Difficult Conversations: How to Discuss What Matters Most

Author: Douglas Stone, Sheila Heen, Bruce Patton
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This Month Reddit 2


by flakyfilibuster   2022-03-03
Lots of good recommendations in the thread.

I found this one to be pretty valuable: https://www.amazon.de/Difficult-Conversations-Discuss-What-M... (sorry, amazon link)

Because, obviously you're going to get into situation as a manager where you have to have difficult conversations.

by yboris   2021-12-22
I think since communication is vital to any professional setting, one of the best impact-per-point-of-improvement may at first come from better communication.

A great book that provides a framework for dealing with difficult conversations is Difficult Conversations, written by a team at Harvard that spent years on practicing and refining conflict-resolution.


by lithasblot   2021-12-10

My SO and I are both super sensitive-- we decided to study NVC together (non-violent communication) and also read this book-- I highly recommend it. Transformative: https://www.amazon.com/Difficult-Conversations-Discuss-What-Matters/dp/0143118447 .

by Cdn_Nick   2021-12-10

I'll add:





by lionhearted   2021-06-08
"Difficult Conversations" was a great read —


The basic idea is that in any difficult conversation, there's actually three sub-conversations happening —

(1) What happened?

(2) How do we feel about it?

(3) What are we going to do about it?

A lot of times people get into cross-talk or can't get on the same page because they mix up what sub-conversation they're happening. This can happen when one person gets right into proposing solutions (#3) while another person is still trying to work out why things went the way they did (#1). Likewise, sometimes a conversation around "we really screwed this up" is meant to be a neutral "what happened" conversation (#1) but is taken as a negative or put-down (#2).

Useful book. Very readable and informative.

by BeetleB   2020-12-16
I would say both. If you had to pick one, go with DC. However, there were some things in CC that I didn't find elsewhere. As an example, it focuses on how a lot of people don't realize they're in a poor/tense conversation until it's too late, and it emphasizes the need to develop the skill to become aware of this.

OTOH, CC attempts to prescribe how to behave are pretty poor. I would not focus too much effort on emulating those.

At first read, all 3 sound like fairly different books. A year after I read them, I was going over all the notes I had made for them, and was surprised to find out that all 3 are mostly saying the same things.

As for the authors:

Difficult Conversations: https://www.amazon.com/Difficult-Conversations-Discuss-What-...

Crucial Conversations: https://www.amazon.com/Crucial-Conversations-Talking-Stakes-...

by vincentmarle   2020-11-21
I can highly recommend this book when it comes to preparing for difficult conversations (aptly named "Difficult Conversations"): https://www.amazon.com/Difficult-Conversations-Discuss-What-...
by sergeyfilippov   2020-06-08
"Difficult conversations" [1] would be the best direction, to my knowledge. It is written by creators of Harvard Negotiation Project that deals with conflict resolution.

Audiobook version [2] is narrated by authors, and it's great.

[1] https://www.amazon.com/Difficult-Conversations-Discuss-What-...

[2] https://www.audible.com/pd/Difficult-Conversations-Audiobook...

by nickpinkston   2019-12-09
I feel you. I think you'd like Good Authority. Very concrete and actionable on all kinds of management practice:


If you're looking for office communications, I've heard good things about "Difficult Conversations":


by aok1425   2019-07-12
My friend had recommended to me a book called Difficult Conversations: https://www.amazon.com/Difficult-Conversations-Discuss-What-...
by maroonblazer   2019-07-12
At least in the U.S. culturally I think we still have a long way to go when it comes to having what some have termed 'difficult conversations'[0]. In essence, confronting people with their behavior but in a way that's respectful and focused on the impact it has on the recipient (me) as opposed to the aggressor. Sure, it may not change their behavior, but processing the experience and the associated emotions - at least in my experience - is more effective than not dealing with them at all.

[0]There's a good book on this subject called "Difficult Conversations": https://www.amazon.com/Difficult-Conversations-Discuss-What-...

by DoofusOfDeath   2019-07-12
I've also heard good things about "The Art of Hard Conversations: Biblical Tools for the Tough Talks That Matter" [0] and "Difficult Conversations: How to Discuss What Matters Most" [1].

Can anyone comment on the relative merits of these articles' / books' approaches?

[0] https://www.amazon.com/Art-Hard-Conversations-Biblical-Matte...

[1] https://www.amazon.com/gp/product/0143118447/ref=oh_aui_sear...

by fab1an   2018-02-26
No framework, but I'd very much recommend reading up on "Difficult Conversations"[1], which has been very helpful for me ever since becoming CEO.

Giving feedback, more often than not, will constitute a difficult conversation, and the concept helps a lot with navigating those in a way where both parties can learn and grow from both emotional and 'semantic' conflicts.

[1] https://www.amazon.de/Difficult-Conversations-Discuss-What-M... Brief summary here: http://www.fscanada.org/wp-content/uploads/2013/12/Difficult...

by fdb   2017-08-20
I recommend "Difficult Conversations", which is an excellent book on this topic. It gives many good examples of difficult conversations, analyzes them and provides great advice.


by dustincoates   2017-08-20
fsniper made a good recommendation with "How to Win Friends and Influence People."

