Career Development Conversation Guide

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

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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?"

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Career / Role / Results Mapping Worksheet

18-Month Milestone Table

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