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Coaching Techniques Reference

Detailed methodology guides for effective founder coaching conversations.

Growth Mindset in Coaching (Carol Dweck Research)

The Core Finding

35+ years of research shows that how you praise matters more than how much you praise.

Mueller & Dweck (1998) - Journal of Personality and Social Psychology - 5th graders given different types of praise:

• Trait praise ("You must be smart"): Students avoided challenges, lost confidence when struggling, performance declined, 38% lied about scores
• Process praise ("You must have worked hard"): Students sought challenges, persisted through difficulty, performance improved

Fixed vs. Growth Mindset

Fixed Mindset	Growth Mindset
Intelligence/ability is static	Intelligence/ability grows with effort
Avoids challenges (might fail)	Seeks challenges (opportunity to grow)
Effort = you're not smart enough	Effort = path to mastery
Gives up when stuck	Persists through obstacles
Ignores useful feedback	Learns from criticism
Threatened by others' success	Inspired by others' success

How Coaching Language Shapes Mindset

Fixed mindset triggers:

• "You're a natural entrepreneur"
• "You're so talented at this"
• "Some people just have it"
• "You're smart enough to figure this out" (implies smartness is fixed)

Growth mindset triggers:

• "Your strategy here was effective"
• "The effort you put into preparation shows"
• "You've improved significantly since we last talked"
• "What did you learn from that setback?"

Reframing Struggle as Growth

Fixed mindset view: Struggle = evidence of inadequacy Growth mindset view: Struggle = evidence of learning happening

Coaching reframes:

• "Finding this hard means you're pushing your boundaries"
• "Confusion is often the first step to understanding"
• "The fact that you're stuck shows you're tackling something meaningful"
• "What's one thing this challenge is teaching you?"

The Effort Paradox

Warning: Praising effort alone can backfire if the effort isn't effective.

Ineffective: "You tried really hard!" (when strategy was wrong) Effective: "You tried multiple approaches—what did you learn about which ones work?"

The goal is to praise effective effort—effort that involves good strategies, seeking help, and learning from mistakes.

Application to Founder Coaching

Situation	Fixed Mindset Response (Avoid)	Growth Mindset Response (Use)
Founder succeeds	"You're a great founder"	"Your approach to customer discovery was methodical"
Founder fails	"Maybe this isn't for you"	"What did this teach you? How will you adjust?"
Founder is stuck	"You should be able to figure this out"	"Getting stuck on hard problems is normal. What have you tried?"
Founder avoids challenge	"That's okay, play to your strengths"	"What would you learn by trying it anyway?"

GROW Model

The most widely-used coaching framework, developed by Sir John Whitmore.

Structure

G - Goal: What do you want to achieve? R - Reality: Where are you now? O - Options: What could you do? W - Will: What will you do?

Goal Questions

Start by establishing what the founder wants from this conversation and longer-term:

• "What would you like to focus on today?"
• "What does your ideal future look like?"
• "Over what time frame?"
• "How will you know when you've achieved it?"
• "What would make this session well-spent?"

Keys to Good Goals

• Specific enough to measure
• Within founder's control
• Positively stated (what they want, not what they don't want)
• Time-bound

Reality Questions

Understand current situation without judgment:

• "Where are you now on a scale of 1-10?"
• "What's happening at the moment?"
• "What have you tried so far?"
• "Who else is involved?"
• "What's stopping you from being at a 10?"
• "What resources do you have?"
• "What's worked before in similar situations?"

Purpose: Create accurate assessment, surface assumptions, identify resources already available.

Options Questions

Generate possibilities without evaluating yet:

• "What could you do?"
• "What else?" (ask 3-5 times)
• "If you had no constraints, what would you do?"
• "What would you advise a friend in this situation?"
• "What are the advantages and disadvantages of each option?"
• "What would happen if you did nothing?"
• "Who else might help?"

Rules

• Quantity over quality first
• No evaluation during brainstorming
• Include wild/unlikely options
• Ask "what else?" until genuinely stuck

Will Questions

Convert options into specific commitments:

• "What will you do?"
• "When exactly will you do it?"
• "What obstacles might you meet?"
• "How will you overcome them?"
• "Who needs to know?"
• "What support do you need?"
• "How committed are you on a scale of 1-10?"
• "What would make it a 10?"

Commitment Checklist

• Is it specific?
• Is there a deadline?
• Are obstacles anticipated?
• Is commitment level high (8+)?

Solution-Focused Brief Coaching

Developed by Steve de Shazer and Insoo Kim Berg. Core philosophy: Focus on solutions, not problems.

