Jacob Morgan | Best-Selling Author, Speaker, & Futurist | Leadership | Future of Work | Employee Experience

The Right Way to Handle Tough Conversations Without Losing Your Team

Do you want to sponsor this newsletter with over 370,000 subscribers, my podcast, or other content? Reach out to me directly and we can explore some options Jacob[at]thefutureorganization[dot]com.

Join over 45,000 other subscribers who get Great Leadership delivered directly to their inbox each week. You’ll get access to my best thinking and latest content. Sign up today.


If you’re a Chief Human Resources or Chief People Officer, then you can request to join a brand new community I put together called Future Of Work Leaders which focuses on the future of work and employee experience. Join leaders from Tractor Supply, Johnson & Johnson, Lego, Dow, Northrop Grumman and many others. We come together virtually each month and once a year in-person to tackle big themes that go beyond traditional HR.

One of the fastest ways to lose your team’s trust is avoiding the conversations that matter most. And who’s to blame when these tough talks require leaders to do a difficult balancing act? On one hand, there’s growing pressure to foster psychological safety, prioritize well-being, and create a supportive work environment. 

On the other hand, leaders still need to drive accountability, manage performance, and address difficult behaviors. Sometimes it’s easier to avoid these conversations than face them. Some leaders are hesitant to give feedback out of fear of being labeled as “too harsh,” misunderstood, or even facing backlash from employees.

This leadership challenge is at the center of our latest episode of the Future Ready Leadership podcast with Paul Falcone, bestselling author and former CHRO of Nickelodeon Animation. Paul breaks down why tough conversations are not the problem, but avoiding them is. He shares how leaders can approach these moments with clarity, confidence, and compassion, without alienating their teams.

Listen to the episode here on Apple Podcast & leave a review!

What Leaders Get Wrong About Tough Conversations

Most leaders’ default response to conflict is often avoidance. It’s a universal truth, and it’s not because they’re careless, it’s the contrary. They don’t want to demotivate their teams, damage relationships, or create conflict. 

But that avoidance is exactly the issue. When managers wait too long to say something, they could let issues fester, and eventually, they end up exploding in frustration, often with no documentation or context to support their case. 

Paul argues that true leadership means leaning into discomfort with clarity, consistency, and compassion. That starts with understanding what a tough conversation really is: it’s not about confrontation, it’s about helping someone see a blind spot that could hold them back.

The Shift from Judgment to Coaching

We’ve been conditioned to believe that dealing with tough conversations always means it’s about punishment. But Paul Falcone challenges us to a mindset shift by reframing feedback as a gift instead. “If you truly care about someone’s growth,” he says, “you owe it to them to be honest in a way that helps, not humiliates.” 

Tough conversations, when done right, are career-development conversations. Instead of criticizing behavior or questioning intent, Paul encourages leaders to connect feedback to coaching. This way, you can course correct and support your people’s long-term success by building their confidence, sharpen their skills, and unlock opportunities. 

He also introduces a powerful framework for navigating feedback conversations: the “Performance vs. Conduct” model. To illustrate it, imagine a circle split in two. 

On one side is performance—what someone achieves. 

On the other is conduct—how they show up. 

Most managers focus too heavily on performance and ignore behavior, but as Paul explains, both are essential for building future leaders. If someone excels on metrics but undermines culture, you’ve got a problem.

Listen to the episode here on Apple Podcast & leave a review!

Building Accountability Without Fear

So how do you deliver this kind of feedback without triggering defensiveness or disengagement? Instead of overwhelming your team with rigid rules or constant confrontation, Paul recommends approaches that open dialogue, reduce defensiveness, and foster growth.

One of the most effective techniques is what Paul calls the “iron hand with a velvet glove” approach. Leaders should maintain clear standards and high expectations (the iron hand), but communicate those expectations with respect, encouragement, and care (the velvet glove)

That means creating safe communication systems (like using a “safe word” such as permission to open honest dialogue), hosting regular development check-ins, and inviting team-led reflections on performance and culture.

In fact, Paul recommends quarterly, employee-led check-ins where the employee, not the manager, sets the agenda. This approach not only reinforces autonomy and accountability but also makes feedback a two-way street. Leaders who model openness and vulnerability are far more likely to receive constructive feedback in return.

Rethinking Psychological Safety

A major mistake leaders make to avoid tough conversations at work is lowering standards to keep the peace. Paul cautions against over-indexing on comfort and sensitivity at the expense of high standards. 

Too much sensitivity can actually weaken performance cultures. When leaders feel like they can’t speak up without being labeled harsh or discriminatory, they pull back. Meanwhile, expectations blur, and standards drop.

True psychological safety isn’t about shielding people from feedback. It’s about creating a space where honesty and growth are possible. The solution isn’t to swing back toward authoritarianism. It’s to be intentional and honest about the kind of culture you’re trying to create. 

As Paul puts it, “Be clear about who you are as a leader. If this isn’t the right place for someone, that’s okay—but don’t try to be all things to all people.”

The Real Work of Leadership: Introspection and Alignment

At the heart of everything Paul shares is a challenge to rethink how we define leadership itself. It’s not just about KPIs or managing deliverables—it’s about building trust, developing people, and having the courage to speak truth when it matters most.

He poses a powerful question every leader should ask: “Would you want to work for you?” If the answer is anything but a confident yes, then it’s time to pause and reflect. Feedback conversations aren’t just about others, they reveal who we are as leaders.

Tough conversations don’t have to be feared. In fact, when handled with care and clarity, they can become the foundation for a stronger, more resilient team. If you want to learn how to give feedback that builds trust, leads with empathy, and reinforces accountability, don’t miss this conversation with Paul Falcone. His frameworks and stories will leave you thinking differently about what it truly means to lead.

Listen to the episode here on Apple Podcast & leave a review!

🎧 Listen here

🎧 Watch on YouTube

Scroll to Top