What’s your strategy for managing up – especially when your CEO or executive peers have unrealistic expectations of what IT can deliver?

Usually a CEO will bring to the table initiatives that he has read in a trendy article. Many times those initiatives they might seem powerful, only in environments that are different from ours actually.

So, I gather data and capabilities our team has to do in a mini-training about that initiative. Maybe with a paid course we can deliver, maybe we can’t. But at least my CEO will understand our constraints about it.

Maybe, we will have to spend $ to deliver that initiative. It’s up to us as a team to understand the scope and constraints of that initiative.

I am a enthusiastic fan of creating some sort of reoccurring Steering Committee type of venue where IT leaders share with CEO and executive peers 1.  "what have you done for us lately', 2.  'what are we working on right now' and discuss 3.  'what would you like us to work on next'?  I think it is important to acknowledge that CEO and leadership team will 'never appreciate what they cannot understand' - so being transparent frequently about the #1 thru # 3 above is vital.  And then yes to what others have replied, provide CEO and executive peers with a 'card sort' exercise to determine what they want done with the resources you presently have and then formally ask if they want to exercise the option for more $$$ to pay to get more resources to get more work/cards done.

Generally, I follow the practices outlined in Gartner research on shifting from Defense to Offense. One of the specific items relates to managing unrealistic expectations. It uses the following template for messaging:

"You have indicated that you want A, B, C. We currently have capacity and capabilities to do B, because we are also doing X,Y,Z. With additional funding, and time to recruit resources, we can meet your expectations. Alternatively, we can pause, defer or cancel X,Y, or Z."

Works like a charm. You don't have to say no (and be seen as resistant), and it puts accountability on leadership to resource the initiative appropriately and prioritize.

Demo's of live and POC use cases helps Senior Management realize the value and potential.

Bring data to the discussion.  The act of gathering the data will give you more confidence in your position- assuming it actually supports your position.  You may find that they're right.

It also gives you a common starting point for discussion.  Ideally, you can shift their "expectation" into an "ask".  Once it's an ask, you can find a way to calculate the investment required to eventually deliver their expectations.  

Once they agree it needs financing, they're suddenly helping you to solve their problem and complicit in the outcome.  They may also decide it's suddenly not so important.