The power of meaningful one-to-one check-in meetings

Check-ins that help people connect and thrive

In fast-paced, operational environments, it’s easy for human connection and wellbeing to take a back seat to task lists and deadlines. One-to-one check-ins are a powerful way to stay connected to both the work and the person behind it.

Regular check-ins also help prevent the hidden costs of poor wellbeing, unclear roles, and disengagement. Without them, organisations face more sick leave, reduced productivity, higher turnover, and lower engagement.

In contrast, regular one-to-ones strengthen clarity, inspire ownership for action, create deeper connection and support, that lifts performance and reduces risk.

Enhance connection and wellbeing

Mental health is now a workplace health and safety issue, not just a personal matter. Employers have a duty of care to identify and reduce psychosocial risks, such as unmanageable workloads, role confusion, isolation, or poor leadership.

These risks when ignored, can lead to burnout, stress, and serious psychological harm. Check-ins, when done with care, help leaders spot early signs of stress, reduce role tension, clarify expectations, and build connection as simple yet powerful ways to enhance wellbeing.

Separate check-ins from work-in-progress

One-to-one check-ins work best when they are intentionally focused on the person, not just the work. These conversations are two-way, curiosity-led, and serve to give the individual space to reflect on their wellbeing, role focus and satisfaction, and performance expectations.

An effective check-in follows an informal agenda of inquiry, compassion, collaborative problem solving and understanding. As leadership author Marcus Buckingham puts it: “check-ins are not in addition to the work of a team leader; they are the work of a team leader”.

Work-in-progress (WIP) meetings serve a different function. These are structured, action-oriented conversations focused on execution: tracking progress, resolving blockages, managing logistics, and aligning stakeholder expectations and risks. An effective WIP benefits from an agenda of Progress, Issues, Plans.

Trying to cover both in one meeting usually results in the operational crowding out the relational. Separating them builds trust, supports psychological safety, and allows full presence for each purpose without switching context mid-conversation.

Take up the role of thinking partner

As manager, a one-to-one check-in meeting is a gift of time and intention to offer yourself as a thinking partner. This means creating a safe, open space where the other person can speak freely and be fully heard. In that space, clarity emerges, decision-making sharpens, and energy is mobilised for action.

When hosting a check-in, aim to listen 80% of the time and talk just 20%. Focus less on telling and more on asking thoughtful questions. Acknowledge that this is their time, follow their agenda, and give them space to reflect. Then support them in deciding and acting from their own perspective.

Lean into silence

Silence in a conversation can feel uncomfortable. For the listener, it may trigger habits of needing to speak, solve problems, or filling the space. For the thinker, it may stir a fear of not having all the answers or needing to appear competent.

Silence can also signal deeper reflection. Moments of stillness often precede insight. Rather than rushing past them, allow the pause. Something important may be coming together.

Practice empathic listening

Empathic listening means being fully present and showing genuine curiosity about the other person's perspective. It's more than avoiding distractions; it involves tuning in emotionally and mentally. This includes:

• Acknowledging and normalising feelings

• Reflecting back what you’re hearing

• Validating experiences without rushing to fix or reframe. 

Ask yourself: how well could you describe the other person’s view on an issue, especially when it differs from your own?

Done with care, empathic listening strengthens connection, builds trust, and makes room for real collaboration.

Experiment with generative listening

Generative listening goes further.  It means being fully open to encourage new ideas and possibilities for and with the other person.

Try approaching the conversation from a place of not-knowing, free from your own assumptions, impatience, judgments, advice, or the urge to fix the other person’s challenge.

This kind of listening encourages divergent thinking, deeper understanding, and joint personal growth. It shifts the dynamic from problem-solving to co-creating. 

Realign expectations

Check-ins can also be a time to revisit and clarify expectations. This might include:

• Reconfirming performance standards and role priorities

• Discussing shifts in focus or resourcing

• Calibrating effort across responsibilities

• Sharing observations and offering constructive feedback for the person

• Identifying new skills needed to meet future demands.

Done well, this supports alignment and gives the individual a clearer view of their development trajectory and readiness for progression.

Share organisational context

Providing context helps people understand why certain priorities matter, and how their work fits within broader organisation dynamics.

Share relevant shifts in direction, emerging risks, or stakeholder expectations. This enables smarter decision-making and helps individuals navigate organisational complexity with greater confidence.

Reinforce Strengths and Values

Use check-ins to recognise what’s going well. Highlight strengths in action and how they contribute to success.

Offer reinforcing feedback, and help individuals recognise when strengths may be overused or under-leveraged.

Revisit behavioural expectations and values-in-action to ensure clarity and alignment.

A simple framework for encouraging reflection

A simple structure to encourage deeper thinking and genuine care:

• What’s on your mind?

• What else? / Anything else?

• What do you want to happen?

• What’s happening now?

• What will you do next?

• What do you need from me?

When asked for your opinion, rather than jump to giving advice, share your observations as an invitation for consideration:

• So, here’s what I’ve heard you say …

• Well, here’s what I’ve noticed …

• So, here’s what I’m wondering …

• For you, it has me feel …

Final thoughts

When done with intention, check-in conversations are a core leadership practice, not a luxury. They promote wellbeing and performance by deepening connection, fostering clarity, and supporting growth. Most importantly, they help people feel seen, heard, and genuinely supported both in their work and as individuals.