Not long ago, I found myself sitting in a room full of people from different backgrounds—different cultural backgrounds, sexual orientation, career paths, and personal experiences. We were there to talk about diversity and inclusion, and I thought, “This is going to be good.” But as the conversation began, I noticed something: people were hesitant to speak up.
When the facilitator asked a simple but thought-provoking question:
“When was the last time you felt truly included?”
Everything shifted. The room grew quiet at first, but then one by one, people started sharing. They talked about their team members, their workplace culture, and the moments they felt seen and valued—or, sadly, invisible.
That one key question opened the door to an honest, heartfelt dialogue that left everyone with a better understanding of each other’s realities.
That’s the power of asking the right questions. It’s not about just ticking a box on a checklist or having a one-time inclusion conversation. It’s about building bridges between different perspectives, giving people a safe space to share, and fostering a more inclusive environment where everyone feels they belong.
Yes, these conversations can feel uncomfortable, but discomfort is where growth happens. To create a diverse workforce and an inclusive workplace, we need curiosity, courage, and a willingness to ask the tough questions that make us think deeper. When we do, we’re not just addressing diversity issues; we’re paving the way for real change.
Why Asking the Right Questions Matters
In the work of diversity, equity, and inclusion, dialogue is everything. It’s the bridge that connects people from different backgrounds and creates a space where diverse perspectives can be shared and valued.
But real dialogue—the kind that drives positive change—requires us to step out of our comfort zones and face our own blind spots. That’s where asking the right questions comes in.
Questions are powerful tools. They help us challenge assumptions, uncover biases we didn’t even realize we had, and understand the lived experiences of others. For organizations, they can reveal gaps in inclusion initiatives, inspire actionable steps in DEI efforts, and ultimately help build a more inclusive workplace. But for individuals, questions can spark something even deeper: connection.
I remember one moment that changed the way I think about inclusion. I was leading a discussion on workplace culture, and someone asked:
“How often do you think about the voices that aren’t in the room?”
It stopped me in my tracks.
I realized that even with my commitment to inclusion efforts, I sometimes focused too much on the people already at the table—those I could see and hear. I wasn’t always thinking about the underrepresented groups or the diverse employees who hadn’t been hired yet because our hiring process wasn’t reaching them.
That question shifted my perspective and deepened my approach. I started pushing for changes to job descriptions and the interview process, making sure they reflected the company’s commitment to equal opportunities and a diverse workforce. I also began encouraging leadership teams to ask inclusion survey questions that went beyond surface-level metrics, giving a voice to employees from underrepresented backgrounds.
This experience reminded me that asking the right questions isn’t just an effective way to foster employee engagement or improve inclusion programs. It’s a way to build trust, spark meaningful conversations, and create a workplace where everyone feels seen. That’s the foundation of a truly inclusive culture.
Key Themes for Thought-Provoking Questions
If we want to foster a truly inclusive workplace, we need to start with questions that go beyond the surface. These aren’t easy questions. They’re the ones that make us pause, reflect, and sometimes squirm… but that’s a good thing.
Growth comes from asking the tough questions and being open to the answers, no matter how uncomfortable they might make us feel. Here are some key themes to explore.
Race and Privilege
Talking about race can be one of the hardest conversations to have in diverse groups, but it’s also one of the most necessary. We can’t address diversity issues or create effective diversity initiatives without confronting the realities of race and privilege.
Why is it uncomfortable to talk about race, and how can we get past that discomfort?
This question challenges us to examine our fears and hesitations. Is it fear of saying the wrong thing? Worry about offending someone? Identifying the discomfort is the first step to moving through it.
What does privilege mean to you, and how does it show up in your life?
Privilege can take many forms—economic status, education level, or simply the ease of navigating a world built for people like you. Acknowledging privilege isn’t about guilt; it’s about awareness and using that awareness to drive positive change.
Bias and Assumptions
We all have biases, whether we’re aware of them or not. The key is to recognize how those biases influence our interactions and decision-making.
How do your biases shape the way you interact with others?
This question invites introspection. Do you gravitate toward team members who share your cultural background or socioeconomic status? Do you make assumptions about others based on stereotypes?
When was the last time you questioned a stereotype you held?
Biases aren’t fixed; they can evolve. Reflecting on a time when your assumptions were challenged is a great way to understand how learning and growth happen.
Equity vs. Equality
The difference between equity and equality is a common topic in inclusion conversations, but it’s one that still trips people up. Equality gives everyone the same resources. Equity ensures everyone has what they need to succeed.
What does fairness look like in your workplace or community?
Fairness doesn’t always mean treating everyone the same. This question encourages us to think about how policies and practices can create truly equal access and opportunities.
Can you think of a time when equality wasn’t enough?
Sometimes, giving everyone the same thing doesn’t address systemic barriers. This question can highlight where inclusion initiatives or action plans may need to go deeper.
Inclusion and Belonging
Diversity efforts are important, but they’re only part of the equation. Belonging is what turns a diverse team into a thriving team.
Have you ever felt excluded? What did you learn from that experience?
Everyone knows what it feels like to be left out. Reflecting on that feeling can build empathy and drive management teams to create a workplace culture that avoids it.
What steps do you take to ensure everyone feels like they belong?
This is where action meets reflection. From team-building activities to inclusion programs, what are you doing, or what could you be doing, to make sure your workplace fosters a sense of belonging for everyone?
These questions aren’t just conversation starters; they’re invitations to dig deeper. When we ask them with honesty and humility, they can lead to the kind of meaningful conversations that transform workplaces and lives.
Truthing Cards
To take these conversations to the next level, why not bring a little structure and a lot of fun to the table? With Randi B.’s Truthing Cards, you’ll have everything you need to spark meaningful conversations that go beyond the surface and help create real connections.
