Managing people well doesn’t require a degree in HR — but it does mean staying connected with your team.
When there’s no in-house HR team to rely on, much of the day to day people admin can fall on managers’ shoulders and juggling everything can feel like working two full-time jobs.
That’s why regular, meaningful conversations are one of the most powerful tools a manager has - not just to catch problems early, but to build trust, clarify expectations, and keep everyone pulling in the same direction.
As the summer season ramps up, it’s that halfway point in the year when workloads shift, holidays loom, and colleagues can start feeling a little jaded.
While every workplace is different, we’re sharing four key conversations every manager should be having right now. The tone may vary depending on your industry or team dynamic, but goals remain the same - to strengthen rapport, reduce holiday firefighting, and help support your business through the rest of the year.
1. “How are you (Really) Doing?” – The Wellbeing Check-In
Why it Matters
As deadlines loom and project work intensifies ahead of the summer break, stress can quietly build — especially for team members covering for others or juggling end-of-quarter goals. A quick, genuine check-in can go a long way. Done right, it’s not just about wellbeing — it’s about preventing burnout, improving retention, and showing valued team members that you’re paying attention.
Get Ahead
Pick up on the signals. A change in tone, a dip in energy, or an increase in unplanned absence can all be cues to check in. Review sick days, back-to-work notes or recent performance reviews — they might highlight someone who's struggling beneath the surface.
“It doesn’t have to be formal,” says WorkSmarter CEO Luke Burton. “Even a five-minute chat, prompted by a quick scan of someone’s absence record or appraisal notes, can help you spot who might need a little extra support.”
2. “Do you Know What’s Expected of you?” – The Role & Goals Conversation
Why it Matters
As the year unfolds, responsibilities can shift. People take on new tasks, priorities evolve, and expectations set six months ago may no longer reflect the day-to-day reality. While flexibility is a strength, unclear roles can quietly erode confidence, create frustration, and leave individuals unsure of how they’re being measured. Often, they won’t raise concerns until things start to go wrong.
Get Ahead
Take time this month to review each team member’s job description, current goals, workload and development needs. Where things have changed, be clear and open about what’s expected now, and make sure it's realistic, well understood and supported by development opportunities - however small they may seem.
“One of the most common causes of performance issues is misalignment — someone thinks they’re doing a great job, but their manager expected something different,” says WorkSmarter founder Luke Burton. “That’s why these conversations matter. When roles, goals and growth plans are clear — and written down — everyone moves forward with more confidence.”
3. How are we Handling Summer Leave? The Holiday Planning Chat
Why it Matters
Between school holiday pressure on working parents and the seasonal increase in time off requests, summer is the most complex period of your leave calendar. It’s essential to plan around overlapping holidays, childcare needs, or workload gaps. A little foresight now can prevent last-minute headaches later.
Get Ahead
Use this month to check in with each team member about their plans for annual leave:
- Remind everyone of your holiday policy and where to find it.
- Explain how leave requests are handled — who approves them, how far in advance they should be submitted, and how clashes are managed.
- Encourage early booking wherever possible, especially if you have team members with school-age children or peak workload periods to consider.
- Discuss cover for critical roles — get people thinking now about how work will be handed over and supported in their absence.
4. “Is Anything Getting in Your way?” – The Barrier Buster
Why it Matters
Small frustrations can quickly become big problems if they’re left unspoken. It might be an outdated process, an unclear instruction, missing equipment, or a team dynamic that isn’t working. People often won’t raise these issues unless they’re directly asked — especially in fast-moving environments where everyone’s under pressure.
Get Ahead
Create space for honest feedback. A simple, open-ended question - “Is anything slowing you down at the moment?” - can reveal problems that are easy to fix but hard to spot. You don’t need all the answers right now — it’s about showing that you’re willing to listen and follow up that builds employee trust.
Whatever might be holding someone back, the sooner you know about it, the sooner you can step in and support them. Don’t forget to note anything raised, and record agreed actions or changes. That way, it doesn’t get forgotten and your team sees that their feedback leads to real follow-up.
Ready to Start the Conversation?
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