{"id":28678,"date":"2021-03-11T16:02:53","date_gmt":"2021-03-11T20:02:53","guid":{"rendered":"https:\/\/www.shortform.com\/blog\/?p=28678"},"modified":"2021-03-26T17:49:42","modified_gmt":"2021-03-26T21:49:42","slug":"challenging-conversation","status":"publish","type":"post","link":"https:\/\/www.shortform.com\/blog\/challenging-conversation\/","title":{"rendered":"The Challenge of Starting a Challenging Conversation"},"content":{"rendered":"\n<p>How do you start a challenging conversation? What can you say to raise the issue in a way that sets the tone for an open and constructive discussion?<\/p>\n\n\n\n<p>Starting a challenging conversation is nerve-wracking. Most of us treat it like we treat swimming\u2014we close our eyes and just jump in, but this is hardly the best way to go about it. <\/p>\n\n\n\n<p>Here is how to start a challenging conversation in a way that sets the tone for an open and non-judgemental exchange.<\/p>\n\n\n\n<!--more-->\n\n\n\n<h2 class=\"wp-block-heading\">How to Start a Challenging Conversation<\/h2>\n\n\n\n<p>The beginning of a challenging conversation is usually the most stressful moment, where we either learn that bad news is coming our way, or that the person we\u2019re talking to is going to get upset. With that in mind, here are the attitudes to take into a challenging conversation:<\/p>\n\n\n\n<ul class=\"wp-block-list\"><li><strong>Replace certainty with curiosity. <\/strong>Don\u2019t believe that your story is the one right story. Challenge why you believe what you do, and ask what you don\u2019t know. Then be curious about someone else\u2019s story and ask questions.<\/li><li><strong>Adopt the And Stance.<\/strong> Embrace that both sides\u2019 stories are valid.<\/li><li><strong>Don\u2019t assume bad intentions of the other person. <\/strong>Just because you feel bad doesn\u2019t mean the other person wanted you to feel bad. Ask what the other person said or did exactly, and what assumptions you\u2019re making about the intention behind it.<ul><li>Even go in assuming good intentions, and phrase things accordingly \u2014 \u201cI was surprised by your comment\u201d or \u201cI thought that action was out of character\u201d imply that you do think they\u2019re a good person.<\/li><\/ul><\/li><li><strong>Question your own intentions. <\/strong>If someone accuses you of harboring bad intentions, avoid being defensive as a reflex. Is it possible you had mixed intentions?&nbsp;<\/li><\/ul>\n\n\n\n<h3 class=\"wp-block-heading\"><strong>Two Bad Openings<\/strong><\/h3>\n\n\n\n<p>These are the two most common ways we start a challenging conversation and the two least helpful ways to do so:<\/p>\n\n\n\n<p><strong>1. We start in directly with our own perspective.<\/strong> If the other person agreed with how we saw things, we wouldn\u2019t be having the difficult conversation. Most of the time, the other person doesn\u2019t know there\u2019s an issue, or has their own perspective on it \u2014 so going in with our own perspective right away can make it seem like we aren\u2019t interested in solving the problem together.<\/p>\n\n\n\n<p><strong>2. We express judgments about their character, and trigger their identity conversation immediately.<\/strong> This is why it\u2019s so important to do away with judgments. The issue is <em>not<\/em> a judgment on the other person\u2019s character, it\u2019s an instance of friction between two people. Especially at the beginning of a difficult conversation, dispensing judgments shows you\u2019re not really interested in a <em>conversation<\/em> or your own contribution.<\/p>\n\n\n\n<p>Sometimes the opening lines are deceptively judgmental, even when you\u2019re trying to discuss your intentions.<\/p>\n\n\n\n<ul class=\"wp-block-list\"><li>What is said: \u201cI was upset by what you said to our boss about our work.\u201d What is implied: \u201cYou are either a betraying scumbag, or you were dumb enough not to realize the ramifications.