# Career Development Conversation Guide

> A facilitation guide for the 1:1 conversation where a manager and rep map the next 18 months of role and earning trajectory together: grounded in the skills that unlock it, not just this quarter's number.

Free guide for sales managers. Topic: [Coaching, 1:1s & Feedback](https://www.peerlab.ai/library/topic/coaching-1-1s-feedback/). Published by PeerLab in the [Sales Enablement Resource Library](https://www.peerlab.ai/library/). Source: https://www.peerlab.ai/library/career-development-conversation-guide/

## How to use it

Send the prep questions 48 hours ahead, run the five stages as a dedicated session (not folded into a pipeline review), and leave the meeting with the mapping worksheet and milestone table filled in and dated for the next check-in.

## What's inside

- When to run this conversation (and how often)
- Prep questions for the rep (send in advance)
- Prep questions for the manager
- Conversation flow, 5 stages with word-for-word prompts
- The Career/Role/Results mapping worksheet
- 18-month milestone table
- Follow-up cadence and check-in triggers

This conversation answers a different question than a normal 1:1. A normal 1:1 asks "how's this quarter going?" This one asks "where is this role taking you, and what has to be true to get there?" Run it as its own session: don't bolt it onto a pipeline review, it will lose to the pipeline review every time.

## When to Run It

- Every 6 months at minimum, as a dedicated 45-60 minute session
- Additionally trigger it: after a rep hits a tenure milestone (6mo, 1yr, 2yr), after a promotion cycle closes (whether they got it or not), or when a rep explicitly raises "where is this going."

## Send These Prep Questions to the Rep in Advance (48 Hours Before)

1. "If you fast-forward 18 months, what role or level do you want to be in?"
2. "What's a skill you have now that you think is underused in your current role?"
3. "What's a skill you don't have yet that you think the next level requires?"
4. "Who in the company (or in the industry) has a career path you admire, and why?"
5. "What would need to be true about your day-to-day for you to feel like you're growing, regardless of title?"

## Manager Prep (Do This Before the Session)

- Pull the rep's most recent Skill-Gap Map (Sales Skills Self-Assessment) if one exists
- Note their current competency level against the next role's typical requirements
- Have a realistic view of the next 2-3 role/level paths actually available in this org (don't promise a path that doesn't structurally exist)
- Know the realistic earning trajectory tied to each path (base/variable/comp-plan changes at each level), vague answers here erode trust fast

---

## Conversation Flow

### Stage 1, Anchor on Where They Want to Go (10 min)

> "Let's start with your answer to the 18-month question, where do you see yourself?"

Follow-ups:
- "What draws you to that, specifically?"
- "Is it the role itself, the money, the challenge, or something else?"
- "What does 'winning' look like to you in 18 months: not just title, but what you'd be doing day to day?"

### Stage 2, Name the Skill Gap Between Here and There (15 min)

> "Let's map the skills that role actually requires against where you are today."

- "Of the skills that role needs, which do you already have strong evidence of?"
- "Which ones haven't you had a chance to build yet?"
- "Where do you think the biggest gap is, and does that match what I'm seeing?" *(Share your honest view here, anchored in specific evidence: this is the moment for real feedback, not vague encouragement.)*

### Stage 3: Career Lens: What This Unlocks (10 min)

> "Let's talk about what building that skill actually opens up for you: not just the next title, but the arc."

- "What roles become realistic for you once this skill is solid?"
- "What does the earning trajectory look like across that path, do you want me to walk through the actual numbers?"
- "Is there a version of growth here that doesn't require a title change: a deeper specialization, a mentor role, a bigger book?"

### Stage 4: Role Lens: What This Means Right Now (10 min)

> "Before we get to 18 months out: what would having this skill change about your current role, starting now?"

- "What situations in your current role would you handle differently with this skill built out?"
- "What would this look like in your next call, deal, or account: not as a script, but as a capability you're carrying in?"

### Stage 5: Build the 18-Month Plan (10-15 min)

> "Let's put dates on this so it's a plan, not just a conversation."

- "What's the first concrete thing you'll work on in the next 30 days?"
- "What milestone would tell us, at 6 months, that you're on track?"
- "What support do you need from me specifically: coaching time, a stretch project, an introduction to someone?"
- "How do you want to check progress on this: same cadence as today, or something else?"

---

## Career / Role / Results Mapping Worksheet

| | Career (18-month arc) | Role (right now) | Results (measurable) |
|---|---|---|---|
| **Target skill(s)** | | | |
| **What it unlocks** | e.g., eligibility for Senior AE / Team Lead track | e.g., handles enterprise objections without escalating | e.g., win rate, deal size, ramp speed |
| **Current level** | | | |
| **Gap** | | | |
| **First action (30 days)** | | | |

## 18-Month Milestone Table

| Milestone | Target date | What "on track" looks like | Check-in method |
|---|---|---|---|
| 30 days | | | |
| 90 days | | | |
| 6 months | | | |
| 12 months | | | |
| 18 months | | | |

## Follow-Up Cadence

- Revisit the milestone table briefly at every regular 1:1 (2 minutes, not a full session)
- Run a focused 20-minute check-in at each milestone date in the table above
- Re-run the full Career Development Conversation at 6-month intervals, or sooner if the rep's stated 18-month goal changes