How To Support A Trans Colleague is Broken (How to Fix)

Last month, during a coffee break with a fellow founder, she shared a troubling story about a trans colleague who felt like an outsider in their own team. This wasn't the first time I'd heard something like this. In fact, just a week prior, I sat in a boardroom as a well-meaning HR executive rolled out a "progressive" policy aimed at supporting trans employees. Yet, the policy fell flat on its face because it missed the mark on what truly matters—understanding and genuine integration.

Three years ago, I believed that a checklist of inclusivity measures was enough. But after working closely with diverse teams across industries, I now see how these well-intentioned efforts often backfire, alienating rather than embracing. The problem? Most support initiatives are built on assumptions rather than real conversations and needs. It's a contradiction that feels almost absurd—companies striving for inclusivity, yet unwittingly creating new barriers.

Over the next few sections, I'll unravel the common pitfalls and share stories of what I've seen genuinely work. It's not about more policies or training sessions. It's about transforming the very fabric of workplace culture through simple, human-centered changes. Stay with me, and I'll show you how a single shift in perspective can create an environment where everyone, regardless of gender identity, feels not just included, but truly valued.

The Day I Realized We Were Doing It Wrong

Three months ago, I found myself in a meeting with our team at Apparate, where we were dissecting a recent project that, quite frankly, didn't go as planned. We had collaborated with a client on a diversity training initiative, specifically aimed at supporting trans colleagues. I remember the excitement we all felt going into it, convinced that our meticulously crafted training modules and workshops would make a significant impact. However, as the weeks went by, feedback from the participants painted a different picture. It wasn't that the sessions were bad—they were just... ineffective.

The turning point came during a follow-up call with the client's HR director. We were reviewing the post-training feedback forms when she said something that stopped me in my tracks: "Your sessions were comprehensive, but they felt like an obligation rather than an opportunity to connect." That hit hard. Here we were, thinking we were helping to build an inclusive environment, but instead, our approach was perceived as a checkbox tick rather than a transformative experience. I realized then that we were focusing too much on the mechanics of training rather than fostering genuine understanding and empathy.

Shifting the Focus from Training to Culture

Reflecting on that feedback, I understood that the issue wasn't just about providing information—it was about changing the culture. This was not something that could be achieved solely through training sessions. We needed to embed inclusivity into the very fabric of the workplace.

• We started by promoting open conversations: Encouraging team members to share their experiences and listen to others.
• Implementing regular check-ins: Not just with HR, but across teams, to ensure everyone feels safe and heard.
• Fostering mentorship programs: Pairing trans employees with allies who can provide support and advocacy within the workplace.

💡 Key Takeaway: Real change begins by embedding inclusive practices into daily interactions, not just during scheduled training.

Listening as a Tool for Inclusion

The more I thought about it, the clearer it became that we needed to listen more than we spoke. One of our team members, Alex, shared a story during a brainstorming session that illustrated this beautifully. Alex recounted how a simple act of listening had made a significant difference in their previous job. A colleague transitioning at that workplace had felt isolated, but a manager's genuine curiosity and willingness to listen created a ripple effect of support and understanding.

• Create spaces for open dialogue: Regularly scheduled, informal meetings where employees can speak freely.
• Train managers to listen actively: Shift from simply hearing to understanding and empathizing.
• Encourage feedback loops: Allow employees to share their thoughts and experiences anonymously if they prefer.

✅ Pro Tip: Encourage managers to ask open-ended questions like, "How can we support you better?" It opens doors to meaningful conversations.

The Emotional Journey of Transformation

Looking back, I can now see the emotional rollercoaster we went through. Initially, there was the frustration of realizing our well-intended efforts weren't hitting the mark. But through discovery and genuine engagement, we began to see validation in the form of increased satisfaction and morale among our clients' employees. Their feedback shifted from obligatory participation to genuine gratitude for a supportive environment.

Here's the sequence we now use to facilitate this transformation:

graph TD;
    A[Identify Pain Points] --> B[Engage in Open Conversations];
    B --> C[Implement Inclusive Practices];
    C --> D[Create Feedback Loops];
    D --> E[Adapt and Evolve];

Ending each project with a feedback loop allows us to refine our approach continuously. As we embed these practices, we see a shift from mere acceptance to active inclusion, where trans colleagues thrive as integral parts of their teams.

As we continue this journey, the next logical step is to explore how we can further develop these insights into a scalable framework, ensuring every organization we work with can foster a truly inclusive culture. Let's delve into that next.

A Breakthrough in Understanding: What Truly Makes a Difference

Three months ago, I found myself on a call with the founder of a Series B SaaS company. They had just gone through a rather painful experience with their team, particularly with a trans employee who felt marginalized despite the company's efforts to create an inclusive environment. The founder was genuinely baffled. "We've implemented all the standard policies," they told me, "but it still feels like we're missing something crucial." As I listened, I could sense a familiar frustration. This wasn't the first time I'd heard a story like this, and it certainly wouldn't be the last.

