Good Enough

Getting promoted to manager is a big milestone—but what happens when nobody teaches you how to lead?

On this episode of Good Enough, host Brittany Greenfield sits down with Jen Silva Boucher, CEO and founder of For the Middle Academy, to unpack one of the most overlooked challenges in business: helping individual contributors become effective people leaders. Drawing on 20 years of corporate experience and nearly a decade leading teams, Jen shares why managers often struggle without the right tools—and how communication, clarity, and accountability can transform team culture.

Together, they explore how to:

● Lead with kindness, not just niceness: Why setting standards and having difficult conversations are essential parts of caring for your team.

● Build connection through communication: How listening, appreciation, and consistent check-ins help people feel supported and motivated.

● Find the balance between hands-off and micromanaging: Why effective managers create alignment, establish accountability, and adapt their leadership to the people they lead.

● Keep the human element in an AI-driven world: How technology can support managers, but can’t replace the human connection that makes leadership work.

Great managers don’t have to be everyone’s best friend. They need to be clear, consistent, and committed to helping their people succeed.

If you’re a first-time manager, a seasoned leader, or someone responsible for developing the next generation of leaders, this conversation will help you rethink what good leadership looks like—and what you can start doing differently tomorrow.

Connect with Jen Silva Boucher

Website: https://www.forthemiddleacademy.com/

Connect with Brittany Greenfield

Website: https://www.wabbi.com

LinkedIn: https://www.linkedin.com/in/brittanygreenfield

What if the biggest thing standing between you and the life you want isn't a lack of talent, time, or opportunity—but your own hesitation?

On this episode of Good Enough, host Brittany Greenfield sits down with Klyn Elsbury, a nationally recognized persuasion and negotiation expert who built a seven-figure business while navigating cystic fibrosis, diabetes, and more than 60 hospitalizations. Klyn shares how facing extraordinary challenges shaped her approach to business and life, helping her turn action over perfection into a powerful philosophy that has generated more than $100 million in new revenue for the companies she's worked with.

Together, Brittany and Klyn explore why waiting until you feel ready can keep you stuck, how the stories we tell ourselves shape our decisions, and why taking imperfect action is often the fastest path to growth.

In this episode, you'll discover:

● Why hesitation holds you back: How perfectionism, fear of failure, and other people's opinions can keep you from taking the next step.

● How to get out of your own head: Why breaking big goals into smaller, manageable actions can help you build momentum.

● The power of connection: How stepping outside your comfort zone, understanding other people's perspectives, and finding the right support system can transform your personal and professional life.

You don't need perfect timing, complete confidence, or all the answers to get started. You just need to take the next step.

Tune in for an honest, hilarious, and inspiring conversation that will challenge you to stop overthinking, trust yourself, and just do the damn thing. Because on Good Enough, done beats perfect.

Connect with Klyn Elsbury

Website: https://leadershipsalestraining.com/

Connect with Brittany Greenfield

Website: https://www.wabbi.com

LinkedIn: https://www.linkedin.com/in/brittanygreenfield

What if the difference between reacting under pressure and leading with intention comes down to just half a second?

On this episode of Good Enough, host Brittany Greenfield sits down with Sandra Haddad, an executive coach with more than 25 years of leadership experience, to explore why emotional intelligence (EQ) is one of the most critical skills a leader can develop. Sandra shares the personal wake-up call that changed her approach to leadership and introduces her “Squeeze First” method—a simple, practical way to pause before reacting, recognize your patterns, and choose how you show up.

Together, they explore why even the best strategies fail when organizations overlook the human side of change, how leaders can build trust and psychological safety, and why perfectionism can sometimes protect your ego instead of improving your work.

In this episode, you'll discover:

● The power of the pause: How half a second can help you interrupt automatic reactions and respond with intention.

● Why EQ is a leadership essential: How empathy, active listening, and self-awareness drive stronger teams, innovation, and results.

● The hidden cost of perfectionism: How to recognize when high standards serve the work—and when they're holding you and your team back.

You don't have to become a different person to become a better leader. Start by noticing your patterns, making space to listen, and finding your half-second. Because great leadership isn't about getting everything right—it's about choosing what comes next.

Connect with Sanda Haddad

LinkedIn:https://www.linkedin.com/in/sandrahaddadeqcoach/

Connect with Brittany Greenfield

Website: https://www.wabbi.com

LinkedIn: https://www.linkedin.com/in/brittanygreenfield

What if better results had less to do with doing more—and everything to do with making better moves?

