Supporting a Mentee Facing Repeated Setbacks

Mentorship & CoachingMid5–10 min

Introduction: What You’ll Learn

In this simulation, you’ll practice supporting a mentee who’s dealing with ongoing challenges. These can affect motivation and confidence, so your role is to help them build resilience, find practical solutions, and regain momentum.

You’ll practice:

  • Creating a supportive and open environment
  • Encouraging reflection and problem-solving
  • Reinforcing strengths and past successes
  • Setting achievable goals to get back on track

Step-by-Step Simulation

Scene 1: Initial Check-In

Mentor: "Hey Jamie, thanks for catching up with me today. I heard things have been a bit challenging lately. Let’s chat about what’s been going on and see how I can help."

Jamie: "Hi, yeah, it’s been a tough few weeks. Every time I think I’ve solved something, another issue pops up. I’m feeling kind of stuck."

Mentor: "That sounds really frustrating. Can you tell me more about what’s been tripping you up?"


Scene 2: Exploring Challenges

Jamie: "First, there was an API issue I thought I fixed, but the tests are still failing. Then, I tried adding a new feature and ended up with more bugs."

Mentor: "Sounds like you’ve got a lot on your plate. What have you tried so far to tackle these issues?"

Jamie: "I’ve been debugging and looking up solutions, but I’m not sure what I’m missing. It feels like I’m running in circles."

Mentor: "That’s tough. Have you thought about breaking the problem down into smaller pieces or maybe getting a fresh perspective from a teammate?"


Scene 3: Encouraging Problem-Solving

Jamie: "I’ve talked to a few people, but I probably need to be clearer about what I need help with."

Mentor: "Good idea. Sometimes a different way of looking at the problem can really help. What’s one new approach you could try this week?"

Jamie: "I think I’ll put together a detailed summary of the issues and ask the team for a brainstorming session. Maybe they’ll see something I missed."

Mentor: "That sounds like a solid plan. Remember, it’s okay to lean on your team. Also, think back to other tough challenges you’ve overcome. What worked for you then?"


Scene 4: Reinforcing Strengths and Setting Goals

Jamie: "I remember breaking a similar bug into smaller parts and tackling them one by one."

Mentor: "Exactly, you’ve got the skills to handle this. Let’s set a small, achievable goal for this week to help you get back on track. How about focusing on just one part of the API issue, and maybe pair programming with someone for feedback?"

Jamie: "Yeah, I can do that. I’ll start with the test failures and see if I can figure it out with a teammate."

Mentor: "Perfect. Keep me posted on your progress, and let’s touch base next week. Remember, setbacks are part of the process, and they set the stage for your next success."


Mini Roleplay Challenges

Challenge 1: Jamie doubts their skills.

  • Best Response: “You’ve tackled tough problems before. Let’s look at what worked for you in the past.”

Challenge 2: Jamie becomes defensive about failures.

  • Best Response: “It’s okay to feel frustrated. Let’s see what we can learn and adjust moving forward.”

Challenge 3: Jamie struggles to see any positive outcomes from setbacks.

  • Best Response: “What’s one thing you’ve learned about handling challenges during this time?”

Optional Curveball Mode

Add one of these scenarios during practice:

  • Jamie becomes overwhelmed and shuts down.
  • A new, unexpected challenge comes up during the session.
  • Jamie questions the value of mentorship and coaching.

Practice staying supportive and guiding without escalating the situation.

Reflection Checklist

Mentorship Approach

  • Did I create a safe and supportive environment?
  • Did I encourage Jamie to reflect on successes and strategies?
  • Did I help Jamie identify actionable next steps?

Communication Style

  • Was I empathetic and patient?
  • Did I actively listen and respond to Jamie’s concerns?
  • Did I reinforce Jamie’s strengths and potential?

Goal Setting

  • Did we set a clear, achievable goal?
  • Did I provide ongoing encouragement and support?

Common Mistakes to Avoid

  • Offering solutions without understanding the full context
  • Dismissing Jamie’s feelings or frustrations
  • Setting unrealistic or demotivating goals
  • Missing chances to reinforce strengths and past successes