Opening Sentences for Tough Conversations
You can avoid tough conversations. You cannot avoid the consequences of avoiding them. The longer you wait, the more courage it takes.
“Clear is kind. Unclear is unkind.” Brené Brown
How to Begin Tough Conversations
Focus on Relationship:
- “I need to discuss something difficult because our relationship matters to me.”
- “There’s something important I’ve been avoiding. I’d like us to talk about it.”
- “I value you. That’s why I need to be honest about something difficult.”
Focus on Growth:
- “I know you care about …. What you’re doing doesn’t serve you.”
- “I care about your success too much to stay silent about this.”
- “I respect your potential. That’s why I need to address something that isn’t working.”
Focus on Conversation:
- “I might not see this perfectly, but I need to share my perspective.”
- “I’ve noticed a pattern that’s creating problems. We need to talk about it.”
Sentences that Derail Tough Conversations
Don’t trigger resistance.
- “You always…”
- “Everybody thinks…”
- “This is probably pointless…”
- “Calm down.”
- “I guess I’m the bad guy.”
- “No offense, but…”
Practical Principle
Start with purpose before problems.
People listen better when they know you care. Stay calm. Be honest. Aim to make things better.
Tough AND Tender
Be kind. Don’t lower standards.
“Be tender with people and tough on standards.” Doug Conant
Too much truth makes you a pit bull.
Too much kindness makes you a doormat.
The cost of tough conversations is less than the price of avoidance.
Which beginning sentence works best for you?
5 Questions to Ask During Tough Conversations
Are You Dreading a Work Discussion? HBR




TOTALLY LOVE your suggested openers for tough conversations! Extremely helpful! Thank you for sharing those with us!
Thank you for your encouragement, Bob. You’re an expert in effective communication.
These opening sentences are not only useful in business life, but are also perfect for everyday personal life situations as well! That serves as a great reminder that quality relationship leadership techniques can serve us well in all aspects of our lives: work, community, and family.
Glad you noticed, Gerry. Practicing good leadership principles leads to the good life at home. Cheers
Don’t make this mistake as I did. I just assumed everyone could see my positive intentions and how much I cared about them. It was self-evident right? Nope. “Willfull Blindness”. People tell themselves wild stories. It’s incumbent on the leader to CLARIFY the intentions. Your intentions are NOT obvious because people tell themselves a story that does not match the facts. My colleague calls this “How they frame it”. Often times you are having a tough conversation because the person is not picking up on all the clues they should see on their own. In other words they are not putting the puzzle together on their own. This includes not being able to see your good intentions. You need to spell it out even though it seems obvious to you. Dan provides the perfect framework for how to do this.
Your insights are so helpful, Brian. “Clarify the intentions.” Sometimes I use the expression, “landing stip.” Create a landing strip for your conversation. That includes clarifying positive intent. I see myself as a fuzzy teddy bear. But I can be intimidating to others. Let out the teddy bear.
So helpful, and about 2 weeks/months/years too late for me. I wish I’d known some of this earlier than today. I’ve been in some tough conversations as a pastor and sometimes my approach has made the matter worse. I’m taking this post to heart – thanks, Dan!
I wish you success, Pete. I’m not sure where you are, but I find many lean toward kindness. They could use more toughness. (I’m not limiting this to church-world.)
Wow, how did you know I needed this article today?!