Crucial Skills®

A Blog by Crucial Learning

Crucial Conversations for Mastering Dialogue

Discussing Gender Transition

Dear Crucial Skills,

My niece recently turned 18 and is planning to schedule an elective double mastectomy. For the past few years she has identified as non-binary, then she legally changed her name, and more recently she has started taking estrogen blockers that make her voice low. Her dad and mom think that she’s brave and strong. My mom is 100% supportive. I think they’re all insane, and I’ve told them perhaps she’s just confused and that maybe we should encourage her to postpone having body parts surgically removed. They think I’m being intolerant and unsupportive. I haven’t shared my concerns with my niece, but I think I need to try to stop her. Should I keep my mouth shut and watch from the sidelines, or tell her what I really think? If so, how?


Dear Opposed,

Conversations don’t get much more crucial than this. There are differing opinions, very strong emotions, and the stakes are incredibly high (family relationships, mental health and well-being, lasting medical interventions). Variations of this conversation are happening in families, doctors’ offices, communities, schools, and legislatures across the country. Often, the conversations are divisive and painful, leaving people emotionally battered, bruised, and deeply disconnected from one another.

Nowhere is this more true than in our family conversations. Families are where we learn so much about who we are, what we value, how to connect with and see others, how to love and support people, and how to hold boundaries. For most of us, families are where the toughest Crucial Conversations of our lives take place because this is where the stakes are highest, and the relationships mean the most.

While your question is specific in nature, it can also be broadly applied. At the heart of your question seems to be this: Someone I care about is doing something I think is wrong, hurtful, destructive, or dangerous. What should I do?

The two questions you are asking are the right questions:

  • Should I have a conversation?
  • If so, how do I have it well?

Too often, people bypass the first question. They have an opinion, a perspective, or a concern about something or someone and jump right into the fray, presuming that their meaning is obviously needed in the discussion. But simply having an opinion, especially an opinion about what another adult should do with their life, does not mean you should express that opinion.

As you consider whether to raise your concerns, ask yourself:

Has this person asked for my opinion? I have learned that, especially with teens and young adults, my influence is greatest when they approach me seeking counsel. This happens when they are secure in our relationship, and they know that I deeply care for and about them. When they feel safe with me, they will be more likely to ask for my opinion when they have a hard decision to make.

Do I have a relationship with this person? Do I have standing to have this conversation? Managers at work have clear standing to talk with employees about concerning behaviors. Parents have the same clear standing to talk with their children about behavior. Outside of specific structural relationships like these, the lines get more ambiguous. Close friend? Yes. Person sitting next to you on the bus? No.

What is my goal—to have a conversation or tell someone why I think they are wrong? From painful experience, I can tell you with certainty that when your goal is to convince someone that you are right and they are wrong, the conversation will not go well. When my primary purpose is to convince others of the error of their ways, I become a preacher giving a sermon, not a friend having a conversation. If I am to truly have a conversation, my goal must be to listen, learn, and love.

Is the behavior a threat to themselves or others? Is it unambiguously harmful? Of course, you should speak up if your niece threatened harm to self or others, especially in an urgent situation. But this situation seems neither urgent nor unambiguously harmful. My guess is that you would argue that yes, your niece is about to engage in harmful, self-destructive behavior. You are not alone in that opinion. However, there are also reasonable, rational, educated people (including, presumably, your niece’s parents and your mother) who would argue just the opposite—that taking hormones and having surgery is not harmful but affirming, and that greater harm would be done by withholding medical treatment. This, then, is not a case of unambiguous harm.

Only you can answer these questions for your situation. While it seems clear from your question that you are deeply concerned about your niece’s choice to have surgery, there is little in your question to suggest that you are deeply concerned about your niece. If that is the case, and your goal in the conversation is to tell your niece what you think and why you are right, I can’t imagine the conversation will go well.