Whether you’re looking to connect within the Black community or foster diverse perspectives in larger groups, these decks are designed to inspire reflection, understanding, and trust.
- Truthing Cards: Questions for The Black Community ($35): Perfect for game nights, family gatherings, or any social event, this deck of 100 questions dives into topics that matter deeply to us. It’s a great way to bring people together and elevate your discussions. Click here to get your deck.
- Truthing Cards: The Black Edition 2 ($35): A brand-new set of questions to keep the conversations flowing. Ideal for everything from intimate evenings to large gatherings, these cards encourage bonding and insight in a relaxed, fun way. Get the second edition here.
- Truthing Cards: The U.S. Edition ($35): Designed to foster inclusive workplace environments and team-building activities, this edition focuses on topics like race, privilege, and gender identity—making it a powerful tool for corporate events, DEI workshops, or as a unique gift.
Click here to get your Truthing Cards.
The beauty of the Truthing Cards lies in their simplicity. There are no complicated rules or setups—just open-ended questions designed to encourage active participation and honest conversation.
Tips for Creating a Safe Space
For these conversations to truly have an impact, the environment matters. Creating a safe space is essential to encourage people to share openly and vulnerably. Here are some tips for building that kind of atmosphere:
- Start with trust: People need to feel they won’t be judged or dismissed for sharing their perspectives. Set ground rules that emphasize respect and confidentiality.
- Listen actively: Sometimes, we listen just to respond, but in these conversations, it’s crucial to listen to truly understand. Let people finish their thoughts before jumping in.
- Stay open: It’s normal to feel defensive when someone challenges your assumptions or brings up a blind spot. Instead of shutting down, lean into curiosity and ask for clarification.
When these elements come together, you create a space where diverse employees, team members, and even entire leadership teams can engage in dialogue that drives positive change.
Thought-Provoking Questions in Action
I’ve seen firsthand how a simple question can transform a workplace. At one company, a manager used the Truthing Cards during a team retreat to spark a conversation about diverse perspectives and privilege.
One of the questions, “How often do you think about your race in your daily life?” led to an eye-opening discussion. Team members from underrepresented groups shared their experiences of navigating a diverse workforce, while others reflected on how rarely they considered their own privilege.
That one conversation shifted the team’s dynamic. It inspired the company to revise its inclusion survey questions, which highlighted areas where inclusion initiatives were falling short. These insights led to action plans that improved employee engagement, retention, and the overall workplace culture.
In another instance, a school district used the Truthing Cards to address biases among staff. A question about stereotypes prompted one teacher to recognize how their assumptions about socioeconomic background were affecting their interactions with students. That moment of self-awareness sparked a broader discussion on equal access to resources and the importance of diversity efforts in education.
These examples show that asking thought-provoking questions isn’t just an effective way to start a conversation—it’s the first step toward a cultural transformation. With tools like Truthing Cards, we can create environments where people feel heard, valued, and inspired to work together for a more inclusive world.
How to Start Your Own Conversations
Let’s be real—talking about diversity, equity, and inclusion can be tough. Whether it’s discussing race, privilege, or gender identity, these are conversations that challenge us to confront our own blind spots and biases.
It’s uncomfortable… and that’s okay. Growth often comes from discomfort. What matters is having the courage to start.
The good news is that you don’t have to have all the answers. In fact, the most impactful conversations often begin with someone admitting they don’t know it all and simply want to listen and learn.
Approaching these discussions with authenticity and humility is key. Be open about your intentions, create a safe space for others to share, and don’t shy away from asking the tough questions that lead to deeper understanding.
Here are a few tips to guide you as you navigate these discussions:
- Start small: Begin with a trusted group of friends, family, or colleagues. Build confidence in sharing and listening before tackling larger settings.
- Be an active listener: Give people the time and space to share their experiences without interrupting or jumping to conclusions.
- Stay curious: Instead of being defensive, ask follow-up questions to dig deeper into what others are saying.
- Acknowledge missteps: If you say something wrong, own it. Apologize, learn from it, and move forward.
To help you get started, here are some conversation starters you can use in your own circles:
- What’s one thing about your cultural background that you wish more people understood?
- What steps can our leadership team take to create a more inclusive workplace?
- How do you think our company’s hiring process could better attract diverse talent?
- When was the last time you learned something that changed your perspective about another group of people?
- What’s a stereotype you’ve had to challenge in your own thinking?
These questions aren’t just great for sparking dialogue—they’re a way to build empathy, foster trust, and strengthen bonds across different backgrounds. Whether you’re at a family dinner, in the workplace, or at a community event, they can help set the stage for real connection and understanding.
Remember, you don’t have to solve every issue in one conversation. The goal is to plant the seeds of change, one discussion at a time. The impact can be far greater than you imagine.
Spark a Conversation
Creating a more inclusive world starts with one simple but powerful step: asking the right questions. When we approach conversations about diversity, equity, and inclusion with curiosity, courage, and an open heart, we create opportunities for real connection and meaningful change.
These conversations won’t always be easy, but they’re absolutely worth it. By sharing our personal experiences, listening to the unique perspectives of others, and challenging our assumptions, we begin to build workplaces, communities, and relationships where everyone feels valued and heard.
As you reflect on the questions shared here, remember that progress doesn’t come from perfection—it comes from showing up, being open, and staying committed to growth. Whether you’re leading a discussion at work, sparking dialogue at a family gathering, or simply reflecting on your own journey, your efforts are a powerful part of creating a more inclusive culture.
So, let’s keep the conversation going. Ask the tough questions, listen with empathy, and embrace the transformative power of dialogue.
If you need a little extra help getting started, Randi B.’s Truthing Cards are always here to guide the way. Together, we can create a world where everyone belongs.
