The Counterintuitive Truths of Leadership

In our latest episode with Rebecca Yang , Director of Engineering at HubSpot , we explored leadership principles that often contradict conventional wisdom. Her insights challenged us to rethink some commonly held beliefs about what makes an effective leader. Here's a deeper look at these uncommon principles.

Don't Trust Your Gut When Receiving Feedback

We often hear "trust your gut," but when it comes to receiving critical feedback, our instincts can lead us astray. Our immediate emotional response is usually defensive – we want to explain, justify, or dismiss the feedback. Rebecca shared how she physically feels this reaction: tunnel vision, racing heart, fight-or-flight response.

Instead of acting on these instincts, try this approach: Thank the person for feeling safe enough to share feedback, ask for time to process it, and commit to circling back. This creates space to move past your emotional reaction and find the truth in what's being shared.

The Art of Selective Micromanagement

"Micromanagement" has become a dirty word in leadership circles. But here's a radical thought: Sometimes it's exactly what your team needs. The key is knowing when to step in and when to step back.

Think of it like teaching someone to drive. At first, you're highly involved – watching every move, providing constant feedback. As they develop confidence and skill, you gradually pull back. The same applies to leadership. The goal isn't to avoid micromanagement altogether but to adjust your involvement based on individual capabilities and gradually grant autonomy as people grow.

Being a "Chaos Vacuum"

Great leaders don't just manage chaos – they actively remove it. Every room you walk into should have more clarity and direction when you leave it. This means:

• Helping teams focus on what truly matters
• Pulling people out of unnecessary rabbit holes
• Finding signal in the noise
• Creating clear paths forward from confusion

This requires fighting against our natural tendency (especially in technical roles) to dive deep into details and edge cases. Sometimes, the most valuable thing you can do is help your team step back and see the forest through the trees.

The Power of Owning the Message

During difficult times – layoffs, reorganizations, tough feedback – many leaders try to distance themselves from unpopular decisions. "This is coming from above" or "I don't necessarily agree, but..." These phrases might make you feel better in the moment, but they severely undermine your effectiveness.

Rebecca shared how during a significant layoff, their CEO's direct ownership of the message – "We are not winning right now" – actually united the team around a clear mission to turn things around.

When leaders own tough messages, they:

• Build trust through honesty
• Create clarity around the path forward
• Enable meaningful action rather than passive acceptance
• Demonstrate true leadership courage

Unity After Decision

While we've gotten better at encouraging healthy debate in organizations, we often struggle with what comes after. The "Debate, Decide and Unite" framework from Hubspot’s CTO Dharmesh Shah emphasizes that once a decision is made, the time for debate is over. Continued resistance or passive disagreement drains energy and creates toxicity.

This doesn't mean blind agreement – it means asking yourself, "Can I get behind this decision enough to support it fully?" If yes, commit wholeheartedly. If no, make the tough choice to find an environment more aligned with your values.

The Ultimate Accountability

"Everything is your fault" might sound extreme, but this mindset creates extraordinary leaders.

When you assume total accountability, you:

• Stop wasting energy on blame
• Focus on solutions rather than excuses
• Model accountability for your team
• Create psychological safety by owning mistakes
• Enable faster learning and improvement

Leadership isn't about being perfect – it's about being accountable. When everything is "your fault," everything is also within your power to influence and improve.

The Emotional Intelligence Paradox

One of the most striking insights from Rebecca's experience is how emotional intelligence manifests in leadership. While we often think of emotional intelligence as being highly attuned to others' feelings, effective leadership requires what she calls "dispassionate empathy" – the ability to deeply understand emotions without becoming entangled in them.

This balance is particularly crucial when:

• Delivering difficult feedback
• Making unpopular but necessary decisions
• Supporting team members through personal challenges
• Navigating organizational change

The goal isn't to suppress empathy but to channel it productively. Great leaders feel deeply while maintaining the clarity to act in the team's best interest.

Creating Safety Through Transparency

Perhaps counterintuitively, psychological safety often comes from radical honesty rather than careful tiptoeing around issues. Rebecca's experience coming out early in her career shaped her leadership approach to transparency.

When leaders model vulnerability and directness, they create an environment where:

• Team members feel safe sharing concerns
• Difficult conversations become normalized
• Innovation flourishes through open dialogue
• Trust deepens through shared authenticity

This transparency extends to admitting what you don't know, acknowledging mistakes, and being open about organizational challenges.

The Role of Identity in Leadership

Leadership principles don't exist in a vacuum – they're shaped by our personal experiences and identities. Rebecca's perspective as a woman in tech, a member of the LGBTQ+ community, and someone with experience across different functions has enriched her leadership approach.

This highlights how diverse experiences can enhance leadership by:

• Bringing fresh perspectives to traditional challenges
• Creating deeper empathy for different viewpoints
• Building more inclusive team environments
• Challenging established norms constructively

The best leaders don't try to fit a predetermined mold. Instead, they leverage their unique experiences and perspectives to create authentic leadership styles that work for their teams and organizations.