It's funny, his very first paragraph hints at what I've found to be the most effective way to handle difficult conversations:
"All my biggest regrets as a founder are around not having difficult conversations sooner. I could have helped team members improve faster, fired people with the wrong fit earlier, had so many more productive meetings. I could have created a more open company culture."
"Sooner". Give difficult information out in small bit immediately. Waiting and letting things bottle up only makes it harder. You also build a relationship with the person receiving the bad news of honesty and openness from the get go.
If I'm managing a report that did something wrong, I address it immediately. They get used to me being honest and prompt with my feedback. Addressing a single issue immediately also mean things don't build up and you're not forced to "bundle" bad news together.
Of course you should also do this with positive feedback but I think you'll find that when you regularly and openly address negative issues, it becomes much easier on all parties involved.
Depends on culture and formality of the relationship. I noticed some key differences working with people in the US, Scandinavia, Netherlands, India, Germany, Russia, and other places.
In the US, people will insist everything is awesome and great right until they get fired. Reason, they can be on the street in under 15 minutes and that kind of puts some filters in place. It also means that you need to follow up with some questions to get a real feel for what is going on. A peculiar thing with Indians I've worked with (superiors even) is that they seem reluctant to say no even when they mean to. So if you ask a direct question and you get an evasive answer, more questions are needed.
"All my biggest regrets as a founder are around not having difficult conversations sooner. I could have helped team members improve faster, fired people with the wrong fit earlier, had so many more productive meetings. I could have created a more open company culture."
"Sooner". Give difficult information out in small bit immediately. Waiting and letting things bottle up only makes it harder. You also build a relationship with the person receiving the bad news of honesty and openness from the get go.
If I'm managing a report that did something wrong, I address it immediately. They get used to me being honest and prompt with my feedback. Addressing a single issue immediately also mean things don't build up and you're not forced to "bundle" bad news together.
Of course you should also do this with positive feedback but I think you'll find that when you regularly and openly address negative issues, it becomes much easier on all parties involved.