Make an Appointment: (512) 669-5892 |   [email protected]

  • An Alternative to the Ultimatum: a Guide for Having a Healthy Hard Conversation

    Relationships. We’ve all got them. We all want them (usually). Humans are social creatures, so frankly, relationships are inevitable, and we need to learn how to navigate them.

    Relationships come in every shape, size, and form: friends, family, work, acquaintances, lovers, partners, teammates, mentors, the list is endless. And because we’re people – each of us unique – we’re going to have our differences. 

    When handled well, these differences can lead to growth and depth of the relationship, building longevity, trust, and connection. When handled poorly – or sometimes not at all – we find ourselves frustrated and resentful. 

    It’s then that we consider throwing down one of the most harmful relationship weapons: the ultimatum.

    Yeah, but How Did We Even Get Here?

    Typically, reaching the point in which you’re considering an ultimatum is the result of having a need, want, boundary or expectation go unmet for an extended period of time.

    Perhaps you’ve expressed the need, perhaps you haven’t. Maybe it’s happened in your head and you’ve even visualized it, so it feels like you’ve done it already – but you haven’t in real life (hello, ADHD and/or anxiety). Maybe you’ve talked around need/want/boundary/expectation, but never truly and explicitly named it. Or maybe you’ve been extremely clear, and nothing has changed.

    Regardless, the situation is this: you need something about the relationship to be different, and that change is not happening. 

    You feel unheard, disrespected, invalidated, and resentful. Gone uncommunicated, these feelings compound and compact, building in pressure and intensity until *BOOM* internal volcanic explosion that can’t be contained.

    So, in an act of desperation, you throw down the ultimatum. 

    The ultimatum usually goes something like this: I love and value you, but  IF you don’t ________, then I will ________. 

    What is an ultimatum actually? A threat camouflaged in good intentions.

    Okay, but you only kind of answered the question. HOW DID WE EVEN GET HERE?

    Right. That. 

    We’re going big picture, so stay with me.

    You got to this breaking point of using an ultimatum to solve an unmet need in a relationship because we as a society are interpersonally conflict avoidant.

    We can talk shit online all day. Hurt people’s feelings up and down through a little blue screen. Spew hate and bigotry without a second thought and damn near no consequence.

    Shit, we can even commit multiple simultaneous genocides from an ocean away and still sleep at night.

    But talking about our feelings one-on-one and having to sit in the discomfort of holding someone we love accountable, thereby making them uncomfortable? Sweet Jesus.

    Hard pass.


    Because we have to look the person we love in the face and tell them they’ve been deficient or disappointing or that they’ve hurt us. We’ve somehow conflated holding someone accountable or asking for change with causing them harm.

    So we put our feelings aside, sacrifice our needs and emotional well-being, and become a martyr to Keeping the Peace. 

    Spoiler alert: the martyr always dies at the end – and it’s usually brutal.

    Pro tip: Accountability and Change ≠ Harm.

    However, when we’re escalated, triggered, or upset, we often revert back to what’s familiar – and what’s familiar is conflict avoidance due to being socialized with a pea-sized threshold for interpersonal responsibility and discomfort.

    Therefore, we put off  having a difficult conversation and we seethe; we try to bring it up and nothing changes – and our frustration and resentment grow; time passes and passes and passes and you try and try and try, and despite your best efforts, nothing changes: your need/want/boundary/expectation remains unmet.  The feelings writhe in your gut, and eventually eat you from the inside.

    See, there are a few things happening here:

    1. In a world where all we crave is stability, change is the only constant. We are living, breathing organisms who are adapting to a world that is constantly evolving – this evolution and adaptation includes our relationships; if we don’t evolve with them, we get left behind. While it feels counterintuitive, developing the flexibility to tolerate and even welcome change is the skill that generates stability and expands our window of tolerance for the inevitable discomfort of change.

    2. As evidenced above, ongoing avoidance isn’t sustainable because it breeds resentment. So if you’ve been avoiding communicating that your needs/wants/boundaries/expectations haven’t been met, it’s no wonder you’ve arrived at Ultimatum Station. You’re pissed and resentful, after all.

