How to Develop Real Empathy in 30 Days (Professor and Therapist Explains)

Most men are told to “listen better,” but almost nobody teaches the actual skills. In this episode, therapist and professor Tim Wienecke breaks empathy down into a practical, trainable system you can improve in 30 days. No personality shift required—just simple tools that help you communicate clearly, stay grounded in tough moments, and understand what people actually need from you.

Tim teaches the same framework he uses with counseling students: a 30-day daily drill that improves emotional recognition, grounding skills to keep you out of fixer mode, and a three-level reflective listening method that makes conversations easier and more productive. You’ll also learn the one question that prevents most difficult conversations from blowing up, plus how to apply these skills in romantic partnerships, leadership, and parenting.

Whether you want to connect better with your partner, lead more effectively at work, or simply be the man people feel safe opening up to, this episode gives you a complete step-by-step system you can start using today.

What You’ll Learn

• The 30-day stranger exercise that builds emotional accuracy
 • Why the Eyes Test is a helpful baseline for empathy
 • How the Emotion Wheel expands emotional vocabulary
 • Grounding techniques that help you stay present
 • The three types of reflections: simple, dual-sided, and summary
 • The question that keeps conversations from going sideways
 • How empathy shows up differently in parenting, leadership, and relationships

Chapters

00:00 Why Empathy Is a Trainable Skill
 00:50 The Eyes Test and Your Baseline
 02:10 The 30-Day Stranger Exercise
 03:10 Using the Emotion Wheel
 04:00 Skill 1: Grounding So You Stop Fixing
 06:40 Skill 2: Reflective Listening (Simple → Dual → Summary)
 12:00 Skill 3: “Am I Helping or Listening?”
 15:10 Applying the Skills: Kids, Leadership, and Partnerships

Tools Mentioned

Reading the Mind in the Eyes Test - https://socialintelligence.labinthewild.org/mite/

Emotion Wheel (vocabulary expansion tool)- https://feelingswheel.com/

Recommended Reading

How to Win Friends and Influence People — Dale Carnegie
If I Understood You, Would I Have This Look on My Face? — Alan Alda
Motivational Interviewing (3rd ed.) — Miller and Rollnick

Get them from delivered by your local bookstore:

https://bookshop.org/lists/amp-32-empathy-and-communication-reading-list

Full Fact Check and Show Notes: www.americanmasculnity.com/amp32-skilled-empathy 

📊 Research Notes:
The 36-item Reading the Mind in the Eyes Test measures emotion recognition accuracy. Studies show empathic accuracy and reflective listening improve with deliberate practice. 
John Gottman's research finds 69% of relationship conflicts are "perpetual"—the goal is

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The American Masculinity Podcast™ is hosted by Timothy Wienecke — licensed psychotherapist, Air Force veteran, and men’s advocate.
Real conversations about masculinity, mental health, growth, and how men can show up better — as partners, leaders, and friends.
We focus on grounded tools, not yelling or clichés. If you have questions or want a tool for something you're wrestling with, leave a comment or send a message — your feedback shapes what we build next.
Note: While this doesn’t replace therapy, it might help you notice something worth exploring.