\u201d<\/li><li>What is said: \u201cIf you move away, it\u2019s going to tear the family apart.\u201d What is implied: \u201cYou\u2019re selfish and don\u2019t care about the family.\u201d<\/li><\/ul>\n\n\n\n<p>Both of these beginnings are common because they\u2019re based in how we see things \u2014 but they also immediately put the other person on the defensive. If the tables were turned, and the other person started a challenging conversation by insulting your character, would you be willing to sit and listen to them explain further?<\/p>\n\n\n\n<h3 class=\"wp-block-heading\"><strong>The Correct First Two Steps<\/strong><\/h3>\n\n\n\n<p>If <a href=\"https:\/\/www.shortform.com\/blog\/your-life-purpose\/\">your purpose<\/a> is to understand the other person\u2019s story, express yourself, and solve the problem together, you need to start the conversation off to set the tone for those things to happen. Start with these two steps.<\/p>\n\n\n\n<h4 class=\"wp-block-heading\"><strong>First, Start From the Third Story<\/strong><\/h4>\n\n\n\n<p>The Third Story is the objective story a mediator or other 3rd party would tell about the current situation. <strong>Mediators try to tell the third story in a way that makes both parties feel understood. <\/strong>The goal of the Third Story is to tell a story that both parties can agree to. It requires them to understand each party\u2019s feelings and use the And Stance to connect the actions and impact that caused the issue.<\/p>\n\n\n\n<p>Mediators know that no one view is right or wrong, they\u2019re just <em>different<\/em>. <strong>The Third Story sets out to illuminate the difference between the views.<\/strong> For example, a mediator working with two roommates on an issue about who does the dishes might summarize it this way: \u201cJason and Jill have different preferences around when the dishes are done and what constitutes appropriate cleanliness. Each is unhappy with the other\u2019s approach.\u201d<\/p>\n\n\n\n<p><strong>To start from the Third Story, you don\u2019t have to know the other person\u2019s story, you can just focus on the difference. <\/strong>\u201cI was taught that dishes should be done immediately after you use them, and that it\u2019s a sign of disrespect to leave dirty dishes in the sink \u2014 but it seems like you have a different perspective.\u201d<\/p>\n\n\n\n<p>Starting from the Third Story doesn\u2019t mean giving up your point of view, it means starting from a neutral place so you can invite the other person to share and participate in the conversation.<strong> <\/strong>Starting from the Third Story shows we <em>care<\/em> about the other person and are trying to improve the relationship for both people.<\/p>\n\n\n\n<p><strong>Even if you don\u2019t get to start the difficult conversation, you can still bring in the Third Story at the earliest opportunity<\/strong>. Use what the other person said as their side of the Third Story, and bring it back around to the difference between your perspectives and your desire to explore the issue.<\/p>\n\n\n\n<h4 class=\"wp-block-heading\"><strong>Then, Invite Them to Participate<\/strong><\/h4>\n\n\n\n<p>Once you\u2019ve told the Third Story in a way that both parties can agree to, you essentially have to <strong>invite the other person to join you in a conversation about mutual understanding and problem-solving.<\/strong><\/p>\n\n\n\n<p><strong>Express your purpose up front.<\/strong> You want to understand their side better, share your side, and then discuss how to move forward. For them to agree to participate, they need to know what they\u2019re agreeing to. This also helps focus them on the right purpose.<\/p>\n\n\n\n<p>But remember: <strong>invitations can be refused.<\/strong> You can\u2019t force someone to participate, no matter how badly you want to. You can only invite, and then it\u2019s up to them to agree or refuse.<\/p>\n\n\n\n<p><strong>Explicitly put them in the role of your <\/strong><strong><em>partner<\/em><\/strong><strong> in the tasks at hand.