Look Before You Leap – CTO look fors in a new job

(Many thanks to my editorial board on this post)

It’s the understatement of the decade to say there’s a lot going on with ed tech in K-12 education. In our BYOD, 1:1, blended learning world, CTOs who are looking to move on to a new role have a lot to weigh: the organization’s propensity for change…support structure…people power – IT and instructional support…does the people power know what they’re doing…past/recent success…past/recent failures…infrastructure…administrative structure…is this place’s infrastructure messed up and if it is am I willing to deal with it?

With the exception of one friend, I have yet to talk to someone who has took on a challenge in a new district and said – “boy this place has it all put together!”

The discoveries of new CTOs is more that like this:

“wait…we’re going one-to-one and there isn’t an access point in every room and the controllers are worthless. And we have no reliable SSID for BYOD kids”


“There isn’t a single system in this district that integrates with another.”


“I’m so sick of people complaining about the wireless, I just want to rip the !@#% out and start over!”


“We have two email systems” (a non CTO friend was telling me that she was spending her night cleaning out messages from her THREE school emails accounts)


“We have a $2 million dollar a year technology budget” but that includes all salaries, telephones, printers, SIS, HR and payroll systems, security systems and everything else that plugs in.


Your office is a converted janitorial closet in a windowless basement. It smells funny.

Is it possible to figure out what is under the hood before saying Yes to the Dress? I would venture a guess that it’s 100% impossible for you to find all the issues large and small before you commit. What one needs is to be observant and to ask good questions. That’s all you really have, unless you have an inside mole in the district to let you know what’s going on.


Where are their priorities? Are they talking a lot about technology or about how they’ll be using technology.

Beware of server rooms that look too tidy. Look closer…those color coded cables might be disguising something.

Listen to how people talk about technology. Any good CTO knows when someone is full of it.

Ask good questions:

Ask how students are using technology to drive their learning.

Ask if the teaching and learning plan are integrated with the technology plan.

My old standard is “what do you want out of a CTO?”

What are your organizations goals?

What kind of service are you all getting from the technology department?

Ask for average ticket open times on help desk requests. Ask for average first response times.

Ask for greatest technology dept strengths. Areas of improvement.

Ask how technology staff are alerted to failing switches, overtaxed servers, issues with connection to the internet.

Ask how staff members monitor the network.

Ask for an org chart.

Ask for detailed budget.

Ask for data/tech security manual.

Ask for tech plan

Ask for record of network outages and downtime

Ask for network diagram

Ask about replacement schedules

Ask to see your office

No one is going to catch everything, but gathering as much intel as possible before making the call is in your’s, and the prospective new organization’s favor. No one wants a bad fit, either way, and good decisions are made with good information. Take the time to give your own vetting process due diligence. Look before you leap!