How to hire an internet-era CTO

(This is part 2 of a series. If you haven’t seen it already, start with part 1: Why hire an Internet-era CTO?)

There’s a pretty important step between recognising your need for an internet-era CTO and reaping the benefits: finding and hiring that person.

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.

Steps 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:
  1. 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.
  2. 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).
  3. 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.
In the next post in this series, I’ll be trying to answer the question: What does it mean to be good at technology?

1 thought on How to hire an internet-era CTO

  1. Why hire an internet-era CTO? What will they actually do? – Public DigitalOctober 19, 2018

    […] Read the next post in this series: How to hire an internet-era CTO. […]

Public Digital