Can you launch initiatives not involved with the IT infrastructure?
What is the role of the CIO/CTO in setting the organization’s agenda?
What’s the level of trust you have with the leaders of the other major functional areas in your office?
How do you balance “fixing the printer” with setting strategic direction?
Do you think of yourself as someone in a customer service job?
How have practices changed within the last 10 years, given the ubiquitous impact of ICT?
What mechanisms do you have in place to listen to people who are not at the management table?
What’s the “right” organizational structure? Why does this matter?
If you had to get your job done with half the head count you have right now, how would you do it? Why not just combine with other NGOs and/or outsource everything?
<ul><li>What is the appropriate role for a CIO? </li></ul><ul><ul><li>Manage the Website </li></ul></ul><ul><ul><li>Manage the Internal technology </li></ul></ul><ul><ul><li>Fix the printers </li></ul></ul><ul><ul><li>Archives and Records Management </li></ul></ul>
Do you (and does technology) play a role in establishing and sustaining strategic relationships with other organizations?
What should drive change – new tools or new needs?
What does a really effective future technology leader looks like? How would you guess which 25 year old at this conference is going to be leading well in the year 2020?
How do you keep grounded – in touch with the user needs?
Tell me why we shouldn’t just make the trains (email, web, voice, video, etc…) run on time? Isn’t the ultimate success be for us to fade into the background so program and communications people can put the technology to work?
What is the appropriate capacity for internal systems development?
Do you spend enough time educating your customers about technology? Who’s responsible for making sure they know?
How do you get out of the tactical morass and into the strategic discussion?
Do you think knowledge management is going to mean anything to non-profits as a distinct, self-sustaining component?
When (if ever) will all these fancy collaboration tools take root and change how we work?
How far out in front of the rest of the organization do you have your research and development efforts? Do you see any value in stealthy, skunkworks projects?
How do we keep up with the pace of change? How do we pick the right path / direction / platform / tool
Will technology ever have any financial significance in your organization beyond the expense line? How accountable are you for ROI, cost recovery, cost reduction?