<\/strong> They\u2019re not solely the problem, and you need them to work this issue out. Let them know that they have equal footing in the conversation (if that\u2019s true), and that finding a satisfactory solution depends on their involvement.<\/p>\n\n\n\n<p>Here are some phrases to use that invite the other person to participate:<\/p>\n\n\n\n<ul class=\"wp-block-list\"><li>\u201cCan you help me understand\u2026\u201d makes them an advisor on what\u2019s going on.<\/li><li>\u201cLet\u2019s work on how we might\u2026\u201d suggests a partnership.<\/li><li>\u201cI wonder if it\u2019s possible\u2026\u201d issues a respectful challenge and allows the other person to ride in and be the hero.<\/li><\/ul>\n\n\n\n<p>The partnership has to be offered genuinely, or it won\u2019t be received well because it won\u2019t seem like you really mean it. <strong>If you\u2019re having trouble viewing them as a partner and not just the problem, be open about that:<\/strong> \u201cThe story I\u2019m telling myself is that you\u2019re being inconsiderate. I know that\u2019s unfair to you. Help me put this in perspective and better understand where you\u2019re coming from.\u201d<\/p>\n\n\n\n<p>Finally, remember to <strong>be persistent.<\/strong> This doesn\u2019t mean you can force them to participate, but you might have to work to get them to understand what you\u2019re asking for. Most people aren\u2019t used to being treated as an equal in a difficult conversation, so it could take some time to shift their mindset about how you\u2019re trying to have the conversation.<\/p>\n\n\n\n<h3 class=\"wp-block-heading\"><strong>General Advice for Starting a Challenging Conversation<\/strong><\/h3>\n\n\n\n<p><strong>Here\u2019s a good structure for approaching the beginning of any challenging conversation:<\/strong><\/p>\n\n\n\n<ol class=\"wp-block-list\"><li>Start with the Third Story.<\/li><li>Try to understand their story.<\/li><li>Share your story.<\/li><\/ol>\n\n\n\n<p>This structure will go the farthest in bringing the other person along with you and easing them into the difficult conversation.<\/p>\n\n\n\n<p><strong>You can also help guide them through the 3 Conversations \u2014 What Happened, Feelings, and Identity \u2014 by asking questions or explaining the conversations to them.<\/strong> Each of you should talk about past experiences that have influenced how you see the current situation. Ask about the other person\u2019s intentions and share the impact their actions had on you. Share what\u2019s going on in your Identity Conversation, and ask what might be going on for them.<\/p>\n\n\n\n<p>Of course, <strong>a real conversation is interactive, and it won\u2019t necessarily go exactly according to schedule.<\/strong> But once you understand the components, you can work with them on the fly. To understand the other person\u2019s perspective, you\u2019ll need to <a href=\"https:\/\/www.shortform.com\/blog\/improve-your-skills\/\">improve your skills<\/a> of asking, listening, and acknowledging. To share your perspective, you\u2019ll have to hone your sense of deserving <em>to<\/em> share your story, and improve your ability to share it concisely. To keep a difficult conversation on track, you\u2019ll have to develop your ability to negotiate it back into the correct focus, if and when it starts to veer off course.<\/p>\n\n\n\n<h3 class=\"wp-block-heading\"><strong>Three Conversations That Might Be More Difficult to Start<\/strong><\/h3>\n\n\n\n<p>Some conversations might feel like they\u2019re harder work than others. Here are 3 common conversations that feel more difficult, and some ways you can make them a little easier:<\/p>\n\n\n\n<h4 class=\"wp-block-heading\"><strong>The Bad News Conversation<\/strong><\/h4>\n\n\n\n<p>Sometimes, you\u2019ve got to be the bearer of bad news \u2014 firing someone, breaking up with someone, and so on \u2014 but you should still aim to have a conversation. It doesn\u2019t mean you\u2019re going to change your mind, but it does mean you respect the other person enough to want them to understand your side and share their side, and to resolve as many of the negative feelings as possible.