Coaching Beyond the Surface: How the Fail Forward Deck Elevates 1:1 Mentoring Conversations
It all begins with an idea.
When you sit down for a one-on-one, it’s easy to slip into status updates and surface-level check-ins. “How’s it going?” “Anything you need?” “What’s your goal for next week?” These are valid, but they’re not always transformative.
The Leap & Learn Fail Forward Card Deck redefines what powerful 1:1 coaching and mentoring can look like. Whether you’re guiding a new team member, coaching a student, supporting a colleague, or mentoring across generations, the deck helps you dig deeper, reflect with honesty, and unlock growth mindsets that lead to real momentum.
Why This Deck Works in 1:1 Coaching
Research in adult learning theory and leadership coaching reminds us that transformation doesn’t come from advice—it comes from self-reflection, psychological safety, and guided inquiry. The Fail Forward cards provide that structure.
According to Harvard Business Review, effective coaching “turns insight into action” and creates reflective thinking environments. That’s exactly what the Fail Forward prompts do—especially in quiet, confidential coaching conversations where trust is already forming or needs to be built.
Instead of just asking “How’s it going?”, you’re now asking:
"What does success look like for you this week—really?"
"What fear is holding you back from trying something new?"
"When did you recover from a moment that felt like failure?"
These aren’t random icebreakers. They’re targeted growth accelerators.
5 Ways to Use the Deck in Coaching & Mentoring Sessions
1. Start-of-Session Reset (Launch Cards)
Kick off with a light prompt to set the tone:
🟦 “What’s a small win you haven’t celebrated yet?”
This signals that the space is non-judgmental and reflective—not performative.
2. Identify Growth Gaps (Leap Prompts)
Use green cards to gently challenge your mentee’s thinking:
🟩 “What belief are you holding onto that might be limiting you?”
This opens up a safe space for self-exploration without defensiveness.
3. Process a Setback (Stumble Stories)
If someone is stuck or frustrated, red cards guide them to reframe it:
🟥 “Share a time when you wanted to quit but didn’t. What helped?”
The cards give permission to talk about failure as a source of data, not shame.
4. Close with Action (Momentum Moves)
After reflection, finish by making it practical:
🟧 “List two actions that will move you forward this week—even if it’s messy.”
This turns the session from insight → execution.
5. Coaching Journal Prompts (Asynchronous Use)
Send a card digitally or give a card to reflect on between sessions:
“Use this green Leap Prompt this week: What story are you telling yourself about your ability to lead? Write your honest response before we meet again.”
This builds continuity and accountability without pressure.
Pro Tips for Coaches and Mentors
✅ Let Them Choose
Spread 3-4 cards and let your mentee pick one. This gives autonomy and taps into intuition.
✅ Use the Same Prompt Twice
Revisit a prompt a few sessions later. See how their thinking has evolved. This builds evidence of growth.
✅ Print a Mini Deck
Have a printed PDF sampler to physically hand out or leave with a mentee. Tangible prompts leave lasting impressions.
✅ Be Vulnerable Too
If appropriate, share your own response. Modeling is powerful. Coaching is a two-way street.
What If They’re Resistant?
They shut down: Pivot to a lighter Launch Card and remind them there are no “right answers.”
They say “I don’t know”: Say, “That’s totally fine. If something comes up later, we can come back to it.”
They try to be ‘perfect’: Gently remind them this isn’t a performance—it’s a partnership.
“This deck isn’t about fixing. It’s about finding—and forwarding.”
Why It Matters
In one-on-one spaces, language matters. The Fail Forward Card Deck invites brave language—language that helps people see themselves not as stuck, but as becoming.
And when people feel seen in that becoming process? They take bigger risks, recover faster, and lead with more clarity.
So bring the cards to your next 1:1. You won’t regret it. You’ll move past check-ins—and step into transformation.