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

I think the key is to join initiatives as soon as they emerge, define their scope from within, and lead them to deliver realistic and reasonable results. We shouldn't just receive requests, but we should also bring together the executive team that will sponsor the project. It's true that vendors often tend to propose a vision in sales meetings that isn't necessarily realistic given each company's digital maturity. However, since we're the ones most in touch with trends, we must always be vigilant, not taking control, but serving as subject matter experts. Instead of saying "No, this isn't possible," we should start a conversation in a positive way like "Yes, that could work, and we also need to consider what other projects we can put on hold," or "Yes, we could achieve something close to what you mention, and we also need to consider that we'll need people, time, and additional budget to achieve what we want." This way, we can regulate expectations while also allowing ourselves to lead and discover what we're capable of.

There are exceptions to everything, but I believe that orchestrating joint work with the C Suite on initiatives is equally, if not more, important than deploying them. 

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.

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