Discipline

• How do you spend your time (e.g. between cold calling, follow-up, upselling, price quotes, etc.)? -- Look for good balance between all these.
  
• Give examples of your having done this -- is there a proven track record
  
• What would former supervisors say about your work? (crosscheck with references)?

Motivation/work style

• How have you handled rejection or a loss? Look for ability to learn from mistakes and move past failures.
  
• What works best for you to keep motivated? Look for internal vs. external source of motivation)
  
• Describe in great detail exactly what you do in a typical day? Look for process orientation, attention to detail, and results vs. activity focus.
  
• Walk me through your most successful deal ever. Look forward motivation, work style, leadership, proactive approach, maturity, etc.
  
• Walk me through your biggest failure (e.g. loss)? Look for lessons learned, and honest appraisal of personal shortcomings vs. company failings.

Skills/Knowledge:

• How do you gain product knowledge? Look for self-starter, quick study.
  
• How do you deal with objections? Look for resourcefulness and listening skills.
  
• What is your strong suit (e.g. closing, contracting, contracting/negotiations, door opening, etc.)? Look for excellent balance between door opening and closing.
  
• What specific tasks have you done in sales (e.g. account planning, contacting, consultative selling, forecasting/reporting, etc.)? Look for depth/completeness.
  
• What areas do you acknowledge need improvement? Look for self-awareness, maturity.
  
• If I called up some of your customers what would they say? Look for comments like “adds value”, “proactive”, “understands my needs”, etc that indicate customer focus, consultative and relationship building not just transactional ability.