Transcript

0:00

Most men are told, listen better, but fewer are told how, and we're taught that empathy is either something you have or you don't have, which is nonsense. I've been training clinicians and aspiring clinicians in empathetic communication since 2017. Learning these skills are gonna help you connect better in love relationships and in your profession. Today I'm gonna break down empathy as a skill and how to use it in the conversations that actually matter. Empathy is a skill, not a personality trait, and we know that because we can measure it, we can improve it, and we can apply it. All empathy is, is successfully identifying the emotions in the room and the people that you're engaging with and ideally within yourself. Since we can do all these things, we know we can progress. Clinicians regularly spend years of our life and rigorous effort to improve this skill to better serve you. That means you can do it too. So first, let's start on how to measure it. The folks in the Ivy League came up with this really powerful empathy test where they show you clips of people's eyes, just this. And have you identify the emotional state. It's a one to 32 point test, and the reason why we start with just the eyes is because it's the one piece of our humanity that doesn't change culturally in how we express our emotions. So it's a really powerful cross-cultural way to impact communication. I have my graduate students do this, and when they do, they generally score somewhere between 22 to 24 on the test on average. By the time they're done doing all the exercises that we're going over today, on average, they go up four points and a lot of them just max out the test. I redo these exercises to make sure I'm staying sharp for my patients. It's gonna be really useful for you. If you're curious about where you're at. Go ahead and pause the video and take the test. I'll link it up here in the video if we can, in order to be in the description. If not, let's go into the exercises that we're gonna use to help you get better. Like any skill improvement, this is gonna take time and repetition. So what I want you to do is for the next 30 days, you're gonna name one stranger's emotional state in your own mind. You're not gonna say it, you're not gonna confirm it, and you're not gonna ask anybody else if you're right. The point of this is to get you paying attention to what the cues are and how to notice 'em. And it's gonna help you develop out emotional language because now that you're thinking about it every day, you're kind of stretching yourself into a place that you probably don't live very often. It's important to start with strangers because you don't wanna start playing with live ammo in your relationships. You wanna go and get good first. Nothing wrong with it. To enhance the exercise, I want you to use something called the emotion wheel. Essentially, our emotions are kind of like colors, where there's primary emotions that then blend together to form more complex emotions. So most guys can start out by saying, sad, angry, fearful, happy, right? If you take those emotions and you blend them together, all of a sudden you get variation, you get excitement, you get grieving, you get pride, lots of things. It's really gonna help you name different emotions, get a little bit more language to it, and it's gonna enhance the exercise because it's gonna make you think about it a little bit longer than just in that moment in time. You don't have to do this one, but it really does help improve the skull a lot faster. So you're gonna do this once a day. You're gonna walk in somewhere, you're gonna identify a stranger's emotion. You're then gonna walk out, and when you get a little time, you're gonna look at your phone and look at the emotion wheel and see where you're at and see if you can just extend it out to one more ring on the wheel. That's it. You're gonna do that every day. This is the exercise that brings up four points in that 32 point scale for most of my students. It's really, really powerful. It's really helpful, and I think you're gonna find that if you do this and you do it consistently, you're gonna get better at this. I do this exercise pretty regularly just to make sure I stay sharp for my patients and for my loved ones. It's a good thing to do. So now that you've got some more emotional vocabulary and a little bit of awareness about what emotions are going on around you, it's time to start talking about how to engage with the people in your life. So the first thing is you've gotta be able to handle yourself. A lot of us, when we're engaging with somebody and they're expressing a powerful emotion, we get really uncomfortable. And then what most of us do when we get uncomfortable is we either shut down or we try to fix it for 'em. We start giving advice, we start telling 'em what to do. And most of the time that's not what people want. People are pretty bright. They know what their problems are, they know where their solutions are. They're usually just looking for some space to be validated, to be normalized, and have some room to talk it out with what's going on with them. I know that you wanna jump in. Of course you do. You care about the person in front of you, you wanna help 'em. This just isn't gonna be the way to do it, and so to get tactical, you have to get grounded. So how do you ground yourself? There's a lot of different tools and a lot of different ways to do it. We can cover three here, but there's tons of 'em, and you probably have some already. Just from being in the world as an adult. The ones that I kind of use in session are I relax my jaw, right? If I get kind of tense, my jaw tends to lock up a little bit and that kind of triggers my body that I'm about to take a hit or that I'm uncomfortable. So just kind of do one of these, maybe a little, pop your jaw and then combine that with it. Like a nice deep breath. Just like a slow, like four count breath in, hold the air, and then four count breath out. Can I get that regulation just going in there where everything's kind of evened out? So it might look like this from the outside. Do you feel how that just kind of calmed the room generally? Like it wasn't even just for me. If we were in the room together, you'd feel that and you'd slow down as well. It's a great way to co-regulate. The