340. Rethinks: Why the Conversations You Avoid Cost You the Most

“Most things that we want in life are on the other side of a difficult conversation.”You want a more successful career, a more fulfilling relationship, a more meaningful life? What if all that’s standing in your way — are the conversations that you’re avoiding? In this Rethinks episode of Think Fast, Talk Smart, Jenn Wynn, a professor at NYU Stern School of Business and previously the director of education at the Obama Foundation, joins Matt Abrahams to discuss how to build the “hard but worth-it skills” necessary for difficult communication. Whether it's asking for a raise, setting boundaries, or addressing conflict, Wynn’s insights show that the conversations you’re avoiding aren’t just holding you back — they’re keeping you from the life you really want.Takeaways: Difficult conversations create opportunities for growth. Speaking up, setting boundaries, and addressing conflict can help us build stronger relationships and move closer to our goals.Confidence comes from communicating through discomfort. Developing the skills to navigate challenging discussions helps us overcome fear and approach difficult conversations with greater intention.Activity:Have the hard conversation. Identify a conversation you've been avoiding and write down what you want to achieve and what's holding you back. Then, take one step toward having it, whether that's scheduling a time to talk or practicing your opening words.Episode Reference Links:Jenn WynnEp.222 Discussing Through Discomfort: Why the Conversations You Avoid Cost You the Most Connect:Premium Signup >>>> Think Fast Talk Smart PremiumEmail Questions & Feedback >>> [email protected] Transcripts >>> Think Fast Talk Smart WebsiteNewsletter Signup + English Language Learning >>> FasterSmarter.ioThink Fast Talk Smart >>> LinkedIn, Instagram, YouTubeMatt Abrahams >>> LinkedIn Chapters:(00:00) - Introduction (01:28) - Understanding Difficult Conversations (03:45) - Developing Emotional Intelligence (04:45) - Self-Awareness, Pause, Reframe (07:00) - Common Communication Barriers (10:04) - Listening for Understanding (13:11) - Feedback to Your Boss (17:04) - Reinforcing Good Behavior (20:04) - Using AI for Communication (21:31) - Lessons from the Obama Foundation (25:07) - Creating Psychological Safety (28:01) - The Final Three Questions (32:42) - Conclusion ********Thank you to our sponsors.  These partnerships support the ongoing production of the podcast, allowing us to bring it to you at no cost.Strawberry.me. Get 50% off your first coaching session today at Strawberry.me/smartJoin our Think Fast Talk Smart Learning Community and become the communicator you want to be. 

“Being present is really at the center of listening. Nothing really happens unless we're present.”Some of the most important things we need to say are often the hardest to put into words. Whether it's expressing gratitude, offering an apology, or saying goodbye, slowing down and taking the time to write can help us communicate with greater thoughtfulness and meaning. In this episode of Think Fast, Talk Smart, Matt Abrahams speaks with Frish Brandt, professional letter midwife and author of Unfinished Business: Writing the Five Essential Letters of Your Life. Brandt shares why letter writing can be as valuable for the writer as the recipient, how to move past the fear of a blank page, and why thoughtful communication requires more than finding the right words.Takeaways:Slowing down makes communication more meaningful. Thoughtful writing helps us process emotions, find the right words, and express ourselves with greater intention.Better listening starts with being present. Setting aside our own thoughts and judgments creates space for empathy, understanding, and stronger connections.Activity:Write the unwritten letter. Write the first few sentences of a letter you've been putting off, whether it's a thank you, an apology, or something left unsaid. Focus on expressing what you genuinely feel rather than finding the perfect words.Printable Expanded Takeaways & ActivitiesEpisode Reference Links:Frish BrandtFrish’s Book: Unfinished BusinessEp.114 Communication Means Paying Attention: The Four Pillars of Active Listening Connect:Premium Signup >>>> Think Fast Talk Smart PremiumEmail Questions & Feedback >>> [email protected] Transcripts >>> Think Fast Talk Smart WebsiteNewsletter Signup + English Language Learning >>> FasterSmarter.ioThink Fast Talk Smart >>> LinkedIn, Instagram, YouTubeMatt Abrahams >>> LinkedIn Chapters:(00:00) - Introduction (01:03) - The Art of Letter Writing (02:00) - The Five Essential Letters (03:19) - Writing for Yourself (04:06) - Slowing Down Communication (05:33) - Getting Started With Letters (06:55) - Writing Meaningful Letters (08:13) - Overcoming the Blank Page (10:21) - The Power of Cathartic Writing (12:21) - Writing Authentic Apologies (13:39) - AI and Writing (15:45) - The Art of Deep Listening (17:58) - The Final Three Questions (22:11) - Conclusion ********Thank you to our sponsors.  These partnerships support the ongoing production of the podcast, allowing us to bring it to you at no cost.Strawberry.me. Get 50% off your first coaching session today at Strawberry.me/smartJoin our Think Fast Talk Smart Learning Community and become the communicator you want to be. 

