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The Success Trap: Live and (Un)learn

What got you here won’t get you there, so how do we unlearn the behaviors that are holding us back? Welcome to Maestro’s new blog series by Go-to-Market Expert, Dean Gonsowski.

September 16, 2025

By Dean Gonsowski

Many of the enterprise software companies that I’m working with to solve their go-to-market (GTM) challenges have hit a wall after years/quarters of success. This struggle is both surprising and, obviously, disconcerting. 

In many instances, the root cause is simple enough and boils down to: “What got you here won’t get you there.”  This notion is similar to Churchill’s famous warning about “fighting last year’s war” and the need for constant reinvention. But, while the problem statement is straightforward, the remedy isn’t.

Marshall Goldsmith wrote a book entitled What Got You Here Won’t Get You There: How Successful People Get Even More Successful, and while it was originally penned almost 20 years ago, his core tenets are just as, if not more, insightful today as they were decades ago. His main theme is that past successes are often enabled by a set of behaviors that can lull you into a “success trap.” 

“One of the greatest mistakes of successful people is the assumption, ‘I behave this way, and I achieve results. Therefore, I must be achieving results because I behave this way.’” – Marshall Goldsmith

This tendency to assume our behavior leads directly to our results is natural, particularly in a GTM sense, where we apply any range of formerly successful experiences, playbooks, frameworks, etc., and they produce results. We then attribute those results to our behaviors, perhaps conflating causation with correlation.

While innocuous enough when the results are positive, what if achievement dries up and the tried-and-true behaviors stop working?  In the face of new setbacks, most seasoned practitioners will look at any number of micro/macro trends to diagnose their challenges, while consciously ignoring their historically successful approaches. This creates blind spots that can be particularly dangerous because they’re difficult to diagnose.

To counter these blind spots and power continuous/ongoing success requires “continuous unlearning and adaptation.” For Goldsmith, continuous unlearning isn’t about forgetting everything you know—it’s about selectively shedding outdated habits and yesterday’s formulas for success so that you can create space to grow into tomorrow’s challenges. Continuous unlearning means stopping what no longer serves you and consciously replacing it with more forward-looking behaviors.

This is the core focus of my blog series, The Success Trap, where I’ll tackle a range of past notions that likely need to be unlearned and then relearned.

Our first deep dive will be into traditional sales qualifications methodologies (BANT, MEDDIC, etc.) to see if they need to be “unlearned….”

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