If you have ever built any sort of software for a set of stakeholders, you have to have heard the term ‘t-shirt sizing’. For those that haven’t, t-shirt sizing is the process of listening to a set of requirements that aren’t fully baked to give stakeholders an idea of what the effort and in reality cost might be.
Full disclosure: I have nothing against this activity. I think any activity that leads to focus, more details, and direction is a good one. However, it is important that everyone involved a t-shirt sizing activity understand its true value. T-shirt sizes are typically given at either the beginning of a project or at major milestones where stakeholders are looking to add significant number of capabilities. This is where the dance starts: stakeholders explicitly want things quickly and cheaper with implied quality and development teams want the proper time to design and build a solution with moments of overengineering sprinkled in. So when it comes to providing the sizes, this all typically combines into a list of features that are all on the bigger side of the scale.
And now that we are done, what have we learned? Nothing. We are no closer to a reality of what the features will actually end up being, when any of it will give done, or how much it will cost. For stakeholders, either a false sense of security is established based on the portrayed confidence of the team along with always being able to tell their stakeholders, “well, that is what the development team said.” For many development teams, these are fear-based activities; fear of being without (time, money, details) and fear of not giving the answer the stakeholders want to hear.
In order to get real value out of a t-shirt sizing activity, the entire team needs to align on a few key items:
What does the team truly value?
Starting with stakeholders, the team needs to understand what the non-negotiables are and some of them may go without saying. Quality, feature accuracy, responsiveness, communication, etc. are just some examples of how the team might prioritize their working environment which will help to make decisions on who the full team might be. These are the items, that when decisions need to be made about where the team will do or how the something will be developed, that are unwavering; that define a team’s personality and morale compass.
The only infinite resource we have is time, but it still needs to be used wisely
For the most part, deadlines are arbitrary. We all understand that as quickly as we understand something, more information can come to the forefront to change our understanding. It is important that every team is built to respond to change while stakeholders appreciate the talents of a team and care about how they get the work completed. Providing constant prioritization in support of an iterative development environment ensures maximum productivity on what is most valuable to the business.
So then what should be achieved with t-shirt sizing?
A valuable direction should be set without absolute commitment. It is an agreement around these are the features we truly care about and that we know we need to learn more and execute against. Also, it establishes how big the bread box is believed to be which can help in finding the highly complex features along with framing the value conversation for stakeholders to have with leadership. T-shirt sizes represent a moment in time just like any other estimation activity. So if the team doesn’t feel like they that have enough details to get to a better level of granularity, then that should be acknowledged and the discovery process continues to help to get what is being looked for.
Teams want to succeed. It is important to remember that when supporting activities like t-shirt sizing; setting up “glass half full” versus a “glass half empty” conversations in the future is the key to long-term team and project success. Trust and understanding are the foundation for making all of this work.