“Sleep is essential to good performance and good communication.”A good night's sleep can make all the difference in how we think, feel, and communicate. But for anyone who struggles to fall asleep, worrying about getting enough rest can become part of the problem. In this Quick Thinks episode of Think Fast, Talk Smart, Matt Abrahams shares his personal struggles with sleep and the strategies that have helped him rest easier. Drawing on advice from past guests, including Cheri Mah and Andrew Huberman, Matt introduces his ABCDE framework for better sleep, offering practical tips for managing bedtime anxiety, calming a racing mind, and building healthier sleep habits so you can show up at your best.Takeaways:Better sleep starts with managing your mind. Journaling, reframing negative thoughts, and practicing deep breathing can help reduce bedtime anxiety and quiet a racing mind.Small changes can make a big difference in sleep quality. Limiting caffeine, creating a comfortable sleep environment, and maintaining a consistent bedtime routine can help you rest better and show up more effectively in your daily communication.Activity:Quiet your mind. Before bed tonight, spend five minutes writing down anything that's worrying you, followed by three things you're grateful for. Notice whether getting your thoughts onto paper helps you feel more relaxed and ready for sleep.Episode Reference Links:Ep.287 Give It a Rest to Do Your Best: The Sleep Habits That Catalyze Your CommunicationEp.274 Choose Connection Over Perfection: Why Happiness Starts with Better CommunicationEp. 109 Simplify! How to Communicate Complex Ideas Simply and EffectivelyEp. 270 Make Belief: The Mindset Shifts That Make Your Communication StrongerEp.33 Hacking your Speaking Anxiety: How Lessons from Neuroscience Can Help You Communicate Confidently   Connect:Premium Signup >>>> Think Fast Talk Smart PremiumEmail Questions & Feedback >>> [email protected] Transcripts >>> Think Fast Talk Smart WebsiteNewsletter Signup + English Language Learning >>> FasterSmarter.ioThink Fast Talk Smart >>> LinkedIn, Instagram, YouTubeMatt Abrahams >>> LinkedIn Chapters:(00:00) - Introduction (01:04) - A: Managing Emotions (01:53) - B: Building Better Sleep Habits (02:37) - C: Managing Your Thoughts (03:34) - D: Deep Breathing Techniques (04:23) - E: Creating the Right Sleep Environment (05:24) - Conclusion ********Thank you to our sponsors.  These partnerships support the ongoing production of the podcast, allowing us to bring it to you at no cost.Strawberry.me. Get 50% off your first coaching session today at Strawberry.me/smartJoin our Think Fast Talk Smart Learning Community and become the communicator you want to be. 

