Marsden Kline

Building a Modern Mom & Pop Shop. Helping 1M leaders level-up.

[Marsden Kline @marsdenkline]

Join us this week ! Make good on your good intentions.

[Dave Kline @dklineii]

I've trained 1500+ managers. Two skills make or break them: setting expectations and holding people accountable. But both take hours to get right, so they rationalize skipping them. AI removes the friction, not the conversation. Here's the old way vs the new way:

[Dave Kline @dklineii]

I've hired hundreds of people. My worst hires didn't fail on skill. They failed on things I could have caught in the interview. Here are 5 hiring mistakes that cost me the most (and how I catch them now):

[Marsden Kline @marsdenkline]

@Codie_Sanchez SMB

[Dave Kline @dklineii]

As a new manager, my biggest regret was tolerating missed deadlines. I thought I was being understanding. I was actually teaching my team that their commitments were optional. And whatever you tolerate becomes your new standard. Here are 3 tests to build real accountability:

[Marsden Kline @marsdenkline]

@dklineii The parallels to parenting are real...

[Marsden Kline @marsdenkline]

@KateBour @TheCoolestCool we did! Loving it...

[Dave Kline @dklineii]

I used to put hard management conversations off. I'd over think them. Or worse, jump into them unprepared. This only made them harder. Now I can prep in 10 minutes with my AI chief of staff and walk in calm and confident. Here's how:

[Marsden Kline @marsdenkline]

My favorite thing about teaching is helping others skip my mistakes.
Live today at Noon ET.
Join us

[Dave Kline @dklineii]

The biggest mistake I made as a manager: Not managing up. I thought my team's impact was obvious. I assumed my boss was plugged in. I was convinced I'd be more valuable if I just "handled it." Wrong! Here's how to stop making excuses and what to do instead:

[Marsden Kline @marsdenkline]

@youderian I have been looking forward to hearing about your adventure. Love this- perhaps the thing I admire most was that you decided it couldn't wait.

[Marsden Kline @marsdenkline]

Give structure to your listening tour.

[Dave Kline @dklineii]

If you want to succeed as a new manager, you must survive the overwhelm of your first 90 days. Driving performance. Making calls. Navigating politics. All while building your own credibility as a leader. Here's the playbook I give to every new manager:

[Dave Kline @dklineii]

When I first started managing, I delegated work terribly. 5 minutes of vague direction and an encouraging "you'll figure it out." Three weeks later, I'd be underwhelmed. The fix wasn't more detail. It was greater precision. Here's are the 5 lines you need to delegate anything:

[Marsden Kline @marsdenkline]

I love a good commencement speech. I have a new favorite.

[Country Sayings @countrysayingss]

Eric Church delivered one heck of a commencement speech before closing it out with Carolina… #EricChurch #UNC #countrymusic

[Marsden Kline @marsdenkline]

I'm a fan of Prompt 4: 'What might they bring up that I'm not ready for?'

[Dave Kline @dklineii]

I used to walk into 1:1s flying blind. Glance at the agenda. Hope the conversation went somewhere useful. Walk out wondering what I missed. Now my AI prep takes 5 minutes. The 1:1 hits different. Here are 5 prompts I run before every 1:1:

[Marsden Kline @marsdenkline]

All in on teaching live. Encouraging debate. Solving real problems. And building the skills file that helps you make good on your good intentions. Harness the power of AI to help you show up in the moments that need you most .

[Dave Kline @dklineii]

https://t.co/lEtHB7YMIp

[Marsden Kline @marsdenkline]

Make the investment up front or pay the cost to swoop in later…

[Dave Kline @dklineii]

95% of work problems are caused by one thing: unclear expectations. The manager is frustrated. The employee is confused. Everyone's stuck. Here's my simple playbook you can run to get (and stay) on the same page in 15 minutes:

[Dave Kline @dklineii]

After several promotions, I was convinced I made great decisions. Strategy. Hires. Big bets. I remembered the ones that worked out. Conveniently forgot the ones that didn't. I started keeping a decision journal. Huge wake up call. Here are 4 prompts to build yours with AI:

[Marsden Kline @marsdenkline]

Help us settle a debate...

[Marsden Kline @marsdenkline]

Sharing the pre-work for Wednesday's workshop.
Join us to build your Management Second Brain

[Dave Kline @dklineii]

Smart leaders learn from their mistakes. Wise leaders learn from the mistakes of others. And AI-powered leaders? They learn from both.

Here's the 30-minutes of pre-work our Management Second Brain students are doing this weekend. Steal it start compounding.

---

# Pre-Work: Generate Your Raw Inputs

**Purpose:** Produce the `/raw-inputs/` folder you'll need for the workshop, with maximum leverage from material that already exists in your world and minimum writing burden on you.

Target: **30 minutes**, most of it pointing at existing artifacts rather than writing new ones.

---

## Before you run the prompt

Gather any of the following you can get to easily. You don't need all of them — the more you have, the less you'll have to type.

