The Power of Side Quests to Level-up Your Team

In the world of RPGs, side quests are optional missions that challenge characters to develop new skills, strengthen relationships, and prepare for the main story arc. In the workplace, side quests can serve the same purpose—particularly when they focus on building soft skills like boundary setting, conflict resolution, and communication.

As a leader, you can use side quests to help team members grow beyond their core technical skills and learn how to manage themselves and others more effectively. These aren’t just helpful tasks—they’re transformational.

What Is a Side Quest?

A side quest is a deliberate developmental challenge. It’s something you assign instead of solving. When a team member brings you a tough interpersonal or emotional issue, instead of taking the lead, you hand them a side quest: a specific, stretch-level task that confronts the problem directly.

This doesn’t mean abandoning them. You guide, model, and support—but they own the action.

The Goal:

Not just resolution, but growth. Not just comfort, but capability.

Examples of Side Quests

Let’s break down some real side quests:

1. Conflict Resolution

Scenario: “Someone on the team said something that really upset me.”

Side Quest Breakdown:

• Ask: What specifically upset you? Help unpack meaning vs. intention.
• Reframe: Could there be another interpretation?
• Equip: Provide a conversation framework—like “When you said X, I felt Y.”
• Assign: Have them speak directly with the other person.

You’re not mediating. You’re mentoring.

2. Boundary Setting

Scenario: “I keep getting pulled into work late at night.”

Side Quest Breakdown:

• Clarify expectations and acceptable boundaries.
• Draft language together for a boundary-setting message.
• Have them send it—and reflect afterward.

The quest builds assertiveness, not just solves the time problem.

3. Feedback Loops

Scenario: “I feel like my ideas don’t get taken seriously.”

Side Quest Breakdown:

• Explore examples together.
• Identify whether it’s delivery, timing, or perception.
• Task them with trying a revised approach and reporting back.

They grow through pattern recognition and adaptation.

What Happens Over Time

When you consistently use side quests, something powerful emerges:

Predictive Self-Coaching

You’ll notice a shift in how team members talk to you:

• Before: “Here’s my issue. What should I do?”
• Later: “Here’s my issue. I think I know what you’re going to say…”
• Eventually: “Here’s what happened. Here’s how I handled it. What’s your take?”

They start anticipating growth-oriented action. They internalize your frameworks. They begin to think like a lead.

From Side Quests to Leadership

That’s your signal.

When someone:

• Recognizes tough interpersonal challenges,
• Applies structure to navigate them,
• Takes ownership of outcomes,
• Reflects and iterates—

They’ve moved from being senior to being a lead. Not because of title or tenure, but because they now elevate others.

Tracking the Journey

Side quests lose their power if they’re forgotten. Growth is incremental, and without a way to reflect, measure, and revisit progress, the opportunity to reinforce learning fades.

That’s why tracking matters—not in a bureaucratic, performance-review sense, but as an intentional act of leadership.

When you assign a side quest, treat it as a meaningful developmental step. Note it. Capture the context, the challenge, and the timeframe. Then, create a thread—something you can revisit in future one-on-ones.

It could be as simple as:

• “Gave feedback to teammate directly after coaching session.”
• “Set boundaries with client on after-hours availability.”
• “Initiated conversation to clarify team expectations.”

By linking conversations over time, patterns emerge: where someone avoids discomfort, where they grow more confident, where they still need nudges.

This doesn’t require a complex system—but it does require consistency. Whether you track in a graph-based tool, a shared doc, or a leadership journal, the key is to make development visible. Not just to you, but eventually to the team member as well.

And during your one-on-ones, revisit those threads. Ask:

• What happened after you took action?
• How did that feel?
• What would you do differently next time?

That’s how you turn moments into momentum. Side quests don’t end when the task is done—they end when the learning sticks.

The Conclusion: Leadership Is Earned in the Side Quests

Technical skill may earn someone seniority. But soft skill—the ability to handle hard conversations, set boundaries, and model emotional resilience—is what earns leadership.

Side quests are how you build that. Not by solving every problem for your team, but by challenging them to solve problems with your guidance.

When they start coming to you less for answers and more to share solutions, you’ll know: they leveled up.