    3. Also, there’s an underlying assumption that asking for a need/want/boundary/expectation to be met automatically leads to conflict. In healthy relationships, giving and receiving consistent feedback – both positive and negative – is a regular and expected part of your interactions. If consistent feedback about each of your needs/wants/boundaries/expectations isn’t part of your current relationship communication routine, it’s time to start developing a new, shared, equitable feedback loop.

    For the moment, let’s continue assuming you’re at the point of issuing an ultimatum. Because you’ve reached this peak emotional strife and desperation, you’re also likely contending with an additional layer of shame. Your internal narrative reprimands that you *just should* have torn off the band-aid and had the hard conversation before the relationship became infected with resentment.

    Yes, you’re right: you *just should* have had that hard conversation and communicated your unmet need/want/boundary/expectation; however, using that specific *just should* language invalidates the significance and difficulty of how vulnerable you become when you communicate a need in a world that prioritizes individualism and self efficacy. Speaking your truth makes it real, which makes the potential that it might continue to go unmet also real.

    Goddess forbid, in this bootstraps-obsessed culture, you have a need/want/boundary/expectation that you can’t meet on your own. You’re a fucking monolith, don’t ya know.

    This, friends, is the cycle of shame and isolation that leads to an ultimatum.


    Consistent, hard conversations come from a place of love.

    • Hard conversations come from a place of self-love because you are affirming that you love yourself enough to be vulnerable and state a need/want/boundary/expectation (which we have been socialized to believe is a weakness, even though it just makes us human);

    • Hard conversations come from a place of self trust and dignity because you value your worth, needs, and boundaries more than your assumptions about someone else’s comfort;

    • Hard conversations come from a place of love for the other person because even if you’re asking them to change, you’re communicating that you believe they can and that you trust them enough to be vulnerable with the soft underbelly of your needs;

    • Hard conversations come from a place of love for the relationship because your vulnerability is the gift that says “I believe in us and our future enough to lay my pride on the line.”

    A few last things about why we avoid hard conversations.

    We avoid hard conversations out of fear of abandonment. 

    We avoid hard conversations because we’re afraid they will confirm that we are not good, valuable, or worthy enough if the person we love is unwilling to change.

    We avoid hard conversations because we grew up believing that our value as humans is tied to the opinions of others.

    We avoid hard conversations because if we’re too needy, we must be burdensome and unlovable.

    We avoid hard conversations because our identities are tied to being in certain types of relationships with specific people, and who would we be if those relationships or people were different?

    We avoid hard conversations because sometimes the chaos of anger and resentment are more familiar than the stability of peace.

    We avoid hard conversations because we’re terrified of being alone – and we’re told by society that we are a failure if we’re not partnered.

    All of these reasons that we use to rationalize avoiding the ongoing difficult conversations that ultimately lead to an ultimatum are deficit-based cognitive distortions. 

    Imagine, instead, these alternatives that address hard conversations from an abundance perspective:

    • I’m going to have this hard conversation because I love and respect this person; if they leave, I will survive and learn to thrive. Where they were casting shade, I will learn to find the sun.
    • I’m going to have this hard conversation because I am worthy of love and respect and the same level of effort and care that I give. I deserve the same amount of tenderness and nurturing.
    • I’m going to have this hard conversation because I value myself and my own opinions more than the opinions of others; often their behavior is more a reflection of them and their insecurities and has nothing to do with me. The opinions of others do not define me.
    • I’m going to have this hard conversation because healthy relationships take work and investment; this effort is not a burden so much as a consistent communication of commitment. Doing challenging tasks in a relationship helps us grow together and learn how to nurture each other’s development.
    • I’m going to have this hard conversation because while I love and support this person, it’s important that we remain independent rather than enmeshed. Perhaps, the issue isn’t that I’m not enough but rather my abundance can’t be contained.
    • I’m going to have this hard conversation because I’m trying to establish new, healthier patterns in my life. I am not responsible for the feelings and behaviors of others, and I can only control my own reactions and responses. I am making this intentional choice to honor my needs/wants/boundaries/expectations because I trust that I will be okay even if it doesn’t go well.
    • I’m going to have this hard conversation because no matter the outcome, I am lovable and valuable and worthy of love all on my own. This self-love and respect will attract people who reflect my own values and worth.

    So how do you have a healthy, hard conversation when you’re at the point of an ultimatum?

    Oof. If you’re at the point of an ultimatum, that means you’re likely upset, frustrated, angry, maybe even resentful. It also means you’re trying to try something new in an already established pattern of behaviors and expectations.