In this episode of Good Enough, Brittany Greenfield sits down with Greg Woodward, founder of Woodward Strategies, to unpack the psychology behind why some sales reps and teams consistently outperform others—even when they’re putting in the same hours and making the same number of calls. Greg explains why consistency beats perfection, how subconscious resistance shapes prospect behavior, and why filling the “tank” with enough data can keep leaders from making costly decisions too soon.

In this episode, you’ll learn:

● Why doing the reps matters more than winning every individual attempt

● How perfectionism can disguise itself as procrastination—and how to move past it

● Why sales teams should focus on precision, personalization, and the right personas instead of simply increasing activity

● How “chunking” and focused time blocks can dramatically improve both productivity and quality

The goal isn’t to make more moves. It’s to make the right moves, consistently—and let small improvements compound over time.

Tune in and discover how to trade volume for precision, embrace the inevitable volatility, and make your next move a little better than the last.

Connect with Greg Woodward

LinkedIn: https://www.linkedin.com/in/gregorycwoodward/

Connect with Brittany Greenfield

Website: https://www.wabbi.com

LinkedIn: https://www.linkedin.com/in/brittanygreenfield

What if the people you think are the problem actually just need more clarity?

What if the thing keeping you from moving forward isn’t perfectionism—but shame?

In this powerful conversation, Brittany Greenfield sits down with Dr. Melissa Robinson Weinmiller to unpack the hidden connection between shame, self-criticism, procrastination, and decision avoidance. Drawing from more than 30 years as a classically trained musician, her experience with toxic leadership, and her work in empathetic leadership, Dr. Melissa reveals why self-empathy—not more pressure—is what can help us break the cycle and regain momentum.

In this episode, you’ll discover:

● Why perfectionism can turn into procrastination and decision avoidance

● The difference between being critical of yourself and judging yourself

● Four steps to practicing self-empathy and breaking the shame cycle

● Why empathy isn’t a “soft skill”—and how it can strengthen leadership, creativity, and

innovation

● How to stay human and authentic as AI takes on more of our cognitive work

At the heart of this conversation is a simple but powerful reminder: being human means being imperfect. Learning to meet yourself with empathy can create the space to learn, lead, innovate, and keep moving forward.

If you’ve ever told yourself, “I should be better,” this episode is for you. Hit play—and discover what becomes possible when you stop letting shame put you in a box.

Connect with Dr. Melissa

Website: https://eqviaempathy.com/

Connect with Brittany Greenfield

Website: https://www.wabbi.com

LinkedIn: https://www.linkedin.com/in/brittanygreenfield

What if the people you think are the problem actually just need more clarity?

In this episode of Good Enough, Brittany Greenfield sits down with Lia Garvin, author, leadership expert, and host of Managing Made Simple, to challenge one of the most common assumptions leaders make: that performance problems are always about the people. Lia explains why clear systems, expectations, context, and communication can transform how teams work—and why even the smallest businesses need systems to succeed.

Together, Brittany and Lia explore:

● Why clarity beats micromanagement: Giving people clear expectations and context helps them make better decisions independently.

● The power of simple systems: Systems don't have to be complicated—they can be as simple as defining the three steps that absolutely need to happen.

● How to make feedback conversations easier: Lia shares a practical “sit-down” approach that combines ownership, recognition or constructive feedback, and a clear action plan.

● Where AI, automation, and hiring fit: Start by identifying the most frustrating, repetitive task in your day and ask whether it should be automated, delegated, or eliminated.

Lia's philosophy is refreshingly simple: good enough systems reduce the number of steps it takes to get something done. You don't need a perfect process—you need a clear one that helps people know what matters, what success looks like, and what to do next.

If leadership feels overwhelming, this conversation is a reminder that the answer may not be to work harder or find better people. Sometimes, you just need to make the work easier to do.

Connect with Lia Garvin

Website: https://www.liagarvin.com/

Connect with Brittany Greenfield

Website: https://www.wabbi.com

LinkedIn: https://www.linkedin.com/in/brittanygreenfield

In this episode of Good Enough, Brittany Greenfield sits down with leadership consultant, executive coach, and author Chuck Wisner to rethink what effective communication really looks like. Chuck explains why great leaders don’t need to have all the answers—they need to create the conditions for better questions, deeper dialogue, and shared understanding. His “open hand” approach to communication helps leaders move away from command-and-control and toward collaboration, curiosity, and trust.

