9 Tips for Having Tough Conversations

9 Tips for Having Tough Conversations


As hard as it can be, I’ve never regretted having a tough conversation.  I’ve always regretted putting it off or waiting until it’s too late.


During tricky market times like these, tough conversations are swirling ALL around us.  We’re hearing a lot of stories about:


  • Layoffs
  • Budget cuts
  • The difficulties founders are experiencing when it comes to fundraising and the tough decisions that come without the much-needed investment
  • Disappointed buyers
  • Delayed projects 


And the list goes on… it’s not an easy time to communicate! 


That said, we can navigate this challenging time or any challenging situation with grace if we’re approaching these conversations with the right mindset.


So, how does that actually translate in real life?..


A Founder came my way needing to hire “the one” reeling from a pretty significant sales leadership mishire.  We had three “meaty,” meaningful conversations that left both of us wanting more…


Needless to say, my heart stopped and my gut clenched when I received an email with a couple of big red flags waving at me.


They’re an international startup with some big differences when it comes to how they view compensation and equity versus the way we do, here in the US.  


He wasn’t budging regard