Curing the Pain of Annual Planning

A time to laugh, a time to cry

For many, autumn signals a time of relaxation. As the year enters the twilight of its final quarter, we prepare for cooler weather, a string of holidays, and some well-deserved relaxation with family members. 

Yet for enterprise leaders, autumn promises the pain of bitterly agonizing processes associated with annual planning for the coming year; a promise as inevitable as death and taxes. While such pain only happens once a year, it’s severe enough to take a step back and ask the question: can we do better?  

Planning pain points

Much of the pain associated with annual planning has to do with lack of structure. Ironically, planning hurts because it’s not well planned. 

 From the get-go, the process are bespoke and thus we encounter phenomenon such as:

  • Vague or high-level goals set by the c-suite without measurable targets
  • A subjective combination of top-down and bottom-up planning
  • Excessive use of zero-based budgeting
  • Lack of clarity, scope, and value pertaining to business asks
  • A different approach taken every year; usually due to executive turnover
  • Restricting planning to an annual process; creating artificial scarcity and a culture of over-asking

When vague priorities hit the VP and director-level leaders, a flurry of blank canvas documents are born. Various formats of scratchpads, roll-ups, and draft documents plague our inboxes and cannibalize our limited time. 

These departmentally dissimilar planning artifacts are then clumsily choreographed into some semblance of structure through nothing more than brute force trial and error. And this is the process that turns everyone’s hair grey. 

Enhancing planning efficiency

Locking and loading fiscal plans across dozens of departments is no small feat, thus I wouldn’t dare over trivialize such a challenge. Nonetheless, there are some seemingly obvious areas for improvement; specifically along the lines of standardization. 

Formalized strategic goals or OKRs

First, there should really be a handful (1-5) measurable goals set by the c-suite which then cascade down to senior leaders for execution. This is the process, and it should ideally be managed within an intuitive performance management tool. 

Standardized planning templates

Large monetary asks require justification, and the delivery mechanism is typically a presentation of some sort. So why not use a standardized template across departments? A template, regardless of the type, establishes the boiler plate components expected from leaders. The problem, solution, and return on investment should be unified across departments. Without rationalizing asks, we end up with a confusing cornucopia of apples and oranges. 

Standardize above the line prioritization 

Everyone believes their budgetary ask is important. To that, I say: prove it. Yet the spoils of budget mustn’t be issued only to the victors of stellar salesmanship. Moreover, the CEO and CFO aren’t the only approvers of business endeavors. A project will often require cross-functional cooperation from horizontal teams such as IT, HR, or facilities. These horizontal teams must also make a call as to whether or not to take on a supporting role, which of course requires human bandwidth and potentially additional dollars as well. Having an objective and agreed-upon prioritization process working across all departments is one way to ensure the entire company is focused on the right priorities. 


It will be difficult to convince all departments to align on a common planning paradigm. Fortunately, one doesn’t need to boil the ocean to realize immediate benefits. When the planning environment is chaotic and bespoke across the enterprise, consider embracing the aforementioned artifacts for your department first. Control what you can first, then convince others when results are prominent.