next one is you want your feet on the floor. I know that sounds kind of dumb, but we feel more secure when we're braced and grounded. So you wanna put your feet on the floor and you kinda wanna push a little bit just so you feel the floor underneath you and you feel what's happening around you. The other thing I want you to do is before you speak at all. I want you to leave two to five seconds of silence. One, it's really powerful in the person having a moment to see if you're listening. And two, it's gonna give you a few seconds to just ground yourself a little bit. See that pause there. It makes things sound more important. We use it aloud as clinicians. We're trained in how to hold silence to make impactful moments for you. So in addition to grounding you, it's leaving space for them. So as you go through this, if you can calm your nervous system, you're not gonna jump in without thinking. You're not gonna start trying to fix things for people that don't need you to fix 'em. You're just gonna be able to be there and hear what's going on for your people. So start with you. Start inside. How are you gonna ground? If you've got other skills you like, go ahead and share 'em in the comments. Some other guys can probably use'em and there's dozens of them. Which ways do you like? The next one we're gonna talk about is reflective listening. If you looked at any kind of communication class at all, you've heard of reflective listening at its core, it's simply repeating back what you hear. We're gonna break that down into a little bit more complicated ways to do it. We're gonna start with simple, move to moderate and move to advanced. It's important to have this kinda framed out. It's a really powerful tool for this. It's something we use in what's called motivational interviewing. It's a wonderful way to give you some breath. Some strategy and some tactics on how you're engaging with people. So let's start with the simplest thing you can do. Say one sentence back, that repeats or reflects something happening with the person. So it's either gonna be content, they really pissed you off. It's gonna be emotional state. You're angry or it's gonna be meaning they really disrespected you. The reason we're keeping it simple is because it's generally used as a way to check in and confirm that you've heard them correctly. So when we just say a simple sentence back, and if we can, we use their direct language, that's called a direct reflection. Right. You say back exactly what they told you, and that does some pretty powerful things. It lets them hear what they're talking about and confirms that you heard them correctly. I know that sounds silly, but it goes a long way and these are gonna be the core of your communication in any kind of event where you're trying to be there for somebody. These simple reflections of the building blocks for everything else you do, so get a little good at them, and they're also great. Let's say that you're talking to a buddy. And he's telling you the same story about his girlfriend, that he's told you 16 times and you kind of check out for a minute because you're just, you know, you've heard this before and he's just repeating himself and you come back and you realize that you've lost the thread in the communication and he's looking at you like he's waiting for you to talk, say back the last thing you remember hearing. So what this does, it kind of cues him as to where you left off and it gives you a chance to kind of reconnect in with what's happening. It's okay. We all drift. It happens, but this way it lets them know where you are and lets you come back to where they're going without making it a thing. It really does work. It's really powerful and it's super simple. So try that next time you kinda zone out in a conversation. For the second kind of reflection we're gonna talk about, it's called a dual-sided reflection. And the reason why this is important is most of us, when we're kind of stuck in ourselves and we need the support of somebody else, it's because two things are happening that we can't reconcile. Two things are happening that don't go together, and it's really hurting us and kind of tearing us apart. And having those moments reflected back at people is really powerful because they're the only ones that can choose which way they're gonna go. You can't choose it for 'em. And so by highlighting that and just sitting there with it, naming it. It leaves space for them to do their own processing. So it's essentially as simple as, so on the one hand, X, on the other hand, Y you really love them, but you're also pretty convinced that they're not gonna change. You really like your current team, but this new job is offering a lot more money. You really wanna work out and get better, but you really embarrassed when you go to the gym. See how these two-sided reflections work. It gives it a little bit more complexity, and it gives them a little bit more room to wiggle around and feel the discomfort of what they're stuck in. And I know that sounds mean, but we're gonna put them in a little bit more discomfort. But what you're doing is you're creating safety for that discomfort. They're gonna feel understood and they're gonna be able to sit with you because you are grounded and sit in that ambiguity and maybe do something with it, and maybe they don't, but at least they get to see where they're at, and it's a really powerful tool. The third one is the most complex one, and it should be used the most sparingly. It's the summary. This is where we take a threat of their conversation and we create a story out of it. This is where we're telling them not just the content of the individual thing they're saying, but the story that we're hearing them tell and the reason why you wanna use it sparingly is because. It's big. It takes a little time and you might get it wrong. So this is where you take what they're telling you and you can just kinda like put it in two to four sentences, right? This still isn't like super long. We're not doing a diatribe, but what we are doing is telling that story. So it's really busy at work. You love your team and you don't wanna leave them in the lurch, but your rent's gone up. You need more money, and this other job is offering a lot more opportunity for you to grow in the future. So you've got this partner, you