Do you ask these bad questions?

Did you know that people can read your mind just based on the questions you ask?

Anyone who’s part of the Pinoy500 insider list knows that in the first email they get from me, I ask them to submit questions. Here’s what I say:

“If you could spend 30 minutes over coffee with me, talking about your freelancing career, what are the top 2 questions you would ask me?”

Why do I encourage readers to ask questions? Why not just go straight to giving them tips about freelancing?

First, before I give any tips, I want to know what you need from me. Second, it helps me read your mind better so that I can figure out the mindset and worldview you are coming from.

See, a person’s questions reveal more about their mindset, barriers, and personality more than statements do. This is because it’s easy to lie or change your image using statements. It’s difficult to lie when you’re asking a question.

Let me illustrate by deconstructing a few common questions and uncovering the hidden assumptions lurking beneath.

Image Credit: JD Hancock

“What is your recipe/strategy/tip for success?”

Hidden Assumptions: This tells me that the person asking this very generic question thinks that success looks the same for everyone. It doesn’t. I know some people already feel happy and successful getting paid $5 per article for SEO articles, while for other freelance writers that scenario sounds like a nightmare.

In my experience, people ask this question for either of the following reasons a) they don’t know enough about the field to ask better questions or b) they assume that the person they’re asking can easily outline the steps to success.

Also, most successful people probably don’t understand why they are successful, so this question is very hard for them to answer tactically. Try asking a successful person this question. Most likely they’ll give you generic answers like “disiplina” or “focus” or “passion” or “lakas ng loob”. Does that tell you what you should do next to be successful?

Better Questions to Ask:

  • “What do most beginners/newbies get/do wrong?” - I asked this question in a gardening forum online, when I was learning how to improve my gardening skills. The answers saved my garden, which was already suffering from my stupid “black thumb” - the opposite of green thumb, I suppose. (Most common answers: overwatering plants and planting things too close together.)
  • “What’s the #1 challenge/problem that you didn’t expect when you got started?” This tells you exactly what to avoid or be worried about. Many new freelancers are worried about the wrong things - business cards, where to look for jobs, how to accept payment - and this makes them blind to the more immediate issues they have to address (what skills/services to offer, how to talk to a client professionally).
  • “When did you know you finally ‘made it’? What were the concrete signs?” Follow this up with “How did you achieve that?” for each concrete sign the interviewee mentions. Rather than vaguely asking for “success tips”, you are asking the interviewee to define success into CONCRETE examples. For example, rather than answer “Focus led me to my success”, your interviewee can answer “I knew I was successful when I finally earned enough to quit my full-time job.” Then you can ask them how they got to that point. That stuff is easier to measure and analyze, unlike things like passion and focus.

“How can freelancers ensure a steady income or survive from one month to the next? Should they have a quota of jobs?”

Hidden Assumptions: Someone asked me this during an interview. Notice that the question is very leading, “Should they have a quota of jobs?” This tells me that the person asking this thinks that more jobs = more money. And that’s just not true. A freelancer with one $50/hour job can easily make more than another freelancer with three $2/hour jobs.

Plus, the person asking this also equates steady income with survival. Getting $100/month is steady income, but is it enough to survive on if you’re the sole breadwinner of a 5-person family? What this person is really asking is “How do I make sure that my freelancing income covers my living expenses?” Notice how different the answers will be:

“How can freelancers ensure a steady income or survive from one month to the next? Should they have a quota of jobs?” Yes. You should always have more than one client working with you and paying you regularly.


“How do I make sure that my freelancing income covers my living expenses?” First, you have to know what your living expenses are. Compare that with you are earning per hour or per output (like an article or a website project). This will tell you how many hours you have to work or how many articles you have to write or how many websites you have to design each month to make ends meet.

Which one is better? The answer that’s just either a Yes or No, or concrete steps that are informative?

Better Questions to Ask:

  • “How do I make sure that my freelancing income covers my living expenses?” We’ve already covered why this works.
  • “Which decisions had the highest returns for your freelancing business? Why?” True, this is a completely different question, but since you’re asking about money, it’s best to learn which decisions or actions will lead to maximizing your income. This also doesn’t box in your interviewee into thinking about just one thing.

