We’ve all said it, and I’m sure many of us have fallen victim to it. A friend, family member or colleague comes to us with a story they’re eager to tell. They start strong (or not, that happens to), but the story starts to fall apart as they forget things, stumble over the delivery, or leave out crucial details, finally trailing off with “you had to be there.”

When I started working with the students at Startup Institute Boston over the summer, I decided to harness the lessons of this infuriating phenomenon for good. I see these students in the fifth week of their eight-week bootcamp program, just before they start making contact with prospective employers and network with people who could be their future colleagues and bosses. And as I think about the nature of these “you had to be there” stories, they have some instructive elements that could help those who struggle in networking, job interview, and other scenarios dependent on connection.

I have them break into groups (typically the ones they use for a separate project they work on), and have them rotate telling the story of something funny that happened to them. I focus less on having them tell a joke, and more on a funny occurrence, because many are intimidated by the burden of having to be funny on command. After they move around the group, I have them designate a “winner” in the circle, and talk through why that person’s attempt was so successful.


This is where the connections start to come together. All the stories we tell one another, no matter the goal (educational, entertainment, informative) are sensitive in a number of ways. And the best ones are brief enough to hold the listener’s attention for their duration, detailed but not exhaustively so, and invite minimal clarifying questions. I encourage students to tell stories with humor as a goal, because funny stories are especially sensitive to missing details; in the absence of these details, they don’t “land.” For anyone desiring to make a good impression, being able to master sharing information in this fashion is crucial; as such, I like this exercise for students (or anyone!) needing to be compelling because it can help them refine strategy.

This conversation, for them, is framed in terms of temperament because each “side” can help the other when participating in this refinement. Introverts, with their natural neural proficiency for listening, can invite meaningful clarifying questions and encourage their extroverted counterparts to include key details while leaving out or changing less important ones. And extroverts, who find more comfort in verbal expression, can coach their introverted counterparts on details of delivery like tone or accompanying body language. Together, working to practice and prepare in advance of high-stakes scenarios, each side can prove highly advantageous to its opposite.

If you’re interested in doing a version of this with your friends, classmates, colleagues, or students, here are a few tips to harness the power of “you had to be there”:

  • Provide individuals time to come up with a story; this story can be about anything, but I find that the exercise is particularly effective if its goal is humor. The few minutes of think time will reduce the particular conversational tics that come with a lack of preparedness. Further, this underscores the idea that one should not go into any scenario where an impression is being made – an interview, a networking social, even speed dating – unprepared.
  • Let each individual tell their story, noting their tone and body language. Sharing focus across words, tone, and body language is crucial for first impressions, because those meeting you will have little else to judge you on.
  • After the story is told, share the questions that arose during it. The storyteller can choose to answer them or not, but it’s important to note the nature of the questions and the bearing of their answers on the final results. For extroverts, their “external processing” tendency may mean that they talked past an important detail without realizing its role in the understanding of the story. Conversely, for introverts who process inwardly, they may have skipped a crucial detail verbally while addressing it mentally. By sharing the questions that arise during these stories, we can pinpoint our individual weaknesses and address them in service of a good final story.
  • Continue to refine the story, addressing questions that arise along the way, and checking in with your “counterpart” or “wingperson” to assess clarity and effectiveness.

What are the qualities of a good storyteller that you admire? What is your favorite story to tell, and why?

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