Jason Osborn: The Critical Growth Phase Between Business Deals

In a recent LinkedIn post, Jason Osborn explores a crucial, yet often overlooked, phase in professional development: the period between closing one deal and starting the next. Osborn argues that true growth and improvement don’t happen during the high-pressure execution of a deal, but rather in the reflective space that follows. He highlights how many professionals bypass this vital stage, leading to recurring issues and slower progress.

According to Osborn, the typical approach involves a relentless sprint from one transaction to another, with little to no time allocated for introspection. This constant forward momentum, he suggests, prevents individuals from learning from their experiences. “During a deal you’re executing what you already know. Focused on closing. Reacting. Too deep in it to see it clearly,” Osborn writes. He posits that this phase is about application, not growth.

The Missed Opportunity for Learning

Osborn emphasizes that the real learning and development occur in the aftermath of a deal. This is when professionals have the mental space to ask deeper, more insightful questions. Instead of merely focusing on the outcome, he advocates for examining the ‘why’ behind the success or failure of a deal. What were the differentiating factors? What almost derailed it? What would be done differently next time? These are the questions, Osborn contends, that drive significant improvement.

He observes that many professionals neglect this reflective process, often because it feels less immediately productive than ‘doing.’ The insights gained from reflection don’t appear on a pipeline report, and the comfort of constant activity can overshadow the value of stillness. “Because busy is comfortable and stillness isn’t,” Osborn points out, explaining the common avoidance of this critical growth period.

Extracting Maximum Value from Each Cycle

The author differentiates between those who close the most deals and those who improve the fastest. The latter group, in Osborn’s view, are those who are adept at extracting the most value from each deal cycle. This involves a continuous process of refinement:

• Sharpening processes by removing ineffective strategies and amplifying successful ones.
• Clarifying positioning by understanding what messaging truly resonated and why.
• Building confidence through the visibility of patterns in wins and losses.
• Nurturing relationships that will form the basis for future opportunities.

Osborn challenges the common perception of the space between deals as a mere ‘waiting room.’ He asserts that this period is, in fact, where the most significant work happens. “But the real work is happening right there. In the reflection nobody sees. In the refinement nobody tracks. In the preparation that makes the next deal look easier than it actually was,” he states.

The Learning Happens Between Deals

Ultimately, Osborn concludes that while deals serve as a test of existing knowledge and skills, it is the time invested between these transactions that fosters genuine learning and adaptation. He encourages professionals to reframe their understanding of productivity, recognizing that strategic reflection and refinement are not passive waiting periods but active components of sustained professional growth.

Osborn prompts his audience to consider their own experiences, asking, “What did your last deal teach you that you haven’t sat with yet?” This question underscores his central thesis: leveraging the space between deals is key to unlocking an organization’s or individual’s greatest potential for advancement.