Morning paper outreach
Use this skill early each morning to turn a curated publication you subscribe to into warm, specific touchpoints. Produces a short list of the day's stories worth sending, who each one goes to and why, and a drafted note for each that you review before sending. Also use for "who should I send this to", "daily reading for client outreach", "turn the paper into touchpoints", "curate and cultivate".
Andrew KappelPrincipal, LeaderLev ConsultingApplies first thing each morning, on a schedule, against a publication you pay for. Produces three to five article-and-person pairs with a drafted note each, for review before anything is sent.
The play
- Read the day's edition of the source you subscribe to, in full, through your own account. One strong curated source beats a feed: the value here comes from the paper being edited by someone good, so the agent is choosing among pieces that already cleared a bar. Other subscriptions can be swapped in; what cannot be swapped in is anything you do not have the right to read.
- Hold a people file: clients, prospects, partners, friends, with what each one works on, what they have said they care about, and when they were last contacted. The fields and how to build the file from scratch are in references/people-file.md. Without it the picks are generic, and a generic send is worse than no send.
- Match stories to people on a specific reason, not a topic overlap. "Logistics person, logistics article" is not a reason. The test, the four kinds of match that work, and the do-not-send list are in references/matching-rules.md.
- Cap the day at three to five pairs. The cap is the discipline that keeps this from becoming a mailing list. If a day's edition yields one good pair, send one.
- Draft a note per pair, two or three sentences, that says why it made you think of them and asks nothing. The patterns, with examples, are in references/note-patterns.md. A note with an ask attached converts the gesture into outreach and the recipient feels the difference immediately.
- Branch by the relationship:
- Client, mid-engagement: only send something that bears on their work, never something that reads as marketing.
- Prospect in an open deal: send sparingly. During a live negotiation, do not send at all.
- Lapsed contact, over a year: acknowledge the gap in a half sentence and move on. Pretending it has not been a year is the thing people notice.
- Friend: looser, shorter, and no business framing at all.
- Anyone who has not replied to the last two sends: stop. The rule is in references/matching-rules.md.
- Review every note before it goes. The skill drafts and never sends, because the entire value is that the recipient believes a person chose this for them.
- Record what you sent, what you edited and what you killed. Tomorrow's picks read yesterday's record. The log format and what each signal changes are in references/feedback-loop.md.
What good looks like
- First thing I check that most people skip: when I last contacted them. A perfect article match to someone contacted twice this month is worse than no send, and the people file is the only thing that catches it.
- The mediocre version: five articles a day to the same twenty people, each with "thought you'd find this interesting". It is a newsletter nobody subscribed to, and it teaches the whole list to ignore you.
- I know a pick is right when the note could not be sent to anyone else without rewriting it.
- I know the system works when people reply about the article rather than thanking you for sending it.
- Red flag: the same five names every week. Either the people file is too small or the matching has collapsed into topic overlap.
Rules
- MUST read the source through your own paid subscription, and never circumvent a paywall.
- MUST link to the article rather than pasting its text, and keep any quoted line short.
- MUST have a specific reason per pairing, naming something about that person.
- MUST cap the day at five, and send fewer on a thin day.
- MUST review every note before sending. The skill never sends on its own.
- MUST check last-contacted before every send.
- NEVER attach an ask, a meeting request or a pitch to one of these notes.
- NEVER send to someone who has not responded to the last two.
references/feedback-loop.md
The feedback loop
The picks improve because yesterday's decisions are recorded and read. Without the log, day 200 is exactly as good as day 1.
Log every pick, including the rejected ones
2026-10-31 | Sam Oyelaran | tariff exposure piece | SENT, edited
edit: cut the second sentence, too explanatory
2026-10-31 | Dana Reyes | ERP post-mortem | KILLED
reason: topical only, she's not replacing anything
2026-10-31 | Mark Liu | freight capacity | SENT, unedited
2026-10-31 | Priya Shah | lab-grown piece | HELD
reason: good match, but contacted 9 days ago
Four outcomes: sent unedited, sent with edits, killed, held. Killed and held matter more than sent, because they teach the boundary.
