Playing To Win
- PHIL JACKLIN
- Apr 13
- 3 min read

When there are multiple choices, particularly on the big decisions that make a difference, how do you make sure you make the right choice? Are you using the frameworks that can help?
Without a framework, you normally find yourself in one of these traps
The “have you also considered” trap, where a senior stakeholder will not make a decision, by putting other options into the mix.
The “this shouldn't be in the mix” trap, where an option will be discounted before consideration, potentially weakening the decision.
Or the “you're using the wrong criteria trap”, where all work to date will be asked to be redone with some new evaluation criteria.
Feel familiar? Try this instead.
Playing to win
In 2013, Alan G Lafferty and Roger L Martin published Playing to win - how strategy really works. Whilst not a book about project decisions, it's insights into strategic decision making can be reused in a project context. Here's how I use it to avoid the popular decision traps.
What is winning?
Firstly, we define the context. What is the situation we face and why do we need to make a decision. This background information helps everyone get on the same page.
Secondly, we define what winning looks like. We want a decision that is a winning decision, not a “meh” decision. So we have to define what winning is. What will a winning situation look like? At this point we are not constraining our choices. So a winning decision is not constrained by budget, or capacity, or time. We simply describe what aspects of the problem need to be solved and how those problem aspects now look in a winning situation. Effectively, were trying to fast forward to the time when the problem is solved and we're describing what that time looks like.
At this point it's good to pause and involve other people. Do we have agreement on the definition of winning? Getting agreement stops the “wrong criteria trap” from appearing later in the cycle.
Sandpits are not just for sandcastles
What are the generic ways in which these problems can be solved? For example, we could build a solution or we could buy a solution. Therefore we have two sandpits - build and buy.
What is a winning solution?
For each of our sandpits, we list the options under consideration that would be winning options. A winning option is an option that meets our definition of a winning solution. If it doesn't meet our definition, you might still note the option, but you also note that you discounted it because it wasn't a winning solution.
Another point at which it's good to pause and check if there are other options that should be under consideration. Pausing and checking here avoids the “have you also considered” trap from tripping us up later in the cycle.
What needs to be true?
The final step in the framework is looking at what needs to be true for each winning solution to actually deliver a win. This is where you put back in any constraints that are necessary to be adhered to. Things often evaluated here include price, timeline, capacity as well as technical feasibility of options under evaluation.
If something cannot be true, there are essentially two options. Either this potential solution is not viable and we strike it off the list, or there’s another set of true conditions that are also acceptable. An example puts this into context.
An option under consideration needs the capacity of another team, in the next quarter. One of the conditions that needs to be true is that the other team has capacity to do the work. On checking, it is apparent that the other team have other priorities and are not going to prioritise our work in the quarter ahead. At this point, we can strike this potential solution off the list, or change our criteria. We might instead add a criteria that says the other team can be influenced through Executive support to prioritise our work in the quarter ahead. Now we have a new condition to go and check.
Did we win?
The Playing to win framework is not a panacea and is not good for all solutions. It excels in solutions where there is genuine disagreement on the best outcome, where analysis is required to inform the choice and where there is time for analysis and consideration. It puts structure and discipline around the process and achieves, in my experience, a higher percentage of buy-in to the decisions that are made.
As an added bonus, this framework is also good for minimising re-litigation of solutions at a point in time. Something that does happen on projects and can be the cause of issues. Decisions should only be re-litigated if one of the things that needed to be true, is no longer true. You now have the bonus of a framework for re-litigation rather than opinion driving re-litigation.
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