Advanced Storytelling For Leaders: Skip The Summary For A Clear Synthesis

Read Time: 3 Minutes

There's an attack on middle managers. But no one is telling them why, only that they're increasingly getting in the way and coming up short.

My hypothesis on the root cause?

"Managing" is no longer the expectation. "Leading" is.

This is why Paul Graham's Founder's Mode essay resonates deeply with the leaders who started companies.

• It's an ethos biased for action.

• It's an approach that prioritizes depth.

• It's an operating system optimized for the resourceful.

While there are many dimensions we will examine that distinguish old-school managers from Founder's Mode leaders, there is one capability I want to zoom in on today:

Storytelling

Managers often offer summaries.
Leaders always author strategies.

Leaders don't summarize. They synthesize.

This is not semantics.
If they sound like identical twins, I promise they’re anything but.

Let's pull apart the key differences.

State vs. Strategy

A summary tells you the state of something. It offers facts. Data. Tables. Done well, it might even provide a Red/Yellow/Green assessment of that data.

A strategy goes a step further. It provides context. It zooms in and zooms out. It connects the dots. Those connections reveal why three yellows are alarming while two reds are positive.

It's data with a direction.

Tip: Don't tell the story like an objective reporter. Tell the story in the context of What Excellent Looks Like.

First Order vs. Second Order

The first order is like the weather report. It'll be a specific temperature. It's likely to rain. This is normal or abnormal for the season.

The second order answers the question, "So what?"

Will this rain cause flooding because of previous storms or be a welcome relief to a prolonged drought?

First-order highlights the cause.
Second-order probability weights the effects.

Reactive vs. Proactive

Knowing "What's True" is necessary but not sufficient to lead.
You need to know "What To Do About It."

"What's True" is reacting to what's happened so far.
"What To Do About It" is anticipating the next best move.

And it's not a surprise. Managers like to be in control. They've learned to fear what could go wrong and prevent the next embarrassing mistake.

Leaders are comfortable yielding control because they're in command. They operate with optimism and abundance.

This posture doesn't mean they're naive. It means they're working backward from the outcome they're trying to create and making their best move, not overreacting to the last move made on them.

Exhaustive vs. Prioritized

When everything is important, nothing is a priority. Are you showing me a map of the world or highlighting the best directions between two cities?

Leaders separate:

• Big from Small

• Urgent from Important

• Must Do from Nice To Have

They may reveal data below the line to test that they didn't draw it in the wrong place. But have no doubts, they drew one.

Nuanced vs. Binary

This one is counterintuitive. As F. Scott Fitzgerald famously wrote,

"The test of a first-rate intelligence is the ability to hold two opposing ideas in mind at the same time and still retain the ability to function."

The problem with nuance is that inexperienced leaders use it to hide. They don't want to have to pick a door, so they leave them all open.

This produces confusion, not confidence.

When sizing something up, choose! Is it good or bad? On track or off track? If you don't lead with a clear headline assessment, it undermines the credibility of everything that follows.  

Objective vs. Directive

Managers are reporters. Here are the facts. Draw your own conclusions.

The problem with this is you're outsourcing the conclusion to managers above you who are less informed or the team below you who have less context and experience.

This is a virtuous abdication of your most important responsibility.

Leaders write opinions. They take a stand. They don't lay out numbers. They add them up to draw conclusions. Doing so elevates the engagement of their manager and team.

They show their work so people can understand the equation. And use that understanding to challenge or support their math.

For You vs. For Themselves

A manager write reports for their boss. And because they write them for someone else, they're prone to telling them what they want to hear.

A leader synthesizes for themselves. They are testing previous assumptions. They are reexamining constraints. They're making a list and checking it twice.

They are writing it for themselves because they are calculating their next move.

Their purpose for sharing it is to have it pressure-tested by people wiser than them. And as a vehicle to get others onboard with executing against their now co-authored strategy.

You see, it's not a story that's told once and forgotten.
It's a story that's written and rewritten every day.

Because every day, we get new data.

Which means every day, the calculus changes.

And every day, we rewrite our story.

Bonus: Two 80/20 Tips For Better Writing

You’re not writing an essay to be graded. You’re sharing ideas meant to persuade.

• Invest in nailing the opening sentence

• Prune every unnecessary word

• One idea per sentence

• Write how you talk

But don’t become a boring writer. You’re telling a story to connect, move people, and evoke a reaction. You want them to push back because you're wrong or follow your lead.

Make your writing sing!

What You Missed

Here’s what you missed from me on LinkedIn:

• 1:1 Meeting Mistakes

• 2x Your Public Speaking Confidence

• Red Flag: A Team That Makes No Mistakes

Here’s what you missed from me on X/Twitter:

• Teams Leads vs Managers vs Managers of Managers

• 5 Types of Leaders People Will Follow

• Strategy vs Execution

I’d also love to know what playbooks would be most helpful to you. Hit reply and tell me your biggest management challenge.

You’ll always remain anonymous unless you tell me otherwise.

Thank you for reading. Appreciate you!

Dave