Later that week, I met with our team at Apparate to dissect this issue. The more we delved into the specifics, the clearer it became that the problem wasn't with the policies themselves, but with how they were interpreted and applied. We had encountered similar scenarios before, where well-intentioned measures fell flat because they didn't address the unique, everyday experiences of trans individuals. The real breakthrough came when we decided to shift our focus from policy to practice—how interactions and support systems could be tailored to genuinely fit the needs of trans colleagues.

As we started exploring this new angle, one particular anecdote stood out. A trans employee at a different client company shared how a simple change in the language used in team meetings made a world of difference to them. Instead of sticking to rigid pronouns and formalities, team members began asking, "How do you prefer us to address you today?" It seemed like a small gesture, yet it signaled a shift from mere compliance to genuine consideration. This subtle change not only improved the individual's comfort but also encouraged others to engage more openly.

Building Genuine Understanding

The first key point we discovered was the importance of building genuine understanding rather than relying solely on procedural inclusivity.

• Listen Actively: Instead of assuming, ask open-ended questions to understand individual preferences and experiences.
• Be Flexible: Encourage adaptability in communication styles and language, recognizing that identity is fluid and personal.
• Provide Resources: Offer access to educational materials and workshops on gender diversity to foster an informed workplace culture.

This approach required a cultural shift from top-down policy enforcement to bottom-up empathy and awareness. It was less about ticking boxes and more about embracing each person's unique identity.

💡 Key Takeaway: Genuine understanding isn't just about policies; it's about adapting interactions to meet the individual needs of your colleagues.

Implementing Tailored Support

Next, we focused on how tailored support could be implemented effectively, drawing from our successful interventions.

One client, a medium-sized tech firm, had struggled to retain their trans employees. We introduced them to the concept of personal mentorship programs specifically for trans employees, pairing them with allies within the company who could provide both professional guidance and personal support.

• Mentorship Programs: Establish mentor-mentee relationships to offer personalized guidance and support.
• Regular Feedback Loops: Conduct regular check-ins to assess the effectiveness of support systems and make necessary adjustments.
• Visibility and Celebration: Celebrate milestones and achievements of trans employees to foster a sense of belonging.

These tailored initiatives not only improved retention but also boosted morale across the board. Employees appreciated the company's commitment to individual support and felt more connected to their workplace.

The Emotional Impact

The emotional journey of this process can't be overstated. Initially, there was frustration—both from leadership and employees. The realization that their efforts weren't producing the desired results was disheartening, to say the least. But as we began implementing these changes, the atmosphere shifted. There was a palpable sense of discovery and validation, as employees saw tangible evidence of their company's commitment to their well-being.

By the end of our engagement, the Series B founder who initially reached out to us expressed newfound optimism. "It's like we've finally found the missing piece," they said. And indeed, they had. By focusing on understanding and personalized support, they'd managed to transform their workplace into one where all employees, regardless of their gender identity, felt truly valued.

As we wrapped up our work with them, it became evident that these principles could serve as a framework for other companies facing similar challenges. In the next section, I'll delve into how we scaled these insights across different industries, ensuring a consistent and inclusive experience for trans employees everywhere.

The Changes We Made: Small Steps, Big Impact

Three months ago, I was sitting across from a Series B SaaS founder who was visibly frustrated. "Louis," he said, "we've been trying to create an inclusive environment, but it feels like we're just spinning our wheels." This wasn't the first time I’d heard this sentiment. His team had implemented all the "right" policies—gender-neutral bathrooms, diversity training sessions, and so on—but something wasn't clicking. Despite their best efforts, their trans employees reported feeling misunderstood and unsupported. The disconnect was subtle, yet palpable, and it was reflected in their retention rates.

Later that week, I gathered our team at Apparate to dig deeper into this issue. We realized that the problem wasn't with the policies themselves, but in how they were being executed. We needed to shift focus from broad, generic initiatives to more tailored support that acknowledged individual experiences. We decided to start small, with changes that were specific, actionable, and could be implemented quickly.

Focus on Individual Stories

The first key change was to actively engage with individual stories. I remember one particular conversation with a trans colleague who shared how a seemingly minor change made a huge difference. They mentioned how being addressed by their correct pronouns in meetings was rare, yet incredibly affirming when it happened.

• Personal Check-ins: We encouraged managers to schedule regular one-on-one check-ins, fostering open lines of communication.
• Pronoun Practices: We implemented a system where everyone shared their pronouns at the beginning of meetings, normalizing this practice.
• Story Sharing Sessions: We initiated monthly story-sharing sessions where team members could share their personal experiences in a safe environment.

💡 Key Takeaway: Prioritizing personal stories over generic policies can lead to meaningful change and deeper understanding.

