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