For a moment, though, let’s assume I got it all wrong. You deeply care about your niece as a full and complete human being. You have a strong and loving relationship. In fact, your niece has asked for your opinion. How can you hold this conversation with care and candor? Here are three tips:

Have and share your good intent. Before engaging in a Crucial Conversation, it is essential to get clear on what it is you want. Ask yourself: What do I really want? For me? For them? For the relationship? If your answers to these questions are “for the other person to hear my concerns and see the error of their ways,” keeping asking. Sometimes it can be more helpful to ask them in the reverse order: What do I want for this relationship? What do I want for the other person? Note that the preposition there is “for” not “from.” We are often well aware of what we want from someone else (we want them to listen, to agree, to change) but much less aware of what we want for that person. Once you have tapped into a good intent that is grounded in respect for self and others, share it. Start by expressing your love for your niece. Make it clear that nothing will change that love. Demonstrate your respect for your niece’s autonomy. This might sound like:

“I love you and I always will. I want the very best for you. I am so grateful to be a part of your life, especially as you are becoming an adult.”

Ask about and listen to your niece’s experience. Let understanding be your agenda. Listen for the truth in what is shared. Listen with empathy. Use phrases like “tell me more about that” and “how has that felt”. Consider stopping the conversation there, with a sincere expression of gratitude that your niece was generous in sharing her experiences. This will give you time to sincerely reflect on what you have learned from listening.

Ask whether your niece would like to hear your opinion. You might say, “I have some different thoughts about this, different from your parents and doctors. Do you want to hear them?” If the answer is no, respect that. If the answer is yes, reaffirm your good intent, start tentatively, and check in frequently. That might sound like:

“I am sharing this with you because I love you and I want you to be able to consider lots of different perspectives and information before deciding. And, if at any point, you change your mind and don’t want to hear my opinion anymore, just say so and I will stop.”

Crucial Conversations are hard. No conversational skill, technique, or phrase can make them easy. What makes them go well is to care more about the person than the problem, to always see the individual before the issue.


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41 thoughts on “Discussing Gender Transition”

  1. Rob Craig

    Wow! (I feel like I need to say “Long time listener, first time caller”). I have found many of these posts in the past to be wonderfully helpful when helping with challenging conversations. And this one is no exception. Creating this post in itself was an act of starting with heart. Thank you so much for sharing.

  2. Luis Gerardo Gonzalez Lopez

    Great article. It was really helpful for many situations that I have faced.

  3. Troy

    Well done!

  4. Cheryl

    Well done! When I read the headline I was worried. As a leader and advocate in the LGBTQ+ community I appreciate the thoughtfulness and clarity of your advice.

    1. Ashley

      This is an excellent article, and I appreciate the authors perspective when it comes to the intent of the advice seeker. Encouraging family members to put the best interests of the niece at the center of their thoughts is a great way to approach this situation with empathy.

  5. audiomind

    “But this situation seems neither urgent nor unambiguously harmful.”

    Not sure how one come to such a conclusion? It’s clear that some young people are being immorally encouraged to irreversibly mutilate and/or medicate themselves at an impressionable time in their lives that later deeply regret it, and yet are forever scarred. Instead of affirming mental health issues, we should be seeking the help and care they need.

    1. Kermit Frogger

      My thoughts exactly! It was hard not to ignore the author’s obvious bias on this issue.

      1. Matthew

        True about the bias and yet, it seems the advice is sound. “Opposed” isn’t in a position to really push their views or concerns on the soon-to-be-adult niece so focusing on the relationship first and going from there is probably the best that can be done in this mixed up world that’s rebranding doctor assisted body mutilation as “gender affirming care”.

    2. Deborah Campbell,%2C%20only%201%25%20regretted%20it.

      Many people think that trans surgery has a significant “regret” factor, but that isn’t actually how it plays out.

      1. Matthew

        You lost me at “CNN” . . . You can look here for a shocking look inside this trend

        But about the advice on how to approach this siuation, I think it’s sound.

    3. Cole

      Regret for trans surgery is ridiculously low. Lower than the regret for knee surgery. If regret was a basis to not get surgery on, we would not be able to do surgery.

