Raj KheraCEO MakeMEDIA • 3x exits to public firms • Host, Executive Signal Podcast, make authentic pipeline-building content just by talking

When executives can't tell a good story, it's usually because of this

Name: When executives can't tell a good story, it's usually because of this
Uploaded: 2026-01-26T12:30:38+00:00
Duration: 14 s
Channel: Raj Khera
Description: In this brief coaching dialogue, Speaker A identifies a common flaw in executive storytelling: the tendency to be overly broad and generic, which…

26 Jan 2026 · 0 min

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In this brief coaching dialogue, Speaker A identifies a common flaw in executive storytelling: the tendency to be overly broad and generic, which prevents vulnerability and learning. Speaker A suggests a concrete technique to deepen the narrative by asking the executive about their internal dialogue at the moment of decision—what thoughts they repeated to themselves while driving home or to work. This line of questioning helps the speaker view themselves from a third‑person perspective, encouraging openness. Additionally, Speaker A emphasizes the importance of anchoring a story to a specific moment, using that moment as a hook to make the story compelling and relatable.

Like, first of all, one of the biggest mistakes I see in storytelling, especially from executives, is that it goes too broad, too generic, you know, like, you know, we made a difficult decision, right? Like, that's not vulnerable, right?
Like saying that feels like the who hasn't, right? And it doesn't feel like you learn anything from it.
Exactly, exactly, exactly. So, so if someone is saying that, and I'm like, oh, I have to get them to go deeper, I might ask them to be like, well, can you talk to me about what your internal dialogue was telling you at the time? Like, what words, what What were, I know you had to do forward-facing to the company and you had to make this really difficult decision, but when you were driving home that night or driving to work that morning, what were you saying on repeat in your brain? And you kind of almost get them to see themselves in a third person and people can often start being a little bit more open with you. But also moments, you always want to hook a story on a moment.