Sales tips, leadership communication skills insight and more from Steve Giglio, sales training professional for more than 25 years.

To Persuade, Timing Matters

There’s a great feeling as a coach to work with a client who is enthusiastic and hungry for knowledge. What makes them a pleasure is their desire and commitment to experiment.

Recently, I worked with a client preparing to present a highly lucrative idea to a group of prospective clients. The concept was strong. It positioned her company as a true solution provider and had the potential to create immediate interest.

The challenge wasn’t the idea itself. It was when she planned to introduce it. I quickly realized her timing was off.

Too often, when we have a compelling story or a breakthrough solution, we rush to share it. We assume the strength of the idea alone will create persuasion. In reality, great communication is rarely about leading with your answer. It’s about first understanding the client’s problem.

Before presenting the solution, I encouraged her to slow down and focus on uncovering the prospective clients’ goals, frustrations, and concerns. Not surface-level concerns but their fears…real fears. What’s at risk if they don’t solve the issue? What pressure are they under? What outcomes are they accountable for?

Strategic listening creates the context that gives your solution meaning. If you worked with me (or are a regular reader of my blog), you know I always recommend listening first, selling second. That was the case here.

Once the client fully articulates the challenge, you stay there for a moment. You size the pain. You understand the commercial impact, the internal pressure, and what success or failure means to them personally and professionally.

Only then do you introduce the idea.

The conversation becomes far more powerful because the client now experiences your recommendation as a solution to their problem, not simply a presentation of your expertise.

It sounds something like this:

“Thank you for this understanding of how mission-critical achieving your goals is, as well as what has been frustrating you.”

That’s the moment to present the “home run” idea.

Then guide the conversation toward the next step by tailoring the solution to their business and asking:

“Can you see this approach making the kind of difference you’re looking for?”

By controlling the timing of your enthusiasm, you increase the impact of your message and position yourself as someone focused on solving the client’s problem — not simply showcasing your capabilities.

The result for this client was exceptional. Not because the idea changed, but because the timing did.

Contribution Is King

An essential responsibility of leadership is seeing potential in others that they may not yet see in themselves—and then helping bring it forward.

That’s the difference between observation and contribution.

It’s one thing to recognize talent. It’s another to activate it.

Recently, I was coaching a high-potential Vice President and posed a simple question: “What’s the next step for you professionally?”

The question was intentional. From what I observed, my client had already developed the judgment, experience, and credibility to elevate his impact with clients. The next move wasn’t about capability—it was about mindset.

After a thoughtful pause, he responded with humility, acknowledging that he had spent years supporting his clients—adding value, solving problems, being dependable—but not necessarily directing them.

I summarized the shift simply: “It sounds like you’ve mastered supporting them, but not yet directing them.”

It was a moment of shared clarity. That distinction changed everything.

What emerged was a realization: the very beliefs and behaviors that had made him successful to this point were no longer sufficient for where he needed to go. Supporting had been his strength. But leadership at the next level required something more—direction.

Through further discussion, we identified multiple moments where he had the opportunity not just to support client decisions, but to shape them. To guide. To challenge. To lead.

Together, we reframed his role: from supporter to director, contributor to catalyst.

We identified specific clients and situations where he could begin making clear, confident recommendations—stepping into a more directive posture to drive stronger commercial outcomes. We aligned on where and how this new behavior would be applied, turning insight into practice.

Leadership is ultimately measured by contribution—both to the business and to the people within it. When an executive helps someone see themselves more clearly, step into a new level of impact, and act on it, that’s meaningful contribution.

It’s what drives results. And that’s what makes the work worth it.

Courage Is the Virtue That Moves Everything Forward

“The virtue of courage carries all other virtues.”
— Winston Churchill

That quote has been sitting with me lately.

Courage isn’t always dramatic. It’s rarely a battlefield moment. More often, it shows up in everyday decisions that quietly shape the direction of our lives and work.

It’s the courage to:

  • Disagree when it would be easier to nod along

  • Defend an idea that hasn’t yet won the room

  • Do what’s right when it costs you something

  • Ask the hard questions and help chart a new course

  • Speak up when silence would be safer

  • Put yourself out there and interview for a job

Different situations. Different stakes. Same requirement: courage.

Churchill’s words resonate with me because they apply so directly to the work I’m doing with several clients right now. Each of them is facing a defining moment. Not a grand, public crossroads—but a personal one. A moment where they must choose between comfort and conviction.

They can swing toward what matters to them. Or they can let the opportunity pass.

To be vital.
To contribute.
To make a difference in your organization—or in the world—requires courage.

And here’s what I’ve observed again and again: when courage is present and a person is resolute, things begin to move. Conversations shift. Leaders listen. Doors open. It’s as if once you commit internally, the external world adjusts in response.