Training with Real Impact

Traditional diversity training often feels more like a checkbox than a transformative experience. We pivoted our approach to focus on empathy-driven training. I recall our first session, where we used real scenarios shared by our trans colleagues to educate the team. This wasn’t about hypothetical situations; this was real-life, raw, and impactful.

• Scenario-Based Workshops: We developed workshops based on real scenarios that our trans employees had faced.
• Role-Playing Exercises: These exercises allowed team members to step into others' shoes and understand their perspectives.
• Feedback Loops: After each session, we collected feedback to continuously refine our approach.

⚠️ Warning: Avoid generic training modules that don’t resonate with personal experiences; they often do more harm than good by fostering resentment.

Building a Supportive Network

The final piece was creating a network of allies within the company. This was about more than just naming a few people as "allies." It was about building a culture where everyone could be an ally. We set out to educate and empower our team to be proactive in their support.

• Allyship Training: We conducted specific training sessions focused on what it means to be an ally and how to provide support.
• Resource Groups: We established resource groups where employees could find community and support.
• Visible Support: Encouraged public displays of support, like wearing pins or badges, to signal safe spaces.

✅ Pro Tip: Encourage visible allyship; it creates an environment where trans colleagues feel seen and supported.

As these changes took root, I witnessed a shift in the office atmosphere. Our trans colleagues reported feeling more supported and valued, and our overall team cohesion improved. The retention rates began to rise, reflecting a healthier workplace culture.

In the next section, I'll delve into how these changes paved the way for even more profound transformations in our company culture. Transformation isn’t just about changing policies; it’s about nurturing an environment where everyone thrives.

Seeing Transformation: How It All Comes Together

Three months ago, I was sitting in a dimly lit office, on a call with the team from a mid-sized SaaS company. They were struggling with internal culture issues after a recent wave of hiring. The frustration in the room was palpable; they had the talent but were losing momentum due to internal friction. As I listened to their concerns, I realized that they were missing a crucial component: genuine support for their trans colleagues. It wasn't that they didn't want to help—it was that they didn't know how.

I recalled a similar situation we faced at Apparate. We had just onboarded a brilliant developer, Alex, who happened to be trans. Despite our best intentions, we quickly realized that our existing support structures were inadequate. Alex felt isolated, and although our team was welcoming, there was a disconnect. This wasn't just about policies or training sessions—it was about creating an environment where Alex could thrive. We needed to see the transformation happen, not just talk about it.

Building Trust Through Authentic Conversations

The first key to supporting a trans colleague is building trust through authentic conversations. At Apparate, we learned this the hard way. After a rough onboarding period, we decided to sit down with Alex and have an open dialogue. This wasn't a one-off meeting; it was the start of an ongoing conversation.

• Listen Actively: Instead of assuming what Alex needed, we asked directly. This approach fostered trust and encouraged Alex to share experiences openly.
• Create a Safe Space: We designated certain team meetings as "safe zones" where anyone could voice concerns without fear of judgment.
• Follow Through: It wasn't just about listening; it was about taking action on what was shared. We implemented changes based on Alex's feedback, demonstrating that their input was valued.

💡 Key Takeaway: Trust is built through ongoing, authentic conversations. Make room for these dialogues and follow through with actions that reflect genuine care.

Implementing Structural Changes

Conversations alone aren't enough; they need to be backed by structural changes. This was a lesson we absorbed after realizing that Alex's challenges were partly systemic.

• Policy Updates: We revised our HR policies to explicitly protect and support trans employees, ensuring zero tolerance for discrimination.
• Resource Groups: We set up an employee resource group focused on LGBTQ+ issues, providing a network for support and advocacy.
• Training Programs: We implemented sensitivity training for all employees, not just management, to foster a more inclusive culture.

These changes weren't just about ticking boxes; they were about embedding support into the very fabric of our organization. Once these structures were in place, we noticed a significant shift in morale and productivity—not just for Alex, but across the board.

Celebrating Wins and Learning from Mistakes

Finally, it was crucial to celebrate the wins and learn from the inevitable mistakes. Supporting trans colleagues is an evolving process, and there are bound to be missteps along the way.

• Acknowledge Mistakes: When we stumbled, we acknowledged it. This transparency encouraged the entire team to keep pushing forward.
• Celebrate Progress: We made it a point to celebrate Alex's achievements and contributions, reinforcing their value within the team.
• Iterate and Improve: We treated this as an ongoing journey. Regular check-ins allowed us to continually refine our approach based on feedback.

✅ Pro Tip: Celebrate every small win to maintain momentum and morale. It's the accumulation of these victories that leads to lasting transformation.

As we implemented these changes, the transformation was remarkable. Alex went from feeling like an outsider to being a key player in several major projects. The team gelled in ways I hadn't anticipated, fostering an environment of genuine inclusion and collaboration.

Now, as we look to the future, the next step is to extend these practices beyond individual cases and truly embed them into our company's DNA. Our journey with Alex taught us that transformation is not a destination but an ongoing process, one that requires constant attention and adaptation.