Illustration: Oscar Ramos Orozco

5 Strategies for Tackling Tough Conversations

One of the hardest parts of being a leader is having difficult conversations: firing someone, getting into it with a client, apologizing for a mistake, or delivering bad news. Many of us choose avoidance as often as possible. That uncomfortable feeling (in your gut, your hands, in the back of the throat) is a warning sign: tough conversation ahead.

In the book Difficult Conversations by Douglas Stone, Bruce Patton and Sheila Heen, the authors write, “Our anxiety results not just from having to face the other person, but from having to face ourselves.”

Whether the source of the conflict stems from circumstance, a challenge to your identity as a leader, or protecting ones turf, stemming the tide of personal emotions and dealing in a direct, measured way can let the air out and diffuse conflict effectively.

Here are some methods to use with your team, your boss, or anyone else in the face of everyday conflict.

1. Draw out possibility.

Instead of using a blunt doorstop of a statement like, “This is the problem!” turn it into a question. “What would you say if…?” or “Could it be that…?” are both great disarming phrases.

2. Share the impact.

One tactic to disengage harsh feelings is to share the anxiety or tension that you feel about the conversation. Andrew Lightheart, who runs workshops about how to communicate in high-stakes situations and writes the blog, A Peaceful Resolution, says communicating your anxiety about the conversation can help you “step out of automatic roles and become a bit more human.” Just stating your discomfort can soften the prickliness.

3. Use silence.

Silence works especially well when facilitating teams of people through rough terrain like a strategy session or a pressure-filled meeting. Throw something out there and wait. See what bubbles up. Most people need to fill up the conversational space with words, so learn to embrace uncomfortable silences. Sometimes it just takes a moment for the important stuff to hatch. Just wait.

Communicating your anxiety about the conversation can help you step out of automatic roles and become a bit more human.

 4. Coax insight.

Not to be confused with giving advice. The phrase, “and what else?” lets your cohort formulate Option 2, usually a more measured and calmer, though less intuitive, response.  “And what else?” is one of the most powerful questions according to Michael Bungay Stanier in his book, Do More Great Work. He offers variations on this theme: “Do you have any further thoughts on this?” and “Can you think of anything else?”

5. Extinguish blame.

The need to blame is a reactionary feeling; it’s quite normal. But blame usually signifies more complicated emotions. In Difficult Conversations, the authors encourage talking in terms of “joint contribution” rather than blame, even though that tactic can feel incomplete. Blame, they say, “is a stimulus to search further for hidden feelings. Once those feeling are expressed, the urge to blame recedes.”

Dealing head-on with your emotions can minimize anxiety and make tough conversations easier to handle. After all, a tough conversation is usually less difficult in hindsight.

How about you? 

What’s in your bag of tricks? How do you deal with tough conversations?

Scott McDowell

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Scott McDowell is a strategy consultant and a coach to new managers & first-time leaders. He wrote New Manager Handbook to help leaders in transition panic less. He also hosts a radio show called The Long Rally on WFMU.
load comments (11)
  • YinMom YangMom Mere

    I just wanted to mention, you should seriously consider making at least 1 image “pinnable” on Pinterest. I loved the article and would most likely return to it if I could pin it rather than Tweet or bookmark it.

  • Sean Blanda

    Thanks for the heads up. A new site design is on its way!

  • Signs Now Fort Wayne

    I have to know that I’m right with myself. I have to get honest with myself first, and then do everything I can to speak from that place of honesty, even if it IS admitting that I am uncomfortable or nervous. I find that this has a tremendous impact on how my message is perceived.

  • KB

    I totally agree!

  • Scott Wagers

    Thanks for the clear guide on handling difficult conversations. It is true that avoidance is perhaps the worst strategy for dealing with difficult conversations.

    I partcularly like your point about silence. Silence is sometimes the most important part of a conversation. I facilitate a lot of teleconferences and teleconferences are full of awkward silences. Yet, it is clear that silences, or pausing to summarize gives people time and space to process the conversation and get past the initial reaction. It also gives them time to be creative.

  • Slim

    Waaw Great !

  • Girl in New Orleans

    I really liked this article/advice. I enjoyed seeing “silence” on there because that is what I do, even outside of difficult conversations. Remember, “A fool can be mistaken for an intellect if he keeps his mouth shut”.
    Also, do you mind if I post a link to this article on my website. Maybe not immediately but I am adding a section/page for articles to checkout. I really liked it thanks!

  • alex ghita

    Drink a glass of GYN TONIC! before the conversation..will be much fun!

  • Aaron Morton

    The trick to handling difficult conversations is to make sure you present yourself as equal within the conversation whilst maintaining control of the situation (the direct opposite to what happened with piers morgan against Alex Jones this week). The other person won’t take on board what is being said if they feel patronised or looked down on.

    Good article and something a lot of people have trouble with.

    Aaron Morton

  • Aaron Morton

    you may need a Gin after as well if you take that strategy!

  • Diana

    I just recently had a few tough conversations with my best friend. I had never really gotten mad at her before and sort of realized after processing and journalling that I *was* mad.. what really helped was saying that I felt afraid and she also reciprocated. Communicating over text is hard… but this is how we dealt with our conflict. The best approach would be to meet in person, granted, but it’s hard when you are cities away. Learning that communicating over text is not always the best way to resolve our conflicts.

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