    4. Crazy Horse Lady

      I respectfully disagree. The phrase you use, “immorally encouraged,” indicates a judgement/opinion on your part. I’d encourage you to re-read Ms. Gregory’s guidance with particular attention to the sections, “What is my goal—to have a conversation or tell someone why I think they are wrong?” and “Have and share your good intent.” This is a deeply personal decision. I’m confident the letter writer’s niece is well-aware of the gravity of her decision.

      I am grateful for Ms. Gregory’s thorough, clear articulation of the considerations necessary *before* embarking on this kind of a crucial conversation.

      1. Crazy Horse Lady

        For clarity, my disagreement was with audiomind’s comments, not with Ms. Gregory’s guidance.

    5. RP

      “But this situation seems neither urgent nor unambiguously harmful.”

      I would think from the standpoint that this young individual is “planning to schedule” the procedure versus the procedure has already been scheduled and is imminent such that time is of the essence.

      In other words, there is still time in this case.

    6. CS

      Let’s say you’re a person with female genitalia. And I tell you your entire life that you are a man and have to act and look like one. Or the opposite. How do you feel? Wouldn’t you think I’m nuts and it’s none of my business? Someone else’s gender is none of your business.

    7. Mark Lawrence Murphy

      I agree that there is a great concern about an impulsive, youthful decisions with long-term impact. I do agree, also, with Emily that having a “standing” is going to be an important factor in the conversation. Perhaps, “Opposed” could research and find some facts about individuals that have regretted making these decisions.

  6. Pam

    When considering whether to share an opinion, I would add a reflection on whether the opinion is well informed. What else might you need to learn about the topic before you can have a helpful conversation? When the topic is very personal, like this one, even your best crucial conversations skills can do great harm if you’re coming from a place of ignorance.

    1. CS

      I agree whole-heartedly.

  7. Amanda Eakins

    This was phenomenally written, I really appreciate the fact that you broke down the real questions that we should always ask ourselves before entering our “opinion” into someone else’s life. Please share this everywhere!

  8. Lee

    So happy to see an article that tackles these kinds of issues. Well done Emily and Crucial Learning.

  9. Deborah Campbell

    Thank you for a really great post on a highly crucial conversation.

  10. Jhenelle Carrawell

    Thank you for this Emily. More of us, myself included, would be successful in difficult conversations by going in with this in mind: “care more about the person than the problem”. Again thank you, your tips are useful and applicable.

  11. Matthew

    I was surprised to see this in my email and that you were willing to take it on. Kudos on that and the general advice. My one concern is the apparent presumption that the asker is more focused on being right than having concern for her niece. But ultimately addressing it both ways was helpful. Thank you.

  12. Kelly Downing, LCSW

    Thank you Emily for coming from a place of care and compassion and above all, empathy. Thank you to Pam’s comment “When considering whether to share an opinion, I would add a reflection on whether the opinion is well informed. What else might you need to learn about the topic before you can have a helpful conversation? When the topic is very personal, like this one, even your best crucial conversations skills can do great harm if you’re coming from a place of ignorance”. When people bring their own personal values and/or religious views into how they believe a person should live their life, it isn’t about caring for that person anymore, it’s about setting your own agenda.
    I have people in my life that come from very diverse backgrounds, different colors, faiths, cultures, gender identities, ages, income brackets and social statuses. What makes us a ‘good’ neighbor? community member? family member? When you approach a tough conversation and lead it with empathy and truly listen without judgement you will learn what that person’s experience is like which will also generate compassion. Granted you may not change your own personal view but you will most likely maintain a relationship and in learning how to listen you learn to create community.

  13. Jaime R

    Going through the exact scenerio with my niece.
    I’m choosing not to get involved but continuing to respect the decisions made by my brother and sister in-law and of course niece.

  14. Steve Yunker

    Wow, Emily! That is exceptionally well handled. It is easy to get discouraged when what is most often modeled is speaking past one another. Thank you!

  15. Rachelwx

    One of the best columns ever on how to have an effective conversation. Demonstrating complete respect for another person’s autonomy is not easy – thank you for breaking it down to the basics.

