The Fog of IT Wargaming

In our podcast, the Calculus of IT , Mike Crispin and I have, in some recent episodes, moved from discussing how to survive your first year as a new IT Leader to capitalizing on that achieved momentum into years two, three, and beyond. Most recently, we have been discussing how to create a new IT budget for your second year and construct a near-term (12 months) and longer-term (18+ months) IT strategy too.? Thematically speaking, what has begun to emerge from these discussions, as is also echoed in the New IT Leader’s Survival Guide , is that the best plans for both budgeting and IT strategic development will incorporate a vital element of flexibility and actively demonstrate your capability to change as needed with little to no surprise.? What is this vital flexibility element?? Wargaming.

When I think about flexibility in IT Strategic Planning, I skew towards considering three major classes of potential impacts:

1. Delay or substantial change of a strategic goal
2. External impact causing a corporate pivot
3. Internal impact causing a corporate pivot

Up until 2011, careerwise, I had never really taken the time to consider the second and third classes of impacts. This was primarily due to not having experienced them, even peripherally, as an IT Leader. I had mostly worked in very stable environments, where I could typically successfully construct and execute a three-year plan with little disruption. It was usually negligible enough not to be disruptive if something did happen. With some easy amendments, we were generally right back on track.

So…what happened?? In short, starting in 2011 (following an unexpected 60% reduction in force in the company I worked at) and continuing through all of my other roles for the balance of my career to date, I have experienced the reality that the only safe bet for IT strategy planning is to assume, by default, that all three can and will happen yearly because, for the most part, they have.

Knowing that these impacts can and will happen did not and does not provide a casual excuse for me to avoid constructing strategic plans.? If anything, it has required a doubling down on creating medium to long-term strategies because I recognized that not only did I need to have a core, flexible IT strategy that aligns with the business goals, but I also needed to consider and make plans for any potential alternative scenario that could impact the company along with a response and the readiness needed to amend the IT strategy.?

Why Wargame?

Wargaming, scenario-planning, bench-testing, prototyping…pick your turn of phrase.? The principal idea is the same.? You have an "A" goal with an idea of how it starts, ends, and what happens in the middle.? Next, you modify your A goal by adding an extra month to the expected completion date.? What happens as a result???

Now...shorten it by a month.? Remove a resource.? Add a cybersecurity attack.? Fire half of your staff.? Have a global pandemic. Upgrade Windows…you get the point.??

Throw enough scenarios at an IT Strategic Plan, and you will become quite good at it, so much so that you will slowly begin to think of every IT strategic goal as always having multiple paths to success.? In that three-dimensional thinking pattern, you may fortuitously find avenues of strategy you had not considered before.? This is just one of the beneficial outcomes of this way of approaching IT strategy design.

Naturally, the greatest benefit is having a playbook for what to do in nearly any scenario where your Plan A goal rapidly becomes Plan C or Plan M, and you can execute it accordingly. The plan you have to execute is not always guaranteed to be ideal, but it will be the ideal scenario for that specific outcome.

The 9 Steps of Effective Wargaming

Below, I have summarized the nine steps of a wargaming model I wrote back in 2013 for my senior IT staff. At that time, it was becoming somewhat of a habit to painstakingly construct a long-term IT strategy only to throw it in the trash due to some significant unforeseen (or unconsidered) event.? It was putting us on a dangerous trajectory of reactivism, which made even the idea, let alone the practice, of IT strategic planning very difficult. This wargaming model finally enabled us to resume creating long-term strategies and have a response to, for instance, a moment when someone accidentally elbows the big red button.?

Whether you are only writing an IT strategic plan for one year, 18 months, or three years+, here are the nine steps you must do to properly wargame for your plan:??