Core Principles

1. If it ain't broke, don't fix it
2. Once you know what works, do more of it
3. If it's not working, do something different

The Miracle Question

"Suppose tonight while you sleep, a miracle happens. The problem is solved. When you wake up tomorrow, what will be the first small sign that tells you the miracle happened?"

Follow-Up Questions

• "What will be different?"
• "Who will notice first?"
• "What will they see you doing?"
• "What will that make possible?"

Purpose: Bypass problem-focus, reveal desired future state, make abstract goals concrete.

Exception Finding

"Tell me about a time when this problem wasn't happening, or was less severe. What was different? What were you doing differently?"

Follow-Up Questions

• "How did you make that happen?"
• "What was different about that situation?"
• "How could you do more of that?"

Purpose: Identify existing solutions, build on past successes, recognize founder's own resources.

Scaling Questions

"On a scale of 1-10, where 10 is the miracle and 1 is the worst it's been, where are you today?"

Follow-Ups

• "What makes it a [current number] and not lower?"
• "What would it take to move from [current] to [current +1]?"
• "When have you been at a higher number?"
• "What was happening then?"

Purpose: Make abstract progress concrete, identify small steps, celebrate progress already made.

Coping Questions

For founders in crisis or overwhelm:

• "How have you managed to keep going despite everything?"
• "What keeps you from giving up?"
• "What's one thing that's still working?"

Purpose: Recognize resilience, identify coping resources, shift from helplessness to agency.

Socratic Method

Named after Socrates. Uses disciplined questioning to stimulate critical thinking and illuminate assumptions.

Six Types of Socratic Questions

1. Clarifying Questions

• "What exactly do you mean by...?"
• "Can you give me an example?"
• "How does this relate to your goal?"
• "What's the connection between X and Y?"

2. Probing Assumptions

• "What are you assuming here?"
• "Is that always the case?"
• "What would happen if that assumption were wrong?"
• "What would need to be true for X?"

3. Probing Reasons and Evidence

• "What evidence supports that?"
• "How do you know that's true?"
• "What makes you say that?"
• "Is that data or intuition?"

4. Exploring Viewpoints and Perspectives

• "How would your co-founder see this?"
• "What's the alternative perspective?"
• "How would this look from your users' view?"
• "What would a skeptic say?"

5. Examining Implications and Consequences

• "If you do that, what happens next?"
• "What are the long-term implications?"
• "How does this affect your other goals?"
• "What's the cost of this choice?"

6. Meta-Questions (Questions about Questions)

• "Why do you think I asked that?"
• "What other questions should we explore?"
• "What question would be most useful right now?"
• "What are you not asking that you should be?"

The Funnel Technique

Start Broad "Tell me about the situation you're facing."

Narrow Focus "Of all those factors, which feels most critical?"

Go Deep "What makes that factor so important to you?"

Surface Insights "What are you realizing as we talk through this?"

Plan Action "Given what we've discovered, what's one small step you could take?"

Michael Bungay Stanier's 7 Essential Questions

From "The Coaching Habit"—designed to stay curious longer and rush to advice less quickly.

1. "What's on your mind?" (The Kickstart Question)

• Open-ended, focused
• Gets to what's actually important
• Better than "How are you?"

2. "And what else?" (The AWE Question)

• Most important question
• First answer is rarely the real answer
• Prevents rushing to problem-solving
• Ask 3-5 times per conversation

3. "What's the real challenge here for you?" (The Focus Question)

• Cuts through complexity
• "Real challenge" = get to the root
• "For you" = makes it personal, not abstract

4. "What do you want?" (The Foundation Question)

• Clarifies desired outcome
• Creates autonomy
• Transitions from reflection to action

5. "How can I help?" (The Lazy Question)

• Places ownership on the other person
• Prevents assuming you know how to help
• Acceptable responses: Yes/No/Alternative/Let me think

6. "If you're saying yes to this, what are you saying no to?" (The Strategic Question)

• Forces prioritization
• Reveals trade-offs
• Creates focus and boundaries

7. "What was most useful for you?" (The Learning Question)

• Consolidates learning
• Builds self-awareness
• Improves future sessions

Radical Candor for Honest Feedback

Kim Scott's framework for giving feedback that's both caring and direct.

The 2x2 Matrix

	Low Challenge	High Challenge
High Care	Ruinous Empathy	RADICAL CANDOR ✓
Low Care	Manipulative Insincerity	Obnoxious Aggression

Ruinous Empathy is the most common failure mode—being nice instead of being helpful.

The CORE Method for Criticism

When delivering difficult feedback, use this structure:

• Context: "In yesterday's investor pitch..."
• Observation: "When you said the market is $50B without citing a source..."
• Result: "The investor visibly disengaged and asked no follow-up questions..."
• Expectation: "Going forward, lead with credible third-party market data."

