Michael Piperno

When Difficult Conversations Go Wrong (and How to Recover) 

You finally decide to have the conversation you’ve been putting off. You sit down with the employee. You start strong. And then… it derails. 

Maybe they get defensive. Maybe you get frustrated. Maybe the message gets lost. Maybe you walk away thinking, “Well, that didn’t help.” 

If this sounds familiar, you’re not alone. 

Why These Conversations Go Sideways 

Most difficult conversations fail for one of three reasons: 

1. The leader jumps straight to the conclusion. 

“You need to improve your attitude.” “You’re not performing at the level we need.” 

The employee hears judgment, not guidance. 

2. The leader focuses on the person, not the behavior. 

This triggers defensiveness instantly. 

3. The leader doesn’t have a clear coaching structure. 

Without a process, the conversation becomes emotional instead of productive. 

How to Get Back on Track 

Here’s a simple reset you can use in the moment: 

Pause. Breathe. Then say: “I want to make sure we’re working on this together. Let me restate what I’m trying to address.” 

This does three things: 

  • Lowers the emotional temperature 
  • Re-centers the conversation on the issue 
  • Signals partnership, not punishment 

The Power of a Coaching Mindset 

When leaders approach these conversations with curiosity instead of certainty, everything shifts. 

Try asking: 

  • “Help me understand what’s getting in the way.” 
  • “What support would help you be more successful?” 
  • “What do you think the next step should be?” 

These questions turn a difficult conversation into a productive one — and they build trust instead of fear. 

If conversations like these tend to go off‑track, you’re not alone — and you don’t have to navigate them by trial and error. With the right structure and coaching tools, leaders handle them with far more clarity and confidence. 

Leaders often feel torn between being supportive and holding people accountable. The truth is, great leadership isn’t about choosing one or the other — it’s about blending both with intention. That balance is the leadership sweet spot. 

Support Without Clarity Falls Flat 

Support builds trust and connection, but if it isn’t paired with clear expectations, teams can drift. People feel cared for but unsure of what “good” looks like. 

Constructive Feedback Without Care Backfires 

Constructive feedback keeps standards high, yet when it’s delivered without empathy, it can create defensiveness or fear. Performance may improve temporarily, but engagement drops. 

Where the Two Meet 

Leaders who operate in the sweet spot do three things well: 

  • They make expectations empowering. Feedback becomes a path forward, not a punishment. 
  • They treat support as a performance tool. Removing barriers helps people rise to the challenge. 
  • They stay consistent. They don’t avoid tough conversations, and they don’t withhold encouragement. 

How to Lead From the Sweet Spot 

  • Ask questions before giving constructive feedback. 
  • Be specific about what needs to change. 
  • Recognize progress. 
  • Invite ownership of next steps. 
  • Follow up reliably. 

The Impact 

Support builds trust. Constructive feedback builds clarity. 

Together, they create teams that feel valued, challenged, and motivated to deliver their best. 

This article originally appeared at WeAreComvia.com and is reprinted here with permission.

Michael Piperno is a communication coach and executive presence expert. His insights empower leaders to communicate effectively and authentically.

When Difficult Conversations Go Wrong (and How to Recover)  Read More »

Podcast show artwork featuring images of Michael Piperno and Kerry Barrett with the title of the show, "I Don't Know Where This Conversation is Going to Go"

Overcoming Fears, Reinvention, and Entrepreneurship with Kerry Barrett

Ever wondered what it really takes to conquer self-doubt, switch careers, or start a business from scratch—especially when you have no clue what you’re doing? In this episode, I sit down with Emmy Award-winning former TV news anchor turned on-camera coach, Kerry Barrett, to unpack the winding road from the newsroom to entrepreneurship.

We both open up about the messy side of pursuing new dreams: overcoming fear of public speaking, dealing with imposter syndrome, learning on the fly, and making peace with failure. You’ll hear how Kerry pivoted her business multiple times, faced a steep learning curve, and discovered the power of relentless self-improvement.

