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A few days ago, I sent out an email to my friends, all brilliant CTOs, hoping for their distilled wisdom to a question that I thought amazingly valuable:

What are THE top 5 or 10 questions you would ask a candidate and/or know answer to in a CTO job interview?

My hope was that I could update my CTOWannabe Interview Questions. Here are 10 of my favorites from that list:

  1. What is it that you monitor or assess to determine your effectiveness in the organization?
  2. What are your top 3 priorities for what you must do well in the first 100 days of this position to be an effective leader?
  3. Please describe an issue in the past 12 months that has tested your ethical being?
  4. Describe yourself in the context of being a reflective leader.
  5. Describe how you see “technology” in the broader context of the school’s core mission of teaching and learning
  6. What accomplishments are you most proud of and why?
  7. How do you stay current with technology issues, apps, innovations? How do you stay current with educational research, reforms, etc.?
  8. How would you direct/handle/deploy a new district wide initiative?
  9. Discuss how frequently and how comfortable you would be asking, “How can I help? What can I do?”
  10. How do you balance providing the electronic resources needed for the classroom environment while securing the network and related technology that you are responsible for?

Unfortunately, in response to my query, my friends and colleagues, jokingly gave me more wisdom than I was prepared to handle.  Given those questions, I’ve decided to try to respond to them seriously, even though they may have intended them as a joke.  While I did get some serious questions, like the ones below, I decided to take a shot at the zany ones featured in this blog entry. For now, here are the sane questions contributed by Nathan Mielke (@ndmielke):

  • Have you built a career pitching a product/platform or have you worked to build systems that support learning? If you pitch a product/platform, why?
  • Have you been to Mountain View or Cupertino? If so, how many times and what did you learn/share with others?
  • Were you a business ed teacher? If so, are you over “kids need to know how to use Word to work in a business?”
  • Can you spell TCP/IP?

What would your responses be to these zany questions–contributors include Doug “Blue Skunk” Johnson (MN) and Mark Gabehart (TX)–below?

1) Are you a masochist?
“Did you know that he installed video cameras in the ceiling above the women’s restroom stalls?” gossiped a secretary. I had just arrived in the school district to facilitate a workshop and this was her way of introducing me to the school district. Of course, she was referring to the technology director, for who else had the knowledge to setup video cameras?

The word “masochist” is one I’ve carefully avoided researching for the simple reason that it appeared to have sexual overtones, and as such, not worth investigating since I am an educator. Since my esteemed colleague suggested this question, I am, with some trepidation, looking up the word:

enjoyment of pain : pleasure that someone gets from being abused or hurt; especially : sexual enjoyment from being hurt or punished

But it is an important bit of wisdom to consider. Obviously, human beings shouldn’t–and an educator cannot, and it’s against the law!–derive any pleasure from others being abused or hurt, or how “sex” might play out in school setting. Consider the cautionary tale of the CTO who would gently caress the back of a female staff member while meeting with her. Sexual harassment NEVER is acceptable. These situations play out in the news every few months, unfortunately.

Of course, this question would never be asked during a CTO job interview. But there are valuable lessons here that any CTO would be wise to heed.

  • Are you willing to endure the pain of leadership to get things done? There can be emotional pain and turmoil resulting from being a leader or being in a management position. I do not believe that leadership is possible without the kind of self-reflection that leads to growth…as one colleague put it, “Remember, you signed up for this!” Still, that can be cold comfort in the midst. That’s why it’s important to reach out to others, build a PLN of leaders. 
  • “No pain, no gain” is a reminder I take to heart when exercising. Pain signals that growth is occurring (or that you’re doing things wrong). Figuring out which is a reflective process that must involve those pesky 360 degree surveys, or at least, the ability to ask others, “Am I nuts or what?”

Masochism for the CTO is learning to step into painful situations, have tough conversations and confrontations, even when you know it will be painful. It means working hard to NOT be pain-averse because, as anyone in a leadership position knows, our first instinct is to back away from pain.


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) Can you turn water into wine and sows’ ears into silk purses?
“We just need you to setup the district’s network, run our phone system, and show everyone how to use technology in the classroom?” There is no doubt that CTOs are expected to be miracle-workers.  But what happens when you can’t afford to pay for miracle-workers, and instead have to make do?

“Home-grown” techs often make great additions to a tech team. I still remember the fondness that two fellow technology directors had for high school students that had grown up “techie” and decided to stay in the school district, either with a degree or not.

“Sow’s ears” clearly doesn’t refer to these folks, but rather, individuals that can be found in any organization who must be helped to work together. I take a particular delight in recent events with the Security Service, the new director being excoriated because he needed to change the culture now…his approach was to build trust and strong relationships with people that now Congress wants to terminate:

“Dude, you don’t have to earn their trust. You’re their boss. They’re supposed to earn your trust,” Rep. Chris Stewart, R-Utah, told Director Joseph Clancy.
Stewart was responding to Clancy — trying to explain why the Secret Service has been caught up in a series of controversies and security incidents — saying it will “take time” to change the culture and he, as director, needs to “build trust” with the workforce. 