"It's been a paradigm shift for me to ask whether I can make my situation my ally rather than just try harder."Trying harder isn't always the answer. Sometimes, the key to making progress isn't changing yourself, but changing the people and environments around you. In this episode of Think Fast, Talk Smart, psychologist and bestselling author Angela Duckworth joins Matt Abrahams to challenge conventional thinking about grit, perseverance, and personal growth. Drawing on insights from her new book, Situated: Find the People and Places That Bring Out Your Best, Duckworth explains why effort alone isn't enough, how asking for help can accelerate improvement, and what deliberate practice really takes. Takeaways:Sometimes changing your situation is more effective than trying harder. The people and environments around you can either support or limit your progress. Seeking help, mentorship, and the right conditions can make your efforts more successful.Better communication takes more than repetition. Deliberate practice requires specific goals, focused effort, and constructive feedback. Knowing what works, what needs improvement, and what to leave out can help you become a more effective communicator.Activity:Change the situation. Think of something you've been struggling to improve despite putting in the effort. Instead of working harder, make one change to your environment, routine, or support system that could help you make progress.Printable Expanded Takeaways & ActivitiesTo listen to the extended Deep Thinks version of this episode, please visit FasterSmarter.io/premium.Episode Reference Links:Angela DuckworthAngela’s Books: Grit / SituatedConnect:Premium Signup >>>> Think Fast Talk Smart PremiumEmail Questions & Feedback >>> [email protected] Transcripts >>> Think Fast Talk Smart WebsiteNewsletter Signup + English Language Learning >>> FasterSmarter.ioThink Fast Talk Smart >>> LinkedIn, Instagram, YouTubeMatt Abrahams >>> LinkedIn Chapters:(00:00) - Introduction (01:09) - The Four Pillars of Grit (05:22) - The Power of Deliberate Practice (08:46) - Giving Effective Feedback (11:51) - Changing Your Situation (13:45) - The Value of Asking for Help (16:55) - The Final Three Questions (24:24) - Conclusion

“Rather than trying to eliminate your nerves entirely, build your own anxiety management plan so you're prepared when they inevitably creep in.”Around Halloween, few things feel scarier than being put on the spot to speak in front of others. Your heart races, your palms sweat, and suddenly the words you planned to say disappear. But while communication anxiety can be frightening, it doesn't have to haunt you. In this special Halloween Rethinks episode of Think Fast, Talk Smart, Matt Abrahams revisits research-backed strategies for managing speaking anxiety, featuring insights from experts including Andrew Huberman, Kelly McGonigal, and Alison Wood Brooks. Through the ABCs of anxiety management, Matt shares practical techniques for managing your emotions, calming your body, and reframing your thoughts. With a few tricks up your sleeve, you can take the fright out of public speaking and treat yourself to more confident communication.Takeaways: Anxiety doesn't have to be the enemy of confident communication. Acknowledging your nerves as normal and reframing them as excitement or a sign that you care can help you approach speaking situations with a more positive mindset.Managing speaking anxiety starts with having a plan. Combining emotional, physical, and mental techniques into a personalized anxiety management plan can help you feel more comfortable, prepared, and confident under pressure.Activity:Build your anxiety management plan. Create your own three-step plan for managing speaking anxiety using the ABCs: one technique to reframe your emotions, one to calm your body, and one to redirect negative thoughts. Test your plan before your next presentation or important conversation, and adjust it based on what works best for you.Episode Reference Links:Ep.18 Managing in the Moment: How to Get Comfortable with Being UncomfortableEp.69 Feeling Nervous? How Anxiety Can Fuel Better CommunicationEp.66 Rethinks: Lessons from Neuroscientist Andrew Huberman to Help You Hack your Speaking AnxietyEp.34 How We Gain — Or Give Away — Authority While SpeakingEp.40 Mindset Matters: How to Embrace the Benefits of StressEp.73 Listen Up: Why It’s Better to Be Interested Than Interesting   Connect:Premium Signup >>>> Think Fast Talk Smart PremiumEmail Questions & Feedback >>> [email protected] Transcripts >>> Think Fast Talk Smart WebsiteNewsletter Signup + English Language Learning >>> FasterSmarter.ioThink Fast Talk Smart >>> LinkedIn, Instagram, YouTubeMatt Abrahams >>> LinkedIn Chapters:(00:00) - Introduction (02:41) - Managing Negative Feelings (04:07) - Reframing Anxiety (05:03) - Managing Physical Symptoms (05:40) - Breathing Techniques (06:25) - Physical Strategies for Anxiety (07:30) - Warming Up to Speak (08:31) - Managing Your Mindset (11:02) - Turning Anxiety Into Excitement (12:20) - Creating an Anxiety Management Plan (14:33) - Testing and Refining Your Plan (15:22) - Conclusion ********Thank you to our sponsors.  These partnerships support the ongoing production of the podcast, allowing us to bring it to you at no cost.Strawberry.me. Get 50% off your first coaching session today at Strawberry.me/smartJoin our Think Fast Talk Smart Learning Community and become the communicator you want to be. 