“Does anyone know of any gigs/jobs out there?”

Hidden Assumptions: I found this question in a Facebook group. The fact that this person is bringing up age requirements tells me that in his or her mind, age is a factor in hiring. Unless you’re in an industry where your appearance is important (acting, modeling, etc.), it’s very very rare that age in itself matters. If it’s a barrier, it’s likely that it’s a barrier in your mind first. Most of the prominent social media and marketing professionals out there are at least 40 years old.

Better Questions to Ask:

  • “I’m a freelance ________ looking for work. I specialize in ___________. Do you know how someone with my expertise can find more work quickly?” Let others know what your forte is. Otherwise you’ll get generic tips and are losing the opportunity to connect with other professionals who are in the same boat. The asker should’ve been more specific about the type of writing he/she does.
  • “I’m a freelance ____________ and I think that age/gender/experience/nationality is a barrier for me to get jobs. Do you know of any examples who are ___ like me and still find work in this industry?” If you think that something is holding you back from getting a job, the best way to destroy that barrier is to find people like you who have “made it”. He/she could’ve said “I’m a freelance writer and I think being 55 years old prevents me from getting jobs. Do you know of any other freelance writers who are 50+? If so, where/how do they get work without age being a barrier?”

“I want to become a _________. How do I start?”

Hidden Assumptions: What this question tells me is that the person hasn’t done any work beforehand to figure out how to start. My impression is that they just thought “Uy, ok ata maging web developer” and just assumed that it was the right path for them, without figuring out what it means to be a web developer.

Also, here’s a bonus assumption: the person is assuming that skilled web developers will actually take the time to PM him. If you’re the one asking for free advice, MAKE IT EASY for the person answering you. Maybe someone did PM him. But he would be getting better and more responses if he just asked for replies in the comments or Googled for web developers and emailed them directly.

Better Questions to Ask:

  • “I’ve tried __________ and __________. Here’s what happened: _________. What am I doing wrong?” In the case of our aspiring web developer, he or she can get better answers by framing it this way: “I want to become a web developer. I’ve tried reading programming books and looking up videos online. Here’s what happened: It was very hard for me to understand the lessons. I just don’t get any of it. What am I doing wrong?”
  • “I’m interested in becoming a ______________. My impression is that this job involves ________________. Is my impression right? How does it compare to your actual work?” A common issue with new freelancers is a mismatch of their expectations with reality. For example, a lot of people claim they want to be freelance writers. But what they really want is to be paid to write about their thoughts, feelings, and experiences. So when they find out - the hard way - that freelance writing requires more skills and business savvy, they easily give up.
  • “I’m interested in becoming a ___________. My current skills are __________________. I’ve done ___________________. Given my background and experience, what would be the best next step for me?” You’d be amazed at how many times people ask me “I want to be a freelancer. How do I start?” WITHOUT telling me what their background is. How should I know how you can start? I don’t know what your skills are!

Also, notice how these better questions tend to elaborate what you’ve already done, studied, or tried. This is CRUCIAL when asking for advice, because it tells the person you’re asking that you take action and any time they spend on you will not be wasted.

How to Ask Better Questions

We’re lucky that the internet allows us to connect with other professionals from all over the world. This makes it easier to find opportunities, mentors, and new colleagues.

BUT it would be a waste of our time and effort if we don’t ask them good questions.

So how do you ask good questions?

First, let go of all assumptions. Don’t try to predict what the answer will be about. You’ll get more interesting and more specific answers that way.

Then, be specific about your endgame. Why are you asking your question in the first place? Do you need guidance? Do you need to achieve a very specific goal? Or are you just looking to confirm what you already believe/know? Understanding why you’re asking the question can help you phrase it better so that you can get the answers you want.

The next time you try to ask a question, write the question out and think:

  • What assumptions are hidden in this question?
  • Why am I asking this? What do I want to get out of it?
  • If I try to answer this question. What would my answer be like?

