The Ask Toolkit
If you don't ask the answer's no — but ask in a way that never risks the relationship.
- Difficulty
- Moderate
- Time to result
- ~weeks to results
- Steps
- 4
- Confidence
- 90%
The Ask Toolkit is Lederman's set of request formats, all designed so the ask increases your odds of a yes while protecting the relationship. The opt-out ask hands the person an easy reason to say no ('if your company allows it'). The make-it-easy family lowers the bar through alternate asks (two equal options), shrinking asks (progressively smaller requests), and convenient asks (you jump through the hoops). The WIIFT ask leads with a genuine benefit to them — never a fake one. The non-ask shares your goal with energy and passion, then invites ideas without requesting anything specific, tapping the other person's generous spirit.
Origin
Lederman teaches the toolkit as the action half of having a clear vision, drilling 'if you don't ask the answer's no' into her own kids and into coaching clients, and evolving her favorite from the opt-out ask to the non-ask over time.
Core principles
- 01If you don't ask the answer is no; asking immediately increases your odds.
- 02The goal is to protect the relationship first, not just to get the yes.
- 03Make saying no as easy as saying yes so the person never has to avoid you.
- 04Different situations call for different ask formats.
How to run it
- 1
Opt-out ask
Attach an easy out to the request — 'if your company allows it' or 'if you have time' — so the person can decline without discomfort.
Pro tip An easy no keeps the person from feeling they must avoid you and preserves the relationship.
- 2
Make-it-easy asks
Lower the bar via the alternate ask (two equal-value options), the shrinking ask (progressively smaller requests until they can say yes), and the convenient ask (you do the work — come to their office, pick their coffee shop).
Pro tip For someone busier than you, bring the times and options yourself — never send a Calendly link or defer to your assistant.
- 3
WIIFT ask (what's in it for them)
Lead with a real benefit to the other person or their organization to create an impetus for action, and combine it with deference and options.
Pro tip Anchor it in something they've said they value, like mentorship, so it's a way for them to act on their own values.
Watch out Don't pretend there's a benefit when there isn't — a fake 'mutually beneficial' pitch reads as empty.
- 4
Non-ask
Share your goal or vision with genuine energy and passion without making a specific request, then follow with 'any advice or ideas for me?' to tap their desire to be helpful.
Pro tip Enthusiasm is contagious — people volunteer help and connections when they catch your excitement.
In the wild
While writing her book, Lederman told a longtime CEO mentor what she was working on without asking for anything. He volunteered 'well, here's an idea' and suggested adding a millennial angle.
→ That unsolicited idea led to her book featuring 30 experts giving readers additional advice and guidance.
Lederman contrasts the empty 'I think it'd be mutually beneficial for us to connect' with a student telling a CEO 'I know you're really keen on mentorship and I'm trying to learn this.'
→ The value-anchored, deferential ask gives the CEO a real reason to engage rather than a hollow claim.
Common mistakes
Cornering the person with no opt-out
Without an easy out, a person forced to say no feels awkward and may avoid you afterward, putting the relationship at risk.
Faking the benefit in a WIIFT ask
Claiming something is mutually beneficial when it clearly isn't destroys credibility; if there's no benefit to them, don't pretend there is.
Making a busy person do the logistics
Sending a Calendly link or deferring to your assistant when asking someone busier than you shifts the effort onto them and lowers your odds.
Is it for you?
Best for
Networkers, job-seekers, salespeople and anyone who needs to make requests without damaging relationships.
Not ideal for
Situations requiring a blunt, take-it-or-leave-it demand where relationship preservation is irrelevant.
From the transcript
“if you don't ask the answers no if you ask you immediately increase your odds”
“you want to make it as easy for them to say no as it is for them to say yes”
“the non-ask is when you're not asking for anything specific instead you're sharing a little bit about your goal or your vision”
From the episode
Michelle Tillis Lederman: Creating Connection, How to Build Strong Relationships in the Networking Age
Michelle Tillis Lederman