How to Ask for Advice (and Make the Most of It)

Reading Time: 19 minutes

A few months ago, a random listener of the show DMed me on Instagram asking for advice.

“I need some guidance on following my dream,” he wrote.

“Sure,” I replied as I watched a little Netflix (and felt guilty about taking time for myself, but that’s another story). In my experience, Instagram DMs represent the bottom one percent of advice inquiries, but I was intrigued and happy to offer someone a few minutes.

Our conversation went something like this (almost verbatim):

Listener: I want to start a clothing line.

Me: Okay, cool. Why?

Listener: Because I see a lot of wealthy people with clothing lines and the margins are really good. Plus where I’m working now sucks and I need to get out.

Me: In my experience, to really succeed, you need to be pulled toward an idea, not running away from something. Do you work in fashion now?

Listener: No. I want to work in apparel. It’s my dream.

Me: My advice would be to work in the industry for a while, learn how the apparel business operates, then use that experience to decide if you really love it and set yourself up to succeed. I’d start in supply chain if I were you — that’s the nuts and bolts.

Listener: No, I wanna design things.

Me: Great. But I wouldn’t start there. Operations is where the problems arise. That’s the real business.

I never got a reply to that last message. Then, three months later, I came across a post from this guy, so I DMed him, curious to see how things were going.

Me: Hey, how’s it going with the line?

Listener: I don’t even fucking listen to you anymore.

Me: Oh, okay. What happened?

Listener: You told me to give up on my dream.

Me (eyes rolling): I did?

Listener: You told me to get a job. I already have a fucking job. I want to do my dream and you told me to give up on it.

Me: Oh, well. No good deed goes unpunished. Best of luck with everything. 🙂

And that was the end of that conversation.

Later that night, a little miffed to be blamed for something I didn’t do, by someone who explicitly asked for my opinion, I suddenly realized that I was the dumbass. This guy didn’t want advice. He wanted encouragement. He wanted permission. Even if it was a terrible idea. Even if his starry-eyed dream-chasing lens on the world would lead him to almost certain failure.

But I’m not in that business. That blind you-can-do-anything-as-long-as-you-really-want-it encouragement, that follow-your-dreams-no-matter-what type stuff stuff — that’s the woo-woo self-help garbage that ends up making you feel terrible.

Me, I’m more practical. I’m direct. I’ll try my best to teach you to be successful at something using the principles that I know work. But that approach comes with some hard truths. Like the fact that you don’t get to kick off your fashion career day one with a CFDA award. Even Kanye took years to build Yeezy, and he had a running start, to say the least.

So how do you start?

You start by becoming a student. By forming a strong opinion. By learning the ropes. By building meaningful relationships. By studying your passion with a passion.

You start by putting your development ahead of your dreams.

You start by accepting that dreams only come true when you develop the right way.

You start by asking for advice correctly from people who are in a position to offer it, and then by actually listening. Which, as we’ll see in a moment, is different from following it.

The Tensions of Good Advice

As you can imagine, I get asked for advice a lot. I enjoy giving it. I’ve made it my career — from providing legal advice (well, kinda) to sharing dating advice to running Feedback Friday on the podcast.

But if I’ve learned one thing from giving so much advice over the years, it’s that a lot of people don’t actually want advice. In many cases, it’s precisely the people asking for advice who don’t want it at all!

Oftentimes, their questions are phrased as advice-seeking. “What would you do if you worked in A but really wanted to work in B?” they might ask. But what they really mean is, “Can you please tell me it’s okay to go after B?” Or they might ask, “Can you confirm that I wasn’t an idiot to rush into B just because I didn’t like A?” But what they really mean is, “Please reassure me that I haven’t made a colossal mistake.” So this can be a tricky dynamic to navigate.

And even if people really are asking for advice, they often don’t want to follow it. They might just want to hear another perspective. Or check the box on their research. Or find out if they’re off-base. But once they receive a piece of advice they don’t like, they reject it — either by dismissing it outright, refusing to internalize it, or failing to execute on the advice in the right way.