Application for Founder Coaching

Before giving hard feedback:

1. Check your intent—are you trying to help them succeed?
2. Use CORE structure to be specific, not vague
3. Focus on behavior and results, not character
4. Make it a conversation: "How does that land for you?"

Common mistakes:

• The "feedback sandwich" (positive-negative-positive) buries the message
• Adam Grant: "When you start and end with positive feedback, criticism gets buried or discounted"
• Better: Direct feedback followed by "What would help?"

Powerful Question Characteristics

Research shows effective coaching questions share these traits:

Open-Ended

• Start with What, How, When
• Avoid Why (too defensive)
• Allow exploration, not yes/no

Good: "What options do you see?" Bad: "Do you have options?"

Future-Focused

• "What do you want to create?"
• "Where do you want to be in 6 months?"
• Not: "Why did this go wrong?"

Generatively Ambiguous

• Allow client to define terms their own way
• "What does success mean to you?"
• Not: "Do you want to hit $1M ARR?"

Short and Clean

• 5-10 words ideal
• No metaphors unless client introduces them
• Minimal interference from coach

Client-Focused, Not Problem-Focused

• "What do you want?"
• "What's working?"
• Not: "What's the problem?" "What's broken?"

Accountability Structures

The Accountability Conversation

Opening (5 minutes)

1. "What did you commit to last time?"
2. "What actually happened?"
3. If completed: "What did you learn?"
4. If not completed: "What got in the way?" (curious, not judgmental)

Middle (20 minutes) 5. "What does that tell you?" 6. "What do you want to do differently?" 7. Continue with GROW or other framework

Closing (5 minutes) 8. "What's your commitment for next time?" 9. "On a scale of 1-10, how confident are you?" 10. "What might get in the way?" 11. "How will you handle that?"

Making Commitments Stick

SMART Format

• Specific: "Talk to 10 users" not "do user research"
• Measurable: Clear success criteria
• Achievable: Within founder's control
• Relevant: Connected to stated goals
• Time-bound: "By Friday" not "soon"

Obstacle Pre-Mortems Before any commitment is made:

• "What might get in the way?"
• "What's happened before when you tried this?"
• "What would make it a 10/10 in commitment?"
• If below 8/10: "What would make it higher?"

Commitment Devices

Research-backed techniques:

• Public commitment: Share goals with someone else
• Implementation intentions: "If X happens, I will do Y"
• Progress documentation: Visual tracking

When to Ask vs. When to Tell

Default to Questions (80%)

Why Questions Work Better

• Founder implements THEIR solution, not yours
• Builds decision-making capacity
• You don't have full context
• Creates ownership, not dependency

When Advice IS Appropriate (20%)

1. Founder explicitly asks: "What would you do?"
2. Safety/legal/ethical considerations
3. Factual information (grants, market data, frameworks)
4. After thorough exploration, founder is genuinely stuck

How to Give Advice Without Undermining

1. Ask permission: "Would it be useful if I shared what I've seen work for others?"
2. Offer options, not directives: "Some founders have tried X or Y. What resonates?"
3. Stay tentative: "I wonder if..." not "You should..."
4. Check fit: "How does that land for you?"
5. Return to questions: "What would you adapt from that for your situation?"

Empowerment Techniques

Reflect Questions Back

Founder: "Should I hire a head of sales?" Weak: "Yes, you should." Strong: "What's making you consider that now?"

Mine Past Successes

• "When have you faced a similar decision? What did you do?"
• "What's worked for you in the past when you were uncertain?"

Expand Options

• "What else could you try?"
• "If that option wasn't available, what would you do?"
• "What would [someone they admire] do?"

Strengthen Decision-Making

• "What criteria matter most here?"
• "What information would help you decide?"
• "How will you know if it's the right call?"

Build Meta-Cognition

• "What's your thinking process here?"
• "How are you approaching this decision?"
• "What questions are you asking yourself?"

Anti-Patterns to Avoid

Solution Dumping

Problem: Immediately providing answers Fix: Ask 3 questions before any suggestion

Vague Questions

Problem: "How do you feel about that?" Fix: Specific questions that advance thinking

Interrupting

Problem: Talking more than listening Fix: Target 20% coach, 80% founder

Making It About You

Problem: "When I was building my startup..." Fix: Share sparingly, return to their situation

Ignoring Emotions

Problem: Pure analysis on emotional topics Fix: Acknowledge before problem-solving

Being Too Nice

Problem: Sugar-coating dilutes value Fix: "I want to be direct with you..."

Generic Advice

Problem: Same advice to everyone Fix: Mine their specific context