“As you're navigating your workplace hierarchy, you're also simultaneously shaping it.”Power shapes the way we work, communicate, and connect with others. But when workplace hierarchies become overly competitive, unfair, or unstable, they can undermine the very teams they're meant to support. According to Stanford professor Nir Halevy, the solution isn't necessarily to eliminate hierarchies, but to rethink how they work. In this episode of Think Fast, Talk Smart, Halevy joins Matt Abrahams to share insights from his new book, Level Up: Why Hierarchies Are Broken and How to Fix Them. He explains how everyday acts of communication can help repair unhealthy workplace dynamics, why recognizing different contributions creates stronger teams, and how humor, empathy, and a better understanding of your audience can help you lead and influence others more effectively.Takeaways:Healthy hierarchies reward more than individual success. Recognizing different contributions, encouraging collaboration, and valuing kindness alongside achievement can create stronger, more supportive teams.Everyday communication can reshape workplace dynamics. Small acts of gratitude, empathy, and recognition help build trust, strengthen relationships, and create a more positive organizational culture.Activity:Give credit where it's due. At your next team meeting, publicly recognize someone whose contributions often go unnoticed. Highlight something specific they did and why it mattered, helping reinforce a culture where different strengths and efforts are valued.Printable Expanded Takeaways & ActivitiesEpisode Reference Links:Nir HalevyNir’s Book: Level UpEp.30 Dissolve Disagreements: How Communication Impacts Conflict  Connect:Premium Signup >>>> Think Fast Talk Smart PremiumEmail Questions & Feedback >>> [email protected] Transcripts >>> Think Fast Talk Smart WebsiteNewsletter Signup + English Language Learning >>> FasterSmarter.ioThink Fast Talk Smart >>> LinkedIn, Instagram, YouTubeMatt Abrahams >>> LinkedIn Chapters:(00:00) - Introduction (00:53) - Understanding Hierarchies (03:14) - Signs of Broken Hierarchies (05:14) - Fixing Unhealthy Hierarchies (06:27) - Building Healthy Hierarchies (09:36) - Competition and Collaboration (11:00) - Communication and Hierarchies (13:34) - Construal Fit (17:07) - Humor and Competence (19:18) - The Final Three Questions (23:56) - Conclusion ********Thank you to our sponsors.  These partnerships support the ongoing production of the podcast, allowing us to bring it to you at no cost.Strawberry.me. Get 50% off your first coaching session today at Strawberry.me/smartJoin our Think Fast Talk Smart Learning Community and become the communicator you want to be. 

“Meetings are often used as band-aids, as ways of covering up for other larger communication challenges.”Few things feel better than seeing a meeting canceled. But what if meetings were something we actually looked forward to? A productive meeting doesn't happen by accident. It starts with knowing whether you need one at all, continues with a clear purpose and thoughtful structure, and ends with everyone knowing what comes next. In this Quick Thinks episode of Think Fast, Talk Smart, Matt Abrahams breaks down what makes meetings work. He shares strategies for creating smarter agendas, making space for every voice, and turning discussions into decisions and action, so your next meeting is worth the time on everyone's calendar.Takeaways:The best meetings start before anyone enters the room. Question whether a meeting is necessary, establish clear goals, and create a focused agenda that respects everyone's time and sets expectations for success.Effective meetings turn discussion into action. Encourage participation, manage time thoughtfully, and close with clear decisions and next steps. Following up afterward ensures conversations lead to meaningful results.Activity:Rethink your agenda. Take an upcoming meeting agenda and rearrange the topics by difficulty: medium first, most challenging second, and easiest last. Give each item a clear outcome, whether it's a decision, discussion, or update, to help keep the meeting focused and productive.Episode Reference Links:Ep.261 Meetings With a Point: How to Design For Better Decisions Connect:Premium Signup >>>> Think Fast Talk Smart PremiumEmail Questions & Feedback >>> [email protected] Transcripts >>> Think Fast Talk Smart WebsiteNewsletter Signup + English Language Learning >>> FasterSmarter.ioThink Fast Talk Smart >>> LinkedIn, Instagram, YouTubeMatt Abrahams >>> LinkedIn Chapters:(00:00) - Introduction (00:43) - Is a Meeting Necessary (01:55) - Set Goals & Create an Agenda (03:56) - Choose the Right Attendees (04:35) - Make the Most of Calendar Invites (05:08) - Optimize Meeting Length & Time (06:56) - Start Meetings Effectively (07:40) - Facilitate Participation (08:21) - Managing Hybrid Meetings (09:23) - End Meetings with Purpose (10:05) - Following Up After Meetings (11:04) - Conclusion ********Thank you to our sponsors.  These partnerships support the ongoing production of the podcast, allowing us to bring it to you at no cost.Strawberry.me. Get 50% off your first coaching session today at Strawberry.me/smartJoin our Think Fast Talk Smart Learning Community and become the communicator you want to be. 

