Initiating difficult conversations - how do you get better?

5 Replies

Taking on difficult conversations is certainly neccessary in pursuing any aspect of REI (e.g not satisfied with contractor's performance, relaying complaints from one tenant about another, etc).

Some people have have the ability to effortlessly launch into these types of discusssions.

For others, it is more of a challenge to initiate these types of conversations. They find these situations awkward or mentally draining. As a result, they engage in difficult conversations less often than they probably should.

I am probably middle of the road on this spectrum - BUT, I want to get better. Any tips, mindgames, motivators from the BP community?

Hey @Dan C. I struggle a little bit with these types of conversations at times too. For some reason, the hardest one for me is to talk about my dissatisfaction with someone's performance. Whether it be crappy contractor or piss-poor service at a restaurant, I've always been the type to just say "I'll never give them my business again". I figure not going back or calling them again is a pretty clear message. I am working on speaking up more often in these situations but it's not easy. I had really poor service at a national restaurant chain like 15+ years ago and I have never been back, I'm showing them ;-)

you get used to it. i have had to fire my share of realtors, contractors. i most of the time think it's my fault for not communicating properly and say something like, "maybe i did not explain it correctly or didn't specify, but...."

just practice. that's the best way to learn.

My problem is that I am too direct and this still causes problems but the other way round. My perception is that tenants already feel resentful for being their landlord. I tend to have my father intervene between any potential disputes and he really does a great job. I also found my last assistant also had a better and calmer approach to disagreements because she was removed and not personally involved in the issues. She was more like an mediator. She also let me know if she felt I was being unreasonable.

Explain things in writing up front as much as possible - expectations and what happens if they are not met. Then follow the process. It should be easier to approach the topic if it's all layed out in advance.

It's tough. I try to assume positive intent with people, and if the result of their labor doesn't meet your standards, it's due to a lack of understanding. Assuming you screened your tenants and contractors properly.

Before you begin any crucial conversation, give yourself at least 30 minutes or an hour to cool down before engaging in this conversation, your emotions will tell you need to handle this right now, but if you're emotional the results will not be good. Once you're cool, ask yourself "What is the goal of this conversation?" I want X result, I want this person to stop doing Y, and etc. During the convo, if anything you think to say moves you away from that goal, don't say it.

Stay away from ad hominems (You screwed up, your work is crappy etc). Build commonality between you and the person (you've done a good job doing X or Y). Try to set a clear vision of what you want and why it's in the persons interest to do so.

Finally, Read this book and this book.

Free eBook from BiggerPockets!

Ultimate Beginner's Guide Book Cover

Join BiggerPockets and get The Ultimate Beginner's Guide to Real Estate Investing for FREE - read by more than 100,000 people - AND get exclusive real estate investing tips, tricks and techniques delivered straight to your inbox twice weekly!

  • Actionable advice for getting started,
  • Discover the 10 Most Lucrative Real Estate Niches,
  • Learn how to get started with or without money,
  • Explore Real-Life Strategies for Building Wealth,
  • And a LOT more.

Lock We hate spam just as much as you

Create Lasting Wealth Through Real Estate

Join the millions of people achieving financial freedom through the power of real estate investing

Start here