<\/p>\n\n\n\n<p><strong>It\u2019s best to deliver the bad news first \u2014 don\u2019t draw out conversations where you\u2019ve already decided.<\/strong><\/p>\n\n\n\n<ul class=\"wp-block-list\"><li>For example, if you\u2019re calling to tell your mother you\u2019ve decided to have your own Christmas instead of attending the family Christmas, start there. \u201cWe\u2019ve decided that we\u2019re going to spend Christmas here. I know it\u2019s important to you that we come home for the holidays and I feel guilty about disappointing you, but it\u2019s just too difficult for us financially and emotionally this year to do that. I wanted to let you know as soon as possible, and maybe talk more about our reasoning and how it makes you feel.\u201d<\/li><\/ul>\n\n\n\n<p><strong>If there\u2019s good and bad news, specify that you have both.<\/strong> There may be a logical order to deliver the news in, or you can let the other person decide what they\u2019d like to hear first.<\/p>\n\n\n\n<h4 class=\"wp-block-heading\"><strong>Asking for Something<\/strong><\/h4>\n\n\n\n<p>Sometimes difficult conversations are focused on our desire for something, such as a raise. It can feel one-sided in a different way: \u201cI want a raise, so I\u2019ve got to talk my boss into giving me one.\u201d But these, too, should be conversations instead of demands.<\/p>\n\n\n\n<p>It\u2019s best to still invite the other person to participate and explore the issue with you. <strong>It isn\u2019t unassertive to approach the conversation this way \u2014 it\u2019s more realistic. <\/strong>If you\u2019re asking your boss for a raise, you can\u2019t strongarm them into giving you one, you need them to <em>agree<\/em> that you deserve one.<\/p>\n\n\n\n<p>\u201cI wonder if it would make sense\u2026\u201d is a great phrase to use in these conversations. \u201cI\u2019d like to explore\u2026\u201d is another one.&nbsp;<\/p>\n\n\n\n<h4 class=\"wp-block-heading\"><strong>Previously Difficult Conversations<\/strong><\/h4>\n\n\n\n<p>Sometimes we\u2019ve already had a difficult conversation where someone reacted badly, so it makes us hesitant to enter into the conversation again and get the same bad reaction.&nbsp;<\/p>\n\n\n\n<p><strong>The first step is to talk about how to talk about it this time.<\/strong> The real issue now is the way this conversation goes based on past experiences.&nbsp;<\/p>\n\n\n\n<p>Start with a Third Story about that: \u201cI know that when I\u2019ve tried to talk to you about how busy your schedule is in the past, you\u2019ve felt annoyed or agitated. That\u2019s not my goal. I\u2019m just worried about you. I wonder if we can talk about how to address this issue for both of us, and if there\u2019s a better way the conversation could be had.\u201d<\/p>\n","protected":false},"excerpt":{"rendered":"<p>How do you start a challenging conversation? What can you say to raise the issue in a way that sets the tone for an open and constructive discussion? Starting a challenging conversation is nerve-wracking. Most of us treat it like we treat swimming\u2014we close our eyes and just jump in, but this is hardly the best way to go about it. Here is how to start a challenging conversation in a way that sets the tone for an open and non-judgemental exchange.<\/p>\n","protected":false},"author":7,"featured_media":18967,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_jetpack_memberships_contains_paid_content":false,"footnotes":""},"categories":[34,43],"tags":[230],"class_list":["post-28678","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-communication","category-self-improvement","tag-difficult-conversations","","tg-column-two"],"yoast_head":"<!