spend a lot of time with them, you love them dearly, and you've been talking to'em about this problem you have, and they're just not engaging with it. They're not changing it, and you don't know what to do. So you wanna feel better, you wanna be healthier, and you know, the gym is the place where you wanna do that, but it's really hard to walk in there outta shape. It's really hard to walk in there looking like you don't belong. And that makes it hard to kinda get over that hurdle. Do you see how these are a little bit long and they kinda tell the story? You're giving them back details and a few of your reflections. So the way this should structure out is in any conversation you're at where you're actually trying to do effective, empathetic communication, the pacing of it is three simple reflections and then either some kind of question, like if you wanna go a little bit more depth so I don't understand what's happening with her. Right, something like that, or one of the other two, the double-sided reflection or the summary. But you always wanna start with that beat of three reflections, bop, bop, bop. And what that does is it gives them time to build up what they're trying to tell you and make sure you understand it. So. Simple reflection. Simple reflection. Simple reflection. Maybe a question, maybe a double-sided reflection, and maybe a summary depending. But these are the structured tools and ways that you're gonna engage to make sure that the person feels heard, feels seen, and that you know what the hell they're talking about. So many times people get lost. They get lost in trying to find the solution. They get lost in their own perception of the person's problem without hearing what's happening to them. And this is the best way to make sure that doesn't happen to you. So take these out into the world, give 'em a shot. There's a lot of different videos on each one of these. They're all pretty good. Combining 'em together though, that's where the mastery, the tool comes in and that's how you get good at empathetic communication. So dive in, try 'em out. They're pretty easy. The reflections are great. If you don't know what else to say, just say back what they said. No matter where you are, no matter what's going on, it works. It gives you a beat to think and it helps them like figure out where they wanna go with it. Use them. It's gonna be fun. The third skill we're gonna talk about is figuring out what the hell it is you're trying to do for 'em. This skill has saved marriages, it's saved relationships, and it saved me a lot of headaches in my life. Sometimes when people talk to you, they just want space to be heard, and sometimes they wanna brainstorm solutions and get help figuring out what to do. The problem is, is that most guys tend to default into fixing because of what we talked about earlier. The reason you gotta ground, you gotta make it so that you feel comfortable enough to give 'em what they need. But why? Guess why? Get stuck in a spot where you're taking a coin flip to see which one you're doing. Ask 'em, Hey, are you looking for solutions right now? Or are you just looking for space to process? Am I listening or am I helping? And what's nice is if you've got an established relationship, you can ask them what kinda language cues they'd like around this. And that's the ways that I've seen marriages saved, right? Somebody comes home, they bring a problem in, but they've got an agreed upon protocol to cue the other person as to what's going on. And the nice thing is, is that it's not particularly gendered as to whether people get this right or wrong. Women do it too. But it's worth checking in on, and it saves so much headache because it makes them think about what they want. How many times you've been talking to somebody you love, they're dumping on you about what's going on with them, and you jump in with something and they get mad at you because it's not what they want. A lot of the time that happens, it's because they don't know what they want. So by asking the question, it cues them to join the conversation in a way that they're looking for. It makes them pause for a minute and say, what am I looking for from this person right now in front of me? It's really, really helpful because then you two are on the same page and then you have an opportunity to be of service. I know it doesn't feel like it, but a lot of times just listening and reflecting back and using those powerful tools that's of service, I know a lot of guys, we don't feel like we're fixing anything. When someone just comes and talks to us about a problem, we are, we're making them feel connected. We're making them feel held, and we're giving them the space and the confidence. To maybe do something about it, and it's of service because it's hard. It's hard to listen to the people you care about in pain. And if you think about it like I'm providing a service, like they're asking me to listen, so I'm just gonna listen. It gives you a lot more gumption and battery to stay grounded and stay connected because you're serving the person in front of you. You're doing it right, you're being there for them in the way that they're asking for, but you gotta ask. Am I helping or I fixing? So now that you've got three skills on how to show up and you've got some awareness on what it is you're bringing, it's time to start talking about the different roles that we use them in. So let's talk about a teaching or coaching role with kids. Kids are really dysregulated a lot of the times and that you use our system to regulate off of. The reason why kids have temper tantrums is because they're overwhelmed and it's the first time they've had to deal with those feelings. They need us to regulate it, and a great way to get them back in their cognition is to reflect back the emotion you think they're feeling. It makes them pause and think about it for a minute, and when you're using that grounding skill with them, they're better at grounding off of you. They're better about using your nervous system to help regulate their nervous system, and then it leaves room for masculine parenting. Masculine parenting is. Teaching and coaching. That's why we love it. That's why dads really start to show up after the kid turns five, because that's how most men wanna show up for kids. We want 'em learning. We