Recently, one client faced a particularly difficult choice. He had developed a thoughtful analysis and a clear point of view. His immediate superior disagreed. The easier path would have been to acquiesce—to soften his stance, to defer, to stay quiet.

Instead, we worked on how he could articulate his reasoning clearly and respectfully. I encouraged him to stand by his principles and, simply put, tell the truth as he saw it.

Within five minutes of presenting his case to the managing partner who oversees the entire firm, that leader agreed with his perspective.

I’m grateful for the outcome. But what heartened me most wasn’t the validation from above. It was my client’s willingness to risk disagreement. His strength of conviction. His decision to show up fully and honestly.

That’s what made the difference.

Courage doesn’t guarantee a specific result. But it does guarantee growth. It builds credibility. It strengthens character. And as Churchill suggested, it carries all the other virtues along with it.

Courage makes the difference.

From Steady Growth to Stronger Leadership

Vias Logo

For several years, Steve Giglio worked with Vias, Ltd, an international wine importer experiencing steady growth. As the company expanded its offerings and extended its reach into new markets, leadership recognized that the evolving demands of the business required a stronger, more aligned team. They turned to Steve once again for support. Here’s what followed.

The Challenge

By 2018, the company had reached an inflection point.

  • Growth had outpaced existing management frameworks
  • Leadership roles were evolving but not clearly defined
  • Sales and management responsibilities needed structure
  • A new generation of leadership was emerging

In particular, Federico Zanella (a key executive and later CEO) needed support developing leadership, sales management, and organizational skills to guide the company into its next phase.

He realized that the company required:

  • A clearer management framework
  • Stronger leadership capabilities
  • Better alignment between strategy, execution, and accountability

The Engagement

Phase 1: Executive & Team Coaching (2018)

Steve Giglio was initially brought in to provide executive coaching for Zanella and two other senior leaders. This included both individual coaching and team coaching sessions focused on leadership effectiveness, communication, and sales management.

Phase 2: CEO Transition & Organizational Transformation (2024–2025)

As Zanella stepped into the role of CEO, the scope of Steve’s work expanded significantly. Over an 18-month engagement, Steve partnered closely with key executives including: 

  • CFO
  • Chief Commercial Officer
  • VP of Distribution

Steve met monthly with the leadership team, immersing himself in:

  • Daily and monthly operational realities
  • Strategic priorities
  • Industry regulations and competitive pressures

His role evolved into that of a trusted advisor, guiding the CEO and leadership team towards shaping a new management structure and operating framework.

Accomplishments Achieved

Over time, Steve partnered closely with the Zanella to bring clarity, focus, and structure to both leadership and operations. By sharpening strategic thinking, aligning the management team, and establishing a shared framework and common language, Steve helped turn complex challenges into clear priorities—backed by defined value, measurable KPIs, and strong accountability across the organization.

  • Helped the CEO put challenges into perspective and address them in an organized, efficient way
  • Facilitated strategic thinking and decision-making
  • Clarified what was truly valuable to focus on—and what was not
  • Defined a shared leadership framework that the CEO shared across the company
  • Supported the development of a new management team
  • Established a clear value proposition, KPIs, and accountability structure
  • Translated leadership and management concepts into a “common language” the CEO could use consistently across the organization

Steve’s ability to deeply understand the wine industry—its regulations, margins, competitive dynamics, and seasonal ups and downs—gave him immediate credibility with the leadership team.

Results

By the end of the engagement in late 2025, the company achieved meaningful and lasting outcomes:

  • Increased CEO visibility and effectiveness across the organization
  • Clearer understanding of company processes, people, and performance
  • Greater confidence that the right people were in the right roles
  • Clearly defined expectations and accountability at every level
  • A management structure capable of supporting future growth

Most importantly, the company now operates with a modern leadership framework designed not just for today—but for the next 40 years.

Team Feedback

Steve was met with zero resistance from the leadership team. Instead, the feedback was overwhelmingly positive:

  • Grateful for his involvement
  • Appreciative of his humility, decisiveness, and respect
  • Valued his strong yet approachable personality
  • Noted his deep preparation and industry understanding
  • Enjoyed working with him on a personal level—“charming, fun, and genuinely invested”

His ability to listen, challenge thoughtfully, and genuinely care about the business made him an integral part of the leadership team.

Long-Term Impact

“As a result of the work we did with Steve, we pivoted from the way we ran the company for our first 40 years to a new way of operating—one that will carry us into the next 40,” noted Zanella.

“The leadership framework, management structure, and accountability systems now in place are already driving the company forward and positioning it for continued national growth.

Steve is viewed not just as a consultant, but as a business partner and trusted friend—someone who remains available, engaged, and invested because he truly cares about our staff, our company and our future.”

 

Lead With Heart: A Better Path for the Year Ahead

Howdy—and Happy, Healthy New Year.