“Be as curious about the other person as you are excited to share about yourself.”What makes you click with someone? For organizational psychologist and bestselling author Adam Grant, meaningful connection isn't just about chemistry. It's about understanding how we relate to others, showing genuine curiosity, and creating interactions that bring us closer. In part one of this two-part Think Fast, Talk Smart episode, Grant joins Matt Abrahams to discuss the science of connection and share lessons from his new book, Vibe: The Secrets of Strong Connections in a Lonely World. From building confidence through practice and seeking advice instead of feedback to finding common ground and creating more dynamic conversations, Grant shares practical ways to strengthen relationships and make our interactions more meaningful.Takeaways:Strong connections are built with intention. Understanding whether you're seeking shared goals, interests, or values helps you approach relationships more thoughtfully and build stronger connections.Better conversations require curiosity and give-and-take. Showing genuine interest, keeping exchanges dynamic, and remembering personal details can turn everyday interactions into more meaningful, lasting relationships.Activity:Make a memory flex. After your next meaningful conversation, note one detail the other person shared. A few days later, follow up with a thoughtful message, recommendation, or question that shows you remembered and helps strengthen the connection.Printable Expanded Takeaways & ActivitiesEpisode Reference Links:Adam GrantAdam’s Book: VibeEp.80 Magic Words: Change What You Say to Inspire and Influence Others Connect:Premium Signup >>>> Think Fast Talk Smart PremiumEmail Questions & Feedback >>> [email protected] Transcripts >>> Think Fast Talk Smart WebsiteNewsletter Signup + English Language Learning >>> FasterSmarter.ioThink Fast Talk Smart >>> LinkedIn, Instagram, YouTubeMatt Abrahams >>> LinkedIn Chapters:(00:00) - Introduction (01:03) - Overcoming Speaking Anxiety (04:03) - Building Confidence (05:28) - Expanding Your Comfort Zone (08:17) - Learning Through Advice (13:45) - Balancing Competence and Connection (15:21) - The Science of Vibing (16:53) - Building Connection Virtually (18:52) - Three Types of Connection (20:17) - Turn Connection Into Collaboration (23:38) - The Final Three Questions (30:34) - Conclusion

“You learn nothing when you’re right.” Effective communication isn’t about having all the answers. As Astro Teller knows, it’s about finding, and sometimes fumbling, your way through the questions. As Captain of Moonshots at X, Alphabet’s Moonshot Factory, Teller embraces what he calls “a learning journey,” where being wrong isn’t the end, but an opportunity to discover something new. In this episode of Think Fast, Talk Smart, Teller and Matt Abrahams discuss how embracing uncertainty drives innovation, why leaders should reward learning over outcomes, and why sometimes being wrong is the best way to learn.Takeaways:Being wrong is where learning happens. Treating failure as useful information rather than something to avoid helps you stay curious, test assumptions, and discover better paths forward. Reward the habits that lead to innovation, not just the outcomes. Focusing on curiosity, humility, and experimentation creates space for people to take meaningful risks and pursue ideas that may not work the first time. Activity:Find the failure faster. Choose one idea or project you’re confident about and identify the assumption most likely to prove you wrong. Design one small test that could challenge that assumption, then treat whatever you learn as progress.Episode Reference Links:Astro TellerAstro’s Book: Sacred CowsEp.237 Mistake It Till You Make It: Learn Faster and Fail