1. Identify potential disruptors: What are the most likely disruptors or unforeseen events that could impact the IT strategy? Consider technological advancements, market shifts, regulatory changes, and global events like pandemics or economic downturns.? Make a list of every single potential disruptor…even zombie attacks.
2. Assess the impacts of each: For each identified potential disruptor, assess the potential impact on the IT strategy. Consider the severity of the impact, the likelihood of occurrence, and the areas of the strategy that would be most affected.? You can use any criteria, such as a 1-5 scale, an HML scale, Smiley and Sad emojis, or make something new.? Regardless of your impact scale, you want to be able to rank your impacts so that you know which ones to focus on first.
3. Construct response plans (the wargaming secret sauce): Based on the identified impacts and their potential disruption to the IT strategic plan, develop specific response plans for each scenario in order of highest (and most likely impact) down to least likely. These plans should outline the steps to adapt to the impact and show how the balance of the IT Strategic plan will change.? I suggest working with your IT Team on this and not just doing it in a vacuum.? Involving your entire IT team in the wargaming process helps generate diverse ideas and perspectives and fosters a sense of ownership and preparedness among team members. This can be crucial when it comes to executing the response plans effectively.
4. (Re)Allocation of resources: When developing the response plans, consider the resources required to respond and adapt to the changes in the IT strategy. This includes personnel, budget, technology, and other assets. Ensure that the necessary resources can be quickly mobilized during a disruption.? Also, consider the what-if scenario where you lose a substantial number of IT staff, yet the IT strategy cannot change.? This scenario is becoming quite common these days.
5. Logistics: Effective communication and coordination are critical during a major change in an IT strategic plan. Consider how information will be disseminated to key stakeholders, including employees, customers, and partners. Establish clear lines of communication and define roles and responsibilities for managing the response. This is especially important if the disruption is caused by the lead communicator leaving the company.
6. Testing and simulation: You should aim to regularly test and simulate the response plans for IT strategic pivots to ensure their effectiveness and identify areas for improvement. This can be done through tabletop exercises, where key stakeholders walk through the response to a hypothetical scenario, or through more comprehensive simulations that test the actual implementation of the response plans.??
7. Continuous improvement: Use the insights from testing and simulation to refine and improve the response plans. Review and update the plans regularly to ensure they remain relevant and effective as the organization and its environment evolve.? This is a great exercise and, if we are honest, should be done for everything in IT, not just strategic planning.
8. Integration with business continuity planning: Ensure that the IT strategy's scenario and response plans are integrated with the organization's overall business continuity planning.? If the company has no business continuity planning, let this be the start of that process and teach others how they, too, can wargame for their respective functions.? Demonstrating the value of wargaming and scenario planning in IT can inspire other departments to adopt similar practices, ultimately leading to a more resilient and adaptable organization.? Even the bare minimum integration will help ensure a coordinated and effective response to any disruption that impacts the entire organization.?
9. Leadership and decision-making: Consider how leadership and decision-making will be handled during a disruption. Clearly define the roles and responsibilities of key leaders and establish protocols for making critical decisions quickly and effectively. Disruptions to IT strategic plans can range from a very slow roll to same-day responses, and you should not automatically assume that every IT leader who plans today will be there to execute that plan when the time comes.

When the War is Over

I would be remiss if I did not also mention that there is one more thing you should do. It is not necessarily a critical step in wargaming (though it is a key component of Continuous Improvement).

Conduct a project post-mortem. After a disruption occurs, thoroughly review the response to identify what worked well and could be improved. Use these insights to refine the IT strategy and response plans further and share learnings with the wider organization.? You may never get past the testing and simulation phase with any one of your scenarios, but let me tell you that it is not wasted time.? Consider it a tremendous positive for so many reasons.? However, should the day come when you have to execute a scenario you planned for due to a disruption, then, after the smoke clears, sit down, grab your peers and some beers, and talk openly and honestly about how well you did according to your scenario plan.? Then, adjust as needed, prepare for the next one, and hope it never comes.

Are you excited about transforming your IT strategy with wargaming and scenario planning? I will be releasing a new (free) book on IT Scenario Planning this summer, so if this article interests you, stay tuned for a greatly expanded version, including templates and adaptable models. You can sign up to get notified at www.longwalk.consulting/library .?