  16. John

    Following are direct and PuBMed links to a recent editorial addressing regret occurrence and a recent report of a mastectomy regret study in the professional literature:

    Postoperative Regret Among Transgender and Gender-Diverse Recipients of Gender-Affirming Surgery

    Long-Term Regret and Satisfaction With Decision Following Gender-Affirming Mastectomy

    PubMed also provides links to, the abstracts for when available and often the full text for similar articles in the scientific literature.

    Great advice on a tough topic, one to clip and keep.

  17. Tough Topic

    Dear Opposed,

    This is an emotionally charged issue for almost everyone. I have a family member who is doing the same. Watching someone who was once young, beautiful, and healthy take medications that are could be damaging her adrenals, other glands, her liver, kidneys, ovaries, and eggs themselves long term is difficult. Her voice has changed, her body has changed, she has gained 50+ pounds of body weight that is not muscle, and her immediate family is being supportive. In other words, I can (up to a point) relate.

    I really do understand your concerns and your fears. Scientifically, during the intrauterine period a testosterone surge masculinizes the fetal brain, whereas the absence of such a surge that results in a feminine brain. In other words, no matter how many hormones are pumped into a body and how many surgeries are done to change the outside of the body, the change that takes place during brain development in the womb cannot be reversed.

    I agree with you. There are tremendous risks to her health.

    I’ve often wondered, why did “gender affirmation” treatment such as cutting off one’s genitalia and pumping a body with hormones it was never intended to process become “medical treatment” when people die from surgical complications and there are risks from the medications?

    I am no longer under the deception that this is just a social issue, it is financially motivated (hundreds of millions of dollars are being spent). Classifying this as “medical treatment” for “gender affirmation” means that our insurance premiums and tax paying dollars (those on Federal support) are being used to fund not only the surgeries but the hormones – indefinitely ($$$$$). Meanwhile, elderly men and women who need hormonal support to treat actual health issues (osteoporosis, brittle bones, bladder and surrounding tissues and more) are denied funding for the necessary medical treatment because they are, well just plain old men and women. Literally not worth the money and where are these proponents then? Are they affirming the choice of women who choose just to be women and need medicine or men? No, definitely not. So, what are they really supporting? Is it really gender affirmation? This has become a politically motivated agenda to have someone else pay their bills, period. If they were really affirming “gender choices” then they would affirm *both* men and women who choose to remain male and female. Such hypocrisy – they in no way lobby for monetary support for treatments for those who choose to keep their sex at birth.

    So where does that leave you with your beloved niece? My family member has not asked my opinion and I have not offered it. She is an adult. She is entitled to make her own choices, regardless of how I feel about them, what I think about them, any risks she is taking with her health, and if she dies on the table or later from some terrible complication, I can do nothing – not one thing – about it. Telling her what I think will not change her mind and quite frankly, she did not ask.

    I know that is not what you want to read. You want someone to support your decision to talk to her, and perhaps prevent any harm that may come from this decision that you believe she may later deeply regret. It is obvious that you love her and want what is best for her not just now, but in her future. What we want when we are 18 is drastically different from what we want when we are 38, 48, etc. Unfortunately, youth cannot understand that.

    That does not mean you have to go along to get along and tell her you support her choices. That would be lying, ingenuine, and unfair to your relationship with her.

    You could consider asking her if she is willing to have a conversation with you and share your concerns. If you do so, know that you take the risk of alienating her and losing that relationship because she has bought into a lie that her sex is her identity, instead of remembering that her true identity is that she is human, like the rest of us.

    Please know that you may incur the wrath of her parents. People who support “gender affirmation” believe they are entitled to rage and even hate those who do not. You become the problem, not your opinion. They will throw away 30, 40, 50 years of relationship because you don’t support “them”. Their entire identity is wrapped up in their external appearance. How dare you question her choices, who do you think you are, and how dare you have an opinion that differs from theirs. You risk immediately becoming public enemy number one.

    These same people refuse to accept you with your beliefs, your concerns, or your thoughts because they feel threatened when yours differ from theirs. They unequivocally believe that they are right and you are wrong. They will judge you as being intolerant, judgmental, and a hater (all the things that they themselves are and claim they are not) all because your opinion differs from theirs. Their hypocrisy is deafening.