I'd also put in a recommendation for a book I stumbled upon when searching through Hacker News called "Difficult Conversations."


I got the same feeling from reading the book as the original recommender ( https://news.ycombinator.com/item?id=7762266 ): reading the book made me feel instantly better at being able to communicate when having difficult or tense conversations. I can't recommend it enough.

by peteforde   2017-08-20
Your friend is lucky to have a friend that is willing to tell them the truth; most people are cowards when it comes to saying the most important things until it's too late. We're pretty much trained from birth to tell people what we think that they want to hear because it feels good to tell someone that they're brilliant. Giving someone the truth even if it's bad feels awful. If we only ever tell someone that their idea is great, what do we do when their next idea is actually great? "This one is really really great!" "Last time I was lying but this time it's actually great!"

I strongly recommend the book Difficult Conversations to everyone, period. It's one of the best books on negotiation that have been written in the past 20 years. It's very hands-on and practical, and after reading it I immediately felt like I had levelled-up in all of my communications. It made giving feedback much simpler.


Instead of telling someone that their idea sucks, you should instead tactfully tell your friend that after consideration you don't think his idea will survive a customer development process. Then suggest he reads The Four Steps to the Epiphany or The Lean Startup (or paraphrase the important concepts) and urge him to validate his concept before becoming too emotionally invested, lest he invest in a solution in search of a problem. Dane Maxwell makes a great point about retiring from having ideas in favour of what he calls "idea extraction":


Your friend should remember that a startup is a temporary business structure that exists only to prove or disprove a hypothesis about a market opportunity in the fewest number of steps (time, money, resources). You don't say why his idea will never work (my wild guess is that it's probably a two-sided marketplace, which is near-impossible to launch because it's actually two businesses at once that both need to succeed at the exact same time == marketing $$$) but rookie founders are often trying to do WAY too much. Maybe there's a gem of an idea there that's good, and it just needs to be simplified to its essence.

You might ask your friend "why you?" both because he might not have any business starting this company where anyone person might. Investors like to see an unfair advantage; wealth, political connections, celebrity status are all examples... but the best is having someone on your team that has deep experience in the domain. Starting a real-estate site and nobody on your team has worked in real-estate? Good luck.

Also in the "why" category is a literal "why are you doing this?" question which many people glaze over. Sometimes people just have a flight of fancy and do things that seem like a good idea without it actually being something that they truly care about. Aside from being a recipe for disaster, Simon Sinek explains that people don't buy what you do, they buy why you do it:


Finally, you might want to explain to your friend how an investor evaluates a startup. In order:

1. Market opportunity 2. Team 3. Traction 4. Product

Most founders HATE this because they don't want to confront that product is the least important criteria for a term sheet. Obviously you need a great product; that's table stakes. Investors have to first be convinced that there is a real market opportunity, and it has to be big enough to matter if the company succeeds. Bad pitches start with a focus on the product and promise that the market opportunity is there. Good pitches are all about how you've put together a great team to attack a large, demonstrable market opportunity. Great pitches are about great teams with a great opportunity that have demonstrated growth through traction.

In the end, products frequently change and investors know this. Very occasionally you can convince an investor that your product vision is so important that it needs to exist even though you have a questionable market opportunity, an unknown team and no sales to date. However, at this point you're actually competing with every other startup pitching that investor because no matter how brilliant that they think you and your idea are, they have a fiduciary responsibility to the LPs to make the best investments that they can. If a VC backs a product they like over a boring product with great traction, team and opportunity, then they are not a very good VC.

In the end, most startups fail and your friend is awesome for being willing to try anyway. Despite his fancy MBA if this is his first rodeo, he owes it to his future self to be honest about what he's doing. He should spend a year at another startup learning by osmosis before he tries to start up.

This is all strong opinions which are strongly held. I think having strong opinions is one of the most valuable things someone can do. In fact, my job is to tell important people awkward truths and anyone who suggests you should not "pile on" negativity is not someone you should go to for startup advice.

by BeetleB   2017-08-19
I just gave a presentation at work about how we're ridiculously overeducated on technical skills, and ridiculously undereducated on social dynamics.

I mean, I solved more complex technical problems in my undergrad than I've ever had to in my career.

My suggestion: While you may want to master a technical skill or two, become good at what they don't teach you:

Negotiation skills:



The Coursera course from the University of Michigan is decent, if you don't want to read. But the other course (from Yale?) - I would not recommend that as a starter.

Communication Skills:






(His work is often cited in other books - especially related to negotiations).



Finally, a word of advice. Most of us here on HN have no trouble reading stuff and grasping its content. Internalizing it, though, will take work. So don't run away reading all these books. Pick one topic (e.g. negotiation), and read up on it. Take notes (I forget 80% of what I've read after a few months). And try to practice it.

Life is a marathon, not a sprint. Just focus on one till you feel you are good at it (perhaps for a year). Then pick another topic.