What each signal changes
| Signal | Tomorrow |
|---|---|
| Sent unedited | That kind of match is working. More of it. |
| Sent with edits | Record what was cut. Edits cluster, and the pattern in them is the real instruction. |
| Killed, topical only | Raise the specificity bar for that person |
| Killed, wrong tone | Adjust the note pattern for that relationship type |
| Held, too soon | Frequency working as intended. No change. |
| Replied | Strongest signal available. Note what the match was built on. |
| No reply, twice | Stop sending to that person, per the people file |
The edits are the lesson
A thumbs down says a pick was wrong. An edit says exactly how it was wrong, which is far more useful. Keeping the before and after of an edited note, rather than just the fact of the edit, is the single highest-value thing in this log.
After a month, read the edits in one sitting. They will cluster into three or four recurring corrections, and those become fixed rules rather than per-note fixes.
Weekly, five minutes
- How many sent, how many replied
- Which names came up more than once, and whether that is right
- Which names have not come up in two months, and whether they should have
- Any edit made more than twice, which is now a rule
The number that matters
Replies per send, over a month. Not sends, not opens.
Under roughly one in five, the matching is generic and the fix is the people file rather than the notes. Well above that, the cap could probably rise slightly, though the discipline is usually worth more than the volume.
What does not go in the log
Nothing the recipient said in confidence, and nothing about them that they did not share with you. The log sits alongside the people file and inherits the same obligation: it exists to help you be useful to them, and it should be something you would be comfortable with them reading.
references/matching-rules.md
Matching a story to a person
The test
Write the reason in one sentence naming something specific about them. If the sentence works for three people in the file, it is a topic, not a match, and the send is generic.
| Fails | Passes |
|---|---|
| "She's in logistics, this is about logistics." | "She said in March they're terrified of tariff exposure on the Mexico lane. This is about exactly that lane." |
| "He's a CFO and this is a finance piece." | "He's replacing their ERP this year and this is a post-mortem on one that went badly." |
| "They'd find this interesting." | "His old company is named in paragraph four." |
The four kinds that work
1. Their stated problem. Something from the said field, addressed directly. The strongest match available and the rarest, because it needs the file to be real.
2. Their world, not their industry. Their customer's industry, their competitor's move, their acquirer, their biggest account's sector. People read endlessly about their own industry and almost nothing about the industries one step away that determine their year.
3. A person they know. Someone they worked with, their old company, an investor, a board member, named in the piece. Nearly always worth sending, and it takes ten seconds to notice.
4. The thing they are not paid to think about. Their hobby, their city, their kid's sport, a book they mentioned. The least business-like and often the most effective, because it is unmistakably not a program.
What never gets sent
- Anything about layoffs, downturns or distress in their sector, unless they raised it first
- Anything where your product or service is the obvious implied answer
- Anything critical of their company, their customers or their investors
- Anything they almost certainly read already. Their own industry's lead story is not a gift.
- Opinion pieces on politics, unless they have an explicit, standing shared interest
- Anything from a source you did not read yourself
That fourth one disqualifies more candidates than anything else. The paper's biggest story in their sector is the one piece they have definitely seen. Value comes from the pages they skipped.
Ranking the day
Score each candidate pair:
| Factor | Weight |
|---|---|
Match is from said, with a date | Highest |
| Match is one step from their industry, not inside it | High |
| A person they know is named | High |
| Story is from deeper in the edition, not the front page | Moderate |
| Last contacted over 6 weeks ago | Moderate |
| Match is topical only | Disqualifying |
Take the top three to five. On a thin day, take one. The cap protects the thing that makes this work.
The relationship branch
- Client, mid-engagement: must bear on their work. Anything else reads as a vendor filling space.
- Prospect, open deal: sparingly, never during live negotiation, and never anything adjacent to what you are selling them.
- Partner: the easiest sends. Referral-relevant pieces are genuinely useful to them.
- Lapsed over a year: half a sentence acknowledging the gap, then the article. No explanation of your absence.
- Friend: shorter, no framing, no sign-off that sounds professional.
references/note-patterns.md
The note
Two or three sentences. Says why it made you think of them. Asks for nothing.
Shape
[The specific reason, referencing something of theirs.]