Being more reflective about the questions we ask helps us get better answers, and may even improve the response rate we get. Go ahead and try it. Try copying and pasting any of the “Better Questions” examples above. Post it on a forum, group, or email it to your mentors. See what happens

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3 thoughts on “Do you ask these bad questions?

  1. Stef Gonzaga @ The Freelance Pinoy

    Each of your points hit the spot, Celine. I especially agree with you about how people who ask for success tips seem to think that any given answer is a one-size-fits-all solution. Hardly. It really depends on his or her resolve, methodology, and how s/he perceives or equates success.

    The common denominators that I see in those generic questions is that these are people who 1) have not done their homework/research/any work at all to answer their own questions, and 2) who are hesitant/unsure/cautious and would like to hear from others first. But just how will these seep into your experience if you haven’t gone out into the wild and given it a try?

    You can have mentors and all these series of tips, but the best way to see if they work is to go out there and execute these ideas.

  2. Charley

    Hi Celine and Stef,

    I’m guessing this post is in line with the Live Q&A on Dec 7?
    Hehe.. naisip k lng parang connected sya so I read this post before replying to your email about possible topics to be discussed in the Q&A.

    I totally agree with all the points stated here.. it’s annoying when I see people asking for jobs in different social media groups without giving readers a bit of background of their skills.

    Admittedly, I sometimes ask questions like this until now especially if I’m not that familiar about a subject. But sometimes my forever inquisitive attitude gets the best of me so my questions tend to be very specific and detailed… It could be annoying (or so some of my friends say) . I guess my question is- Where do you draw the line? I have a lot of questions swirling in my head but then, I don’t want to offend people or make them feel that I’m digging in too deep into their “trade secrets” or professional lives. I’m not afraid of asking the wrong questions, but I don’t want to offend my mentors either.

    1. Celine ( Post author

      Hi Charley!

      Actually it’s a coincidence I wrote this a while back, and it was the most “complete” among my drafts when I had to publish a new post, so I just went with it.

      To answer your question:

      “Where do you draw the line? I have a lot of questions swirling in my head but then, I don’t want to offend people or make them feel that I’m digging in too deep into their “trade secrets” or professional lives. I’m not afraid of asking the wrong questions, but I don’t want to offend my mentors either.”

      Personally, as someone who receives dozens of questions via email or Facebook each week, I draw the line if the person wants to be spoonfed. I’ve been doing enough of this that I can tell early on if the asker is some kind of flake who just wants to leech information or if he/she is someone who actually deserves the time and attention I put into answering them.

      My experience so far:

      - Flakes are unclear about what exactly they want (their endgame) AND when you push them to be clear they will not take even a few minutes to sit down and really think about the specifics of what they want. They’ll ignore it when I ask for specifics and will keep prodding for tips/answers.

      - Awesome people (let’s call them that because it’s true) might not always be clear about what they want, but when I ask them to get specific about it their attitude is VERY DIFFERENT (“Oh wow, I’ve never thought about that before. Let me think about this more clearly and I’ll get back to you.” And almost always they do get back to me with awesome answers.)

      - Flakes don’t like answering questions. So one of the first things I do when I get an email asking for help is to ask the other person questions. If they ignore my questions and keep asking more questions, it’s clear to me that the Flake is turning into a Leech.

      - Awesome people love questions. The end.

      - Flakes don’t say thank you.

      - Awesome people say thank you and you can tell they mean it.

      There are some people out there who might feel like you’re asking for their deepest secrets, but the way to compensate for that is to give FIRST and ask questions later. (Show them links they might appreciate, give them - mostly positive - feedback on their work, anything you sincerely think they’d like as long as you’re being genuine about it.)

      I’m not worried about anyone “stealing” anything from me so that’s not something I think about, but busier, more professional people than myself might care about that. As long as you give them something first, and you’re sincere about it, they’d be more than happy to answer your questions.

      Especially if they’re so sick of the bad questions they keep getting.

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