In this episode, Stephen Cann (Director of Enterprise Sales, Avoma) and Yaag discuss how and when to challenge your prospect during a deal? Stephen shares his experience on how to challenge the prospect across stages such as prospecting, discovery, indecisive moments, and more. ➡️ Key Points⁣ covered 00:00 - Intro 01:37 - Challenging the prospects all the time 03:05 - Challenging at the prospect stage 04:15 - The key is to understand the problem 04:35 - Qualify and turn down meetings 06:10 - What to look for in the discovery stage 07:59 - Challenging during prospecting vs discovery 08:30 - Need to identify the perceptions of the prospect 10:20 - Helping to surface the problems 11:37 - Digging into the problem 2-3 levels deep 14:40 - Go beyond symptoms to understand the pain 15:40 - Don't be a Labrador rep :) 16:18 - Getting something in return for specific requests 19:48 - What to do when you sense indecision? 22:56 - What gives you the authority to challenge? 26:34 - Key takeaways