Source: FoxNews 3/17/2015 

The phrase, “Turn sows’ ears into silk purses” is particularly relevant for CTOs in small districts where they must depend on staff that lack the professional certifications and/or degrees required in larger organizations. This means finding ways to setup learning situations for staff who may not typically rely on “conventional” learning opportunities, such as university studies. It may mean finding self-paced, just-in-time training opportunities…as well as expensive training that is wholly relevant–which is key for these adult learners who provide service–to to their work.

Sow’s ears into silk purses goes to the heart of being a transformational leader. And, unlike what we might imagine from watching fairy tale movies, it doesn’t happen in an hour or with a thunderclap. Rather, it is a slow, plodding process that empower people to move ahead one deliberate step at a time. That takes time. Unless you’re Miracle Max, you have to nurture those around you.

3) Can you provide tech support to your spouse without losing your patience?
“Honey,” my wife woke me up at 5:00am, 30 minutes ahead of my alarm clock. “Can you help me print this out? I can’t get it to work!” Boy, was I hot about that awakening. I had stayed up a little later past my bedtime, while my wife dropped off to sleep a little earlier. Why couldn’t she have asked me for help the night before? I would have pointed this out to her, but it wouldn’t necessarily have done any good–we’ve had the same situation happen throughout our marriage. She’s a morning person, while I’m a night owl. If I had lost my temper, what would it have gained at that moment? I resolved to have a crucial conversation at a time that we were both awake and on equal footing.

Crucial conversations are important, but trying to have them when offering just-in-time, much needed support is a waste of time. The person whom you are trying to have a conversation with doesn’t want to listen to why now isn’t a good time, and you have to ask yourself what you really want–to be perceived as the person who gets the job done in a time of need, or the person who is going to complain about it while doing it and get people mad at you?

Not surprisingly, I had a situation like this come up recently and I had to deal with it. One set of expectations had been communicated and agreed upon, but somehow, the project was now dependent on me getting things done quickly. I could dig in my heels and complain, or just get the work done, then have the crucial confrontation–since I was disappointed that the expectations had changed or not been met by the other party. Fortunately, the confrontation went well.

It’s too easy to lose one’s patience. Instead, I ask myself, What do I really want? and when it comes to technology work, it is the good of the organization that trumps all.

4) Mac or PC?
Mac or PC, the age-old debate of which device is the one-size-fits-all. Some of the reasons why folks often pick the PC include:

  • Easy to maintain, reimage and support
  • Easy to update and manage remotely using solutions like SCCM, PDQ Deploy, “FOG,” Clonezilla and others.
  • Compatibility with Windows world, especially MS Office Suite, Visio, etc.
The Mac is often selected because it’s “ease-of-use” reputation, integrated video/audio and operating system. “Apple does it’s own thing,” I’ve heard it said (and said it myself), while PC can be managed easily and cost is lower.
Of course, you can make similar arguments between iPads and Chromebooks and Android devices. And, for fun, I have. The truth is we are no longer stuck with one-size-fits-all tools. Let’s enjoy the argument, but focus on the needs we are trying to serve.
Another important point is standardization. Should you standardize technology across a school district? I’ve often pointed out that you standardize some things (e.g. computer labs, library computers, laptop carts) to ensure equity and ease of support across the District in support of learning goals. However, you must also find a way to allow diversity and individuality. This point of view has been argued against quite frequently by my colleagues.
They argue for standardized technology in every classroom, from ceiling-mounted digital projectors or wall-mounted television screens, the type of operating system on computers/laptops/tablets. The ultimate in this was one district’s effort to run Windows OS on iPads they issued to every student and staff member, including custodians. Wow.
The problem with standardization is that a lot of people aren’t going to like what you pick. That’s why there has to be a committee of stakeholders, a group of people who are going to come together to make that decision…and, own it. Each community, each school district, will have a different take on it and the decision should reflect that. The importance of this can’t be under-stated–you can’t make that call as a technology director and expect things not to explode in your face.

5) What is your most embarrassing Facebook photo?
“I recommend you block everyone you work with so they can’t read or see what you’re doing,” shared a colleague a few years ago. I found myself disagreeing. In truth, you don’t want to put anything out ANYWHERE that couldn’t be shown on the evening news.

So, if by embarrassing Facebook photo, we’re referring to a picture that shows one in a situation where you’re drinking a margarita with a sombrero, you better not be doing so wearing the school district t-shirt featuring the District’s logo or mascot.

and, a bonus question,

6) Do eat Thai food?
“Let’s go out to lunch,” said one boss I worked with. He had a craving for Thai food and I learned that from him. I was a bit reluctant to go out to eat with my boss at the time; he was a workaholic and I knew lunch would be about work. And, I had this new book I wanted to read during lunch.

Believe it or not, I had never had Thai food until that day and I can’t imagine what would have happened if I wasn’t “open to new experiences.” As a CTO, you have to be open to new experiences that will change your perspective…and, perhaps more importantly, you have to find ways to create–or facilitate the joint creation–of experiences for those you work with.

There are many real questions that could be asked when interviewing for a CTO position. I’ve run into some pretty inventive ones, but I will have to share those at a future date. For now, I’m happy to say that I’m surprised at how insightful my friend’s questions were, even though I doubt I would ever encounter them in an interview panel’s list!

Everything posted on Miguel Guhlin’s blogs/wikis are his personal opinion and do not necessarily represent the views of his employer(s) or its clients. Read Full Disclosure