Managing Up Playbook

Purpose

Your relationship with your boss determines your success as a manager. This skill helps you communicate effectively upward - getting support, surfacing problems, and building trust with leadership. You will create specific strategies for your situation.

When to Use

Use this Skill when you need to:

• Tell your boss about a problem without looking incompetent
• Ask for more resources, headcount, or support
• Push back on unrealistic expectations
• Get clearer direction or priorities
• Improve a difficult relationship with your boss

Step-by-Step Process

Step 1: Understand Your Boss

Map your boss to work with them effectively.

Ask these questions:

• "How does your boss prefer to receive information? (written, verbal, data, stories)"
• "What are they measured on? What keeps them up at night?"
• "How much detail do they want? Big picture or specifics?"
• "What is their communication style? Direct or diplomatic?"

Boss Preference Matrix: | Preference | Adapt By | |------------|----------| | Data-driven | Lead with numbers, then narrative | | Big picture | Summary first, details available | | Detail-oriented | Thorough docs, anticipate questions | | Relationship-first | Small talk, build trust, then business |

Output Variable: boss_profile

Step 2: Identify Your Managing Up Goal

What do you need from your boss right now?

Common goals:

• Surface a problem: "I need to tell them we are going to miss the deadline"
• Request resources: "I need another engineer on my team"
• Push back: "The scope is unrealistic for the timeline"
• Get clarity: "I do not know what success looks like"
• Build relationship: "My boss does not know what I do"

Ask:

• "What specific outcome do you want from this conversation?"
• "What is making this conversation feel difficult?"

Output Variable: managing_up_goal

Step 3: Frame the Message

How you frame it determines how it lands.

Surfacing Problems - The Bad News Formula:

1. State the situation clearly (no burying the lead)
2. Own what you can own
3. Present options or recommendations
4. Ask for what you need

"We are going to miss the March deadline. Here is why, here is what I have tried, and here are our options..."

Requesting Resources - The Business Case:

1. Start with the business need (not your pain)
2. Show the math/impact
3. Present options at different investment levels
4. Make a clear recommendation

"To hit the Q2 targets, we need X. Without it, here is the risk..."

Pushing Back - The Tradeoff Conversation:

1. Confirm the ask
2. Show current commitments
3. Present tradeoffs clearly
4. Ask them to prioritize

"I can do X or Y by that date, but not both. Which is higher priority?"

Output Variable: message_frame

Step 4: Anticipate Their Concerns

Think like your boss:

• What will they worry about?
• What questions will they ask?
• What do they need to tell their boss?

Prepare for:

• "Why is this happening?"
• "What have you tried?"
• "What do you recommend?"
• "How does this affect [their priority]?"

Output Variable: anticipated_concerns

Step 5: Choose the Right Moment

Timing matters more than you think.

Good timing:

• Regular 1:1 (expected, private)
• Right after a win (capital to spend)
• Early in a problem (not when it is a crisis)

Bad timing:

• Right before their big meeting
• When they are stressed about something else
• Via Slack for important topics
• Sprung on them publicly

Ask: "When and how will you raise this?"

Output Variable: timing_approach

Step 6: Script the Conversation

Build the actual language you will use.

Include:

• Opening line
• Core message (using the frame from Step 3)
• Responses to anticipated concerns
• Clear ask

Output Variable: conversation_script

Step 7: Generate Managing Up Plan

Create the complete document.

Create a document titled "Managing Up: [Goal]" with full strategy.

Output Format

Managing Up Strategy: [Goal]

BOSS PROFILE:
- Communication style: [preference]
- Cares most about: [priorities]
- Adapt by: [approach]

GOAL: [What you want]

MESSAGE FRAME:
[Chosen frame and approach]

SCRIPT:
Opening: "[Exact words]"
Core message: "[Key points]"
The ask: "[Specific request]"

ANTICIPATED QUESTIONS:
Q: "[Question]"
A: "[Your response]"

TIMING:
When: [Moment]
Setting: [Context]

FOLLOW-UP:
[Next steps after conversation]

Tools

• basile_create_document - Save your managing up strategy

Example

Input: Need to tell boss that a key engineer is leaving and we will miss the roadmap

Output:

BOSS PROFILE:
- Communication style: Data-driven, wants solutions not problems
- Cares most about: Q2 roadmap commitments
- Adapt by: Lead with impact and options, not just bad news

GOAL: Surface the departure risk and get approval to backfill immediately

MESSAGE FRAME: Bad News Formula
- Situation clear: Alex gave notice, last day March 15
- Own what I can: I did not see this coming, retention conversation too late
- Options: Backfill, redistribute, cut scope
- Ask: Approval to start recruiting now

SCRIPT:
Opening: "I have some difficult news about the team. Alex resigned yesterday."
Core: "He owns the payments integration, which is critical path for Q2. His last day is March 15. I have three options to discuss..."
Ask: "I need approval to open a req immediately and potentially adjust the Q2 scope. Can we talk through the tradeoffs?"

ANTICIPATED QUESTIONS:
Q: "Why is he leaving? Could we have prevented this?"
A: "Comp was part of it, but honestly he wanted to try a startup. I should have had the retention conversation earlier."

Q: "What does this do to the roadmap?"
A: "Payments slips 4-6 weeks unless we either backfill fast or cut scope elsewhere."

TIMING:
When: Tomorrow morning 1:1
Setting: Private, not over Slack

FOLLOW-UP:
- Send options doc after conversation
- Set up recruiting kickoff if approved