How NOT to Sell like Gil from The Simpsons

The Simpsons’ Gil Gunderson is an unsuccessful salesmen with a good heart. Turn his sales strategy failures into your successes with this post from LinkedIn.

April 25, 2014


Gil Gunderson can hardly catch a break. The recurring Simpsons character, modeled after Jack Lemmon’s Shelley Levene from Glengarry Glen Ross, appears as a bumbling salesman who peddles everything from real estate to Coleco computers.

Gil’s always a step away from losing everything – his job, his family, his house, etc. He takes every odd job he can find, becoming a one-man punchline whenever he appears. Despite all this, Gill still finds the drive to keep trying – remaining eternally optimistic that the next sale will provide security for himself and his family.

Gil is an animated walking example of what not to do when selling to prospects – yet we can still take some lessons from his determination and dedication. Gil never seems to be able to close the sale -- primarily due to his uncomfortable sales techniques. He makes the same mistakes, but you don't have to do that. Here's how you can avoid being a Gil in your sales strategy.

Aw, c'mon, do it for ol' Gil!

Gil always appears desperate, no matter what he’s selling. In one particular Simpsons episode, Gil attempted to sell newspaper subscriptions over the phone. The customer, sensing Gil’s desperation, asked him to dance for the sale. Despite being on the phone, Gil danced anyway.

Prospects can smell desperation from miles away – even on social media. Confidence and authority help establish trust, which fosters healthy business relationships. Social selling powerhouses proactively communicate with their prospective clients, and update their profiles with new skills as acquired. Presenting a strong social front can help establish the confidence you’ll need to land the sale.

What’s Gil gotta do to sell you this car?

With Gil, everything is about the sale. His tactics always focus on closing deals, regardless of the relationships with his potential customers. The one-off nature of his character is designed this way for comedic effect – he’s back off camera when the deal goes awry. Without rapport, his sales fall flat.

Building pre-sale relationships is essential for closing deals – and for maintaining good interactions moving forward. Those ice-cold leads can be warmed with an initial understanding of prospect needs and value opportunities. The discovery phase is crucial for kickstarting a productive sales process.

It’s also helpful to widen the relationship beyond a few contacts within a client’s organization. Such a multi-threading approach can help maintain relations if prior contacts leave or shift internally. Do the research on your customer’s internal network to prevent workflow disruptions in the future.

Doesn’t Gil get a lick?

Given Gil’s tendency to refer to himself in the third person, it’s clear that he doesn’t place the customer’s needs above his own. Desperation is likely part of that sordid formula, but he always tailors his sales pitches to reflect his issues.

This is perhaps the most direct lesson you can take from Gil’s hapless strategy. Everything – from your own personal profile to the content and discussions you share – should be focused on answering client concerns and questions. Solution-based selling frameworks help place the focus on the customer, rather than whatever needs the salesperson holds.

Despite all his faults, Gil maintains a never-ending optimism about his selling practices. If there is one trait to take from Gil, it’s his dedication. Just make sure to keep these tips in mind – and never dance for someone while on the phone. Follow @LinkedInSelling  for more selling tips!