You Need a Field Guide to Working with You

• Record 100 calls you hold with your team.

• Point an AI agent at the transcripts.

• Ask it to create a “Field Guide to Working with You” based on the transcripts.

Here is mine:

Working with Jon: a field guide for Sagan executives

This is an operating guide, not a personality diagnosis. It is based on how Jon communicates, makes decisions, and applies pressure in the meeting transcripts.

Understand the job

Jon creates speed through conviction, urgency, humor, and strong opinions. He sees leverage early and gets restless when work becomes administrative or procedural.

Your job is not to imitate his intensity. Your job is to turn it into clear decisions, sound execution, and a team that can sustain the pace.

He will value you most when you can take a big idea and make it real.

Bring him things this way

Lead with the point.

“We have an opportunity to increase referral revenue. We have three partner candidates, one signed agreement, and a live test we can run this week.”

Then cover:

• What problem are we solving?

• What evidence do we have?

• What will it cost?

• What could go wrong?

• What is the smallest useful test?

• Who owns it, and when will we know if it worked?

Do not bring him a long process explanation before telling him what matters.

He responds well to people who think in terms of outcomes, economics, and momentum.

Learn to distinguish his statements

Jon often thinks out loud. Not everything he says is a decision.

Listen for the difference between:

• a decision: “We are doing this.”

• a preference: “I would probably do it this way.”

• a hypothesis: “Maybe this is the model.”

• a provocation: “What if we replaced the whole process with agents?”

If you are unsure, ask:

“Is that a decision, or do you want me to develop the idea?”

Then confirm the owner, next step, and deadline. Otherwise, the company can waste a lot of energy operationalizing half-formed thoughts.

How to disagree with him

Do not respond with vague caution. He is unlikely to respect “I’m not sure this is the right time” unless you can explain why.

A better structure is:

“I agree with the goal. I think this version creates a delivery risk because of X. I recommend we test Y with Z customer by Friday.”

He is more likely to accept a fast, evidence-based disagreement than a slow, abstract objection.

Do not confuse his confidence with certainty. He can be directionally right and operationally early.

What he is looking for in executives

He wants people who:

• find problems before they become excuses;

• use AI without outsourcing their judgment;

• create movement without waiting for permission;

• understand customers and commercial consequences;

• turn ambiguity into a test;

• tell the truth early;

• improve the people and systems around them.

He is skeptical of activity that looks impressive but produces little. “We sent the messages,” “we held the meeting,” and “we followed the process” will not satisfy him if the customer outcome has not improved.

What “what’s new and exciting?” really means

It is partly a joke, but it is also a test for agency.

He wants to know:

• What have you noticed?

• What did you improve?

• What did you learn?

• What are you testing next?

• Where is there leverage?

You do not need a dramatic breakthrough every day. A useful answer might be:

“We found that low-budget leads never convert, so we cut those calls by 10%. Next we’re testing whether the same filter improves close rates.”

That is better than manufacturing enthusiasm or giving a status report.

Expect pressure to be personal

Jon often frames work in terms of identity and value. Are you a trusted advisor? Are you solving problems? Are you adding something a machine cannot?

That can be motivating. It can also feel threatening.

Do not take every sharp comment as evidence that he has decided you are failing. Pressure is his default management language. Still, executives should not normalize every form of pressure. If the team starts hiding problems, copying his opinions, or working around his moods, the system is becoming unhealthy.

Handle the humor carefully

Jon uses humor to build energy, flatten hierarchy, and make difficult messages easier to deliver. It is part of his leadership style.

If something serious needs to be understood, he’ll say it plainly after the joke.

“Joking aside, the expectation is that this process moves within 24 hours.”

The best way to work with him

Bring him leverage, not maintenance.

Bring him the customer insight he has not seen, the risk he has not considered, or the system that turns his idea into repeatable output.

Keep your communication direct. Keep your own judgment. Move quickly, but do not pretend that every idea is already a plan.

The ideal executive relationship with Jon is neither obedience nor resistance. It is translation: turning his urgency into something testable, measurable, and humane.

Yallah Habibi,

Jon