    Fair warning: having a hard conversation when you’d rather lash out with an ultimatum is very doable, and also extremely challenging. Here are the steps:

    1. Regulate yourself. Try to approach the conversation with a regulated central nervous system. Basically, don’t broach the topic if you’re wildly upset or frustrated. Staying cool, calm, and collected is important because as you escalate, so will the person you’re speaking to – and once people are upset, we get defensive and stop listening; sometimes we even attack, and then things devolve quickly from there.

      • Here are some quick and easy methods for staying embodied and within your window of tolerance prior to making the ask.

        1. Work out prior to the discussion so you’ve got some feel-good endorphins coursing through your body. Also, it’ll help work out some of the nervous energy you feel about the outcome of the conversation. Specifically, exercises that incorporate cross-body movements like running, biking, swimming and dancing are great at keeping both hemispheres of your brain connected while also encouraging deep breathing.

        2. Consider your senses:

          1. Wear comfortable clothing while you’re having the hard conversation. No one likes dealing with a scratchy tag or an uncomfortable waistband while also being emotionally uncomfortable. 

          2. Have a beverage (or two or three) that help you regulate. This usually looks like something hot, something cold, and something comforting.

          3. Be aware of the environmental temperature. When we’re upset, our body temperature rises, so consider lowering your thermostat a couple degrees. This helps your body literally stay cooler, which in turn helps you keep a cool head.

          4. Choose a location that is neutral but comfortable for both of you. This eliminates the inherent power imbalance that comes with being in someone else’s space while providing a sense of safety that overrides the urge to escape (reptilian brain: fight/flight/freeze/fawn).

          5. Basically, you want to create a situation where you’re not trying to multitask managing both your physical and emotional regulation because the aggravation of being physically uncomfortable will always take precedence and exacerbate your emotional discomfort.

        3. Go on a walk while you have the conversation. Same concept as exercising before the discussion – walking helps the hemispheres of your brain stay connected and uses gross motor skills, which keep you embodied. Additionally, it’s easier to say hard, vulnerable things when you don’t have to look the person in the eye.

    2. *Optional* Name It to Tame It.  A while back, a therapist named Dan Siegel coined this catchy phrase as a reminder that by naming our emotions, we’re able to de-escalate ourselves relatively quickly. When approaching a hard conversation, this hack can be used to create a bridge of trust and vulnerability while also modeling to the other party that it’s safe for them to communicate their feelings as well. Name It to Tame It might sound something like “I have something important that I want to talk with you about, and I’m so nervous that my palms are sweaty and I haven’t had an appetite all day.” Simply, by naming what you are feeling and how it shows up in your body, you release that feeling into the universe and it no longer holds the same power it had when contained in your mind; physiologically, naming your emotions re-engages your prefrontal cortex (the part associated with logic and higher thinking) when your brain might be flooded with stress hormones.

    3. Approach with an observation and genuine curiosity. Often, we reach the point of ultimatum because at least one party in the relationship isn’t communicating clearly or consistently about what is happening for them. You might even have asked why they’re doing – or not doing – the thing(s) that have led to you feeling like you need an ultimatum. However, we often receive WHY as an accusation rather than genuine curiosity. For instance, how does “why would you do that?” feel when you say it in your head? Not great, right? That’s because tone matters. 

      Consider this alternative instead:

      “Hey, I noticed that you’re doing _______ and I was wondering what that’s about.”

      This language is neutral and lands a lot softer than the accusatory tone that comes with why. This approach also helps you hold empathetic space for the other person’s experience that may change how you feel about what’s been happening. Their response won’t alter the fact that you have an unmet need/want/boundary/expectation, but it might help you feel more empathy and understanding on their behalf, which lends itself to a more successful conversation.

    4. Start the Shit Sandwich. The title isn’t cute, but you’ll remember it. Basically, the Shit Sandwich couches an “I” statement in love. It strokes the ego, lowers defenses, and makes negative feedback more palatable. Here’s how it goes:

      • Start from a place of love and appreciation. Upon the transition from curiosity – in which you incorporate the information you’ve just learned – you might say something like “I’m asking because I really love and appreciate our relationship – and I’m truly grateful that you’re in my life.”

