who will make smart decisions about assembling a team around them.
Equally importantly, you need to hire for aptitude and attitude. This person needs to not only capture your confidence that they can run your technology, but inspire you and teach. You need someone who can help you achieve more while also bringing people along with them on what could be a long and bumpy journey.
Know how to tell
Importantly, you’ll need people in the mix who can help you verify these skills. You’re hiring this person to fill a gap in your organisation, so it’s likely that you won’t start out equipped to assess their skills.
You’ll need a trusted advisor who can help you with that. They will probably help you refine your expectations and what you’re going to ask, and do some deeper dive sessions with the best candidates themselves.
Your advisor will can also help you spot aspects of your normal way of hiring people that might get in the way. Then help you get rid of them, or route around them. (This is something we help our clients with pretty regularly.)
Go where they are
The sort of people you’re looking for should always be looking to learn, so it’s a good idea to get out to the sorts of places where they might do that. Get your team sharing what you’ve learned so far (both what worked and what didn’t) at good conferences. Encourage them to write blog posts and contribute to online discussions.
That starts to set the expectation that you’re trying to change, that you’re keen to learn, and just raises your profile. There’s also a reasonable chance that the person you’re looking for is already speaking at, or at least attending, the same events.
The people you’re looking for will want to make an impact at pace, to keep learning, and to have a chance to reinvent things. Allow them to do all of these.
Don't forget to look inside
Before you spend a lot of time and money searching the world for the right candidate, it’s worth checking whether they’re already working for you. It’s surprising how often most organisations have good, but overlooked, candidates in-house. Seek out this hidden talent first.
Make a point of looking out for people who are quietly making things better, the people everyone else goes to when they have a problem or a question. Incentivise managers across your organisation to look out for them. Give them opportunities to take on new challenges, and find them mentors. Make sure that the people who show you work are the people who did the work. (See point 8 in Tom’s recent post about internet-era ways of working.)
It’s rare, but not unheard of, to find your next CTO that way, but it’s well worth the investment. Even if you don’t find a new CTO, you’ll uncover potential members of the new CTO’s team, people who know the organisation, have the right skills, but just need some leadership. Finding this team gives the new CTO a useful head-start, and significantly increases their chances of success.
Ways to get started
There’s a lot to do to find your internet-era CTO and set them up to be successful, and in most cases it will involve approaching things in ways that are unfamiliar (or even uncomfortable) for your organisation. It could easily be one of those “radical org change, incremental delivery change” moments. So here are a few things you can get started on right away:
- Start to tell the story of where your organisation is now, where it needs to be, and why that journey is exciting. Do this openly and in the right places. That’s the hook that’s going to attract the people you want.
- Kick-start the change this person will be part of: be visible maybe by starting to blog, unblocking a few things that frustrate without good reason, and making sure your recruitment process isn’t going to get in your way (surprisingly common).
- Get the right advisor(s): if you don’t know how to assess potential new CTOS yourself, or where you might find them, find internal advisors who are almost the right candidate, or seek help from someone outside.
Written by
James Stewart
Partner and CTO