- **Your last 2–4 weeks of 1:1 notes** (any format — Notion, Notes app, Google Docs, a text file, photos of a notebook)
- **Your 1-2 weeks of manager-related Slack DMs or channels** (exports, screenshots, or just paste the relevant threads)
- **Important manager-relevant email threads** from the last month
- **Your calendar** (last 2–4 weeks)
- **Existing docs** about your team, roadmap, OKRs, strategy, re-orgs
- **Performance review notes** on your direct reports (if you have them)
- **Staff meeting or all-hands notes**
- **Any doc or Slack thread about a decision you made recently** (promotion, reorg, scope cut, hire/fire, etc.)

If you have almost none of this, that's fine. The prompt handles that case too. It will just ask you more questions directly.

**One non-negotiable:** have your phone or a way to dictate a short voice memo handy. The "signature move" question is much easier to talk through than to write.

---

## The Prompt

Paste everything below into Claude, with your source materials linked or pasted in the `[PASTE OR LINK]` slot. Run it in a fresh chat.

```
I'm preparing for a Management Second Brain workshop. I need to generate a /raw-inputs/ folder that captures enough about my team, my boss, my org, and my decisions that a workshop-level brain can be built from it.

**I want MAXIMUM leverage from what already exists. Don't make me write polished pre-work. Pull from the artifacts I give you and ask me targeted questions only where you genuinely can't infer the answer.**

Here are my source materials:

[PASTE OR LINK TO YOUR ARTIFACTS — 1:1 NOTES, SLACK, EMAILS, DOCS, CALENDAR. Paste whatever you have. It's OK if it's messy. It's OK if some is irrelevant. Don't curate — just dump it.]

---

Your process, step by step. Do not skip ahead.

### Step 1 — Inventory

Read everything I've pointed you at. Tell me what you found:

- How many people appear frequently enough to plausibly be on my team (names + rough frequency of mentions)
- Who my manager appears to be (based on calendar + communication patterns)
- What projects / decisions have been most active in the last 6–12 weeks
- What signals you see about organizational pressures (hiring freezes, reorgs, strategy shifts, tension between teams)
- What's MISSING from what I've given you. Examples: "I see 1:1 notes for three people but they only appear in your calendar twice each — are there other directs I should know about?" or "I see a name 'David' in your emails a lot but you don't seem to have 1:1s with him — peer? Boss's peer? I need to ask."

Wait for me to confirm the inventory is roughly right before moving on. I'd rather correct you here than let errors propagate into 5 files.

### Step 2 — Draft what you can, then ask what you can't

For each input file below, draft what you can from the source material first. Then — and only then — list the specific questions you need to ask me to complete it.

Files you're producing in /raw-inputs/:

- **team-notes.md** — one section per direct report covering: role, tenure, 2–3 specific strengths, 1–2 growth edges, motivation (surface vs deep if there's a distinction), communication style (ESPECIALLY what to AVOID), what I'm currently coaching them on, recent concerns or wins.

- **boss-notes.md** - my manager's current top priorities, communication preferences (including any "language tells" — phrases they use that signal specific meanings), relationship dynamics, open asks I have from them, sensitivities (what would damage the relationship if I got it wrong).

- **org-notes.md** — company at a glance, my unit's mission, current pressures, key stakeholders beyond my boss (peers I compete or cooperate with, cross-functional partners, executives who matter), political dynamics (who has momentum, who has air cover, who doesn't).

- **decisions-notes.md** — 2–4 significant decisions I've made or am making in the last 6–12 weeks. For each: situation, options I considered, what I chose, why (INCLUDING the gut reasoning — not just the analytical version), expected outcome.

- **signature-move.md** — one management move I do well. One that's mine, not textbook.

### Step 3 — Ask me questions in BATCHES, not all at once

Ask me 3–5 questions at a time, not a giant list. After each batch of my answers:
1. Update the relevant draft files
2. Briefly show me what changed (one or two lines per change, not full re-drafts)
3. Ask the next batch

**Rules for your questions — this matters:**

1. **Be specific. Anchor every question to something you actually saw in my material.**
- Bad: "What's Jordan's communication style?"
- Good: "I see your 1:1 note with Jordan on [date] was short — just 'fine, numbers on track.' For some people 'fine' is 'actually fine.' For others it's a tell. Which is it with Jordan?"

2. **Offer multiple-choice or quick-format when possible.**
- "Quick gut check on Jordan: (a) checked-in and happy, (b) flight risk, (c) frustrated but staying, (d) I don't know. Pick one — you can elaborate in one sentence if you want."

3. **Suggest voice memos for things easier spoken than typed.**
- "This one is easier to talk through than write. If you've got 60 seconds, dictate a voice memo and paste the transcript: what's something you do well as a manager — a specific move you make that works? Describe it in your own words."

4. **Don't re-ask what I've given you.** If I've already told you something in the source material or in an earlier answer, move on. Don't make me re-confirm obvious things.

5. **If I can't answer a question, mark the gap explicitly in the draft file and move on.**
- Write: `[UNKNOWN — Dave couldn't recall or didn't have an answer. Revisit after first workshop pass.]`
- Don't get stuck waiting for a perfect answer. An 80% file is what we want.

6. **Batch your questions by person, then by topic.** Don't jump around. It's easier for me to answer 4 questions about Priya in a row than 4 questions across 4 different people.

### Step 4 — Handle the signature move question with care

The signature-move question is the hardest one for most people to answer about themselves, because the move is usually tacit — you do it without noticing.

If I haven't volunteered one in my source materials, ask this:

> "What's one move you make as a manager that you're genuinely good at — something that works for you repeatedly, that you've done enough times to trust it? It might be a specific question you ask when someone's checked out, a way you handle a hard conversation, a particular approach to setting expectations, a way you sequence difficult news. Don't try to be generic or textbook. Describe one move in your own words, in 3–5 sentences, in the language you'd actually use."

If I say "I don't know" or "I can't think of one," don't let me off the hook. Offer these three prompts, one at a time:

1. "Think about the last time a 1:1 went well with someone who was struggling or checked out. What did YOU specifically do that made it go well?"
2. "Think about a time a peer or report told you that something you did was helpful. What did they name specifically?"
3. "Think about what a former boss or mentor has told you that you're good at as a manager. What was it?"

If I still can't find it, mark signature-move.md as `[UNKNOWN — dig for this during the workshop]` and move on. Don't let this block the rest of the work.

### Step 5 — Produce the final output

Once I've answered enough to fill the files with reasonable completeness:

1. Save all five files to /raw-inputs/
2. Show me a summary: for each file, how complete is it, and what's still marked UNKNOWN
3. Flag which of the five files is the weakest and would benefit from more source material if I can dig some up
4. Tell me whether I'm ready for the workshop, or whether the gaps are big enough that I should add more source material first

### Ground rules for you throughout this process:

- **Don't invent.** If I didn't give you evidence for a claim about someone, don't write it as if I did. Plausible-sounding fabrications are the main failure mode here, and it's worse than leaving a gap.
- **Don't ask broad, generic questions.** Every question should be anchored to something specific you saw or something concrete I can answer in under 2 minutes.
- **Don't make me read long outputs before answering.** Show drafts when I explicitly ask or at the end of each batch — not in the middle of a question cycle.
- **Don't over-ask.** If a field is low-value and I haven't given you anything about it, leave it blank with a placeholder rather than asking about it. The workshop prompts will surface what matters.
- **If I'm providing very little source material, tell me early** — within the first two messages. Say: "You've given me [X]. The brain will be thinner than if you'd also given me [Y]. Do you want to provide more, or proceed with what's here?"

Start with Step 1. What did you find?
```

