3 Conversations Every Leader Should Have Before the Holiday Break

3 Conversations Every Leader Should Have Before the Holiday Break

By late November, the pace changes.
Teams are closing out the year, leaders are reforecasting budgets, and focus starts to shift toward the next six months of the financial year.

It’s tempting to slow down, switch off, and wait for January to reset.
But the most effective leaders know this is the moment that defines how their people begin the new year.

Because before the break, there’s one thing every leader can still do that drives engagement more than any system or survey:
have the right conversations.

At Pupal, we call them the three conversations that keep your culture aliveRecognition, Reality and Reset.

Why Conversations Matter More Than Dashboards

According to Gallup’s 2025 State of the Global Workplace, only 21 percent of employees strongly agree that they receive meaningful feedback that helps them improve. And PwC’s Workforce Hopes and Fears Survey found that nearly two-thirds of employees say they would feel more motivated if their managers simply took more time to listen.

In scaling environments, where leaders are stretched and priorities constantly shift, these missed conversations carry real cost.

Engagement, retention and energy aren’t lost in data, they’re lost in silence.

That’s why now, before the holidays, is the perfect moment to pause and reconnect through dialogue.

Conversation 1: Recognition — “I See You”

Recognition is more than a thank-you.
It’s a moment of acknowledgement that connects effort with impact.

Data from McKinsey’s 2024 Organisational Health Index shows that employees who feel recognised are four times more likely to be engaged and five times more likely to stay beyond two years.

As your team approaches the end of the calendar year, take time to say:

  • “Here’s what you did that made a difference.”
  • “Here’s how your work contributed to what we achieved.”
  • “Here’s what I value most about how you show up.”

These aren’t grand gestures — they’re human ones.
Recognition creates belonging, belonging builds trust, and trust fuels performance.

Recognition turns effort into meaning.

Conversation 2: Reality — “How Are We, Really?”

Once recognition opens the door, reality keeps it honest.
This is the space to discuss what’s working, what isn’t, and what needs to change before the next half of the financial year.

According to PwC’s Future of Work Pulse, 74 percent of employees believe their leaders underestimate the pressure teams are under during high-growth phases.
This disconnect widens when leaders assume positivity equals resilience.

The “Reality” conversation is where you invite truth.
Ask:

  • “What made this year harder than it needed to be?”
  • “Where did we lose clarity or connection?”
  • “What support or change would make the biggest difference next year?”

The goal isn’t to solve everything on the spot.
It’s to make honesty safe again.

When teams see their leaders listen without defence, performance conversations stop feeling like reviews and start feeling like relationships.

Reality builds respect.
Respect builds momentum.

Conversation 3: Reset — “Where to From Here?”

The final conversation is forward-facing.
It’s about clarity and renewal, giving people a sense of direction before they switch off for the holidays.

Gartner’s 2024 Leadership Outlook found that employees who have clear goals and understand the company vision are 70 percent more likely to feel energised returning to work in January.

The Reset conversation focuses on alignment:

  • “Here’s what success looks like for the next six months.”
  • “Here’s what we’re keeping, changing or improving.”
  • “Here’s how your work connects to that bigger picture.”

When people leave for the break knowing where they’re heading, they come back with purpose, not uncertainty.

Reset turns reflection into readiness.

The Cost of Skipping These Conversations

For startups and scaleups, these discussions aren’t a “nice to have”. They’re a retention strategy.

When leaders skip them, engagement slides quietly through December.
By February, that silence shows up as turnover, disengagement and lost confidence.

But when leaders close the year with Recognition, Reality and Reset, they create alignment, optimism and loyalty that last well beyond the break.

The Pupal Perspective

At Pupal, we help founders and leadership teams build communication rhythms that scale with growth.

Our frameworks turn feedback into dialogue and dialogue into culture, equipping leaders to hold conversations that connect performance with purpose.

Because sustainable culture isn’t created through surveys or slogans.
It’s created one conversation at a time.

Final Thought

Before the year ends, ask yourself:

“What will my team remember — the metrics I shared, or the conversation I had with them?”

As leaders, we can’t control everything. But we can control connection. And that’s what keeps people coming back, not just after the holidays, but for the long haul.

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