When to challenge a prospect?

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