Win-Win Versus Win-When

Win-win’s are the gold standard of deal-making. We all want to do business where everyone is getting something valuable out of an interaction. The problem is every deal isn’t a win-win. We need to able to dissect the good from the bad and understand how to navigate them in real-time. Whether it’s a complicated business combination or a simple transaction one-on-one with a client, it helps to also be familiar with the win-when.

A win-when is a variation on the win-win that we probably encounter much more often than we realize. It’s a win-win with a pre-condition. Both smart and crafty people will attach these contingencies to a deal or a service as a way of keeping some type of edge (usually without calling it that).

When we start paying attention to win-when’s, we’ll notice some turn into win-wins and some don’t. At first, you might think it’s all about motivations, but it runs deeper than that. It gets straight into intentions and design. We want to carefully examine the contingency and exactly how it’s being positioned to us or by us.

Take an artist who accepts an offer to do a free public class or showing. The person offering might think it’s a win-win because they’re giving the artist free exposure. But, the artist should know better. The naive assumption of a win-win is that some art-related work would follow the “free” exposure. The smarter observation is that this is a win-when.

The smart artist will think about how the showing could turn into actual business for them and then position themselves accordingly in advance. It’s only a win-win WHEN the free offering converts into paid business. Maybe this is through mailing list editions or future commissioned works, but it all requires the artist to have a strategic plan before accepting the “free” offering.

And, let’s also point out the motivations of the person offering the space for the class or showing as good. They sincerely want to help the artist as well as solve some problem for themselves. However, it’s the intentions and then the design of how the artist accepts and executes that determine if their win ever materializes. In a best-case scenario, both sides can discuss this reality upfront.

Win-win’s are great but they don’t just fall into our laps. Most situations are win-when’s and it’s up to us to reverse engineer if, how, and when the win will occur. We want to notice them, with all of their variations, and let the best opportunities for growth guide our work.

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