Making requests that work and build relationships.
Why Asking Matters
Many people avoid asking for help, viewing it as weakness. In reality, asking well is a skill that strengthens relationships and unlocks opportunities. Most people genuinely want to help others when asked appropriately.
The Fear of Asking
| Fear | Reality |
|---|
| "I'll seem weak" | Asking shows self-awareness |
| "They'll think less of me" | People respect those who seek growth |
| "I'll be imposing" | Most people enjoy helping |
| "They'll say no" | No is just information, not rejection |
| "I should figure it out myself" | Smart people leverage networks |
| "I haven't earned the right" | You won't know until you ask |
Benefits of Asking
| Benefit | Explanation |
|---|
| Accelerates learning | Learn from others' experience |
| Opens opportunities | Access things you couldn't alone |
| Deepens relationships | People like to be helpful |
| Builds reciprocity | Creates healthy exchange |
| Signals ambition | Shows you're proactive |
| Honors their expertise | Recognition of their value |
The Principles of Good Asks
Before You Ask
| Principle | Application |
|---|
| Do your homework | Research first, ask informed questions |
| Exhaust other options | Try to solve it yourself first |
| Be clear on what you need | Vague asks get vague responses |
| Consider their perspective | Why would they help you? |
| Respect their time | Make it easy to say yes or no |
| Ensure relationship standing | Have you given before asking? |
The Relationship Bank Account
| Action | Deposit or Withdrawal |
|---|
| Giving value | Deposit |
| Making introductions | Deposit |
| Celebrating their wins | Deposit |
| Offering help | Deposit |
| Making a request | Withdrawal |
| Taking without reciprocating | Major withdrawal |
Before making withdrawals, ensure you have made deposits.
What to Ask For
Types of Requests
| Request Type | Example | Time Investment |
|---|
| Quick question | "How did you handle X?" | 5 minutes |
| Advice conversation | "Can we discuss my challenge with Y?" | 30 minutes |
| Introduction | "Could you connect me with Z?" | 15 minutes |
| Recommendation | "Would you write a reference?" | 30-60 minutes |
| Mentorship | "Would you advise me periodically?" | Ongoing |
| Job referral | "Could you refer me internally?" | Variable |
| Expert input | "Could you review my work?" | 30-60 minutes |
Matching Ask to Relationship
| Relationship Level | Appropriate Asks |
|---|
| New acquaintance | Quick questions, light advice |
| Active connection | Coffee conversations, introductions |
| Established relationship | References, meaningful favors |
| Close relationship | Large requests, ongoing mentorship |
How to Ask Well
The Anatomy of a Good Ask
| Element | Purpose | Example |
|---|
| Context | Why you're asking them | "Given your experience in X..." |
| Specific request | Exactly what you need | "I'd love 20 minutes to discuss Y" |
| Reason | Why it matters | "I'm trying to decide between..." |
| Time boundary | Respect their time | "Just a quick call this month" |
| Easy out | No pressure | "Totally understand if you're too busy" |
| Gratitude | Appreciation | "I'd really appreciate your perspective" |
Good Ask Examples
| Situation | Good Ask |
|---|
| Career advice | "I'm considering a transition to X. Given your experience making a similar move, would you have 20 minutes to share your perspective? I have specific questions about timing and preparation." |
| Introduction | "I noticed you're connected to [Name] at [Company]. I'm exploring opportunities there and would love an introduction. Would you be comfortable connecting us? Happy to write a draft intro for you." |
| Job referral | "I saw [Company] has an opening in [role]. I've prepared my resume and believe I'm a strong fit because [reasons]. Would you be willing to submit an internal referral? I've attached my materials." |
| Expert advice | "I'm working on [project] and would really value your input on [specific aspect]. Could I send you a brief summary and get your thoughts? Even a few bullet points would be helpful." |
Bad Ask Examples
| Bad Ask | Why It Fails |
|---|
| "Can you help me find a job?" | Too vague, too big |
| "I want to pick your brain" | Unclear, devalues their time |
| "Let's grab coffee sometime" | No specific purpose |
| "Can you connect me with everyone you know?" | Unrealistic, lazy |
| "I need this tomorrow" | Disrespects their time |
| "You probably can't help, but..." | Undermines the ask |
Structure Your Request
| Step | What to Include |
|---|
| 1. Hook | Why you're reaching out to them specifically |
| 2. Context | Your situation and background |
| 3. Specific ask | Exactly what you need |
| 4. Scope | Time and effort required |
| 5. Value | Why it matters to you |
| 6. Easy out | No pressure if they can't |
| 7. Gratitude | Thanks for considering |
Request Email Template:
Subject: [Specific, clear subject line]
Hi [Name],
[Hook - why them specifically]
[Brief context - your situation]
[Specific ask - exactly what you need]
[Time boundary - 15 minutes, one question, etc.]
I'm asking because [why it matters].
No pressure at all if you're too busy or this isn't
a good fit. I really appreciate you considering it.