As we step into a new year, many of us are thinking about goals, growth, and how we want this next chapter to unfold. Strategy matters. Execution matters. Results matter.

But before we race ahead, it’s worth pausing to reflect on a simple idea captured beautifully by Ralph Waldo Emerson:

“The only way to have a friend is to be one.”

This isn’t about over-sympathizing or trying to win friends by being agreeable. It’s about recognizing that everyone you work with is carrying something—pressure, ambition, uncertainty, hope—and choosing to lead with awareness and heart. When leaders acknowledge struggle without judgment, they build trust. And trust is the foundation of any high-performing team.

The easy route in leadership is to become singularly focused on outcomes—driving harder, pushing faster, and expecting others to simply keep up. Many leaders can achieve short-term results this way. But the better route—the one that sustains growth—is to include others by making space for their own development and actualization.

When people feel seen, heard, and valued, they don’t just comply; they commit. They begin to see themselves in the path you’re laying out. That’s when leadership turns into followership—not because you demand it, but because you’ve earned it.

And the truth is, none of us gets anywhere meaningful alone. Every successful leader stands on the shoulders of a team that understands the vision, believes in the direction, and feels respected along the way. Alignment isn’t created through authority alone; it’s built through connection.

When you lead with empathy and purpose, you create momentum. People are more willing to walk the road with you—and when the next turn comes, they’ll be ready to follow you there as well.

As you set your goals for the year ahead, consider not just what you want to achieve, but how you want people to experience the journey with you. The results will speak for themselves.

Work Worth Doing

Far and away the best prize that life has to offer is the chance to work hard at work worth doing

-Theodore Roosevelt

This blog is significant to me because Teddy Roosevelt was a hero of mine and the inspiration for the beautiful collage portrait of him you see, created by John Morse, a dear friend of mine who passed away days ago, all too soon.

Roosevelt was dogged with just about everything. More importantly, though, he brought a zeal to his work every day.

As we close out the year, be thankful for the work that you do and the solace that comes with a job well done. There are so many others who don’t have the self-actualization we have.

As we forge into the new year, take stock of the difference you make and use the next two weeks to clarify what you want to manifest and give to others.

I promise, you’ll be excited about it.

I wish you and your family a very joyful holiday, with hope for a splendid 2026!

For Thanksgiving, Give Thanks to Your Team

I recently read a crucial—yet admittedly tough—New York Times piece by Jessica Grose: “Young Workers Are Miserable for Good Reason.”

One line jumped out at me:
“Young people feel jobs now offer far less mentorship and more micromanaging.”

Ouch.
But also… fair point.

Because whether an employee is Gen X, Y, or Z, one truth spans all letters of the alphabet:
Everyone deserves mentorship.

Mentorship says, “I care about you, and you matter here.”
It says, “Let’s invest in your growth—not just your output.”

And here’s the beautiful, slightly magical part:
When people know you genuinely care, they become more responsive, more committed, and yes—more human.

It doesn’t require a lot of effort on your part…just time and enough curiosity to ask:

  • What’s important to this person?

  • What challenges are they carrying quietly?

  • What do they want for themselves (even if they’re hesitant to say it out loud)?

In return, mentors often get these reinforcing moments for themselves. There’s nothing like an employee saying,
“Thanks… I’m more organized and confident now. I realize my voice matters.”

It could bring you to tears.

So this Thanksgiving, take a moment to thank your team—
for their loyalty, their effort, their patience, their ideas, and the simple fact that they show up every day trying to make something work.

Thank them for trusting you.
Thank them for allowing you to lead, guide, and learn right alongside them.

Do that, and I promise:
They’ll pay you back in ways that will surprise you.

What to Do When You Know Your Team Won’t Hit Year-End Targets

It’s the fourth quarter. You’ve reviewed the numbers, triple-checked the forecasts, and the reality is clear: your team is not going to hit the year-end targets.

First, don’t panic. This is not the time for blame, knee-jerk reactions, or hasty changes in direction. Missed targets happen — even to high-performing teams. The real opportunity lies not in the outcome, but in your response as a leader.

Here’s how to lead with purpose and turn a challenging situation into a foundation for future growth:

1. Diagnose, Don’t Deflect

Before you react, ask the critical question: Why?

Was the target realistic to begin with? Did market conditions shift unexpectedly? Were there execution gaps, resource constraints, or alignment issues across departments?

Resist the urge to jump to conclusions. Instead, gather data, talk to your team, and seek input from cross-functional stakeholders. A calm, objective post-mortem now will help avoid repeating the same mistakes later.

2. Communicate Transparently

Your team already knows the numbers aren’t adding up — what they’re waiting for is your leadership. Be honest about where things stand, what the shortfall means, and how you plan to move forward. Transparency builds trust and keeps morale from eroding.

