Checking In With Your Team

February 28, 2025

Two young businesswomen having a meeting in the office sitting at a desk having a discussion with focus to a young woman wearing glasses

This is the fourth in a series on workplace conversations.

Even if your team spends eight or more hours a day together, it is essential to engage with them on a deeper level. While daily collaboration often happens organically, leaders can sometimes focus too heavily on task completion, overlooking the importance of personal check-ins.

Employees can easily become absorbed in their day-to-day responsibilities, but are they discussing their career aspirations, challenges, or personal struggles? Do they feel empowered to share when they need help or guidance? These conversations often do not come up in casual, task-focused exchanges.

The Power of Individual Meetings

One powerful strategy to foster a deeper connection with your team is to hold quarterly meetings focused solely on personal and professional development. These meetings provide a dedicated time to discuss each employee’s goals, progress, challenges, and areas where they need support.

It is also an important follow-up from individual performance reviews to ensure that an employee is improving in areas identified as needing improvement and to check in on the status of goals assigned during the review.

Investing in these one-on-one sessions shows your team that you care about their growth and long-term success within the company. This creates a safe space for employees to openly discuss any concerns or obstacles they face, whether related to their work, personal lives, or professional development.

In addition to quarterly meetings, regular one-on-one check-ins are crucial. These more frequent, shorter sessions offer an opportunity to build rapport, discuss progress on specific tasks, and address challenges on a personal level. One-on-ones help create a supportive environment where employees feel heard, valued, and empowered.

These meetings are especially vital if you are cultivating future leaders. They help to:

  • Build Stronger Relationships: Consistent check-ins foster trust between leadership and employees, which contributes to a healthier work culture and better retention rates.
  • Identify Struggles Early: Regular meetings provide the chance to spot potential issues before they grow. By identifying areas where employees are struggling, you can offer the guidance and resources they need.
  • Boost Employee Retention: Employees who feel valued and supported are more likely to stay with the company for the long term. Showing a genuine interest in their growth and well-being reinforces their commitment to the organization.
  • Assess the Right Fit: Quarterly reviews and one-on-one meetings allow you to evaluate whether an employee is truly aligned with their role or the company’s objectives. If an individual is struggling or not fully engaged, these meetings provide an opportunity to explore possible solutions, such as additional training or transitioning into a different role within the organization.

Creating a Culture of Ongoing Feedback

While structured meetings are vital, fostering an open dialogue about career development throughout the year is equally important. By encouraging ongoing conversations about personal growth, you can offer clarity on employee goals and establish a stronger, more cohesive team that feels supported and engaged.

Routine check-ins allow employees to reflect on their professional aspirations and challenges, leading to better alignment with company objectives and, ultimately, a more motivated, committed workforce.