Thanks so much,
[Your name]
Asking Different Types of People
Asking Peers
| Approach | Why It Works |
|---|
| Frame as collaboration | Equal relationship |
| Offer reciprocity | "Happy to help you with X" |
| Be direct | Less formality needed |
| Reference shared experience | Common ground |
Asking Senior People
| Approach | Why It Works |
|---|
| Be very respectful of time | They're busy |
| Be extremely specific | No ambiguity |
| Show you've done homework | Respect their expertise |
| Make it easy to help | Reduce friction |
| Reference their work | Show genuine interest |
Asking Strangers (Cold Asks)
| Approach | Why It Works |
|---|
| Establish credibility quickly | Why should they care |
| Explain why them specifically | Not random |
| Start very small | Lower the barrier |
| Provide maximum context | They don't know you |
| Make it easy to say no | No obligation |
Asking for Introductions
The Double Opt-In
| Step | Action |
|---|
| 1 | Ask your contact if they'd be comfortable making intro |
| 2 | Provide context for why the intro would be valuable |
| 3 | Make it easy by drafting the intro email |
| 4 | Let them check with the other person first |
| 5 | Introduction only happens if both agree |
Introduction Request Template
Hi [Connector],
I noticed you're connected to [Target Name] at [Company].
I'm [brief relevant background] and I'm interested in
[specific reason - learning about X, exploring opportunity at Y].
Would you be comfortable introducing us? I'd love to
learn about [specific topic] from their perspective.
Happy to draft an intro email if that would be helpful.
And totally understand if you'd rather not - no pressure.
Thanks for considering it,
[Your name]
Making Their Job Easy
| Help You Can Provide | Benefit |
|---|
| Draft the intro email | Saves them time |
| Explain mutual value | Easier to pitch |
| Be specific about topic | Clearer introduction |
| Offer to reach out directly | Alternative if they prefer |
| Express clear gratitude | Makes them feel good |
Asking for References and Recommendations
Setting Up the Ask
| Preparation | Purpose |
|---|
| Ask in advance | Give them time |
| Provide context | What it's for |
| Share relevant info | Remind them of your work |
| Make it specific | What you'd like highlighted |
| Give an out | Only if they can speak positively |
Reference Request Template:
Hi [Name],
I'm applying for [position/program] and need to provide
references. Given our work together on [project/context],
would you be comfortable serving as a reference?
[Brief context on the opportunity]
If you agree, they may ask about [topics]. I'd be happy
to provide any additional context that would be helpful.
Only say yes if you can speak positively about my work.
Totally understand if this isn't the right fit.
Thanks for considering,
[Your name]
After They Help
The Importance of Follow-Through
| Action | Impact |
|---|
| Thank immediately | Basic gratitude |
| Update on outcome | Shows their help mattered |
| Thank publicly when appropriate | Recognition |
| Find ways to reciprocate | Build ongoing relationship |
| Remember who helped | Never forget |
Thank You Best Practices
| Do | Don't |
|---|
| Be specific about what helped | Generic "thanks for everything" |
| Explain the impact | Leave them wondering if it helped |
| Thank promptly | Wait too long |
| Update them on outcomes | Disappear after getting help |
| Look for ways to reciprocate | Take without giving |
Thank You Template:
Hi [Name],
Thank you so much for [specific help]. It made a real
difference because [specific impact].
[Update on outcome - what happened, what you learned]
I really appreciate you taking the time. If there's
ever anything I can do to help you, please don't
hesitate to ask.
Gratefully,
[Your name]
Handling Rejection
When They Say No
| Response | Action |
|---|
| Direct no | "Completely understand. Thanks for considering." |
| Too busy now | "No problem. May I check back in a few months?" |
| Wrong person | "Thanks for letting me know. Any suggestions for who might help?" |
| Unclear reasons | Accept gracefully, don't push |
Moving Forward After No
| Mindset Shift | Explanation |
|---|
| No is information | Not personal rejection |
| Try someone else | Other paths exist |
| Reflect on the ask | Could you have asked better? |
| Maintain relationship | Don't let no damage connection |
| Ask again later | Circumstances change |
Common Asking Mistakes
| Mistake | Why It Fails | Better Approach |
|---|
| Asking too soon | No relationship capital | Build connection first |
| Being too vague | They can't help effectively | Be specific |
| Asking for too much | Overwhelming | Start small |
| Not doing homework | Wastes their time | Research first |
| No easy out | Feels pressured | Always offer escape |
| Not following up | Appears ungrateful | Thank and update |
| Asking without giving | Transactional | Give first |
| Over-apologizing | Undermines request | Ask confidently |
Key Takeaways
- Asking is a strength - Smart people leverage their networks
- Give before you ask - Build relationship capital first
- Be specific - Vague asks get vague (or no) responses
- Respect their time - Make it easy to say yes or no
- Provide an easy out - No pressure reduces friction
- Do your homework - Show you've tried before asking
- Match ask to relationship - Big asks need strong relationships
- Make their job easy - Provide context and materials
- Follow up with gratitude - Thank them and update on outcomes
- Handle rejection gracefully - No is information, not personal