What I keep thinking about underneath your four points is the question of why this pattern is so persistent in technical leaders specifically. The over-reliance on details, the caveat before every claim, the inability to leave context out these are not communication failures. They are survival behaviours that worked in a previous context.
Most technical people were rewarded, for years, for comprehensiveness. The person who caught the edge case. The one who flagged the caveat nobody else had thought of. The one who never got caught out. That pattern was reinforced in code reviews, in architecture debates, in every room where being technically correct was the highest form of credibility.
Then they get promoted. And suddenly the room needs a different thing. Not completeness. Momentum, the skill that made them indispensable now makes them difficult to follow.
The "well, technically" impulse is not bad thinking. It is good thinking, in the wrong room. The hardest part is not learning the new skill. It is unlearning the identity that the old one built.
As you grow in your technical career, every project is like defending your thesis. You get peppered with 100 questions before approval. It's technical people selling ideas to other technical people.
For larger scale projects, it becomes cross functional and that audience doesn't want to hear about every detail; they want to understand what's the point, what is the core story. This goes double for when you're selling to executive audiences.
To this day, I keep all my technical detail in the appendix, should I get a highly-technical question that needs a highly-detailed answer. :)
This maps directly to what I see in founder pitch conversations... the same instinct that makes a technical founder great at building (precision, comprehensiveness, covering edge cases) is exactly what makes them lose the room when they're pitching investors or selling to enterprise buyers.
The hardest shift isn't learning to tell a better story, it's accepting that the simplified version is more true to your audience than the comprehensive one. An investor doesn't need to understand your architecture to believe in your company. They need to understand how you see the market and why you're the one to win it. That's the better signal, right?!
Some technical founders see this challenge, understand their limitations, and appoint a CEO... look at HashiCorp! Mitchell Hashimoto and Armon Dadgar built, and still have, serious tech cred, but they hired someone else to lead the ship, Dave McJannet.
People say 'well, technically' because they don't actually know what their audience is asking for. They think being a subject matter expert means sharing everything they’ve learned. But at the senior level, leadership isn't your peer—they are looking for a specific signal. There’s a time for the deep dive, but a high-stakes review isn't it. If you can't tune your response to the moment, you aren't leading the meeting; you're just presenting to it.
The 'well, technically' reflex is the one that kills most LinkedIn posts too. You write a clean insight, then hedge it into meaninglessness. The instinct to preempt every edge case is real but it costs you the story.
Storytelling is one of those skills that isn't valued enough. Plenty of leaders struggle to master it without the right tools or awareness. Great piece!
“If you’re telling a story about your camping trip, don’t start when you were brainstorming options for tents and carpooling. Start right before you almost get eaten by a bear on a 13 mile hike.”
This is so well-articulated. I need to make this quote my screen background!
I really appreciate the call out of storytelling being a craft that someone really needs to hone over time and to not put yourself in the position where you need extensive storytelling skills that you really don’t have.
I used to read a lot of books about fiction writing and one model about plot that stuck with me was a diagram of a set of branching paths moving from left to right. The start of the story is on the left and the end of the story is the tip of one of the branches on the right. The point of this model was that, viewed from left, the plot appears unpredictable with suspense, but viewed from the right, when the reader is closing the book, the plot feels inevitable. There is only one path back to the beginning. The satisfaction of the plot comes from the experience of moving from suspense to inevitable. (I can't find where I read this originally. Janet Burroway's excellent textbook on fiction writing maybe?)
What I keep thinking about underneath your four points is the question of why this pattern is so persistent in technical leaders specifically. The over-reliance on details, the caveat before every claim, the inability to leave context out these are not communication failures. They are survival behaviours that worked in a previous context.
Most technical people were rewarded, for years, for comprehensiveness. The person who caught the edge case. The one who flagged the caveat nobody else had thought of. The one who never got caught out. That pattern was reinforced in code reviews, in architecture debates, in every room where being technically correct was the highest form of credibility.
Then they get promoted. And suddenly the room needs a different thing. Not completeness. Momentum, the skill that made them indispensable now makes them difficult to follow.
The "well, technically" impulse is not bad thinking. It is good thinking, in the wrong room. The hardest part is not learning the new skill. It is unlearning the identity that the old one built.
100% spot on. You must adapt to the audience.
As you grow in your technical career, every project is like defending your thesis. You get peppered with 100 questions before approval. It's technical people selling ideas to other technical people.
For larger scale projects, it becomes cross functional and that audience doesn't want to hear about every detail; they want to understand what's the point, what is the core story. This goes double for when you're selling to executive audiences.
To this day, I keep all my technical detail in the appendix, should I get a highly-technical question that needs a highly-detailed answer. :)
That's a great idea, keeping all your technical details in the appendix.
This maps directly to what I see in founder pitch conversations... the same instinct that makes a technical founder great at building (precision, comprehensiveness, covering edge cases) is exactly what makes them lose the room when they're pitching investors or selling to enterprise buyers.
The hardest shift isn't learning to tell a better story, it's accepting that the simplified version is more true to your audience than the comprehensive one. An investor doesn't need to understand your architecture to believe in your company. They need to understand how you see the market and why you're the one to win it. That's the better signal, right?!
Some technical founders see this challenge, understand their limitations, and appoint a CEO... look at HashiCorp! Mitchell Hashimoto and Armon Dadgar built, and still have, serious tech cred, but they hired someone else to lead the ship, Dave McJannet.
People say 'well, technically' because they don't actually know what their audience is asking for. They think being a subject matter expert means sharing everything they’ve learned. But at the senior level, leadership isn't your peer—they are looking for a specific signal. There’s a time for the deep dive, but a high-stakes review isn't it. If you can't tune your response to the moment, you aren't leading the meeting; you're just presenting to it.
The 'well, technically' reflex is the one that kills most LinkedIn posts too. You write a clean insight, then hedge it into meaninglessness. The instinct to preempt every edge case is real but it costs you the story.
Storytelling is one of those skills that isn't valued enough. Plenty of leaders struggle to master it without the right tools or awareness. Great piece!
“If you’re telling a story about your camping trip, don’t start when you were brainstorming options for tents and carpooling. Start right before you almost get eaten by a bear on a 13 mile hike.”
This is so well-articulated. I need to make this quote my screen background!
I really appreciate the call out of storytelling being a craft that someone really needs to hone over time and to not put yourself in the position where you need extensive storytelling skills that you really don’t have.
Great piece.
I used to read a lot of books about fiction writing and one model about plot that stuck with me was a diagram of a set of branching paths moving from left to right. The start of the story is on the left and the end of the story is the tip of one of the branches on the right. The point of this model was that, viewed from left, the plot appears unpredictable with suspense, but viewed from the right, when the reader is closing the book, the plot feels inevitable. There is only one path back to the beginning. The satisfaction of the plot comes from the experience of moving from suspense to inevitable. (I can't find where I read this originally. Janet Burroway's excellent textbook on fiction writing maybe?)
Let’s just kill 90% of adverbs
This is great. Definitely need to cut out the backstory but that’s the meat of the pitch 🍔