    5. Start Your “I” Statement. The start of an “I” Statement is a declaration of the behavior that’s been triggering you. You’ll want the transition from the Statement of Love & Appreciation to be connected with the word AND because it allows for the duality of love AND imperfection. For example, “I really love and appreciate our relationship AND when you talk over me in front of other people…”

    6. Add the Feeling. Emotional vocabulary and nuance are extremely important. The better you accurately articulate your feelings, the easier it is to create a plan for managing them. Also, generalized feelings like mad and sad can become nebulous and overwhelming. The more specific you can be, the more succesful your conversation will be. It looks like this: “I really love and appreciate our relationship and when you talk over me in front of other people it feels like you don’t respect me or what I have to say.”

    7. *Optional* Add in a Consequence. Adding the consequence of the behavior after the feeling can sometimes shed light on how this looks in real time. It also might help preemptively answer some questions from the other party.

      “I really love and appreciate our relationship and when you talk over me in front of other people, it feels like you don’t respect me or what I have to say. So I shut down and pull away because my feelings are hurt.”

    8. Make Your Ask / State Your Need. THIS IS THE MOST IMPORTANT (and difficult) PART OF THE WHOLE EXERCISE because it makes you vulnerable and informs the other person that they haven’t been up to snuff. Again, be specific about your need/want/boundary/expectation. State the need in a way that suggests the change you want to see.

      “I really love and appreciate our relationship AND when you talk over me in front of other people, it feels like you don’t respect me or what I have to say. So I shut down and pull away because my feelings are hurt. I need you to listen when I speak and let me finish what I’m saying before you join the conversation.”

    9. Close the Shit Sandwich. This is an opportunity to repair any perceived harm and to reinforce that you value the relationship and the other person. Think of it as a salve for an open wound. Here’s what the whole thing looks like:

      “I really love and appreciate our relationship and when you talk over me in front of other people, it feels like you don’t respect me or what I have to say. So I shut down and pull away because my feelings are hurt. I need you to listen when I speak and let me finish what I’m saying before you join the conversation because what I have to say is important and because I also want to hear what you have to share. We have so much fun together, and I really appreciate your listening just now and working on this.”

    Another way of thinking about this strategy is like a math equation (bear in mind I’m a social worker who only made it through Algebra II):

    Self Regulation ((Genuine Approach (Start Shit Sandwich + “I” Statement + End Shit Sandwich)) = Successful Hard Conversation

    Now it’s time to practice.

    Using nonviolent communication and “I” Statements can be a hard shift when you’re in the unintentional habit of providing feedback and criticism through a deficit-based or negative lens. So I’ve got an assignment for you:

    Think about a conversation in which you asked for a need/want/boundary/expectation to be met that didn’t go well. You might even want to pull out a notebook and write it down.

    Start at the beginning, with setting and environment and do a SWOT (strengths, weaknesses, opportunities, and threats) analysis of the interaction using our new Hard Conversations strategy as a guide. Specifically, think about:

    • What went well?

    • What didn’t go well?

    • What were some missed opportunities?

    • What would you change if you could?

    Now give yourself a mental do-over and visualize the interaction in your mind using the Hard Conversations template. Stay curious, practice your language, remember to be specific and to name the behavior or change you need to see, and reinforce that you’re having this tough conversation because you love this person and care about the future of the relationship.

    Any new skill takes time, commitment, and practice. Changing how you communicate is no exception – especially because we start communicating and developing these patterns while we’re literal babies. However, as you continue to use these tools, you’ll rewire your brain (through cognitive restructuring) to learn that discomfort can be safe, that feedback comes from a place of hope, and that you are deserving of loving, respectful, and equitable relationships.

    One of the most effective places you can practice safely having hard conversations and establishing new communication patterns is therapy. Your therapist is someone who can help you break down and analyze different interactions as well as role play and practice different communication methods. If ultimatums routinely appear in your romantic relationship(s), couple’s counseling would be a fantastic place to work on moving from harmful to nonviolent methods of communication while in a safe and controlled environment with the immediate guidance and feedback of a trained and licensed professional. 

    Additional Resources:

    Cognitive Distortions – Seigel and Name It to Tame It –

    RADAR Communication Check-in Tool –

    Distress Tolerance TIPP Skills –

    Center for Nonviolent Communication –

    SWOT Analysis Tool –

    Cognitive Restructuring –