Just Ask – Day 27

30-Day Writing Challenge

I’m constantly surprised by how open and willing people are to have a conversation with a complete stranger (e.g. me). 

I always thought that reaching out to someone working at an interesting company, in an interesting industry, with an interesting job would be overwhelmed with requests for “virtual coffee chats”, but I’ve proven myself wrong. By simply sending a connection request via LinkedIn with a genuine message, most people are happy to jump on a 30-minute call to tell their story. 

The key here is to never ask for anything in return, meaning when you connect with them never ask for a job. That’s where most people go wrong, they’re immediately thinking about themselves and the short-term outcome. 

My approach here is different, I think about the people I contact and the conversations I have as primary research, similar to an author writing a book. My goal is to understand the person’s “story”… I’ll repeat that… I’m asking for the “story” and nothing else. 

Within the “story” I’m asking questions about their journey, some questions could be… 

  • Tell me a bit about your “story”, how has your life unfolded up to this point? 
  • What inspired you to choose this path for work? 
  • Within the first 2 – 3 years of embarking on this journey, what surprised you both negatively and positively? 
  • If you were to start over at the beginning of your journey today would you take the same path or try something different? 

These are obviously generic questions. When speaking with someone I always tailor the questions to that person based on what’s available publicly online. Another important thing to remember is “follow-up questions”.

The questions I’m asking above should have at least 2 – 3 follow-up questions each because I’m actually listening to them, instead of trying to force all the questions I’ve prepared down that person’s throat. A high-quality conversation should be similar to dancing, if you and your partner are in the moment then the conversation should flow. The prepared questions are just starters to get things kicked off, once we begin to flow they’re no longer needed because we’re feeding off each other’s interest. 

For those of you that think certain people or companies are out of reach, I disagree. 

If you’re willing to just ask, showing genuine interest in the human you’re speaking with and not just their role, company, or industry, then you’ll discover how open people really are. 🙂