Last time we talked about two high-­‐level skill sets schools look for in a CTO: capacity to manage change, and capacity to lead all areas of technology. Now we’ll examine components of the hiring process and where candidates fail. I call these the five pivotal P’s.
1)  Paper (aka PDF)
Technology candidates love to volunteer websites, videos, and portfolios. At the start, it’s your résumé and philosophy statement that usually matter more. Why? First, hiring managers need to quickly assess and compare applicants. Second, they often have a preconceived notion that technologists are only good with technology. The mystery is whether you can articulate coherent ideas in writing.
Present yourself in a forward-­‐thinking context. If you can’t frame your own professional experience into a written document, how will your management team expect you to draft an executive summary of a three-­‐year IT plan to the board?
In your documents don’t go overboard listing every completed project. Focus on synthesized skills and organizational leadership. Having led a technology steering committee is more relevant than your experience with LDAP, because as a CTO you’d presumably have an IT manager reporting to you.
2) Pithiness
The rambling technology candidate is a disaster. Phone conversations are especially hard because of the lack of visual cues. After two minutes it’s time to wrap up.
Remember, another stereotype is that technology professionals lack interpersonal skills.
In practice, consider the following opening question. “Tell me about what you’ve been doing, what you’re looking to do, and how it all ties to the job you’re applying for.” Translation: connect the past, present, and future, and stay at the macro level. Or try this one: “Is coding a fundamental skill?” Here, your answer should be artfully crafted to not only show an understanding of and an opinion on the issue but also leave room for alternative views. This is not easy, but that’s why most people don’t get the job. End every answer with a gymnast-­‐like dismount, inspiring your audience to ask follow-­‐up questions.
3) Presentation
A bad presentation is painful to watch yet sadly a frequent occurrence. Basic skills matter most: stay relaxed, take control of the room, and be engaging. Keep it simple. The good news is that you’re a technology professional, so use that stereotype to your advantage. Don’t artificially demonstrate prowess by creating a Prezi with violent motion effects, leaving your audience seasick.
Whether asked to or not, share your technology management framework during your presentation. What’s that, you ask? Time to develop one.
When I consult with schools, I utilize a 2×3 matrix juxtaposing three major areas of school technology (IT, systems, and instructional) against two levels of management oversight (strategy and tactics). My goal is to provide a mental model for senior management less fluent in technology. Now I have a contextual return point when addressing tough questions. Develop a framework that is authentic for you and then watch how it both engages your audience and elevates your answers—two things every CTO needs to do.
4) Politics
This one vexes so many leadership candidates, and it’s probably the number one reason some finalists keep coming up short. Technology issues in schools are often politically charged because other departments are the stakeholders, and the CTO has to navigate the waters. If the registrar wants a new SIS, how will that affect other departments? If the academic head wants a 1:1 program or maker lab, how will those initiatives be conveyed to parents? In these scenarios, the CTO is often called upon to lead public-­‐facing presentations or broker backroom compromises.
These aren’t topics that you necessarily need to proactively address. Rather, be aware that each school has its own set of political situations for which your evaluators seek a skilled navigator. Any blunders you display—be they in words, actions, mannerisms, attitude, or attire—can be your downfall.
5)  People
People — your references — are invaluable. I can find out more about an applicant’s capacity as a CTO by talking to references than by talking to that applicant. The best references are current and previous managers. Above all else, find people who are your true champions. Mediocre references are a death sentence.
In conclusion
Have patience with the process; you’re not going to improve overnight. Moreover, you can’t change your fundamental characteristics. But you if reflect hard on each failed search and make a sincere effort to address your gaps, you just might find yourself in the CTO’s office sooner than you think.
Read part 1 of Gabriel’s blog here
Gabriel Lucas is principal of Ed Tech Recruiting, an international firm helping educational organizations hire for senior technology administrators. He is a former educator and director of technology.