Whether you’re thinking about your own career leap, struggling with self-confidence, or just craving an authentic peek behind the scenes of working for yourself, I think you’ll find our conversation insightful. Plus, we share some practical wisdom on the importance of building a support network, testing your ideas, and (finally) not letting other people’s opinions define your story.

Tune in for an empowering conversation loaded with real talk, lots of laughs, and actionable takeaways for anyone on the journey of reinventing themselves.

Links mentioned in the show:

Kerry’s LinkedIn Profile: www.linkedin.com/in/kerrybarrett/
Check out Kerry’s YouTube Channel: www.youtube.com/@IAmKerryBarrett
Kerry’s Website: www.kerrybarrett.com
Michael’s Website: MichaelPiperno.com

Listen on Apple Podcasts or Spotify.

Oh, and there’s a video version on YouTube 😉: https://www.youtube.com/@michaelpiperno

Overcoming Fears, Reinvention, and Entrepreneurship with Kerry Barrett Read More »

Taming the Advice Monster: Why Great Leaders Listen Before They Lead 

Most leaders have an “advice monster.” That instinct to jump in, fix, direct, or diagnose the moment we see a problem. 

I know mine well. 

In a recent conversation with Steve Swan, I talked about how quickly I can slip into advice‑giving mode. I’ll walk into a room, observe a group of leaders, and within minutes see where they could grow — how they present, how they handle Q&A, how they make their audience feel. 

My instinct is to help immediately. 

But over the years, I’ve learned something important: 

Just because I’m ready to give advice doesn’t mean someone is ready to receive it. 

And that gap, between my readiness and theirs, is where leadership either strengthens or breaks down. 

The Trap of Leading Through Advice 

Many leaders are promoted because they’re exceptional at what they do. They’re problem‑solvers. They’re experts. They’re the ones people rely on when something needs to get done. 

But expertise can create a blind spot. 

When leaders default to giving advice too quickly, a few things happen: 

  • People feel evaluated instead of understood 
  • Trust takes longer to build 
  • The real issue often stays hidden 
  • Team members become dependent instead of empowered 
  • Feedback lands flat because the timing is off 

Advice isn’t the problem. Premature advice is. 

Curiosity Builds Readiness 

Steven and I talked about how important it is to read the room — not just for what people need, but for what they’re ready for. 

Before someone can absorb feedback, they need: 

  • Psychological safety 
  • A sense of being heard 
  • Confidence that you understand their context 
  • Trust that your intention is to help, not judge 

Curiosity creates those conditions. 

When leaders ask thoughtful, open‑ended questions, they signal respect. They show they’re invested in understanding, not just instructing. And once someone feels seen, they’re far more open to guidance. 

Advice That Lands vs. Advice That Falls Flat 

The difference isn’t the quality of the advice. It’s the timing and the relationship

Advice that lands: 

  • Comes after listening 
  • Is tailored to what the person actually needs 
  • Respects their readiness 
  • Builds confidence instead of diminishing it 

Advice that falls flat: 

  • Comes too early 
  • Solves the wrong problem 
  • Feels like criticism 
  • Creates defensiveness 

Leaders who understand this shift from “fixer” to “partner” see their teams grow faster and with more ownership. 

Leadership Isn’t About Having the Answers 

It’s about creating the conditions where answers can be heard. 

When leaders slow down, get curious, and resist the urge to jump straight into solution mode, they build stronger relationships and more capable teams. 

Your expertise matters — but sometimes your timing matters more. 

This article originally appeared at WeAreComvia.com and is reprinted here with permission.

Michael Piperno is a communication coach and executive presence expert. His insights empower leaders to communicate effectively and authentically.

Taming the Advice Monster: Why Great Leaders Listen Before They Lead  Read More »

Podcast artwork featuring images of Michael Piperno and Tami Wong

The Power of Sharing Your Story with Tami Wong

In this episode, I caught up with Tami Wong, and we had a wonderful conversation that touched on a variety of themes, including vulnerability, resilience, and personal growth.

Tami is the founder of Hair Loss Pride and author of the children’s book “Hair Pride.” In our conversation, she shared her personal journey of living with alopecia since her teens, detailing the struggles she faced with confidence, shame, and self-acceptance, as well as the turning points that led her to become an advocate for women experiencing hair loss. 

