M1E3: How to Have First Time Conversations When There’s Specific Context

In this episode, Georgie and I focus on first-time conversations with someone when a specific context has been layed out. These types of chats often happen when you’ve been directly introduced to someone or have met someone because you are each representing organisations with a specific objective in mind. We still label these conversations as forming because there is an opportunity to build a relationship with the other person, but sometimes the context takes centre stage and you forget to explore other ways to connect meaningfully with them.

Georgie and I try out 3 different ways of having the conversation with context:

  • First, I dive directly into the reason for us meeting and bypass any exploratory conversation
  • Second, we create space at the beginning of the discussion for exploration before shifting gears to the intended context
  • Third, we meander our way through the discussion and touch on the initial context for the conversation at a high level, but there’s no abrupt transition from the exploratory portion of the conversation to the planned focus
  • Like last time, we talk about what we noticed in the dialog after each example. We highlight the pros and cons of each strategy and how it might influence outcomes.


  • First conversation example, diving directly into the context [2:34]
  • First conversation analysis start [6:47]
  • How it feels to be directed through a conversation [7:17]
  • What happens when there’s not enough context or understanding of motivation [7:43]
  • Importance of building rapport [8:34]
  • Transferrable trust from the introduction will only get you so far [9:28]
  • Useful questions to ask [10:13]
  • Second conversation example, exploring first before pivoting into the context [11:41]
  • Second conversation analysis start [19:11]
  • The feeling that exploratory conversation creates [19:34]
  • Finding opportunities for mutual value exchange [20:00]
  • Connecting the dots between the exploratory conversation and the specific context [20:41]
  • How the ‘hard pivot’ impacted the conversation [21:11]
  • How worrying about time changes the energy of a conversation [22:00]
  • The importance of thinking about the conversation as the first of many [22:34]
  • What makes these types conversations boring and draining [23:50]
  • Weaving information we’ve learned about the other person into the conversation [24:49]
  • Third conversation example, meandering from exploratory conversation to context [25:54]
  • Third conversation analysis start [34:16]
  • Getting the other person to tell a story that answers some of your questions [35:01]
  • Moving from story to concept rather than the other way around [35:34]
  • How you do something is how you do everything [36:23]
  • Landing on a way to exchange value [37:30]
  • Sharing the motivations and challenging the brief [38:13]
  • Episode key takeaways [39:09]