    Please, Opposed, know that you may very well incur their wrath if you do speak up. That is how they keep you (and the rest of us who have a different view of this) in check. It is a calculated, trained, political response. Because if they really were gender affirming, they would support everyone’s opinions and sex choices both financially, and socially. They don’t and they never will.

    Please count the costs before you say anything. You may very well lose your relationship with the entire family. If you do choose to have a conversation, start by telling her you love her. Tell her you will love her if she looks like the most feminine woman in the world or the most masculine man on the planet. That your love for her is not dependent upon how she looks on the outside but who she is on the inside. If she is willing to hear your fears own them as that – your fears, such as I’m so afraid you might regret these choices and I wonder if you are too. What is that like for you? How can I support you? Reiterate at the end of the conversation again that love her and always will for who she is on the inside, regardless of the outside.

    I sincerely hope that the decision you make gives you peace and brings you and your beloved niece closer.

    I also hope this enlightened those who claim they are supporting what is in reality a one-sided “gender affirmation” agenda in our society.

    1. Mary

      Your response took courage and was very well articulated. Thank you.

    2. CS

      So many incorrect assumptions and statements here. It is a life-saving procedure for the patients. They’re simply trying to make their outside body look like their inside mind.

  18. Elizabeth

    I agree that this was a good post! Emily, you seem to be doing a good job here of focusing on the larger principles of relationships and dialogue, and avoiding, for the most part, the specific debate about gender. (Unlike some commenters, I don’t think you’re showing a bias toward gender-affirming care. I believe that a very similar reply would have worked, for example, for a niece struggling with mental illness but refusing to seek professional help; adults get to make their own choices and your opinion will only go as far as your relationship with them.)

    The one way in which you could be said to be playing into the asker’s anti-trans bias is by continuing to use the terms “niece” and “she” or “her” to refer to the person in question. We as readers don’t know whether the person objects to those terms or has asked the questioner to use other terms, and I can see that raising that issue might have made it harder for you to connect with “Opposed,” so I respect your choice in writing the reply. However, for anyone who is trying to take Emily’s suggestion to reflect on whether they can or cannot enter a crucial conversation with love and respect for the whole person when talking to a trans family member, I would suggest this: Try using that person’s preferred name, pronouns, and relationship words for a while before you have that crucial conversation, even when talking about them in your head. For example, if the person doesn’t want to be called your niece, you might try calling them your “nibling” (analogous with “sibling”). Even if you believe that this person is misinformed, misled, or mentally ill, meeting them on their own terms will most likely help you “start with heart” and create safety in the conversation in a way that you may not be able to if you are insisting on using terms that they dislike.

    For anyone who is wondering, I am a cisgender woman and happy with that! Nevertheless, I believe that I am first and foremost a human being, and I would generally want people to treat me as a human first and a woman second.

    1. Crazy Horse Lady

      Excelllent points about preferred name, pronouns, and relationship words!

  19. Maureen Neall

    WOW! LONG time user, probably last time. This is the most biased response that I have ever seem from crucial learning! The comment -“For a moment, though, let’s assume I got it all wrong. You deeply care about your niece as a full and complete human being” – from this “advisor” CLEARLY indicates her disagreement with the questioner. She already had a strong view point on this issue and then acts as though she is giving real advice. – as this group in the past has always seemed to do, honestly and unbiasedly address questions. She gave her advice as a physician who already thinks that mutilating your body is GREAT! She judged this questioner becuase of her wrting style, actually indicating she doesnt REALLY care about her neice. If this is your NEW direction; to becoming just one more CRT, DEI political pusher, Im done with Crucial Learning.

    1. CS

      You do realize the topic isn’t the point, right? The point is HOW to have difficult/crucial conversations.

  20. Just Me

    I, too, am tremendously disappointed in the negative bias written by Ms. Gregory towards the OP ☹

    “But this situation seems neither urgent nor unambiguously harmful.”

