AI Guides › Playbooks
By Nigel Guy · 7 min read
Most people use AI to do one thing in a job search: paste in the advert and ask for a CV that echoes it. Everyone else with the same tool is doing the same, so the hiring manager sees a pile of near-identical, keyword-matched documents. It feels productive because the output is polished, and it fails because polish is exactly what AI makes free.
The rule: stop proving you match the advert; show the manager you have already looked at their problem. Send a short plan built on one real gap, not a rewritten CV.
This is a playbook for a small number of well-chosen roles, not a way to apply to two hundred. It takes a few evenings per target, and that is the point.
The Gap Memo is a one-page document with four fixed parts. You build it in five stages.
| Part | What goes in it | What it must not be |
|---|---|---|
| 1. The gap | One specific problem or missed opportunity you can see from outside | A generic complaint ("your social presence is weak") |
| 2. The evidence | Two or three things anyone could check: a page, a listing, a public figure, a customer review | Anything you cannot point to |
| 3. The first fix | A small piece of work you have actually done, attached or linked | A promise or a mock-up you are passing off as finished |
| 4. The ninety days | Three blocks (learn, contribute, own), each with one outcome | A list of activities |
| 5. The ask | One sentence: a 20-minute conversation | A request for a job |
Choose roles where the output is visible from outside: a website, a product, a public-facing process, a published report, a job advert that describes a pain. If you cannot see anything from outside, the role is a poor fit for this method. Three to five targets is plenty.
Read the advert for what it is worried about, not what it lists. Phrases such as "improve", "build from scratch" or "reduce" point to the real problem. Then look at the company's public footprint for evidence. Write the gap as one sentence in the form: "[Observation], which probably costs you [consequence], and I can see it from [source]."
AI is useful here as a sparring partner, not an oracle. It can help you list candidate gaps and challenge your reasoning. It cannot know what is true inside the company, and it will happily invent plausible-sounding problems. Every claim in the memo must trace to something you checked yourself.
Make one small, real piece of work that addresses the gap: a rewritten onboarding email, a cleaned-up spreadsheet of their public data, a prototype, a short audit. Keep it to what you can do in an evening or two. If it needs their private data, do not guess; say what you would need and leave it out.
The ninety-day format is a familiar shape: learn in the first month, contribute in the second, take ownership in the third. Use it, but write outcomes, not activities. "Meet the team" is an activity. "Agree with you which two metrics define success for this role" is an outcome. Be honest that your first thirty days are about listening: you are working from outside information, and the plan should say so.
Find who the role reports to. Company websites, the advert itself and professional networking profiles usually tell you. Messaging people you are not connected to on LinkedIn is limited. According to LinkedIn's help page, you can message non-connections through certain routes (shared groups, current coworkers, or Premium members with Open Profile enabled), and InMail is part of paid plans. Check the current rules and the £ price at checkout before paying for anything. Email is often simpler if you can find an address legitimately.
Send the memo as a short message with the file attached or linked. Also apply through the official route if there is one, so you are not bypassing a process; mention the application in your message.
Use this after you have done the research yourself. It structures your notes; it does not do the looking.
You are an experienced hiring consultant helping a candidate prepare a one-page proposal for a hiring manager. Your job is to organise facts the candidate has already verified, not to add new ones.
Inputs from me:
- Role and company: [ROLE_AND_COMPANY]
- Hiring manager's name and title (if known): [MANAGER_NAME_AND_TITLE]
- The gap I think I have found, in one sentence: [GAP_SENTENCE]
- Evidence I have checked myself (with where I found each item): [EVIDENCE_LIST]
- The piece of work I built and what it shows: [FIX_DESCRIPTION]
- My relevant experience, honestly stated: [MY_EXPERIENCE]
- What I do not know about the company: [KNOWN_UNKNOWNS]
Steps:
1. Check my inputs. If any evidence lacks a source, or my gap sentence makes a claim the evidence does not support, list those problems and ask me questions before writing anything.
2. Write the memo with these headings: The gap, The evidence, The first fix, The ninety days, The ask.
3. In "The ninety days", give three blocks (days 1-30, 31-60, 61-90), each with one outcome, one way of knowing it worked, and one dependency on information only the company has.
Constraints:
- Maximum 450 words. Plain, direct British English. No flattery of the company, no buzzwords.
- Use only the facts I supplied. Do not invent figures, internal details, or company plans.
- Where I have not given you something, write "[NEEDS INPUT]" instead of guessing.
- The ask must be a 20-minute conversation, not a job.
Before answering, check each sentence against my inputs and remove any that you cannot trace to them. Then list anything you removed.
Fill in the square-bracket fields with your own notes; keep the "known unknowns" honest.
Act as a sceptical hiring manager at [COMPANY_TYPE] who receives about thirty unsolicited messages a week. Here is my memo: [PASTE_MEMO].
1. Say in two sentences what you would take away from it.
2. List the three weakest claims and why you would doubt each.
3. Say what would make you reply, and what would make you delete it.
4. Flag anything that sounds generic, flattering, or too certain about things I could not know from outside.
Do not rewrite it. If something is unclear, ask me one question first.
Fill in the type of company and paste your draft.
Say you are a customer-support lead applying to a small online retailer that is hiring a "Head of Customer Experience to improve response times". Hypothetically, you notice that their returns page gives no timeline and their public reviews repeatedly ask when refunds arrive. That is your gap and your evidence. Your fix is a rewritten returns page and a three-email refund-status sequence. Your ninety days: month one, agree what "response time" means and read a sample of tickets; month two, ship the sequence and measure repeat contacts; month three, document the process so someone else can run it. Your ask: twenty minutes to find out whether you have read the problem correctly. Nothing in this is a claim about a real company.