Now, to be fair, I made all these same mistakes when I was younger. (And I probably still do from time to time, which is why I’m obsessed with this topic.) But the costs of handling advice poorly today have increased exponentially. If you acted a fool 30 years ago, only a few people knew about it. Now if you pull some bullshit, the people involved text about it, tweet about it, and decide what to make of it in a super connected world. Someone like me uses your story in an article, and now everyone knows that your narcissistic hangups are getting in the way of your growth. (Of course, I’d never use someone’s real name, but you know what I mean.)

All of this has taught me a lot about advice — how to give it and how to get it — which are really two sides of the same coin. The way you ask for advice determines the type of advice you get. And the type of advice you get in turn shapes the way you receive it. So to make the most of it, we need to understand a few key principles about soliciting advice.

Starting with the idea that you need to…

Know what you need and ask for it clearly.

The guy who wanted to chase his fashion dream committed the first cardinal sin of advice-seeking: asking for overly general advice.

Any inquiry that begins with “I need help chasing my dream,” “I want to start a new chapter but need some guidance,” or any variation on this vague, global, template-y request is problematic. It usually means that the person hasn’t done enough internal work to seek advice, doesn’t have a clear grasp on their own needs or external reality, and doesn’t respect the advice-giver’s time.

To get meaningful advice, you need to be specific, intentional, and explicit in what you need.

That usually means zeroing on very specific and practical questions. “If I pursue an MBA, do you think I’d be in a better position to rise up in the supply chain world?” “When you edited your own podcast, was that time well spent, or do you think I should outsource that work?” “I’m feeling apprehensive about leaving my job to pursue a new one. Should I listen to that feeling, or should I ignore it and just take a chance?” These are all grounded, actionable questions that will generate much more meaningful guidance.

In some cases, of course, you might not know the exact question to ask. Sometimes, it’s when we’re lost that we need advice the most. But you can still be intentional, even when you’re confused. “I’m feeling a little lost about what I should be doing and asking to make the right decision. If you were me, what would you be asking? What options would you be exploring?” Even that question is more specific than, “Ahhh! Help! I need advice navigating my fEeLiNgS!” Which, sadly, is a question I get all too often.

Whatever the particulars of the situation, this kind of object-oriented question will always generate more meaningful advice. Of course, to ask good questions, you’d have to have done some work on your own — which is exactly the point.

Most people seek advice when they don’t know where to go. The smartest people seek advice when they’ve gone as far as they can.

Only then does another person’s advice really become valuable. Because then it helps you make sense of the work you’ve already done, and points you in the right direction to keep building on it.

So how do you go as far as you can on your own? In short, by doing your homework. Which usually means pursuing a few key activities on your own.

First, Google the question, challenge, or topic in question. Read every single relevant article, interview, tutorial and course on the question you have. (And I don’t just mean the first page of search results. I’m talking a deep Goog — 10, 12, 20 pages deep if necessary.) 90 percent of questions can (and therefore should) be answered this way. If you find a couple of expert courses or e-books along the way, check them out — it’s usually worth buying them if they’re good. If they’re bad, ask for a refund (you’ll often get it). Along the way, you’ll probably come across books, lectures, and other sources that will be helpful, and you should explore those too, using the library, Amazon, Google Books, and document databases.

When you’re looking for advice, it’s your job to become a student first, to educate yourself on the world you’re exploring before you turn to the people operating within it. Then, and only then, do you ask an expert for advice.

Doing your homework will transform the advice you receive.

For one thing, you’ll communicate that you’re not wasting the advice-giver’s time by asking questions that you could have answered on your own. (You’d be amazed how many people ask me which hosting site to use or which equipment to check out.) You’ll come across as proactive, responsible, well-informed, and respectful, which will attract people who can offer advice in the same spirit.

At the same time, you’ll signal that you don’t have your head so far up your own butt that you won’t listen to the person’s advice. You communicate openness, curiosity, lack of ego, initiative. You show that you aren’t too entitled or lazy to make good use of the advice you’re seeking. You show that you are someone who takes advice seriously, and therefore wants to hear the truth.

