Am I Saying the Right Thing? – The Hidden Pressure Behind “Sensitive Conversations”

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Insights from a recent workshop with law firm leaders

“Just having time to step back and think about it was the most useful part.”

That was one of the most repeated takeaways from a recent Managing Family-Related Leave workshop we ran with senior leaders at a major law firm. And it says so much.

When it comes to supporting employees through life-changing moments like parental leave or caring responsibilities, most managers aren’t lacking compassion — they’re lacking clarity. They’re wondering, Am I saying the right thing? Am I being too flexible… or not flexible enough? Can I balance empathy with business needs?

And those questions carry weight — not just in policy terms, but in people terms.

These are moments that matter. The way a manager handles a single conversation about returning to work after parental leave can impact how included, supported, and motivated someone feels for years to come.

So why are we still expecting managers to get it right with no training, no toolkit, and no space to talk about it?

Beyond Checklists: What Managers Really Need

Managers told us they found the workshop helpful, not because it taught them something brand new, but because it gave them time to navigate what they already suspected was complex.

Rather than being a tick-box training on policies, the session gave them room to pause, reflect, and hear from peers.

“The interactive elements were really valuable — the materials gave us a framework, but it was the open discussion and shared experiences that helped the most.”

They appreciated hearing real examples, where things had gone well, and where things hadn’t. They valued having honest conversations about the messiness of real-life situations: when someone’s return doesn’t go to plan, when flexibility clashes with workload, when a colleague is silently struggling with loss or fertility treatment.

They also appreciated a rare thing: acknowledgement that this is hard.

“There was probably some fear in the group beforehand — that it would always be wrong not to accommodate someone’s wishes. The session helped us understand that it’s okay to balance business needs, as long as communication is clear and fair.”

This is key. Many managers want to do the right thing — but don’t always feel equipped, confident, or reassured that they’re allowed to navigate that grey area.

Behind Every Successful Return, there is a Manager Who Made it Work

Managing family-related leave isn’t just about knowing the process. It’s about showing up to emotionally loaded conversations with care — and clarity. Conversations that can include:

• Telling someone their flexible working request can’t be fully accommodated
• Supporting a colleague through miscarriage or fertility treatment
• Planning a phased return after a year of parental leave
• Responding with empathy, but also with honesty

These are sensitive, high-impact moments. And while employees often prepare for them — coaching before returning from leave, reading HR policies — managers are left to navigate it in real time.

We’ve heard this from managers across sectors, especially in fast-paced, high-performance cultures like law and finance. They want to get it right. But they don’t want to overstep, or under-deliver. They just want someone to say: Here’s how you can approach this. Here’s how you can communicate fairly and consistently.

Creating Space Builds Confidence

What our recent workshop showed was that giving managers even 90 minutes of dedicated space to explore this topic — without pressure, without judgment — had a significant impact.

They left feeling:

• Reassured that others were facing similar challenges
• More confident in their ability to manage complex scenarios
• Clearer on what “good” communication actually looks like
• Better equipped to balance business needs with empathy
• Validated that perfection isn’t the goal — clarity and fairness are

One attendee summed it up:

“The facilitators were great listeners and brought real examples — it didn’t feel like a lecture.”

Why Manager Confidence Builds Culture

It’s easy to centre support on the individual taking leave — and of course, that matters. But we also need to widen the lens.

Because every thoughtful return-to-work experience, every well-handled flexible working request, every compassionate conversation about family circumstances — starts with a manager who was ready to manage it. And that doesn’t happen by chance.

Too often, we assume managers will just know what to say or how to handle sensitive, high-stakes situations. But in reality, they’re balancing competing pressures, trying to get it right, and often second-guessing themselves.

When we invest in supporting managers with space to reflect, tools to guide conversations, and confidence to act fairly and consistently — we shift the culture.

We create:

• More open, honest conversations
• Greater clarity and consistency
• A better experience for everyone involved

That’s why our coaching and workshops don’t just walk through the policy. They lean into the realities managers face. The grey areas. The curveballs. The “What do I say now?” moments.

Because when we support managers well, we don’t just improve the experience of leave — we strengthen the culture behind it.

Looking Ahead To 2026?

If you want to create a culture where parents and carers feel genuinely supported — start with the managers making it happen.

Because good policy might set the direction. But confident, supported managers turn it into something meaningful.

Book a discovery call: https://parentandprofessional.co.uk/contact or email us at info@pandpcoaching.co.uk.