stephenrogan/manager-one-on-one-prep

Manager 1:1 Prep

Structures your manager 1:1 so it is a 30-minute working session, not a 30-minute status update. The 1:1 is the most valuable recurring meeting in your calendar -- it is your direct line to support, coaching, and career advocacy. Most CSMs waste it by walking in unprepared and defaulting to account status recaps.

How to Use

Provide:

• Your portfolio highlights this week (what changed, what matters)
• Any specific accounts you want to discuss (with context on why)
• Blockers or asks (things you need from your manager)
• Wins (things that went well -- your manager needs to know these for their own reporting)
• Development topics (skills you are working on, feedback you want)
• Time since last 1:1 (what happened between then and now)

The 1:1 Structure

Block 1: What Changed (5 minutes)

Not a portfolio review -- a curated highlight of what is different from the last 1:1.

| Category | What to Share | What Not to Share | |----------|-------------|------------------| | Risks surfaced | New at-risk accounts, escalations initiated, competitive signals | Stable accounts with no change | | Wins | Accounts saved, expansions closed, milestones achieved, customer praise | Routine completions (calls made, emails sent) | | Status changes | Accounts that moved health bands, renewals that progressed or regressed | Accounts that are exactly where they were last week |

Rule: If nothing changed since the last 1:1, say so in one sentence and move to Block 2. Do not manufacture updates.

Block 2: Accounts to Discuss (10 minutes)

Bring 1-3 accounts where you need your manager's input, not their awareness. The test: "I need your help thinking through X" qualifies. "I wanted you to know about Y" does not (put that in your weekly status update).

For each account:

[Account Name] -- [ARR] -- [Health] -- [Renewal: date]
Situation: [2-3 sentences]
What I have done: [1-2 sentences]
Where I am stuck: [the specific question or decision I need help with]
What I think I should do: [your recommendation -- bring a proposal, not just a problem]

Your manager's value is not in telling you what to do. It is in seeing patterns you cannot see, challenging assumptions you are not questioning, and providing resources or connections you do not have. Frame your discussion around the judgment call, not the operational detail.

Block 3: Blockers and Asks (5 minutes)

Things you need from your manager that you cannot get on your own:

| Ask Type | Example | How to Frame | |----------|---------|-------------| | Resource | "I need engineering to prioritise the Acme API fix" | "Can you raise this with [engineering lead]? I have escalated through support but it has stalled for 10 days" | | Decision | "I need approval to offer a 10% discount to save the Beta renewal" | "Here is the commercial context. My recommendation is [X]. Do I have authority to proceed?" | | Introduction | "I need a VP-to-VP call with the Delta CFO" | "I have the account brief ready. Can you or [VP name] make the outreach?" | | Air cover | "The Gamma escalation may come up in the leadership meeting" | "Here is the situation and what we are doing. You may want to know this before [meeting]" | | Coaching | "I am struggling with executive engagement on my top accounts" | "Can we use 10 minutes to walk through my approach to the Acme executive conversation?" |

Rule: Every ask has a reason, a recommended approach, and a specific request. "Can you help with Acme?" is not an ask. "Can you escalate the Acme API fix to [engineering lead] by Thursday? I have the brief ready" is.

Block 4: Development (5 minutes)

Reserve the last 5 minutes for your growth. This is the time most 1:1s lose because the account discussions run over. Protect it.

| Topic | Example | |-------|---------| | Feedback request | "I led the Delta QBR last week. What feedback do you have on how I handled the competitive question?" | | Goal check-in | "My goal this quarter is to lead 3 executive conversations independently. I have done 1. I want to debrief on how it went" | | Career discussion | "I want to talk about what the path to [next role] looks like and what gaps I need to close" | | Skill development | "I am working on commercial acumen. Can you point me to opportunities where I can practise building business cases?" |

Rule: Do not wait for your manager to bring up development. They are busy. If you want coaching, ask for it. If you want career guidance, initiate the conversation.

Block 5: Close (2 minutes)

• Confirm action items from the discussion (yours and theirs)
• Confirm the next 1:1 date
• Flag anything you need before then

Output Format

## 1:1 Prep: [CSM Name] -- [Date]

### What Changed
- [Change 1]
- [Change 2]

### Accounts to Discuss
**[Account Name]** (EUR [ARR] | [Health] | Renewal: [date])
Situation: [summary]
Stuck on: [specific question]
My recommendation: [proposal]

### Asks
1. [Specific ask with context]
2. [Specific ask with context]

### Wins
- [Win 1]
- [Win 2]

### Development
Topic: [what I want to discuss]
Ask: [specific coaching or feedback request]

### Carry-Forward from Last 1:1
- [Item manager committed to last time -- status]

The Carry-Forward Hack

Track what your manager commits to in each 1:1. Not to hold them accountable passive-aggressively -- to gently close the loop:

"Last week you mentioned you would raise the Acme escalation with [engineering lead]. Any update?"

This signals that you take the 1:1 seriously and that you are tracking outcomes, not just having conversations. Managers respect this.

Quality Gates

• Do you have at least one account to discuss (not just report on)? If you are only sharing status, you are using the 1:1 as a report, not a working session
• Is every ask specific? "I need help" wastes time. "I need you to escalate X to Y by Z" uses time well
• Have you brought a recommendation, not just a problem? Managers coach better when you propose an approach for them to react to rather than presenting an open-ended situation
• Is there a development topic? If development is absent from every 1:1, your career growth is not being discussed with the person who has the most influence over it
• Is the prep under 1 page? The prep is a tool for the conversation, not a document to present. Bullet points, not paragraphs

Principles

• The 1:1 is your meeting, not your manager's. You set the agenda, you bring the topics, you drive the conversation. If your manager fills the 1:1 with their agenda, you are not preparing well enough
• Status updates belong in writing, not in the 1:1. Send a weekly status update by email or Slack. Use the 1:1 for the things that require discussion, judgment, or a decision
• Your manager cannot help you if they do not know what you need. Most managers do not ask "how can I help?" unprompted. If you need something, say it directly. They would rather know than wonder
• Consistency compounds. A well-prepared 1:1 every week builds your manager's confidence in you, gives them the data to advocate for you in leadership meetings, and creates a pattern of proactive communication that distinguishes you from peers who only surface problems when they are crises