Finally — and most important — doing your homework will lead you to the right questions to ask. You can’t get specific in your request until you’ve identified the gaps in your knowledge. When people ask overly vague questions, like the fashion guy, it’s not just because they have a faulty mindset. It’s because they haven’t done the legwork that would reveal the gaps in their knowledge, which they could then fill in with good advice.

Once you do your homework, then you’ll be in a position to actually ask for meaningful advice — which all depends on asking for it in the right way.

Formulate a great question.

A great question embodies all the work we’ve talked about so far, then builds on it by posing a meaningful, specific, open-ended inquiry.

Consider, for example, the difference between these two advice requests.

Advice request #1: “I need advice on launching a podcast. How do you book good guests? How do you keep people coming back to listen to more?”

Advice request #2: “I’ve spent the last two months learning everything I can about podcasting, from marketing to audio engineering to interview prep. I’ve even recorded some pilot episodes and gotten feedback from friends and colleagues. I now understand that I need to work on my interview questions and my outreach emails, so my first question is…”

These two requests represent opposite ends of the advice-seeking spectrum.

The first is a recipe for poor advice at best and a non-starter at worst. It immediately signals ignorance, amateurism and a lack of respect. It betrays a profound lack of research and self-awareness, and puts the advice-giver in the uncomfortable position of either being unhelpful or rude. It’s the product of not taking the gift of advice seriously.

The second question is a launching pad for a conversation — a conversation that will, in all likelihood, answer the person’s specific questions and open up into additional territory, such as the art of interviewing and the audience relationship. As a bonus, it will also create a meaningful relationship with the other person — which is why asking for advice is also one of the most powerful ways to network.

(That relationship, by the way, can continue to develop as you implement the advice over time. One of the greatest networking tools I’ve learned is to share the impact of the advice I put into practice. Weeks, months, or even years later, I’ll reach out to the people who counseled me and tell them what happened as a result. I’ll share my appreciation for their wisdom, they’ll know that it was put to good use, the good advice will keep flowing, and our relationship will grow even deeper. This is how you can generate even more dividends from the advice you get — and use the advice as an organic way to nurture a meaningful connection.)

A great question has a few key elements.

Generally speaking, a great question is:

• Specific (about the answer it’s designed to elicit, which means that it often includes a brief summary of or quick nod to the homework you’ve done up till now)
• Goal-oriented and productive (about the action it’s designed to inform, which means that it’s not just aspirational or overly broad, but practical in its purpose)
• Open-ended (in that the question doesn’t just lead to yes/no responses or purely tactical advice, but also opens up an opportunity to have a conversation with the person beyond the immediate request)
• Well-articulated (in style, diction, and grammar)
• Kind, respectful, open, confident, and passionate (in tone, spirit, and overall handling of the question and the advice — not just in the initial request by throughout the exchange)

If you articulate a question that hits all of the above elements, then you’ll maximize the chances of receiving advice when you need it the most — and the odds that the advice you receive will be as meaningful as possible. Top experts can give bad advice when it’s poorly solicited, and mediocre practitioners can give great advice when it’s masterfully solicited. So much of advice comes down to the person asking for it — both in terms of how they pose the request, and what they do with the advice once they get it.

Which brings us to the next principle.

Don’t argue.

Amazingly, some advice-seekers will ask a very specific, well-articulated question — which is great — but don’t actually want to listen to the answer. I recently got one of these requests (again, surprise surprise, on Instagram), which I’ll share more or less verbatim with you here.

Listener: Hey Jordan. I’m going around to different people trying to promote my idea for an interview talk show where people share their core values with other people. Do you know any marketers or editors? If you could help me that would be great.

Jordan: Cool. What’s your budget for editing?

Listener: Great question. I’m not a rich man at all. I’m just trying to get some guidance and advice to start out.

(A-ha. Notice how the very specific question quickly devolved into the vague “I need advice, brah.” Feeling less generous than I was a few months ago with fashion guy, I didn’t respond, because this response wasn’t what I asked. A few days later, this person followed up with:)

Listener: If you can direct me to anyone you know…I can take any help I can get.