We also talked about Tami’s transition from a corporate career in biotech and healthcare to launching her own business—one that offers not only coaching, wig consultations, and support groups, but also a powerful online community where women can share their stories and feel less alone. The conversation covers the significance of breaking silences around topics often considered taboo, including estrangement, anxiety, and grief. 

We delved into the challenges and rewards of entrepreneurship, the importance of representation in beauty and fashion, and the ripple effects created when people are brave enough to step forward and speak openly about their experiences.

It’s a great conversation about the transformative power of connection, sharing personal struggles, and embracing your story.

Links Mentioned:

Listen on Apple Podcasts or Spotify.

Oh, and there’s a video version on YouTube 😉: https://www.youtube.com/@michaelpiperno

The Power of Sharing Your Story with Tami Wong Read More »

Podcast Art with images of Michael Piperno and Erin Davis. The text says, "I don't know where this conversation is going to go."

Inclusion, Connection, and Lessons from the Rink with Erin Davis

In this episode, I sit down with Erin Davis to dive into a candid and wide-ranging conversation about connection, inclusion, and embracing change—both in and outside of the workplace. From stories about childhood belonging (or lack thereof) to how we make people feel in our everyday interactions, this episode explores how our lived experiences shape the way we form relationships and communicate across differences.

You’ll hear Erin share her journey from being a hockey skeptic to lacing up her own skates as an “elder millennial” and how trying something new on the ice turned into powerful lessons about leadership, teamwork, and building truly inclusive spaces. Michael and Erin also share honest reflections about networking, communication challenges among generations, and how recalibrating our beliefs can be healthier than relentlessly pushing forward.

Tune in for practical wisdom, a few good laughs, and a reminder that we all just want to feel included.

Links Mentioned:

Listen on Apple Podcasts or Spotify.

Oh, and there’s a video version on YouTube 😉: https://www.youtube.com/@michaelpiperno

Inclusion, Connection, and Lessons from the Rink with Erin Davis Read More »

Supportive Constructive Feedback: The Skill Most Leaders Never Learn 

Let’s be honest: the word feedback makes most people tense up.   

We’ve all had those “Can we talk?” moments that felt more like a warning than support. 

But supportive constructive feedback — the kind that actually helps someone grow — is one of the most valuable tools a leader has. 

The problem?   

Most leaders were never taught how to give it in a way that feels clear, kind, and helpful. 

So, what is supportive constructive feedback? 

Well, here’s what it’s not

*   A lecture 

*   A judgment 

*   A list of everything that went wrong 

*   A surprise that catches someone off guard 

And here’s what it is

*   Clear 

*   Specific 

*   Respectful 

*   Focused on the future 

*   Something you work on together 

A Simple Way to Make It Easier 

Here’s a structure that keeps things grounded and positive: 

1. Describe the behavior. Stick to what you observed — not assumptions, not opinions. 

2. Explain the impact. Help them understand how it affected the work, the team, or the outcome. 

3. Ask for their perspective. This is where the conversation becomes a conversation, not a monologue. 

4. Collaborate on the next step. Create the plan together. People support what they help build. 

This doesn’t just improve performance. It strengthens trust. It deepens connection. It shows you’re invested in them, not just the output. 

The Bottom Line 

People want to do well.   

They want clarity, support, and leaders who help them grow. Supportive constructive feedback gives them exactly that. 

And when leaders get good at it, everything improves faster — performance, morale, relationships, all of it. 

And when leaders learn how to deliver it well, performance improves quickly, often faster than they expect. 

If you’re curious what supportive corrective feedback looks like in real conversations, there are proven coaching methods that make these moments far more effective and far less stressful. 

This article originally appeared at WeAreComvia.com and is reprinted here with permission.

Michael Piperno is a communication coach and executive presence expert. His insights empower leaders to communicate effectively and authentically.

Supportive Constructive Feedback: The Skill Most Leaders Never Learn  Read More »

Podcast show artwork featuring Greg Ippolito of IMA and Michael Piperno

Music, Marketing, and Meaningful Relationships with Greg Ippolito

In this episode of I Don’t Know Where This Conversation Is Going to Go, I sit down with my longtime friend and colleague Greg Ippolito — someone I’ve known for so many years that our conversations tend to zig, zag, loop back, and somehow land exactly where they’re supposed to.

