Most leaders don't spend a lot of time thinking about and developing strategy, so when it comes time to do so, the mindset, skills, processes and optimization points can be a bit rusty.
Also, with the average time spent within an organization steadily declining, leaders are oftentimes not around for more than one iteration of a strategy process, limiting the ability to iteratively improve the strategy game of both individual leaders and the organization as a whole.
The purpose of this checklist is to help a leader assess the completeness and quality of a strategy document, through the means of human reflection or AI-assisted assessment.
Here is an example of an AI-assisted analysis of the 2018 - 2025 strategy document of NTNU.
I would like to assess and evaluate the quality of this strategic document. I would like for you to be critical of its structure and contents, and assess to which extent it matches the criteria I determine through my upcoming questioning.
Let's start off by reviewing the strategy document and familiarizing yourself with its contents.
Different strategy documents cover different aspects of strategy. Here is a top-level view of what a strategy document might contain:
Please give a detailed analysis of the scope of this specific strategy document, and to which extent it goes into detail on these different sections. Also, if you have identified the document to contain multiple strategies, please list which ones.
In what way does the document describe how the organization envisions the future, meaning what will happen if the strategy succeeds?
In what way does the document describe the organizational core mission/assignment driving the need for this strategy?
In what way does the document describe the values or other core behavioural concepts that inform the strategy?
In what way does the document describe the core challenges faced by the organization that the strategy needs to take into account and navigate?
In what way does the document describe the core opportunities that the strategy needs to take advantage of?
In what way does the document describe the scope of the strategy document? What is considered outside the scope of the document?
Which time period does the strategy cover?
In what way does the document describe where this strategy fits into the hierarchy of strategies, meaning if it is it a top-level (corporate strategy), or a lower level strategy (like the strategy for a region, department, team or area of responsibility)?
In what way does the document describe the key stakeholders of the strategy, the impact the strategy has one them and why they should care?
In what way does the document describe who has a role in the strategy, meaning who is responsible for designing, aligning, operationalizing, executing, enabling and evaluating it?
In what way does the document describe the why this specific strategy needs to exist, and what it's purpose is?
In what way does the document describe the the desired results and outcomes of the strategy?
In what way does the document describe the insights or trends the the strategy based on, and how these insights inform the strategy?
In what way does the document describe what the strategy believes is the right approach, and the justifications for those beliefs?
In what way does the document describe what the strategy believes is the wrong approach, and the justifications for those beliefs?
At it's core, strategy is how we will positon ourselves on the battle field so we win. In what way does the document describe the position taken by the strategy?
In what way does the document describe the uncertainties or risks that make the strategy a gamble?
In what way does the document describe on which north star perspectices, objectives and metrics the strategy will be evaluated?
In what way does the document describe the evaluation regime of the strategy, including how often the strategy will be assesed, by whom and how the success of the strategy will be evaluated?
In what way does the document describe how the organization plans to ensure that the strategy is understood, executed upon and operationalized by the different parts and individuals within the organization?
In what way does the document describe what would need to happen in order for the organization to reconsider the strategy?
In what way does the document describe how the learnings from the process of designing, executing and evaluating the strategy will be collected and organized for the purposes of improving future strategy processes?
In what way does the document describe the resources (capital, manpower, roles, competence, processes, systems) required to succeed with this strategy?
In what way does the document describe how the elements of the strategy will be embedded into the processes, systems and structure of the organization?
In what way does the document describe how the strategy will be broken down into objectives and projects?
Based on your assessment of this strategy document, please provide a detailed and comprehensive list of suggestions on how this strategy can be made more explicit, clear or otherwise increase the likelihood of it's practical success.
For each suggestion, describe what should be done and the motivation for doing it.