Me: What’s your budget for editing?

Listener: Can you help me?

Me: I’m trying. What are you looking for?

Listener: You already asked me that. I’m not sure if this is a bot or a person.

Me: I can assure you it’s not a bot. I’m getting the impression that you’re avoiding the question here, maybe because you haven’t done the homework to know what you really need right now. Podcasting is tough but very fun. I hope you enjoy it.

Listener: Okay but how do I get started? How do I get the right connects? The right target audience?

…and so on.

You can imagine how differently the conversation would have gone if this person had reached out with specific questions that they actually meant, and were willing to actually hear the answers. Instead, they did something even worse than fashion guy: They asked a decent question that was really just a Trojan horse for a bad one — and then doubled down on the overly vague request by asking for introductions that were completely unearned.

Asking for advice the right way is half the battle. The other half is being willing to listen to it.

Getting advice is a delicate process. Even when we ask for it — even when we crave it — it can still be intimidating, overwhelming, or confusing. Sometimes, it’s not what we want to hear. Oftentimes, it’s difficult to accept. That can make the best advice quite threatening to the ego, which is designed to push back in order to protect itself. That temptation is another major obstacle to capitalizing on good advice.

This might seem painfully obvious — after all, how many of us actually want to argue with advice that we explicitly asked for? — but it happens all the time. Worse, it happens in ways that often don’t sound like arguing. The mind is very clever at pushing back without seeming like it’s pushing back.

One common way to subtly argue with advice is to pose questions that chip away at it.

“But do you really think I’m not getting ahead because I’m not building relationships? I mean, isn’t the quality of my work more important than who I know?” These aren’t bad questions, of course. But you can see how someone could pose them in an effort to avoid accepting the reality that they need to become better at networking.

You see this type of resistance even with top performers. Many of them have great questions about the advice they receive, but end up using those questions to distance themselves from the feedback in question. In fact, top performers sometimes argue with advice the most, because they have a strong drive to protect their reputation and sense of self.

Another common way to argue with advice is to internally resist it.

This is also a difficult form of resistance to diagnose, because it’s completely silent. This type of arguing often takes the form of mental chatter while the advice is being given.

“My manager doesn’t know what he’s talking about. He’s not even giving me credit for leading that project last month! And I do take initiative; I’m the only one around here who’s looking for solutions! Do I really need to be taking advice from someone who doesn’t understand me?” This mental monologue acts as a bulwark against the advice, usually without the person consciously realizing it.

Later, this resistance gets even stronger when the person discusses the advice with another party. They might editorialize it into a story about how the manager is wrong and you are right, coloring the story and manipulating the facts. Meanwhile, the person is missing the precious opportunity to see if the advice is actually true before rejecting it out of hand.

The only way to avoid these forms of resistance is to consciously commit to opening yourself up to advice, fully and genuinely.

If someone gives you advice, accept it completely in the moment.

Accepting advice completely means cultivating the self-awareness, openness, and curiosity to tolerate a new perspective on your life. It means creating a space where that perspective, positive or negative, can exist without resistance or validation. It doesn’t mean that you have to agree with it, or that you have to put the advice into practice. It just means that in the moment you’re receiving the advice, you are allowing it to be without judgment.

Later on, you can decide whether you agree with the advice. You can accept the parts that work for you and set aside the parts that don’t. You can celebrate the advice that is dead-on and reject the advice that is misguided.

But before you do any of that, you have to make an agreement with yourself to listen first and judge later.

That’s the key. In the moment you’re receiving feedback, your job is simply to accept, listen, and understand. Later on, in an hour or a day or a week, your job is to question, assess, and decide whether you agree. Most people collapse these two stages, judging as they listen, which usually means not listening at all. In the process, they miss the real value of the advice, and remain stuck in their own concepts, needs, and defenses.

The ability to separate out these two steps has the potential to transform your life. And it’s an ongoing practice.