-- This site is optimized with the Yoast SEO Premium plugin v24.3 (Yoast SEO v24.3) - https:\/\/yoast.com\/wordpress\/plugins\/seo\/ -->\n<title>The Challenge of Starting a Challenging Conversation - Shortform Books<\/title>\n<meta name=\"description\" content=\"Starting a challenging conversation is nerve-wracking. Most just close our eyes and jump in. But here&#039;s how to start more productively.\" \/>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/www.shortform.com\/blog\/challenging-conversation\/\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"The Challenge of Starting a Challenging Conversation\" \/>\n<meta property=\"og:description\" content=\"Starting a challenging conversation is nerve-wracking. Most just close our eyes and jump in. But here&#039;s how to start more productively.\" \/>\n<meta property=\"og:url\" content=\"https:\/\/www.shortform.com\/blog\/challenging-conversation\/\" \/>\n<meta property=\"og:site_name\" content=\"Shortform Books\" \/>\n<meta property=\"article:published_time\" content=\"2021-03-11T20:02:53+00:00\" \/>\n<meta property=\"article:modified_time\" content=\"2021-03-26T21:49:42+00:00\" \/>\n<meta property=\"og:image\" content=\"https:\/\/s3.amazonaws.com\/wordpress.shortform.com\/blog\/wp-content\/uploads\/2020\/11\/how-to-change-someones-mind-influence-scaled.jpg\" \/>\n\t<meta property=\"og:image:width\" content=\"2560\" \/>\n\t<meta property=\"og:image:height\" content=\"1707\" \/>\n\t<meta property=\"og:image:type\" content=\"image\/jpeg\" \/>\n<meta name=\"author\" content=\"Darya Sinusoid\" \/>\n<meta name=\"twitter:card\" content=\"summary_large_image\" \/>\n<meta name=\"twitter:label1\" content=\"Written by\" \/>\n\t<meta name=\"twitter:data1\" content=\"Darya Sinusoid\" \/>\n\t<meta name=\"twitter:label2\" content=\"Est. reading time\" \/>\n\t<meta name=\"twitter:data2\" content=\"11 minutes\" \/>\n<script type=\"application\/ld+json\" class=\"yoast-schema-graph\">{\"@context\":\"https:\/\/schema.org\",\"@graph\":[{\"@type\":\"Article\",\"@id\":\"https:\/\/www.shortform.com\/blog\/challenging-conversation\/#article\",\"isPartOf\":{\"@id\":\"https:\/\/www.shortform.com\/blog\/challenging-conversation\/\"},\"author\":{\"name\":\"Darya Sinusoid\",\"@id\":\"https:\/\/www.shortform.com\/blog\/#\/schema\/person\/0421cce75bc249b11e2517b3a91f9c46\"},\"headline\":\"The Challenge of Starting a Challenging Conversation\",\"datePublished\":\"2021-03-11T20:02:53+00:00\",\"dateModified\":\"2021-03-26T21:49:42+00:00\",\"mainEntityOfPage\":{\"@id\":\"https:\/\/www.shortform.com\/blog\/challenging-conversation\/\"},\"wordCount\":2113,\"commentCount\":0,\"publisher\":{\"@id\":\"https:\/\/www.shortform.com\/blog\/#organization\"},\"image\":{\"@id\":\"https:\/\/www.shortform.com\/blog\/challenging-conversation\/#primaryimage\"},\"thumbnailUrl\":\"https:\/\/www.shortform.com\/blog\/wp-content\/uploads\/2020\/11\/how-to-change-someones-mind-influence-scaled.jpg\",\"keywords\":[\"Difficult Conversations\"],\"articleSection\":[\"Communication\",\"Self-Improvement\"],\"inLanguage\":\"en-US\",\"potentialAction\":[{\"@type\":\"CommentAction\",\"name\":\"Comment\",\"target\":[\"https:\/\/www.shortform.com\/blog\/challenging-conversation\/#respond\"]}]},{\"@type\":\"WebPage\",\"@id\":\"https:\/\/www.shortform.com\/blog\/challenging-conversation\/\",\"url\":\"https:\/\/www.shortform.com\/blog\/challenging-conversation\/\",\"name\":\"The Challenge of Starting a Challenging Conversation - Shortform Books\",\"isPartOf\":{\"@id\":\"https:\/\/www.shortform.com\/blog\/#website\"},\"primaryImageOfPage\":{\"@id\":\"https:\/\/www.shortform.com\/blog\/challenging-conversation\/#primaryimage\"},\"image\":{\"@id\":\"https:\/\/www.shortform.com\/blog\/challenging-conversation\/#primaryimage\"},\"thumbnailUrl\":\"https:\/\/www.shortform.com\/blog\/wp-content\/uploads\/2020\/11\/how-to-change-someones-mind-influence-scaled.jpg\",\"datePublished\":\"2021-03-11T20:02:53+00:00\",\"dateModified\":\"2021-03-26T21:49:42+00:00\",\"description\":\"Starting a challenging conversation is nerve-wracking. 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