Asking for Help Well
Ask for advice, not answers — the counterintuitive skill that separates who rises from who stalls.
- Difficulty
- Easy
- Time to result
- ~ongoing to results
- Steps
- 4
- Confidence
- 90%
A reframe and method for asking for help as a career and job-search superpower. Asking well is a giving activity that invests others in your success and builds independence; asking poorly (demanding others do your work, or asking people you haven't earned access to) backfires. The method: do your homework, be open and vulnerable, ask people with relevant expertise for their perspective ('how would you approach this if you were in my shoes?'), and be honest that you're asking a favor. Terry extends it to 'dead or distant mentors' you study deeply and to structured peer-coaching calls.
Origin
Phil Terry learned it from his mother and teaches it across his product/CEO councils. He cites data from his book: 85% of people who reached senior roles credit asking for help, while 85% of junior people are afraid to ask because they think it signals weakness. Examples span Marissa Mayer, Brad Smith (Intuit), Ken Chenault (American Express), Warren Buffett, and Sundar Pichai's early Google mentoring of Bradley Horowitz.
Core principles
- 01Asking for help is a sign of confidence, not weakness — it requires and strengthens confidence
- 02It's a giving activity, not a taking one — done well, people feel honored and invested
- 03It makes you more independent, accountable, and responsible, not less
- 04It improves your reputation rather than harming it
- 05Do your homework first and ask for advice/perspective, not for someone to do the work
- 06Be honest about the favor; use emotional intelligence to choose whom to ask
How to run it
- 1
Do your homework before you ask
Come prepared with your own thinking so the ask is for perspective and advice, not for the other person to solve it for you. This is what makes people want to help even more.
Pro tip Frame it as 'I'd love your perspective and thoughts — how would you approach this?' rather than 'can you fix/get me this?'
Watch out Asking a stranger to do something for you (e.g. 'introduce me to Marissa to buy my software') without earned relationship is 'asking poorly' and gets ignored.
- 2
Choose whom to ask with emotional intelligence
Pick people with relevant expertise whom you can trust, and read the relationship and your own emotions before being open and vulnerable. Practice asking in the safe 'council format' first.
Pro tip Do a 'gratitude house' exercise — list everyone who helped you get here — which both builds confidence and surfaces people worth talking to.
Watch out Don't get open and vulnerable with someone your emotions say you can't trust; some people will take advantage.
- 3
Ask honestly and openly
Be transparent that you're asking a favor: 'I have a favor to ask — would you be willing to do this? You can say yes or no.' Never disguise a request as if you're doing them the favor.
Pro tip Most people say yes to an honest, low-pressure favor ask; hidden agendas (fake introductions, disguised asks) erode trust.
Watch out Cold intros made without asking, or asks dressed up as favors to you, are dishonest and rarely welcomed.
- 4
Use structured peer-coaching and 'dead or distant' mentors
Run peer-coaching calls (e.g. a 'first 90 days' call with people in the target role, or a 'career evolution' call with people one level up) and adopt dead-or-distant mentors — figures like Warren Buffett or Steve Jobs whom you study deeply, not just admire.
Pro tip Studying a mentor means real study — e.g. Jobs's 1997 'start with the customer, not the technology' moment — so it can inform your actual decisions.
Watch out Being a fan or reading one biography isn't mentorship; shallow admiration won't inform your decisions.
In the wild
Even as a Google leader at a public company, Mayer told the council she was developing a new product to present to the board and wanted their feedback first. Members were 'blown away' and happy to help.
→ Demonstrated that senior people asking for help makes others feel given to, not that they look weak.
Newly-joined, intimidated director Bradley Horowitz sensed Sundar Pichai was approachable and low-guile, so he asked open, vulnerable questions after meetings — starting with 'is this meeting intense or is it just me?' and building to a candid question about Pichai's remit.
→ Built trust that eased his entry into Google and contributed to reaching the VP of product role.
As a GM at Intuit, Brad Smith ran a project poorly and lost $300M. Asked his lesson, he said he'd been pigheaded and hadn't asked for help. He later became CEO, joined a council, asked for help, and the stock rose sevenfold in his tenure.
→ Internalizing the ask-for-help lesson preceded his rise to CEO.
Common mistakes
Asking someone to do the work for you
Requesting favors from people you haven't earned access to, with no homework done, is the 'dumbest' kind of ask and gets ignored.
Believing it signals weakness
85% of junior people avoid asking because they fear looking weak — the exact belief that keeps them junior.
Disguising the ask
Pretending a favor for you is a favor for them (e.g. dishonest cold intros) breaks trust; honesty about what you're asking is essential.
Is it for you?
Best for
Anyone — job seeker or in-role professional — who avoids asking for help and wants to build the relationships and perspective that drive advancement
Not ideal for
Situations where you haven't done your own homework, or where your read on the person says the relationship isn't safe for vulnerability
From the transcript
“asking for help is not a sign of weakness it's a sign of confidence it both requires confidence and strengthens it”
“it's not a taking activity it's a giving activity if you do it well you're actually being giving to the people you ask”
“85% of the people get to a senior role credit asking for help”
“85% of the people in a junior role say they're afraid to ask her out because they think it's a sign of weakness”
“I really want you to be honest with people about what you're asking I never want you to hide”
“you can get what I call a dead or distant Mentor like Warren Buffett is my mentor he just doesn't know it”
“when people get a new job by the way I tell them do a first 90 days pure coaching call”
From the episode
Land your dream job in today’s market: negotiation tactics, job search councils, and more
Phyl Terry (Author, “Never Search Alone”)