wanna prepare 'em for the world, but we forget that nurturing their communication, their self understanding and their empathy is a way that's gonna help 'em in the world. So by modeling this, you're gonna make better men in the future and you're gonna show up better for your kids. It's wonderful. So remember ground, let them ground off of you. Name what's happening in simple language, and then help 'em tell the story of what's happening to them so they can get better at the skill they're trying to pick up. It's gonna go great. Next one is a leader and manager. So a lot of times what I hear when I'm working with my C-Suite guys is they don't have empathy and they can't keep employees. They have a huge amount of turnover because they're bad at checking in and getting the pulse of their team. That's where this empathetic communication comes in so handy. If you're in that position already, you know the processes, you've got the skills on the task being done. So if it's not happening, it's because you're not connecting with where your people are at and giving'em what they need to do the job. Imagine you're sitting there in a meeting and you're just fried. You all just did a major push. Everybody just pulled a 65 hour week to meet this deadline, and then the boss comes in super happy over the moon and says, we're gonna do it again. What happens to everybody in that room? They start to resent him'cause he missed the queue. You all just about killed yourself to get him through this deadline. Why isn't he taking the time to acknowledge that? Why isn't he giving you time to recover? Let's say that they're frustrated because they're just not getting together and working together. But instead, the manager comes in and starts berating them about how lazy they are by understanding what's happening with them on an emotional level, it helps you find the tactical ways to join and bring in solutions to the problems. Remember, as a leader, you're there to help find solutions to problems, not make more. And so you're gonna use that new empathy that you've got. You're gonna use those reflections to make sure you're hearing your employees, and you're gonna use those summaries to tell the story of what's happened with the team so they know where they're going. If you do those things, you're gonna have a lot better retention with your employees. A lot less turnover and just a better fricking weak man. It's hard to be around people that are unhappy. It's way easier when you can validate where they're at and give 'em what they need to go forward better. Empathetic communication is key to that. Anybody who says otherwise isn't paying attention. The last one is in your partnerships, your romantic partnerships specifically. This is where most guys come into therapy. They're trying to do better for their partners. They're trying to connect better and be there for the people in their life that they're romantic with. Here's the trick. 70% of the arguments that we have in relationships like that never change. After your first year together, you kind of know where the rubs are. They just keep rubbing because they're usually a preference thing. They're usually something that's a competing need or competing desires that don't line up and everybody's got 'em. And so the goal isn't to not have the argument. The goal isn't to resolve the argument. A lot of times in these, the goal is to have the argument better and faster and resolve it more quickly. Empathetic communication is gonna be key to doing that. And so this is where you get in with that partner, right? You try these skills out, you start using emotional language with them. I've had so many patients come in and report to me after we go through these skills that their wife cried the first time. They used empathetic communication because it was what she's been needing from him for so long. Using these tools, using these cues, and getting buy-in on what you're talking about with your partner is gonna be key to having a lasting, effective partnership. So try these out. Either your relationship's gonna get better, or those rubs are gonna get big enough that you just know that this relationship isn't where it's gonna work for you. And you go find somebody who's a little bit better for you. It's gonna be powerful as you bring these things into the world. Now you've got some different avenues to use these skills in. You've got some more awareness coming in. Let's say that you wanna delve deeper and learn more. There's three books I generally recommend. The first one is The og, how to Make Friends and Influence People. You can't go wrong with that book. There's a reason why everybody's used it for so long. It's super short and it's something that everybody should read. It's just a really great way to enter the world. If you want something a little bit more involved in that, that Alan Alder book, if I understood you, would I have this look on my face. It's a great simple way to break down empathetic communication and skills, tbit with storytelling. Alan Alder tells the stories. Great. If you're an audio book guy, he's great at telling the stories. And the last one, let's say that you're super into this. You really wanna go deep. You wanna get the motivational interviewing manual. It's a manual on how to do empathetic communication, spot this thick, and it's what I teach graduate students with. It's one of the most established and powerful tool sets to operationalize empathy. You can't go wrong with it. Now. You've got a plan of action. You've got a 30 day exercise on how to build awareness. You've got three sets of skills that you're gonna learn and practice and engage with people in your life, and you're gonna go get good. Who are you most excited to get better at your communication with? Leave it in the comments and tell us which of these skills you think is gonna be most helpful. I really wanna get the conversation going so guys see all the different ways that these things impact 'em in their life, and we can normalize some of these things. If this conversation was helpful for you, do me a favor. Give us a like and a subscription. It's gonna help you stay informed about what we're doing next, and it's gonna help other guys find this. Thanks so much for being here. This is Tim with American Masculinity, hoping you have a great day.