How do you help the CEO get comfortable with the company IT spend? What do you do different when larger items need to be discussed and funded?
For the last 13 years of my IT career, this has always been a matter of contention. I was a Systems admin before a Director. I can attest to what worked for me.
While some IT spends were easy to justify (Anti-Virus, printers, hardware,etc) because they are part of the normal business requirements, expenses that are new or outside the scope of a CEOs knowledge were harder to quantify. Every systems administrator remembers explaining the need for virtual infrastructure the first time. They knew the value, but struggle to explain it without getting technical.
Personally, I give these types of expenses a larger lead time. Have staff do an ROI on requests. This is just good for them to see teh business side. Examples are hardware or software with additional functionality. Like network copiers vs laserjet printers. Or things to improve process like a CRM solution. I feel the only way my can speak the truth to value on these propositions is to understand the business and its internal processes. Be sure they can explain how this can make employees work better. If they don't know how staff operates on given day, its hard to explain how the addition of a tool will make them more efficient.
Allow them to take opportunities when presented. If I ask how "security" is in their environment, the knee jerk reaction is to say 100%. Allow them to be honest. They should be able to say that while you are comfortable with your current operations, additional measures could be taken to provide more.
Go easy deploying technology. Don't sign off on 3K ultralight laptops for mid level managers because someone "wanted" one. IT has a responsibilities to rein in users before the proposal gets to the top. If your an SMB and you decide to deploy the kind of hardware to make a Fortune 500 green with envy. That may come back to haunt you because you have set a precedence. I have seen companies sign off on outlandish expenses because someone told them they needed it. Trust gets lost, IT departments go crazy with expenses. Again they should be able to explain the real value of stuff.
Help build a budget. I would want to see where the dollars are going and they should be able to sit down, review it and explain what everything is.
I find it important to always be communicating the possibilities. Not all at once and not necessarily always in a formal presentation. If there is a significant spend on the horizon and you can make some small talk about it with the CEO well before the actual ask, he/she will be much more informed and and likely will have provided what insights would be helpful. So I recommend changing the game by starting with informal dialogue in advance, nurturing topics that will need a little extra care. I have found that doing this usually finds the CEO helping to champion those items when formally presenting to the full exec team.
Some great feedback from members on this topic. A common theme rises on the importance of having a define technology strategy along with a consistent message to Executives. Others are quick to point to the value of story telling. Who doesn’t like a good story and the lessons from it? As I reflect on my career, I can recall those senior leaders who where really good at this practice. And they most often were the more respected and admired leaders in the company.