[One line on what the piece says, in your words.]
[Link.]
No greeting beyond their name, no sign-off beyond yours. Anything longer starts to look like an email you wanted to send anyway.
Examples
From something they said
Sam, you mentioned the Mexico lane tariff exposure back in March. This is the first thing I've read that puts a number on it. [link]
A person they know
Dana, your old boss at Tessera is quoted halfway down this. Thought you'd want to see it before someone forwards it to you. [link]
One step outside their industry
Mark, this is about what's happening to their customers rather than to them, which I suspect is the part that actually hits your pipeline next year. [link]
The non-work one
Hey, this is just a good piece about the Leafs' goaltending problem. No business content whatsoever. [link]
Lapsed contact
Priya, it's been far too long. Saw this on the lab-grown side and remembered you were sceptical of the whole category two years ago. Curious whether you still are. [link]
That last one carries a question, which is allowed because it is about the article. The forbidden thing is an ask about you.
Never in these notes
- "Hope you're well" and anything else that fills a line
- "Thought you'd find this interesting". Says nothing, and signals a template
- Any ask: a meeting, a call, a reply, an introduction
- Your product, your service, your availability
- A pasted paragraph from the article. Link to it, say one line about it
- A summary longer than the note
- More than one article in a single note
Length
Under 50 words. Over that, the recipient reads it as an email rather than a passing thought, and the whole premise is that it was a passing thought.
The copyright line
Link, never paste. One short quoted line at most, in quotation marks, and only when the exact wording is the reason for sending. The recipient either has a subscription or does not; forwarding the full text of a piece you pay for is not a favour you are entitled to do.
The review step
Every note is read before it goes. Three checks:
- Could this be sent to anyone else in the file without edits? Then it is not specific enough.
- Is there an ask hiding in it, including an implied one?
- Would it read as odd if they had not heard from you in six months?
The edits made at this step are the most valuable training signal the system produces, which is what the feedback log is for.
references/people-file.md
The people file
The matching is only as good as this. Everything else in the skill is mechanical; this is the part that takes a month to get right and then pays out for years.
Fields
| Field | Example | Why |
|---|---|---|
name | ||
relationship | client / prospect / partner / friend / alumni | Sets the tone and the frequency cap |
company and role | VP Ops, 200-person freight brokerage | The obvious layer |
works on | Replacing a TMS by Q3 | The actual matching surface |
cares about | Hiring in a tight market, his daughter's hockey | What makes a send personal rather than professional |
competitors and customers | Names | Their industry news is their competitor's news |
said | "We're terrified of the tariff exposure" | Verbatim, with a date. The highest-value field. |
last contacted | date, and whether they replied | The guardrail |
do not send | Anything about layoffs | Earned the hard way |
works on and said are what separate a specific match from a topical one. A role tells you their category; a quote tells you their week.
Building it
Do not try to fill it for 200 people. Start with 25, the ones where a well-timed note would actually land, and let it grow as conversations happen.
Sources, in order of value:
- Things they said on calls, verbatim, with dates
- What they post themselves
- Their company's announcements, funding, hiring pages
- What mutual contacts mention
- Their title and company, which is the weakest and the one most systems stop at
Keeping it current
Two minutes after any real conversation: update works on, add anything to said, update last contacted. Done weekly instead, it rots, because the specific phrasing is gone by Friday.
Once a quarter, read the file end to end. Entries whose works on has been the same for a year are stale, and anyone with no said entry has never actually been talked to.
Frequency caps
Per relationship, sends of this kind only, not all contact.
| Relationship | Maximum | Note |
|---|---|---|
| Client, mid-engagement | Once a month | They hear from you plenty already |
| Prospect, open deal | Once a quarter, never during live negotiation | |
| Prospect, no open deal | Once every 6 weeks | |
| Partner | Once a month | |
| Friend | No cap, but it should not feel like a system | |
| Lapsed, over a year | Once, then wait for a reply |
The stop rule
Two sends with no response of any kind: stop sending to that person. Not a pause, a stop, until something else happens between you.
Unanswered sends do not accumulate goodwill. They accumulate evidence that you are running a program, which is the one thing this whole approach is trying not to be.