But honesty isn’t just about facts. It’s about tone. Acknowledge the team’s efforts and avoid placing blame. Focus on what you’ve learned and what can still be achieved in the time that remains.

3. Refocus on What’s Still Possible

Even if the original goal is out of reach, the remainder of the year is not a loss. Set short-term, achievable objectives that drive momentum. Focus on high-impact areas: deepening customer relationships, clearing backlogs, or investing in foundational work that sets up a strong Q1.

Momentum, even in small doses, matters — especially in times of disappointment.

4. Support Your People

Disappointing results can lead to burnout, disengagement, or fear — particularly if the team feels they’ve given their all. As a leader, your job is to provide clarity, encouragement, and support.

Celebrate the wins, however small. Highlight the progress made. And make sure your team knows that one missed target does not define their value or your confidence in them.

5. Recalibrate for the Year Ahead

Finally, use this moment to think forward. What did this year reveal about your assumptions, strategies, and team dynamics? Were your KPIs aligned with your actual capacity and priorities? Where can you improve agility and foresight?

Set time aside for structured reflection and planning. This isn’t just about better forecasting — it’s about becoming a more resilient and adaptable team.

Final Thought:
 Missing a target is never ideal, but it’s also not the end of the story. Leaders are remembered not for perfection, but for how they navigate imperfect situations. Stay calm, stay focused, and lead your team through the close of the year with clarity, empathy, and purpose.

 

Finishing Strong: The Leadership Mindset for Q4

As we enter the fourth quarter, it’s time to reflect—not just on the numbers, but on the people behind them. While performance metrics and KPIs matter, a strong leader knows that year-end reporting isn’t just about hitting targets. It’s about understanding how your team got there—and what that journey reveals.

Start by asking the right questions:

  • Who on your team stepped up and showed leadership this year?
  • Who consistently solved problems independently?
  • Who thrived under pressure and became someone you could count on during a crisis?

Recognizing these contributions isn’t just about praise—it’s about identifying your future leaders. These individuals are shaping the culture of your team and laying the groundwork for continued success.

At the same time, you need to take an honest look at underperformance:

  • Who struggled to meet expectations?
  • Who needed more support or clearer direction?
  • Who faltered when the pressure increased?

These insights are just as important. Q4 isn’t just a finish line—it’s also your last opportunity to course-correct. Whether that means offering additional coaching, shifting responsibilities, or setting new expectations, there’s still time to make an impact before the year ends. I recommend that you meet with direct reports. Begin the conversation by highlighting their strengths and areas for improvement. Ask them what they would like to make for a strong end to the year. A client of mine just completed this conversation and is enjoying a new level of transparency with their direct report. The person is more candid now and is beginning to offer his own solutions.

Strong leaders use the fourth quarter not only to measure success but to shape it. Ask the right questions now, and you’ll be better equipped to report the kind of progress—and potential—that drives your organization forward.

When Your Boss Won’t Talk to You

Make Them Want To!

In our ongoing series about standing out, speaking up, and avoiding obsolescence in an AI-saturated world, another headline from the Wall Street Journal jumped out: “Your Boss Doesn’t Have Time to Talk to You.”

That’s a tough truth—but also a wake-up call.

Managers today are pulled in every direction. Time is scarce, and who do they make time for? Their high performers. If you’re not getting the attention you want, the challenge is clear: make yourself unmissable.

You might be thinking, “Sure, but that’s easier said than done.” To that I say: only if you say so. So stop saying it. Do something about it.

High Performers Aren’t Born—They’re Built

It starts with a decision. A personal commitment. Instead of waiting for your manager to change, look inward. Review your recent work and how you’ve been showing up—for your boss, your clients, and your teammates. Then ask: what needs to change?

5 Steps to Earn—and Keep—Your Boss’s Attention

Here’s a practical approach to shifting how you’re perceived:

  1. Pick One Behavior to Improve
    Look back at your last review or feedback session. What’s one behavior, if changed, that would immediately elevate how you’re seen?

  2. Experiment With It
    Growth starts with trying new things. As leadership expert Marshall Goldsmith says, “Without experimentation, there is no growth.”

  3. Declare Your Intent
    Tell your boss the behavior you’re working on. Not only does this set the expectation—it invites them to start noticing the shift.

  4. Apply It in Real Situations
    Choose three current relationships or communications where you can apply this new competency. Make sure they’re visible and impactful.

  5. Reflect and Iterate
    After each interaction, evaluate what worked and what didn’t. Use this to strengthen your approach in the next one.

Recently, I worked with a new client who was laser-focused on being seen as a high performer. He was anxious—but determined. With some coaching, he began experimenting, and he nailed it. He’s now on to his next behavior shift, building on his momentum.

If you’re ready to start changing how you’re seen—and want a guide along the way—give me a call.

Let’s make your boss want to talk to you.