Written by James Chae — Co-Founder, Expert Sapiens
Platform expertise: Professional training & instruction · Reviewed June 2026
Session Prep
Professional skills sessions are most effective when you bring a specific challenge, not just a general area you want to improve. The more concrete your input, the more targeted the coaching. Before your session, identify one or two situations where you felt your skills fall short — a presentation that didn't land, a negotiation where you gave ground you didn't need to, a project that went over budget. Bring the actual situation, not an abstraction. Real examples unlock real coaching.
1.Based on what I've shared, where am I strongest and where is the biggest gap relative to my goal?
A trained instructor will hear things in how you describe your work that reveal gaps you may not be aware of. Ask for an honest diagnostic.
2.What mistakes do people at my level most commonly make in this skill?
Common mistakes are predictable — an experienced instructor has seen them repeatedly and knows exactly how to correct them.
3.What would someone watching me [present, negotiate, manage a team, write code] notice first as an area for improvement?
External perspective is one of the most valuable things an instructor provides. Ask for the honest outside view.
4.Can you walk me through how you would handle [a specific scenario I've struggled with]?
Seeing an expert model the skill in a real context is more instructive than abstract explanation.
5.For [a specific technique I'm trying to develop], what are the most common mistakes people make when learning it?
Knowing the failure modes in advance helps you avoid them rather than discovering them through repeated errors.
6.What should I practice between sessions, and how will I know if I'm doing it correctly?
Deliberate practice between sessions is where skills are actually built. Ask for a specific protocol and a way to self-evaluate.
7.How do I know when I've genuinely internalized this skill versus just knowing it intellectually?
There is a difference between understanding a skill and being able to execute it under pressure. Ask how to tell which side of that line you're on.
8.What's a realistic timeline for me to reach [your specific goal] at the pace we're working?
Honest expectations prevent both complacency and discouragement. Ask for a direct answer with a basis.
9.How would you recommend I track my progress between now and our next session?
Progress tracking is a skill in itself. Ask for a specific method, not just 'practice more.'
10.What's the single most important thing I should focus on before our next session to make the most progress?
Forces prioritization. The most effective instructors know which lever moves the most for a specific learner at a specific moment.
Written by James Chae — Co-Founder, Expert Sapiens
Platform expertise: Professional training & instruction · Reviewed June 2026