Coaching a Teammate Through an Unfamiliar Task

Mentorship & CoachingMid5–10 min

Introduction: What You’ll Learn

In this simulation, you'll practice coaching a team member through a task they haven't done before. The focus is on providing guidance and support while encouraging independence and building confidence.

You’ll practice:

  • Assessing the mentee's current understanding and comfort level
  • Providing clear, actionable guidance and resources
  • Encouraging questions and proactive problem-solving
  • Balancing support with independence, fostering growth

Step-by-Step Simulation

Scene 1: Setting the Stage

Coach: "Hey Jamie, I heard you're tackling the database migration for the first time. How are you feeling about it?"

Jamie: "I’ve read through some docs, but I’m not exactly sure where to begin."

Coach: "That's totally fine. We can break it down together. First, let's start by checking out the current database schema and see what changes we need to make. I'll walk you through the beginning, and then you can take over as you get more comfortable."


Scene 2: Initial Guidance

Coach: "Do you have the database client open? Let's take a look at the tables."

Jamie: "Yeah, I’m looking at them now."

Coach: "Awesome. Can you figure out which new fields or tables we need to add based on the project requirements?"

Jamie: "We need to add a ‘user_profile’ table and a ‘last_login’ column to the ‘users’ table."

Coach: "Spot on. Let's write up the SQL statements for those changes. If you're unsure about the syntax, the documentation can be handy."


Scene 3: Encouraging Independence

Coach: "Now that you've got the SQL statements, let's test them in a development environment. How do you plan to handle any errors that might come up?"

Jamie: "I’ll run each statement one at a time and check the error logs if something doesn’t work. I’ll also verify the data integrity after each step."

Coach: "Great strategy. If you hit a snag, try troubleshooting it first. Of course, I’m here if you need an extra pair of eyes, but I’m confident you’ll handle most of it."


Scene 4: Wrapping Up and Reflection

Coach: "You did really well today, Jamie. How do you feel about tackling the rest on your own?"

Jamie: "I’m feeling much better about it now. I have a clearer understanding of the process and what to look out for."

Coach: "That's great to hear. Remember, I’m just a message away if you need help. Let’s catch up after you finish the migration to go over what you learned."

Jamie: "Sounds like a plan. Thanks for your help!"


Mini Roleplay Challenges

Challenge 1: Jamie seems hesitant to ask questions. What do you do?

  • Best Response: “Feel free to ask any questions as they come up — no question is too small.”

Challenge 2: Jamie encounters a persistent error and seems frustrated.

  • Best Response: “Let’s take a look together. Can you walk me through what you’ve tried so far?”

Challenge 3: Jamie completes the task but is unsure if it was done correctly.

  • Best Response: “Let’s review the work together and see if there are any areas we can improve or clarify.”

Optional Curveball Mode

  • Jamie misunderstands a key requirement and starts heading in the wrong direction.
  • Jamie is interrupted by an urgent request and needs to switch tasks temporarily.
  • Jamie completes the task but doesn’t document the process.

Practice handling each situation while maintaining a supportive coaching approach.

Reflection Checklist

Coaching Approach

  • Did I provide clear and actionable guidance?
  • Did I encourage questions and independent problem-solving?
  • Was I supportive and patient throughout the process?

Outcome & Learning

  • Did Jamie complete the task with a good understanding?
  • Did I offer constructive feedback and celebrate progress?
  • Did we identify any areas for further learning or improvement?

Overall Experience

  • Did I foster a positive and open learning environment?
  • Did Jamie feel more confident and prepared for future tasks?

Common Mistakes to Avoid

  • Overloading Jamie with too much information at once
  • Solving problems for Jamie without encouraging independence
  • Failing to check in on Jamie’s understanding and comfort level
  • Not providing a clear path for follow-up and reflection after the task is completed