We talk about a lot — connection, marketing, music, creativity — but it all comes back to one simple truth: people. How we show up for each other. How we communicate. How we build trust. And how, despite all the digital noise we navigate every day, the most meaningful moments still happen one human at a time.

Greg and I riff on where marketing is headed. We also get into why genuine, personal connection matters more than ever — not as a tactic, but as a way of being.

Some of my favorite parts of our conversation are about music. We swap stories about rediscovering it during the pandemic, the strange comfort of gathering around a piano, and the science behind why certain songs make us feel seen, understood, or simply less alone. We even wander into the nostalgia of vinyl. You’ll see.

We also talk business. The messy blend of sales and marketing. The power of referrals. The magic that happens when you experiment with content instead of overthinking it. And the humble, often invisible ways people help shape our lives without us realizing it until years later.

It’s a thoughtful conversation, and it’s a reminder that connection — real connection — is still at the heart of good work and a good life.

Takeaways:

  • Real connection always beats slick, surface-level marketing.
  • Revisiting old passions (like music) can bring people closer.
  • Creativity thrives when you’re willing to experiment and not take yourself too seriously.
  • Many of the moments that shape us don’t look significant until we look back.

Links Mentioned:

Listen on Apple Podcasts or Spotify.

Oh, and there’s a video version on YouTube 😉: https://youtu.be/TF81YkEfSKs

Music, Marketing, and Meaningful Relationships with Greg Ippolito Read More »

The Leadership Sweet Spot

Leaders often feel torn between being supportive and holding people accountable. The truth is, great leadership isn’t about choosing one or the other — it’s about blending both with intention. That balance is the leadership sweet spot. 

Support Without Clarity Falls Flat 

Support builds trust and connection, but if it isn’t paired with clear expectations, teams can drift. People feel cared for but unsure of what “good” looks like. 

Constructive Feedback Without Care Backfires 

Constructive feedback keeps standards high, yet when it’s delivered without empathy, it can create defensiveness or fear. Performance may improve temporarily, but engagement drops. 

Where the Two Meet 

Leaders who operate in the sweet spot do three things well: 

  • They make expectations empowering. Feedback becomes a path forward, not a punishment. 
  • They treat support as a performance tool. Removing barriers helps people rise to the challenge. 
  • They stay consistent. They don’t avoid tough conversations, and they don’t withhold encouragement. 

How to Lead From the Sweet Spot 

  • Ask questions before giving constructive feedback. 
  • Be specific about what needs to change. 
  • Recognize progress. 
  • Invite ownership of next steps. 
  • Follow up reliably. 

The Impact 

Support builds trust. Constructive feedback builds clarity. 

Together, they create teams that feel valued, challenged, and motivated to deliver their best. 

This article originally appeared at WeAreComvia.com and is reprinted here with permission.

Michael Piperno is a communication coach and executive presence expert. His insights empower leaders to communicate effectively and authentically.

The Leadership Sweet Spot Read More »

How Avoiding Conflict Slowly Tears Teams Apart 

Teams rarely fall apart overnight. They fall apart quietly, through small moments of avoidance. 

A comment that goes unaddressed. A conflict that gets brushed aside. A performance issue that “isn’t worth the fight right now.” A high performer who gets tired of carrying the load. 

Over time, these moments accumulate. And the team starts to fracture. 

The Hidden Consequences of Avoidance 

When leaders avoid conflict or difficult conversations: 

  • High performers lose trust 
  • Low performers lose direction 
  • Resentment grows 
  • Communication breaks down 
  • Turnover increases 
  • Culture erodes 

People don’t leave companies. They leave environments where problems go unaddressed. 

The Myth of “Keeping the Peace” 

Many leaders believe that avoiding conflict protects morale. In reality, it does the opposite. 

Silence sends a message — and not the one leaders intend. 

It tells the team: 

  • “This behavior is acceptable.” 
  • “Your concerns aren’t important.” 
  • “Accountability is optional.” 

