Uncomfortable Questions

The Workplace Questions You’re Afraid to Ask—Answered.

A safe space to ask and learn about leadership, workplace culture, and inclusion—because growth starts with curiosity.

What is Uncomfortable Questions?

Uncomfortable Questions began as a simple idea: What if leaders had a safe space to ask the questions they’re afraid to ask aloud?

It started with people reaching out to me privately, unsure how to navigate sensitive topics like DEI, leadership, and workplace culture without fear of saying the wrong thing. Now, it has evolved into a trusted platform where professionals and organizations can learn, grow, and build psychological safety in the workplace.

📩 Every two weeks, I answer real, anonymous questions in the Uncomfortable Questions newsletter. Sign up to get insights straight to your inbox.

🎥 Want to see past questions? Visit my LinkedIn Newsletter Series or explore video responses on YouTube.

✉️ Have an uncomfortable question? Submit it anonymously here.

For Individuals

A Safe Space to Ask & Learn

You have questions—but you don’t know where to ask them. Maybe you’re afraid of looking uninformed. Maybe you don’t feel psychologically safe at work. That’s why Uncomfortable Questions exists.

✔️ Sign up for my email newsletter to receive answers to the latest workplace questions.
✔️ Browse past editions on LinkedIn to explore real-world leadership and workplace insights.
✔️ Submit your own question anonymously—because learning starts with curiosity.

CTA Button: Sign Up & Start Learning

For Companies & HR Leaders

Build a Culture of Trust & Learning

Psychological safety is a key driver of engagement, retention, and innovation. Yet, many employees feel unsafe asking critical workplace questions—leading to confusion, miscommunication, and distrust.

That’s where Uncomfortable Questions for Organizations comes in.

📊 Culture Compass: A workplace trust and engagement audit to uncover what employees truly think—but are afraid to say.

🔐 Private Uncomfortable Questions Platform: A company-branded, anonymous platform where employees can submit workplace questions safely—fostering psychological safety and trust.

💡 Workshops & Speaking on Psychological Safety: I work with organizations to help leaders and teams build a culture where questions and learning thrive.

CTA Button: Bring Uncomfortable Questions to Your Organization (Links to Consulting/Speaking Inquiry Form)

See it in Action

Watch Real Answers to Uncomfortable Questions

Explore past uncomfortable questions & responses with video clips:

Want more? Visit my YouTube Channel for the full library.

Submit a question

Got an Uncomfortable Question? Ask It Here.

✔️ Completely anonymous. No names, no judgment—just real answers.
✔️ Get insights from workplace experts & research.
✔️ Your question might be featured in a future edition of Uncomfortable Questions!

Stay Connected & Explore More

Let’s build a workplace where questions lead to growth. Sign up today!

Keep Learning & Growing

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  • Find them in the Free Resources Library

  • In Speaking and workshops