For most of us, processing advice in this way is not natural. We all have egos, narcissism, defenses, wounds. We all want to look good and feel secure. We’re hard-wired to reject experiences that threaten us, even in small ways. That’s why we need to constantly commit to inviting advice in before we evaluate it. I still struggle to do this, but now that I know how crucial it is, I consciously choose to approach feedback in that spirit. If I don’t, I know that my limited mind will try to defend itself, preventing me from accessing the advice I need to thrive.

Does this mean you can’t ask follow-up questions when you’re receiving advice? Does it mean that you have to remain absolutely silent when you hear feedback? Of course not. Asking the right questions is an important part of processing feedback.

But you have to cultivate enough self-awareness to know when asking questions is a way to understand advice and when it’s a way to subtly resist that advice. “So when you say that I’m not listening as well as I could be, do you mean that I should be taking people’s opinions more seriously, or focusing more in the moment?” is a question designed to understand a piece of advice better. “So when you say that I’m not listening as well as I could be, are you keeping in mind all those times I held Q&A sessions with my team?” is a question designed to challenge the advice and protect your sense of self. If you probe your response to advice, you’ll usually find when your questions are productive and when they’re actually defensive.

Agreeing not to argue signals that you take advice seriously.

Whenever I come across someone who resists my advice — especially if they explicitly asked for it — I learn a lot about their character. Resistance usually tells me that this is a person who doesn’t have enough self-awareness or curiosity to improve, who doesn’t want to do the work to get better, who is more concerned with appearance than with growth, and who doesn’t respect the value of advice. I have compassion for these people up to a point — like I said, it took me years to un-learn these instincts — but at the end of the day, I find it difficult to fully invest in people who resist the advice they clearly need to hear.

The key practice here is listening, plain and simple.

Listening is the necessary and powerful first step in processing any type of data. Listening means leading with curiosity, empathy, and a genuine desire to understand. It means wanting to hear potentially uncomfortable or surprising views, appreciating why the other person has arrived at that view, and identifying exactly what that view means. Then — and only then — are we in a position to ask ourselves whether we agree with the advice, and to arrive at the right answer.

This might sound tough, and it often is, especially if the advice is difficult to accept. But it’s actually liberating. It means that we don’t need to listen and judge at the same time. It means that all we have to do is take in feedback as an observer, so that later we can take it in as a participant. When we do, the advice becomes a lot more meaningful — and a lot easier to act upon.

Put the advice into practice.

Once you assess the advice you receive, then you’re in a position to act on it. Again, this might sound painfully obvious, but I’m constantly amazed by how many people solicit advice only to let it go to waste — by not understanding it, not processing it, or not taking it seriously. Advice is just words until the advice seeker finds a way to put it into action. If you don’t put it into action in some shape or form, you’ve missed something crucial.

Acting on advice means using it to decide the best course of action for yourself.

That doesn’t necessarily mean following the advice to a T, or even following it at all. It means considering the advice carefully, drawing your own conclusions from it, then factoring those conclusions into your decision, whatever your decision ultimately is.

Say you get a piece of advice to quit your corporate job, enroll in a culinary institute, and become a chef. If you agree with that advice, then putting in your two weeks’ notice at your bank and signing up for the Cordon Bleu would be an obvious way of honoring the advice.

If you disagree with the advice, on the other hand, then you might hold off on quitting, sign up for cooking classes at night, apprentice in a kitchen on weekends, and take some time to find out if you really love being a chef.

In both scenarios, you’ve acted on the advice — in one case, by following it literally; in the other case, by realizing that you only agree with part of it, and applying it in your own way.

You don’t have to follow advice to the letter to make the most of it. Some of the best advice I’ve ever received was advice I totally disagreed with. The value of the advice in those cases was in challenging my perspective, forcing me to revisit my assumptions, and considering the risks of my decision.

The value of advice doesn’t lie in whether it’s “right” or “wrong,” but in the way you process and act on it.

