Session material
The twenty-five questions behind a $5,000 first session
In the order they get asked, with what each answer is actually for and the follow-up a good strategist uses when your first answer was too smooth. Run it on yourself in half a day, or hand it to whoever you are paying and watch whether they ask the follow-ups.
25 questions · 5 movements · 3 hrs 45 mins · free
The agenda · one question from each movement, ungated
Five movements, in this order, for a reason
The sequence carries most of the value. Each movement makes the next one answerable, and running them out of order produces confident answers to the wrong questions. One question from each is below. The other twenty are in the list.
Outcome and audience
What you want to be true, and who has to know you for it to happen. Nothing later means anything without this.
What do you want to be true in twelve months that is not true today?
Positioning and differentiation
The lane, the stance, and what the stance costs you. The longest movement and the one that produces the sentence everything else hangs on.
What do most people in your field believe that you think is wrong?
Credibility inventory
What you have actually done, what you got wrong, and what you are allowed to say about either.
What have you learned in the last year that you have not told anyone?
Voice and boundaries
How you sound, what you refuse to say, and how far you are willing to go under your own name.
What is the most controversial thing you would say publicly under your own name?
The dread-topic check
Last, deliberately. It asks whether you should do this at all, and by now you know enough to answer honestly.
If nothing measurable happened for ninety days, would you continue?
On the number in the headline
Where five thousand a month comes from
That figure sits at the top of the band for personal brand retainers, and it is the level at which you get a properly structured discovery session rather than an intake form. Below roughly two thousand you are generally buying execution and briefing it yourself. The band comes from our own rate research and should be read as a market range rather than a quoted price. If that number is not a real alternative for you, this list is still useful and the rest of the page will not try to convince you otherwise.
Two ways to use it
Both outcomes are fine with us
Run it yourself
Half a day and you have done the session
The list includes the four rules for self-facilitation, which exist because the hard part of running this alone is that nobody pushes back when you give a comfortable answer. Answer out loud before writing. Take the printed follow-up seriously. Write the unflattering version. Do not skip ahead to movement five.
Hand it to whoever you hire
You will get a better session than you would have
Because you will know what should be asked and you will notice if it is not. That is a genuinely uncomfortable thing for us to publish, since we would rather you used our system. It is also true, and a list that only works if you buy from us would not be worth forwarding.
Get the list
Eleven pages, twenty-five questions, nothing held back
- All twenty-five questions in session order across the five movements
- What each answer unlocks, and the follow-up a good strategist asks when your first answer was too smooth
- The four rules for running a discovery session on yourself
- What a strategist does with the answers afterwards, which is the part the retainer actually buys
- The honest time ledger for enforcing the answers on your own
Get the playbook
Where should we send it?
Twenty-five discovery questions in session order, with what each answer is for and the follow-up a good strategist asks when the first answer was too smooth.
One email with the download, and whatever you choose to receive after that. No sequence starts without you opting into it.
Forward the PDF to anyone you like, including a consultant you are considering. It is designed for that.
The honest part
The session is the cheap half. Enforcement is the retainer.
Answering these twenty-five questions well takes a focused half day, and you now have that part for nothing. What a retainer mostly buys is not the session. It is somebody whose job is to remember what you said in it, for months, while you are busy.
Doing it by hand
What enforcement actually costs
Agent Craft’s own time estimate, not a published statistic. Twelve hours is not the obstacle. The obstacle is that it is twelve hours of catching yourself, on your own material, in the weeks when you are pleased with something that quietly breaks a rule you set in March. A consultant charges the retainer largely because they are not you and therefore notice.
Agent Craft
Answer them once. They govern everything after.
These are the questions Agent Craft’s strategy layer asks during onboarding, built on best practice and twenty years of leading global brands. The difference is not the questions. It is what happens to the answers afterwards.
- Your outcome, audience, stance, banned words, off-limits list and dread topic become standing rules rather than a document you never reopen
- Drafts that drift off the position get caught before you see them, including the ones drifting toward the topic you named in question twenty-two
- Your banned words from question eighteen are enforced on every draft, permanently, which is a rule no human retainer reliably holds
- You record a two-minute voice note a week and it comes back as finished content in your voice across LinkedIn, X, TikTok, and YouTube
30-day free trial · no credit card required
Before you ask
Reasonable questions
Why publish the questions if you sell the thing they lead to?
Because they were never the defensible part. Any competent strategist asks roughly these, and a list that only worked if you bought from us would not be worth forwarding to a colleague, which is the main thing we want this document to do. What is hard to copy is enforcing twenty-five answers on every post for a year, and that is what the last two pages are about.
Can I use this to interview consultants?
That is one of the two intended uses and it is stated on page two of the PDF. Watch whether they ask the follow-ups or accept your first answer, and whether they ask question twenty-five at all. Both tell you more about what you are buying than any case study will.
Do I need to answer all twenty-five?
Movements one and two are load-bearing and the rest degrade gracefully. If you have ninety minutes rather than four hours, do questions 1 to 11 properly and come back. Doing all twenty-five badly is worse than doing eleven of them honestly.
Is this the same as the Brand Positioning Workbook?
No, and they work well in sequence. This is a discovery session: someone else asking you questions, in an order, with follow-ups. The workbook is eight structured exercises you complete on paper. This one is faster and more diagnostic. That one goes deeper and produces fillable output.
Who is this not for?
Anyone hoping to be handed conclusions, since the document only asks. And anyone for whom a five-thousand-a-month retainer is not a real alternative, because the framing throughout assumes you are weighing that against doing it yourself. The list still works, it is just not written for you.