Together, Brittany and Chuck explore:

● The “open hand” approach: How revealing your thinking, concerns, and standards can turn confrontation into collaboration.

● The four questions leaders should ask: What do you want? What are your concerns?

● What are the power dynamics? And what standards are shaping your judgment?

● Why leaders need to say “I don’t know”: The higher you climb, the more you have to rely on the expertise of others and learn together.

● How to recognize your own patterns: Learning to notice when defensiveness, assumptions, or old habits are driving the conversation.

Chuck offers a simple practice you can use tomorrow: pick one of the four questions and use it to open the conversation rather than close it. Because leadership isn't about being the smartest person in the room—it's about creating the space where everyone can think, contribute, and move forward.

Connect with Chuck Wisner:

Website: https://www.chuckwisner.com/

Connect with Brittany Greenfield

Website: https://www.wabbi.com

LinkedIn: https://www.linkedin.com/in/brittanygreenfield

What if the thing holding you back isn’t a lack of ability—but an outdated definition of success?

In this episode, host Brittany Greenfield sits down with Ashley Rudolph, who went from individual contributor to VP in just five years, often as the only woman, Black woman, or youngest person in the room. Now, after a decade of studying what helps high achievers advance, Ashley coaches senior leaders at companies including Airbnb, Meta, and Citi to stop

being the “best kept secret” and start getting recognized for the leadership they already possess.

As Ashley explains, the skills that make you successful early in your career—being the best at your individual work—aren’t necessarily the skills that make you successful as a leader. The conversation explores the pivotal shift from proving what you can do to creating impact through

others, and why invisible contributions can be some of the most valuable work a leader does.

In this episode, you’ll discover:

● Why high achievers often struggle when they reach senior leadership

● How to redefine success beyond individual accomplishment

● Why the “invisible work” leaders do can create enormous impact

● How to become more intentional about the way you show up as a leader

If you’ve ever wondered why working harder isn’t translating into the recognition or influence you want, this conversation will help you rethink the game—and give you a new way to play it.

Connect with Ashley Rudolph:

Website: https://www.workwithashleyr.com/

Connect with Brittany Greenfield

Website: https://linktr.ee/brittanygreenfield

What if letting go of perfection is the key to doing your best work?

In this episode, host Brittany Greenfield sits down with Ann Dux for an honest conversation about perfectionism, progress, and the pressure we put on ourselves to get everything right.

Ann shares her perspective on embracing imperfection, moving forward before you feel completely ready, and redefining what success looks like when you stop chasing an impossible standard.

In this episode, you’ll discover:

● Why perfectionism can keep you from making meaningful progress

● How to embrace “good enough” without lowering your standards

● The power of taking action before you have everything figured out

If you’ve been waiting for the perfect time, perfect plan, or perfect version of yourself, this conversation is your reminder that progress starts when you’re willing to begin.

Connect with Ann Dux:

Website: https://duxcommunications.com/about/

Connect with Brittany Greenfield

Website: https://www.wabbi.com

LinkedIn: https://www.linkedin.com/in/brittanygreenfield

What if the one decision you’re avoiding is the one that changes everything?

In this episode, Brittany Greenfield sits down with Amy Lessinger, a leader who built a billion-dollar real estate brokerage during one of the worst market crashes in history. Instead of playing it safe, Amy made a bold, irreversible decision that not only saved her business—but reshaped how she thinks about leadership, risk, and growth.

Together, they unpack why most leaders get stuck at critical inflection points—not because they lack strategy, but because they’re avoiding the uncomfortable decision they already know they need to make. Amy shares how embracing failure, owning risk, and letting go of perfectionism can unlock momentum and drive real progress.

Key Takeaways:

● Why inaction—not failure—is the biggest regret for leaders

● How “zero-failure cultures” quietly kill growth and innovation

● The power of making irreversible decisions that move you forward

If you’ve ever felt stuck, overanalyzed your next move, or waited for the “perfect” moment—this conversation is your wake-up call. The path forward isn’t clearer—it’s just waiting for you to choose it.

Connect with Amy Lessinger:

Website: https://www.amylessinger.com/

Connect with Brittany Greenfield

Website: https://www.wabbi.com

LinkedIn: https://www.linkedin.com/in/brittanygreenfield