The Best Way to Handle a Difficult Conversation At Work - Deepstash
The Best Way to Handle a Difficult Conversation At Work

The Best Way to Handle a Difficult Conversation At Work

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Start with caring personally

Based on Radical Candor, you have to start by caring personally:

  • You need to know someone on a personal level, know their dreams, fears, and struggles, as well as what matters to them in life.

Knowing what drives a person and their goals give you what you need to address them in a way that will strike a chord. Whatever you’re about to share needs to resonate and align with their personal core values.


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Tell people what they need to hear, not what they want to hear.

Tell people what they need to hear, not what they want to hear.

Easier said than done, but once you do it, you’ll never go back to being a word-mincing mush mouth again.

  • It’s truth time. And it’s starting to feel good.
  • There are plenty of reasons to put off the hard talk or telling someone you care about that it’s time to face the music.

When you reframe what you’re doing as giving someone the benefit of knowing the truth, rather than calling someone out, it might take the sting out for both parties.


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Tell the truth

Tell the truth

None of this candor stuff works unless you’re telling the truth. That’s job one. Since the truth can be a bitter pill, we tend to embellish it a little bit, and before you know it, it bears little resemblance to the actual truth.

  • That doesn’t mean that you should zing your words with a poisonous arrow, but rather, make sure they are factual, don’t exaggerate to make a point and be kind about it.
  • Being honest when you’re sharing will be appreciated. Sometimes it may take a bit of time, but in the long run, your friend or colleague will see it as the caring act that it was intended to be.


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Point out the good

Point out the good

Compliment sandwiches don’t really work because everyone knows what’s coming after the first bit of praise. However, there is something to be said for finding the good and highlighting it.

  • Compliment, hammer, then reframe the compliment. Ugh.
  • It’s important to note is that there is always something good you can point out, even if it’s just the effort or intent. Just because something doesn’t work out or was a flop doesn’t mean everything about it was a fail.
  • Find the good and recognize it.


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Clarify why

  1. What’s the reason for dropping this truth bomb? Is it to address their career growth, their health, their relationship? You need to be crystal clear & make sure it is at the heart of the conversation.
  2. Why does it matter to them & why does it matter to you? If you’re telling a hard truth because you’re giving insight that will help them advance in their career, that’s a great reason for them. 
  3. You should also address why it matters to you: In this case, the reason for your candor on your part may be that you’ve set a personal goal to be better at developing others instead of throwing in the towel


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Rinse and repeat (pay it forward)

Rinse and repeat (pay it forward)

The bottom line is that once you begin the practice of being radically candid, it will become your new way to operate. That’s likely to be your nerves at play, so just hang in there and you’ll improve.

The more you follow this practice, the more you build that muscle for yourself, but you may also be inspiring others to do the same so they can also become great, candid, communicators.

Keep this in mind:

  • It makes sense to address things directly and clearly.
  • It’s helpful and honest.
  • It’s the right thing to do.


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QA @deepstash "Fall down seven times, get up eight!"


No one likes to have the hard talk. If you handle it right, it will make you the best leader in a company, and the best friend anyone could have.

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