Healthy Teams Aren’t Conflict-Free — They’re Conflict-Capable 

The strongest teams aren’t the ones with the least conflict. They’re the ones where leaders know how to address issues early, clearly, and respectfully. 

Coaching skills give leaders the confidence and structure to do exactly that. 

When leaders learn how to have these conversations well, teams become: 

  • More aligned 
  • More accountable 
  • More resilient 
  • More engaged 

And turnover drops — because people stay where they feel supported, challenged, and heard. 

If you’re seeing signs of quiet friction or disengagement on your team, it may be time to strengthen the way conflict and performance conversations are handled. With the right coaching tools, leaders can address issues early and keep teams connected and thriving. 

This article originally appeared at WeAreComvia.com and is reprinted here with permission.

Michael Piperno is a communication coach and executive presence expert. His insights empower leaders to communicate effectively and authentically.

How Avoiding Conflict Slowly Tears Teams Apart  Read More »

Respecting Time and Effort: Why Thoughtful Communication Matters More Than Ever 

Picture it: You spend hours crafting a proposal. Thinking through the right approach, writing, making sure every detail is perfect. You hit “send” and wait. Days go by. Weeks. Nothing.  

Or maybe you clear your calendar for an important meeting, only to have it canceled five minutes before it starts—with no explanation or apology. 

Sound familiar? Sadly, we’re seeing this more and more. Last-minute cancellations, ghosting, and one-line rejection emails have become common. And here’s the thing: these behaviors don’t just feel rude—they send a message: “Your time and effort don’t matter to me.” 

Here’s the Problem 

Time and effort are two things we can never get back. When someone invests them, whether by preparing for a meeting, creating a proposal, or contributing ideas, they’re giving you something valuable. Ignoring that investment erodes trust and damages relationships. 

And it’s not just about feelings. Poor communication trends like ghosting or dismissive responses have real consequences. They create frustration, disengagement, and even resentment. Over time, these behaviors weaken collaboration and tarnish reputations. 

The Ripple Effect 

  • On Individuals: When people feel their work isn’t valued, motivation drops. They’re less likely to go the extra mile next time. 
  • On Organizations: Disrespectful communication can cost opportunities. A talented vendor or partner who feels undervalued may walk away. Clients and colleagues notice when courtesy is missing—it reflects on your brand. 

What Good Looks Like 

Small, intentional actions can show you value someone’s contribution. For example: 

  • Thoughtful Declines: Take declining a proposal, for example. A one-line “We’ve decided to go in a different direction” feels abrupt and dismissive. Instead, try something like this: 
     
    “Thank you for the time and effort you put into this proposal. We can see the thought and detail that went into your work, and we truly appreciate it. After careful consideration, we’ve decided to move forward in a different direction because [insert reason—budget, priorities, timing]. We hope to stay connected and explore opportunities to collaborate in the future.” 
     
    You see — a few extra sentences can turn a rejection into a relationship-building moment. 
     
  • Timely Responses: Even if you don’t have an answer yet, acknowledge the effort: 
    “I’ve received your report and need some time to review. I’ll follow up by Friday.” 
     
  • Respectful Scheduling: Emergencies happen, but last-minute cancellations should be rare. If you must cancel, apologize, explain why, and reschedule promptly. 

Some Additional Tips for Thoughtful Communication 

  1. Respond—even when the answer is “no.” Silence isn’t neutral; it’s damaging. 
  1. Say thank you. A simple “thank you for your time and effort” goes a long way. 
  1. Communicate early and clearly about changes. Don’t leave people guessing. 
  1. Treat every interaction as an opportunity to build trust. Courtesy compounds over time. 

Take the time to show people their time and work matter. In a world that moves fast, courtesy is an advantage.  

When you value peoples’ efforts, you strengthen relationships. 

This article originally appeared at WeAreComvia.com and is reprinted here with permission.

Michael Piperno is a communication coach and executive presence expert. His insights empower leaders to communicate effectively and authentically.

Respecting Time and Effort: Why Thoughtful Communication Matters More Than Ever  Read More »

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