SmarterEp.70 Ideas Fuel Innovation: Why Your First Ideas Aren't Always the BestEp.20 Question Your Questions: How to Spark Creativity in Your Communication  Connect:Premium Signup >>>> Think Fast Talk Smart PremiumEmail Questions & Feedback >>> [email protected] Transcripts >>> Think Fast Talk Smart WebsiteNewsletter Signup + English Language Learning >>> FasterSmarter.ioThink Fast Talk Smart >>> LinkedIn, Instagram, YouTubeMatt Abrahams >>> LinkedIn Chapters:(00:00) - Introduction (01:33) - Defining a Moonshot (03:35) - Building a Learning Mindset (06:15) - Learning vs. Productivity (07:50) - Sharing Learning Across Teams (10:04) - Rewarding Habits, Not Outcomes (12:32) - Destigmatizing Failure (15:12) - Moonshots in Action (18:51) - Storytelling for Understanding (20:11) - Using Analogies Effectively (22:15) - Fostering Creativity Through Play (25:20) - Hiring for a Moonshot Culture (27:57) - The Moonshot Podcast (29:44) - The Final Three Questions (34:19) - Conclusion ********Thank you to our sponsors.  These partnerships support the ongoing production of the podcast, allowing us to bring it to you at no cost.Strawberry.me. Get 50% off your first coaching session today at Strawberry.me/smartJoin our Think Fast Talk Smart Learning Community and become the communicator you want to be. 

“Boredom is just the enemy of conversation.” Small talk doesn’t have to be boring. For matchmaker and dating coach Rachel Greenwald, better conversations start with a little preparation and a willingness to move beyond predictable questions toward the stories that make people memorable. In this episode of Think Fast, Talk Smart, Greenwald joins Matt Abrahams to share strategies for building stronger connections in dating, networking, and the workplace. From bridging small talk toward more meaningful topics to navigating taboo subjects and showing more vulnerability, she explains how to create conversations that bring out the best in others and ourselves.Takeaways:Better small talk starts with a little strategy. Preparing a few topics and finding natural bridges toward what makes you unique can turn routine exchanges into more memorable, meaningful interactions. Connection comes from stories, not just information. Asking questions that invite people to share experiences and emotions can reveal more than factual answers and help deepen relationships.Activity:Build a better bridge. Turn three standard small-talk questions into openings that lead somewhere more interesting. For example, instead of answering “How are you?” with “Good,” practice a response that naturally introduces a story, interest, or experience someone could ask you about.Printable Expanded Takeaways & ActivitiesTo listen to the extended Deep Thinks version of this episode, please visit FasterSmarter.io/premium.Episode Reference Links:Rachel GreenwaldEp.89 Listen, Listen, Listen: How to Build Deep Connections Connect:Premium Signup >>>> Think Fast Talk Smart PremiumEmail Questions & Feedback >>> [email protected] Transcripts >>> Think Fast Talk Smart WebsiteNewsletter Signup + English Language Learning >>> FasterSmarter.ioThink Fast Talk Smart >>> LinkedIn, Instagram, YouTubeMatt Abrahams >>> LinkedIn Chapters:(00:00) - Introduction (00:50) - Strategic Small Talk (04:27) - Building Your Personal Brand (08:21) - Mastering the First 60 Seconds (10:54) - Starting in the Middle (12:17) - Navigating Taboo Topics (15:36) - The Final Three Questions (23:33) - Conclusion ********Thank you to our sponsors.  These partnerships support the ongoing production of the podcast, allowing us to bring it to you at no cost.Strawberry.me. Get 50% off your first coaching session today at Strawberry.me/smartJoin our Think Fast Talk Smart Learning Community and become the communicator you want to be.