You can follow “good” advice into failure, and you can follow “bad” advice into success. At the end of the day, advice is just advice until you put it into action. Great counsel doesn’t guarantee great outcomes. Great execution leads to great outcomes — and that has little to do with the advice itself, and everything to do with the person who’s following it.

Another way to fail to make the most of advice is to anticipate the outcome before you even try.

This is almost always a form of avoidance, cleverly hidden behind reasonable objections.

I see this quite a bit with people who email me about our Six Minute Networking course. Many of them assume that the principles of the course won’t work before they even try it. “I don’t want to do Connect Four,” they’ll say about one of the main exercises, “because I don’t want to be texting people all day and booking coffee dates every weekend.” “Just wait,” I’ll say. “You’ll see that half the people you text will respond, and the rest won’t engage. Just try it and see what happens to your relationships.”

Without fail, everyone who goes ahead with the course emails me back and says, “Oh, my God, you were right. Sorry I put up such a fight.” They realize that their concerns never came to pass, and that their objections were really ways to avoid doing the work they knew they should have been doing.

Smart people are especially good at playing this kind of “what-if” game. Because they can think their way out of any situation, they have a tendency to spin up all kinds of implications. “If I apply for this job right now, then they might realize that I’m not as experienced.” “If I launch this company on my own, then I’ll ruin my chances of attracting a partner down the line.” “If I spend all my time building relationships, then I won’t have as much time to actually do my work.”

These implications — real or not — are virtually endless. They either keep us paralyzed or let us off the hook. That’s why people tend to invest so much in them — because they want to believe these problems will arise, or because deep down they don’t want to do the work.

That’s why acting on advice is so important. In some cases — like launching a company, getting engaged, moving countries, and so on — you do need to take the time (months or even years) to consider all the available advice, anticipate the risks and problems, and make a decision. In other cases — like signing up for a class, building a networking system, interviewing for a new job, and so on — you don’t need to anticipate every angle. You only need to listen and act on the advice in front of you.

When you do, you usually discover that the problems you think will exist don’t materialize at all. Instead, other problems crop up — but they’re rarely the problems you could have anticipated.

So what good does overthinking advice really do? When does overthinking advice go from responsible to avoidant?

The answer is when you catch yourself overthinking advice in order to avoid doing some hard work. That’s usually a dead giveaway. Processing advice is key, but only when it’s in service of actually acting on it. If your deliberation is moving you closer to the best decision, then it’s time well spent. If it’s moving you away from the best decision, or keeping you stuck in one place, then it’s time to stop thinking and choose a course of action — whatever action is most appropriate for you.

Ask (Correctly) and Ye Shall Receive

Asking for advice the right way is one of the most important skills we can master. It’s an asset that sharpens our instincts, exposes us to guidance, and brings us closer to our goals, our abilities, and our purpose. Soliciting it the right way — and then processing and putting it to good use — is the difference between ignorance and understanding, failure and success. So it’s no surprise that top performers take this skill very seriously.

But asking for advice isn’t just a skill in and of itself. It’s also at the heart of so many other skills, habits, and mindsets that elevate our lives and careers.

Asking for advice, for example, is one of the easiest ways to start a new relationship, especially if you’re looking for a mentor. Soliciting advice is also one of the most powerful ways to deepen a relationship, because it amplifies social capital in both directions, in the form of knowledge, trust, intimacy, and better decisions. (It’s also a form of value you can give and receive when you’re just starting out, which makes it carry even more of an impact.) Seeking out advice also serves as a powerful hedge against the downsides of following your gut, while helping you avoid the kind of self-help that doesn’t actually help at all. Of course, knowing how to ask for advice also makes you better at giving it — by understanding what it’s like to be on the other side of the conversation.

So knowing how to ask for, listen to, process, and apply advice is actually part of everything we do. Which is why we need to build this muscle over the course of our lives, by constantly embracing these skills, mindsets, and principles. Like most important qualities, this is an ongoing process. It depends on your willingness not just to put in the work, but to allow someone else’s work to fully reach you. That’s when you start getting the best kind of advice: the kind that you truly want, and that someone else truly wants to give.

[Featured image by Artem Maltsev]