At the risk of letting you all guess how old I actually am (somewhere between 27 and 108), I will tell you that I have been advising CIOs on their careers for more than 20 years and recruiting them into their roles for 15.\n\nWith all of that CIO executive search experience, along with two decades of writing for CIO.com and CIO magazine (remember print?), I must have interviewed thousands of CIOs. Along the way, I have learned to differentiate the operational CIOs from the strategic, the project managers from the team leaders, and the isolationists from the collaborators. I have learned to ask the right questions to elicit what I really want to know and then turn around to Heller Search clients and advise them on which CIO to hire.\n\nWhile for every CIO search my team and I conduct, we have specialized attributes we are after (experience working for a private equity portfolio company, for example, or a track record of optimizing the supply chain), we are always in hot pursuit of one general set of skills.\n\nWhat are the skills that every company needs in its CIO? How does an experienced CIO recruiter assess those skills during candidate interviews? For answers to those questions, read on.\n\nTransformation\u201cTell me about a transformation you\u2019ve led.\u201d When a candidate answers with a successful CRM implementation, I think, \u201cThat\u2019s not transformation, that\u2019s technology implementation.\u201d Consider the fact that digital technologies are changing customer behavior and disrupting businesses far faster than a company\u2019s ability to change culture, processes, and behaviors. If today\u2019s companies don\u2019t transform, they will die. Yes, technology implementation is important (and we\u2019ll get to that later, I promise), but the kind of transformation that I\u2019m looking for is a strategic change to the IT environment \u2014 and the company\u2019s culture \u2014 that creates end-to-end processes out of legacy silos, establishes a data-driven mindset, or puts the customer at the center of business operations.\n\nBusiness acumenWhen I walk through a CIO candidate\u2019s background, I will ask an open-ended question like, \u201cWhat was happening at your current company when you joined?\u201d When the candidate responds with horror stories about outages and legacy technologies, I know I cannot check the business acumen requirement off the list just yet. But when a candidate tells me about shifts in customer behavior, slowing sales, or new product lines, I am more optimistic. Yes, I will probe into how the candidate improved the technology environment, but I am looking for an initial response that is close to how a CEO would answer the same question.\n\nTeam developmentDid you improve delivery in your last CIO position? Of course, you did! That\u2019s the price of entry. What I am after under \u201cteam development\u201d is cultural change. Did you shift from a project to a product management culture? Did you focus your team on business outcomes rather than delivery deadlines? In a world where software and data are more central to your business operations than ever, building a solid team is not enough. \n\nStrategic thinkingWhen I interview for strategic thinking, I expect to hear a great strategy about new revenue or improved performance or decreased costs, but that\u2019s just half the story. How did the candidate articulate the vision, business outcomes, end state, and all of the operational changes that have to happen to get from here to there? We can all come up with great strategies. Ideas are cheap! The real work is getting that idea all the way from your brain and into production.\n\nProject executionWhen CIOs that my firm is replacing were asked to leave the job, our clients typically tell us of projects that were \u201con fire.\u201d So, \u201cCan you tell me about a failing project that you turned around?\u201d is something I tend to ask in an interview. Every CIO I have ever met has a great answer, whether it\u2019s landing an SAP implementation plane that has been in flight for three years or resuscitating an e-commerce platform that went down just before the holidays. Again: price of entry. Once you put out the proverbial fire, did you improve the project management capabilities of your team? Did you change incentives to ensure continual business benefit from completed projects? The real question is, \u201cWhat changes did you make to ensure that failing projects are a thing of the past?\u201d\n\nTransparencyTransparency does not mean having an open-door policy or inviting all of your business partners to your project update meetings. Transparency is a collaborative process whereby you turn your user community from IT consumers into co-investors. It\u2019s creating an investment management culture that drives more decisions to the part of the business where the return on those investments is actually realized.\n\nBusiness partnershipYou attend every marketing meeting, and on Tuesdays you grab lunch with the CHRO. But what does partnership look like a level below you? And a level below that? The strongest answers to the business partnership question describe an IT organizational re-design that balances enterprise services with leaders dedicated to a business unit or function, and a CIO who pre-sells the new structure to ensure the success of those new relationships, rather than letting the org chart do all the work.\n\nCommunicationShould my team or I interview you about a CIO opportunity, please don\u2019t tell us about your newsletter. As the proud author of The Heller Report, I am a big fan of newsletters, but I know they cannot carry the weight of a CIO\u2019s communication goals. What frameworks have you employed to educate the executive committee on the true cost of legacy technologies and the value of increased investment? How are you ensuring a tight feedback loop from your business partners back to IT? How are you \u2014 in collaboration with your colleagues \u2014 driving digital literacy throughout your company?\n\nDataHow can four little letters define the future of our world? For such a short word, data is the new currency of our businesses. While I definitely want to know about your data lake and AI engine, what our clients need is a leader who, yes, can implement the tools, but can also can work with his or her business partners to change behaviors to create a data-driven business.\n\nTechnical depthWhen our client is satisfied that our CIO candidate is an experienced and talented leader who builds teams, creates partnerships, and drives transformation, they will ask, \u201cBut is he technical?\u201d What is technical depth to a CIO? For a small company with a small team, it might mean leading custom development and acting as project lead on a cloud migration; for a F500 company it might mean understanding the advantages of one architecture over another and knowing how to hire the right CTO. But it always means the ability to dive deep on technology when you need to and having an acute knowledge of the provider marketplace.\n\nInformation securityOur clients do not expect their CIOs to be technical experts in network security, but they do expect them to hire the right CISO, someone who can talk to the board about risk profile and security investments that will not cause a coronary event. The language of the board is the language of finance, so whether or not the CIO wears the CISO hat, as many do, I am interested in clear articulation of security investments.\n\nVendor managementIn the old days (which were not that long ago), vendor management was all about contract negotiation, ensuring SLAs, and driving costs down. Those activities still matter a lot, but consider this: in the past year, my team and I have had a number of clients tell us that their business model is evolving to the point where they can no longer rely on their traditional vendors for their technology roadmap. These companies need their CIOs to make smart bets on new vendors that provide a niche solution for the business they are becoming. Vendor management involves a venture capitalist\u2019s eye on the emerging technology market. \n\n* * * * *\n\nThe CIO skillset is rich and varied, and I'm bound to have missed something. Are there skills you rely on in your own CIO role that you believe belong on the list? Please tell me, dear reader, what are the three skills you rely on most in your CIO job?\n\nChime in! For 20 years I have relied on you to contribute to the knowledge base that I am building about your role. Let me know your thoughts: firstname.lastname@example.org.\n\nAnd as always, thank you for reading!