Imagine there is a critical client meeting in Las Vegas. You plan to attend and think it would be important for your IT leader, Ted to join. You’re excited to use the opportunity to take a cross-country roadtrip and you ask Ted to drive. On day 2, a number of hours into the trip, you notice signs for Oklahoma City and wonder how that path will end up in Las Vegas in time for the meeting tomorrow. After driving through the night, you wake up in Denver and miss the meeting. You ask Ted what he was thinking, and he says “Oh, I decided to take a much more scenic route, I thought you would be excited to see the mountains.”

Do you think you would ever let Ted drive again? 

Delivery is not about the journey, it’s about the destination - the Key Initiatives that will ultimately build real value for the business. 

IT Leaders sometimes get so wrapped up in the Delivery journey - the tools, methodologies, and cool new technologies, that they can lose sight of the real business destination. And business leaders sometimes assume that their destination is clear. When you wondered about going to Oklahoma City, why didn’t you say something? Both parties need to work together to ensure predictable delivery on the initiatives that matter most.  Business leaders should invite IT leaders into the planning conversations, and IT leaders need to learn all they can about the business goals and objectives. Ideally, the IT leader is a part of the core leadership team and can contribute to the strategic planning conversations directly.  This will ensure that both parties get to the right destination on time.

Are your IT Key Initiatives clear and aligned with the business destination, or are you more engrossed in the Delivery scenery?  

Here are a few of the most important foundations that should be in place to ensure alignment between Business and IT leadership:

• Project Identification and Assessment: Use a single list to capture and evaluate ALL projects in terms of business value (ROI and/or other quantitative and qualitative measures), including long term maintenance of deployed capabilities, not just new development. Assign an effort sizing estimate using a consistent approach to build the Demand pipeline.
• Demand/Capacity Analysis: Build a clear understanding of how much capacity for IT work is really available. Often production support and maintenance activities are not properly tracked and undermine the perceived capacity for new capabilities.  Using the Demand from the single list described above, determine how much of the list could be completed based on the real Capacity available.  This can be complex given the broad range of IT skills required.  
• Project Prioritization: Demand always outpaces Capacity, so priority decisions must be made in the context of a combined business/IT strategy. This can occur in different ways depending on the business size, complexity, IT alignment (Agile or not), but ultimately there should be a single decision maker with the authority to move projects up or down in priority in the pipeline.  
• Technical Lifecycle Management (TLM). Decommissioning end of life capabilities to make room for new products is another strategy that is often overlooked, but is just as critical. This means that all technical assets must be inventoried and assessed to determine their investment posture - whether to Buy (invest more), Sell (decommission), or Hold (maintain as is) an asset. This assessment then drives projects into the pipeline for prioritization.
  

This list might seem obvious to some, but in my experience they are much easier said than done. Establishing these foundational processes and building collaborative and consistent execution among Business and IT leaders will ensure you Deliver on Key Initiatives!