    – Since when is major surgery, in particular something as serious as an elective double mastectomy – on a teenager – not considered harmful? I have family members who had medically necessary reductions performed by highly esteemed and experienced plastic surgeons. I witnessed serious medical complications that ensued and can assure you that this statement is false and extremely biased. One of them was in treatment for a year afterwards and she was in perfect health prior to the surgery :\

    “greater harm would be done by withholding medical treatment. This, then, is not a case of unambiguous harm”
    How is elective surgery and prescription meds with all the associated risks considered medical “treatment” unless you are accusing this young person of having a mental illness? Are you now switching to the other bias, that this is in fact a mental illness in need of “medical treatment” Ms. Gregory?

    “there is little in your question to suggest that you are deeply concerned about your niece.”
    She is clearly concerned about her niece’s well-being and this accusation is undeserved, Ms. Gregory

    “For a moment, though, let’s assume I got it all wrong. You deeply care about your niece as a full and complete human being. ”
    – A second prejudiced accusation that the OP that does not deeply care about her niece, Ms. Gregory

    Lastly, Ms. Gregory, it seems evident that your experiences were negative and have tainted your perspective:

    “When my primary purpose is to convince others of the error of their ways, I become a preacher giving a sermon, not a friend having a conversation”

    – The only message Jesus preached to the people (not to the hypocritical religious leaders of the day) was the good news, the Gospel of peace, of reconciliation to God and the love of God. I don’t know what you heard in your sermons but that is not the message of the Bible. For God so loved the world that He gave His only begotten Son, that whoever believes in Him should not perish but have everlasting life. For God did not send His Son into the world to condemn the world, but that the world through Him might be saved. Greater love has no man than this, to lay down his life for his friends. Jesus said if you have seen me, you have seen the Father. He loves us, unconditionally, and simply asks us to trust in what He did for us.

    I encourage you Ms. Gregory to read what the scriptures say for yourself, starting with the gospel of John. I think you will be pleasantly surprised to discover the true nature of God.

    PS Bravo Tough Topic. I hope that goes viral.

    1. CS

      This is about having crucial conversations, not about forcing your opinions on someone else. Perhaps you should take the class and learn about this.

  21. P Satyanarayan

    Very helpful perspective for conventional people who often face such ‘new Age issues’. Thanks for the insights on how to steer healthy objective conversation without bitterness and bias.

  22. Connie

    This was a tough topic but approached with a thoughtful and balanced viewpoint. I appreciate your team willing to have this conversation with the questioner, and hope that they do think about this in this way.

    It’s clear the commenters picked up on some phrases that they cherry picked to support their point of view, not taking in the entirety of what Ms. Gregory’s advice was.

  23. CS

    I would take this even a step further and say this isn’t even a conversation that should happen. If it isn’t your body, it’s none of your business. According to the Trevor Project, suicide rates among trans/queer kids is FOUR TIMES that of non trans/queer kids. That is why gender-confirming surgery is a medical procedure worth having. Oh, the suicide rate isn’t due to being trans or queer, it’s all about being at higher risk because of mistreatment and victimization by society – and families of birth – less than 40% of trans/nonbinary kids live in a gender-affirming home. Read up on it if you care to:

    LGBTQ youth often face bullying, threats of injury, and sexual violence. The following data on LGBTQ teenagers comes from the Youth Risk Behavior Survey:

    10 percent were threatened or injured with a weapon on school property
    34 percent were bullied on school property
    28 percent experienced cyberbullying
    23 percent who had dated someone during the 12 months before the survey had experienced sexual dating violence
    18 percent students had experienced physical dating violence
    Another 18 percent had been forced to have sexual intercourse at some point in their lives.

    This kind of surgery isn’t whimsical. It is life-saving.

  24. Julie

    I absolutely love the advice given in this article! Honestly, I have mixed feelings about the specific issue that was asked about. There are reasonable, rational, caring people with varying thoughts about it. But the advice was great for discussing any issue that is controversial, emotionally charged, and important! Don’t go into it with the goal of changing the person’s mind. Go into it from a place of caring and with the goal of learning what their thoughts, feelings, and experiences are. Of course you can share your own thoughts and feelings as well, but as the author said, not preaching.

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