Too often, learning and development initiatives are seen as one-and-done events detached from day-to-day work.

Most employee development efforts emphasize formal training. But real growth typically happens during the day-to-day: in conversations, coaching moments and consistent feedback by a direct manager. As a team leader, one of the biggest factors in whether your team grows or stalls often comes down to you being in their corner on an ongoing basis.

Below, you’ll find tips on how to implement coaching and encouragement of small, high-impact development behaviors in meetings with your direct reports. The advice below is drawn directly from an LLR Collaborate session with a group of our portfolio company managers.

Align on goals to accelerate and reinforce learnings

Prioritizing alignment

Whether your direct report is preparing for formal training or focused on building a new skill, your involvement as a manager can make the difference between short-term exposure and long-term development. Even if formal learning moments are limited, your team is immersed in your orbit every day.

Lay the foundation by investing time to understand their goals. A 10-minute skim of a curriculum or a quick sync to talk about individual growth priorities can equip you to speak the same language and connect the dots to how it all applies in the flow of day-to-day work. Use a portion of your 1:1s to align on what success looks like and co-own the outcomes.

In Practice: Example Questions to Cover During Check-Ins

  • “What’s one skill or habit you’re hoping to build on through this experience?”
  • “How do you/I think this training or initiative aligns with our broader team priorities?”
  • “What will success look like for you after completing a training or developing this skill?”

Reinforcement

The way you follow up after aligning on goals with your direct report can help shape whether learning translates into action. Too often, learning and development initiatives are seen as one-and-done events detached from day-to-day work. But real growth is iterative and reinforced over time. Incorporate follow-ups on their development into your regular check-ins.

In Practice: Example Questions to Reiterate During Check-Ins

  • “How can you put a new skill or learning into action this week/this month?
  • “Which part of a training or skill exploration feels most relevant to your current challenges?”
  • “How can we measure this?”

By making time for alignment and reinforcement conversations, you’re signaling that development is a priority, follow-through matters and measuring development in day-to-day “wins” will happen.

Spot ongoing development and provide space for failure

Coaching with a stretch mindset

Effective coaching is also about identifying opportunities for your direct report that are aligned to their development goals and can allow them to grow through experience, take smart risks and build confidence by doing. This also involves creating space for honest conversations on the support they’d like from you when working through these stretch opportunities. Ask yourself: What stretch assignments can I provide that are tied to their/our team’s goals?

In Practice: Example Questions to Align on Stretch Goals During Check-Ins

  • “What stretch assignments can I provide you that are tied to your and our team goals?”
  • “Is there anything you’ve been unsure how to try or where to start?”
  • “Where can I give you more room, or more feedback for this initiative?”

Normalizing failure

Development and learning often begins where comfort ends. As a manager, your role isn’t just to evaluate outcomes. When a direct report steps into ambiguity, takes on a challenge without a clear playbook or tries something for the first time, one of your goals should be to provide space for “thoughtful failure.”

In Practice: Example Prompts to Normalize Risk and Failure During Check-Ins

  • “This project/initiative is a test kitchen, not a performance review. If it fails, we’ll learn fast as a team.”
  • “What’s one thing you’ve tried recently that didn’t go as planned?” What did you learn from it?

Another way to reinforce failure is by being open and honest about yourself. Model vulnerability by sharing a recent mistake or development lesson with your team. That kind of candor creates the psychological safety that fuels experimentation. One of the most powerful things a manager can do is be human. Talk about your own learning curve and how you bounced back from it to model that failure is necessary and a shared journey, not a solo project.

Celebrate progress and “wins”

Progress typically doesn’t come with a drumroll. Most times, it shows up in subtle shifts: tone, presence and follow-through. If you want positive behaviors to stick, don’t hesitate to call them out when you notice them. When recognition is timely and tied directly to development, it reinforces the idea that progress is visible, valued and worth continuing.

In Practice: Examples of Celebrating Progress During Check-Ins

  • “I appreciated how you asked for feedback on x project last week.”
  • “I noticed how you lead the call today confidently. Great job.”
  • “Great job leading the y portion of the project. I know it was your first time doing so.”

Here’s the bottom line.

Real employee development isn’t a one-time event. It’s fostered and built over time by your consistent attention. Impact happens when you align on goals, provide opportunities for development, measure the outcomes and celebrate progress. If you want your team to grow, show them that growth is the ongoing expectation and that you’re in it together.