DeSantis Trusted Advisors

10/13/2026

Every business reaches a point where what got you here won’t get you there.

For more than a decade, I’ve worked alongside CEOs, founders, and executives as a catalyst, strategist, and advocate, helping them navigate business strategy, talent development, board relations, leadership transitions, and exit planning. Whether you’re scaling a growing company, stepping into a bigger role, or preparing for what’s next, having a trusted advisor in your corner can make all the difference.

Learn more about how DeSantis Trusted Advisors creates pathways to success for leaders and their organizations:

https://desantistrustedadvisors.com/

10/12/2026

AI is changing the speed of business, but the real gap isn’t technical. It’s how leaders think.

This HBR piece explores the mindsets leaders need now: adapting quickly, staying steady under pressure, and thinking creatively when the playbook keeps changing. The tools will keep evolving. Our leadership has to evolve with them.

AI is changing not only what leaders need to know, but how they need to think. Yet many are struggling to adapt to the speed, uncertainty, and emotional complexity of an AI-driven workplace. To keep pace, you need to shift the mindsets that shape your behavior in three important ways: from certainty...

10/08/2026

Great thinkers don’t just contribute to a field—they can change the way we understand it.

Howard Stevenson helped transform the study of entrepreneurship by shifting the focus beyond founders and business creation to a broader way of thinking about management: pursuing opportunities beyond the resources currently at hand. His work influenced generations of students, educators, entrepreneurs, and business leaders.

This Harvard Business Review tribute reflects on Stevenson’s lasting impact and the ideas that helped reshape how entrepreneurship is taught and practiced.

Howard Stevenson transformed entrepreneurship from a study of founders’ personalities and business formation into a way of managing: pursuing opportunity beyond the resources currently controlled. His approach emphasized testing ideas, committing resources in stages, assembling teams, and rewardin...

10/06/2026

When uncertainty is high, the pressure to act quickly—or avoid making a decision altogether—can be just as high.

Effective leaders know that navigating uncertainty isn’t about predicting exactly what comes next. It’s about slowing down enough to examine assumptions, consider different possibilities, and make thoughtful choices with the information available.

This Harvard Business Review article offers four questions that can help leaders approach difficult decisions with greater clarity and confidence.

In today’s perma-crisis world, waiting for stability is like waiting for a train that’s never coming. When everything around you feels unsteady, four questions can serve as strategic tools to help you work through ambiguity, reframe risk, and strengthen your decision-making muscles: 1) What deci...

10/05/2026

The role of the chief communications officer is changing—from telling the company's story to helping shape what that story should be.

Today's communications leaders are expected to bring a broader lens, connecting government affairs, reputation, and risk while serving as trusted advisors to the CEO. Technology can make teams faster, but judgment, instinct, and perspective remain irreplaceable.

As issues grow more interconnected, the communicators who see the full picture are the ones who stay at the table.

What does it take for communications to lead, not just support? Read more.

Communicators are evolving from scribes restating others' priorities to trusted strategists directly counseling CEOs.

10/01/2026

We often associate success with independence and having all the answers. But sometimes, one of the most powerful things a leader can do is ask for help.

Knowing when to seek another perspective, ask the right questions, or lean on the experience of others isn’t a weakness—it’s an important part of strong leadership and sound decision-making.

In my latest newsletter, I explore why asking for help can be especially valuable for senior leaders, how going it alone can limit our perspective, and why the right conversation at the right time can make all the difference.

Read my latest newsletter for more on the power of seeking counsel—and why you don’t have to navigate every challenge alone: https://conta.cc/4hkWYnS.

09/29/2026

Career transitions can test even the most experienced professionals—especially when opportunities feel limited and the job market seems to be standing still.

In uncertain times, patience isn’t about doing nothing. It’s about staying focused, continuing to build relationships, sharpening your skills, and remaining ready for the right opportunity. This article explores how professionals can navigate a challenging job market with resilience, perspective, and purpose.

Summer has a way of creating space. Even in the busiest organizations, there's a natural shift in pace. For many of the CEOs, founders, and senior leaders I work with, this season sparks reflection of the kind that’s harder to access in the thick of meetings, deadlines, and decision-making. Maybe ...

09/28/2026

Boards today are balancing more priorities than ever—and the pace of change isn't slowing down.

Deloitte's Board Governance in 2026 report highlights emerging technology, human capital, geopolitical volatility, and cybersecurity as top areas of focus for directors. Leadership continuity is also front and center, as CEO transitions accelerate and companies explore new leadership models.

The boards that thrive will be those that treat succession, risk, and strategy as ongoing conversations rather than periodic check-ins.

How is your board building the agility to lead through change? Read more.

There's no one blueprint, but co-CEOs are hot right now.

09/24/2026

Great leadership isn’t just about having the right answers—it’s about creating the right conversations.

The way leaders frame discussions, ask questions and make space for different perspectives can shape how teams solve problems, make decisions and move forward together. This Harvard Business Review article explores how intentional conversations can become a powerful leadership tool.

Every strategy, decision, and transformation begins as a conversation. Yet leaders rarely think intentionally about how those conversations unfold. The highest-performing teams steward conversation through three elements—goals, roles, and soul—creating greater clarity, stronger trust, and better...

09/22/2026

As AI becomes a bigger part of how we work, leaders have a new challenge to consider: How is it changing the way employees communicate, speak up and share concerns?

AI can create new opportunities for employees to explore ideas or voice perspectives they may hesitate to raise directly—but it can also reshape trust and psychological safety in unexpected ways. This Harvard Business Review article explores four patterns leaders should watch as AI becomes more integrated into the workplace.

The technology may be evolving quickly, but creating a culture where people feel heard, respected and safe to contribute remains a fundamentally human responsibility.

AI’s perceived neutrality plays a role in reshaping how psychological safety is experienced in organizations. When employees use AI to surface concerns they don’t feel safe raising directly, they are sending signals about the culture. Four patterns reveal how AI interacts with psychological safe...