Tactics for Hard Conversations

Some days, real estate investing feels easy – you’ve invested well, the market is going great, and all the pieces are falling into place.

Then – a market cycle hits.  Or a tornado.  Or you find out a contractor was stealing from you.  Or you just need to let a valued partner go because they can’t beat a competitor’s prices.

It’s time to have a hard conversation.

Effective communication is crucial in the world of real estate, especially when dealing with investors and contractors.  Here are my favorite tactics drawing on Chris Voss’ work as a hostage negotiator.

[Chris Voss has books, podcasts, Masterclasses, and so much more if you want to dive deeper.  Highly recommended no matter your industry.]

Change Perspective

Before you have the conversation, do what you can to understand the situation from all perspectives.  Take your ego out of the equation – really think like you were an investor or a contractor coming at this from a different angle.  The more you know about them the easier this is.  Your goal is to build empathy and trust.  That way you can figure out how to explain your position from their perspective while getting them to trust you.

However, recognize if you DON’T know something too.  Maybe a family member just died, or they had another project go under that they won’t tell you about.  These unknowns can impact the conversation just as much, so try to think of at least a few of them beforehand.

Changing perspective is crucial in being able to preserve a relationship even after the hard conversation.


I struggle the most with this one. In hard conversations, both sides are struggling to control emotions with logic.  It’s a tough place to be mentally.  Letting the other party have their say, then asking them follow-up questions to really understand their position, helps a lot with building trust, getting to the real root of the problem and keeping the emotions under control on both sides.

Mirroring and Labeling

These super simple techniques are helpful even in normal conversations.  I use them all the time now. In hard conversations they help defuses tension between the different parties.

Mirroring is just saying the last few words the other person said.  That’s it.  The technique shows you listened and gives the other person an opportunity to talk about it further if they want.

Labeling is just naming what emotion you think the other person is feeling.  “Sounds like you are stressed” or “Sounds like you are frustrated” for example.  Say it, then let the other person talk again to see if they agree or not.  Repeat until both sides understand what is really going on.

Really simple and effective.  Try it on your friends and family to see what happens.

Navigating hard conversations with investors and contractors in real estate requires a strategic and empathetic approach.

By incorporating tactics such as changing perspective, active listening, and mirroring, you increase the likelihood of a productive outcome in challenging discussions.

Effective communication is not just about reaching an agreement; it’s about building long-lasting relationships that contribute to the success of your real estate ventures.

P.S. All the situations in the intro are ones I’ve either been in or heard about in the past month.  These are not hypothetical – and they are becoming more frequent.  Improving your soft skills now will lead you through the inevitable hard conversations down the road.

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