---

## After the prompt finishes

You should have five files in `/raw-inputs/`:
- `team-notes.md`
- `boss-notes.md`
- `org-notes.md`
- `decisions-notes.md`
- `signature-move.md`

Some fields may be marked `[UNKNOWN]`. That's fine. The workshop prompts will often surface what's missing in a way that's easier to fill in later. You don't need perfect inputs — you need honest ones.

**One sanity check before the workshop:** skim each file for 30 seconds. Does it sound like you? If it reads like a management textbook, some of the AI's guesses survived that shouldn't have — flag them in the file with `[CHECK]` and we'll address them during the workshop.

---

## If you get stuck

**"I don't have any 1:1 notes, emails I want to paste, or anything structured."**
Tell the AI that up front: "I don't have good source material — I've been operating mostly from memory. Ask me questions directly." It will switch modes and run a longer question-and-answer session with you. Budget 45 minutes instead of 30.

**"I have too much material — my Slack alone is thousands of messages."**
Don't dump everything. Give the AI just the last 2 weeks of Slack plus the last month of 1:1 notes. More material is not more useful past a certain point, and it will slow down the inventory step.

**"The AI keeps asking me questions I don't think it should need to ask."**
That's a signal. Usually means either your source material is thinner than it looks, or the questions are anchored to the wrong details. Push back: "You already have X in my 1:1 note from March 15 — re-read before asking me about that person's motivation." The AI should recover and move on.

**"The AI's draft is wrong about one of my people — they've mischaracterized them."**
Correct it specifically and in the AI's voice. Not "that's wrong" but "your draft says Jordan is 'struggling with confidence' — that's backwards. He's overconfident, which is actually his risk. Fix that and also check whether it propagates anywhere else in the file." The correction trains the AI's read on the rest of the person.

[Marsden Kline @marsdenkline]

How to transform a chatbot into your Chief of Staff.

[Dave Kline @dklineii]

https://t.co/XNvycK71o0

[Dave Kline @dklineii]

I used to think setting goals for my team was just picking targets. Numbers. Deadlines. Milestones. Then I learned the target matters less than the right mix of goals. Choose poorly and your team's excellent work is wasted. Here are the 3 kinds of goals that actually move teams: