How to Predict Job Interview Questions (And Answer Them), with Max Chan

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You don’t have to be nervous about interview questions if you know what to expect. But how can you predict what the hiring manager will ask? It’s simple, says Find Your Dream Job guest Max Chan. Most positions have common questions that are asked in every interview, so prepare for those ahead of time by studying the job ad. Then, have some general career success stories that you can pull out and tweak to answer any questions you don’t have an answer prepared for. 

About Our Guest:

Max Chan is a career coach, podcaster, and founder of  Chan With A Plan

Resources in This Episode:

Are you ready to stop searching for your dream job and start working it? Find out how Max can help you by visiting

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Find Your Dream Job, Episode 353:

How to Predict Job Interview Questions (And Answer Them), with Max Chan

Airdate: June 22, 2022

Mac Prichard:

This is Find Your Dream Job, the podcast that helps you get hired, have the career you want, and make a difference in life. 

I’m your host, Mac Prichard. I’m also the founder of Mac’s List. It’s a job board in the Pacific Northwest that helps you find a fulfilling career.

Every Wednesday, I talk to a different expert about the tools you need to get the work you want.

Find Your Dream Job is brought to you by TopResume.TopResume has helped more than 400,000 professionals land more interviews and get hired faster. 

Get a free review of your resume today. 

Go to 

Every job interview is different. 

However, you can also expect employers to ask many of the same questions. 

But which questions? 

Max Chan is here to talk about how to predict and answer job interview questions. 

He’s a career coach, podcaster, and founder of Chan With A Plan. 

Max helps frustrated professionals become more focused and confident in order to excel in their careers.

He joins us from Toronto, Canada. 

Well, let’s jump right into it, Max. How common is it for employers to ask many of the same job interview questions? 

Max Chan:

Yeah, so if you are applying for the same type of role, for example, a marketing manager, if you do a few interviews targeting that role, they tend to ask the same type of questions. For example, talk about a time you’ve managed multiple marketing campaigns. Tell me about a time that you had to manage client expectations. So, if you’re staying in the same type of role, their questions do tend to get repetitive. 

Mac Prichard:

And why do employers do that? Why do you see these patterns happen? 

Max Chan:

It’s based off the job ad, and what I mean by that is, when you apply for a marketing management position, the responsibilities tend to be the same, and they’re – the reason why it’s the same is that a marketing manager needs a specific skill set. So, for example, if they need someone to manage the marketing budget, as a marketing manager, you will be doing that responsibility regardless of what marketing manager job you’re gonna interview for. So, that’s why it gets repetitive because they’re looking for a specific skill set that a marketing manager generally needs. 

Mac Prichard:

How can knowing this pattern, knowing that you can expect questions based on these principles, help you as a candidate, Max before you walk into the interview room? 

Max Chan:

Yes, a common mistake that a lot of professionals make when it comes to an interview is they always complain that they don’t know what questions are gonna come up. But it’s fairly easy to find out what it is. You look at the job ad, because not only is the job ad a guide in terms of what they’re expecting in a candidate or the new hire; it’s also the type of questions that they’re gonna ask you to ensure that you are the right fit for the job. 

Mac Prichard:

I know you have a process that you take your clients through that helps them look at the job ad, see those patterns, and prepare for likely questions, and I want to walk through how that works. Before we do that, Max, I wonder, what has been your experience with employers? Sometimes the interviewer isn’t formally trained in hiring or interviewing. And what happens when that’s the case? Can questions go sideways? 

Max Chan:

Yes, that’s why it’s always essential to not try to guess what the question’s gonna be, but have good career stories in your back pocket. A good example is of your experience that you can pivot in various ways in various angles. So, even if it’s a question you weren’t really expecting, you’re able to pull some of your experience to customize and tailor the answer to what they’re asking. 

Mac Prichard:

And I do meet candidates who walk into interviews, and they don’t prepare. They wing it. What’s wrong with that approach, Max? 

Max Chan:

The problem with winging it is, first off, if you’re winging it, you haven’t prepared any career stories that you can share. So, you’re talking off the cuff, and when you talk off the cuff, it doesn’t matter how confident you are. You are going to speak a bit fast, your thoughts are not gonna be organized, so it might be all over the place. 

A common complaint that I’ve heard from recruiters and hiring managers is that the answer is not structured and fluid. That’s easy to follow. It’s also not specific in detail. People tend to talk very generally at a very high level, and it doesn’t really dive deeper into their experience. So, that’s why it’s much better to prepare because then you can practice the little details that will make you a standout candidate compared to someone that is talking off the cuff or talking in a high level. 

Mac Prichard:

And when you do speak off the cuff or you wing it, you’re often competing against candidates who are prepared, aren’t you? 

Max Chan:

Absolutely, and one of the things, when you are moved on to the deeper rounds of an interview, it’s generally between you and potentially three to four other people, and obviously, a decision usually doesn’t get made on the spot. What happens is they take notes, they evaluate how good the answers are. So, that’s why it’s so important to have details in your answers. Because if your answers are more detailed than everybody else’s, you are gonna have a higher chance of being hired compared to someone who is trying to wing it and talking in generalities. 

Mac Prichard:

Well, let’s talk about the approach that you share with your clients about how to predict and answer job interview questions and the first step, Max, is that you recommend using a job ad as a cheat sheet for your interview questions. Tell us more about this. 

Max Chan:

Yes. So, again, as I mentioned earlier in our conversation, a lot of professionals complain in terms of, like, they don’t know how to prepare for an interview because they don’t know what questions are gonna come your way. Obviously, there will be the standard questions you get at every interview, regardless of what position you’re applying for, you’ll get. Such as tell me about yourself, why you’re interested in this role or company. But it’s more of the behavioral experience questions that they have trouble guessing. So the job ad is a great guideline in terms of preparing effectively on how to answer questions or prepare your stories, that you know what question’s gonna come your way. 

So, for example, let’s go back to the marketing manager example. The marketing manager position has a common amount of responsibilities that you’ll see in a lot of marketing manager job ads. So first is, again, as I mentioned, managing a marketing budget, client management if you work on the agency side. There’s also different tactics, for example, SEO (which is search engine optimization), social media, websites, website content management, and then there’s the qualifications section of the job as well, and that’s so, let’s say, five-plus years of project management experience, two-plus years of agency experience. So, those bullet points can be the foundation of potential questions they’re gonna ask you. 

So, for example, the project management one. They could ask you about juggling multiple projects because, in a marketing landscape, you’re going to be working with multiple campaigns. So, if the bullet point for the qualification is two-plus years of project management experience, the question they could ask is, tell me about your project management experience, or the other way is, tell me about a time that you had competing priorities or competing projects. What did you do? And how did you handle it? 

So, by looking at the job ad and trying to position these bullet points into possible questions is gonna make you a lot more prepared and a lot more confident heading into your interview.

Mac Prichard:

Job descriptions can be lengthy. What’s your best advice, Max, about how to determine what might be the most important responsibilities or qualifications that you’re most likely to get questions about?  

Max Chan:

Usually, when hiring managers or recruiters write job ads, the introduction to the job, like the first paragraph or so, that’s the main part, that’s the foundational piece, and then you could possibly rank the bullet points in order. So, the ones that are listed at the top, obviously, there’s two sections. Right? So, the responsibilities that are listed at the top, those are probably the main priorities in that role, and then the qualifications section, the higher bullet points ranked, those will tend to be more important. 

So, and there’s also numbers, too. Right? So, you also want to look at keywords in the qualifications sections as well. So, going back to like the marketing manager example, if they say four-plus years of social media management, they’re most likely gonna ask about your social media marketing management experience. Especially if there’s a number involved, and it’s a higher ranked bullet point compared to the other bullet points they have in the job ad. 

Mac Prichard:

So, you look at the ad, and you make decisions about which questions are most likely to come. 

What do you do with that information? How do you begin to prepare your answers? And I know that there are two different kinds of questions you’re likely to get, and I’d like to talk about those two different kinds of questions in the second segment. 

But when you’re doing this research and this preparation, how do you recommend to begin thinking about and preparing your answers? 

Max Chan:

Yeah, so that’s a great question. So the common format is the STAR format – which is situation, task, action, and result, and how you prepare your career stories and your answers is go through a career example in that STAR format. 

So, going back to the marketing manager example, again. Let’s say one of the bullet points is managing a budget. So, the situation would be, during my time at X company as a marketing manager, I had to manage multiple budgets for clients. Specifically, this one that was budgeted at one million dollars. So, that would be the situation. The task is I have to optimize their budget to generate X ROI or X KPI, based off the objectives that were agreed upon, and then the action step. 

A common mistake that a lot of professionals make is that they gloss over the action part. They might highlight one or two steps, and then they go to the result. You want to be very detailed in the action part. So, I usually recommend to clients to try to have three to five good points of your methodology on how you do certain things. That will give enough detail and enough flow, so the interviewer can understand your thought process and how you do things. 

And then the result which is straightforward. If you can add a quantifiable metric, that would be great as well. If you can’t, that’s okay, too. But just show your impact on the work that you did beforehand, which was the situation, task, and action. 

Mac Prichard:

Alright, let’s pause, and we’re gonna take a break, Max, and when we come back, I want to dig into the two different kinds of questions you’re likely to get. 

So, stay with us when we return, Max Chan will continue to share his advice on how to predict job interview questions and answer them. 

Here’s a prediction you can rely on. 

Employers will ask for your resume.

Is yours ready? 

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TopResume will tell you how to fix your resume yourself. 

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Now, let’s get back to the show.

We’re back in the Mac’s List studio. I’m talking with Max Chan, founder of Chan With A Plan. 

He’s a career coach and podcaster. Max helps frustrated professionals become focused and confident in order to excel in their careers.

He joins us from Toronto, Canada. 

Now, Max, before the break, we were talking about how to predict job interview questions and answer them, and you have found that there are two common types of questions you’re likely to get. 

One is a “tell me about a time when you’ve done something” question, and the other is “how would you approach a job responsibility?” Tell us more about those two types of questions, Max. And why do hiring managers like to ask them? 

Max Chan:

Yes, so, as you mentioned, there’s two types of questions. There’s the behavioral, which is tell me about a time when you had this situation, and then hypothetical, walk me through the approach. So, the reason why they ask you behavioral is that they want to know that you’ve done this specific situation before. 

You’ve, for example, talk about a time you had a conflict with a manager, or with a colleague, or with a client, and the reason why they’re asking this is not to trick you. Like, behavioral questions aren’t trick questions. They’re asking you because this is going to happen if we hire you. How are you going to handle it? So, by asking these behavioral questions, they have a frame of reference in how you deal and resolve those types of situations. So, that’s why they ask you from a behavioral perspective. 

From a hypothetical perspective, which is, walk me through how you would do something, they want to see your thought process on how you evaluate situations and what you do to move forward and resolve them.  

Mac Prichard:

And, with a behavioral question – the tell me about a time when you did X, they’re looking for examples, and the kinds of stories you’ve been referencing, that show that you’ve actually, not only that you think you can handle this problem, but you’ve actually done it in the past. Aren’t they? 

Max Chan:

Absolutely. That’s why it’s so important to have examples in behavioral questions because if you’re just answering, again, winging it without a proper example, they might think you’re making it up on the spot or you don’t know what you’re talking about, and that’s going to lose confidence in the interviewer. That’s why it’s so crucial when they ask you about, tell me about a time that something happened, that you provide a very specific example, and walk them through it. 

Mac Prichard:

Well, let’s talk about career stories you can use to answer the “tell me about a time when you did” something question or the behavioral interview question. How do you collect these stories, Max? And how do you prepare them so that you have them ready when you walk into the interview room? 

Max Chan:

So, this is why it’s so important to have a well-written resume. I’ve worked with clients before, and they had trouble in the interview process, and what I’ve realized is that when the resume was all over the place or wasn’t clear and concise, they had a hard time articulating their achievements and responsibilities. But when the resume is well-written, with a strong action verb such as achieved, directed, drove, initiated, accomplished, they feel more confident in what they’ve done, which makes talking about their experience a lot easier. 

So, you start off with the resume and go through your bullet points, and at that point, you look at the job ad that you’re going to be interviewing at, the job that you’ll be interviewing at, you look at the job ad. And then, you go through your resume and say, what bullet points in my resume, in that experience that I can use to provide an example in these bullet points? 

So, for example, if you are applying for a project coordination job, they might talk about creating statements at work. Or requests for proposals. You would go through your resume and see where in that resume, what bullet points that you had done those responsibilities? And then, you would create a story targeted towards that bullet point.

Mac Prichard:

How do you work with your clients, Max, to help them prepare stories that can answer not just one question, behavioral interview question rather, but multiple questions? In other words, stories that can be adapted and used to answer a lot of different behavioral interview questions. How does that work? 

Max Chan:

Yeah, so how it works is, the client would give me the job they’re going to the interview for, and I’d look through all the bullet points of the job ad. Secondly, I would go through the resume, and then I would take a bullet point from the resume. 

For example, let’s say managing a marketing campaign. So, there’s a lot of aspects in managing a marketing campaign. You have to work with vendors. You have to work with your manager to get approvals; you gotta work with creatives; you also have to make sure that the budget’s optimized because no clients gonna just give money to you and spend it without a return. So, there’s a lot of moving parts inside of managing a marketing campaign. 

So, what I would do is take that story and then go through the bullet points in the job ad and ask myself, how can I pivot this story into multiple angles? So, for example, if one of the questions was about, talk about a time that you had a conflict with a client, there’s bound to be some time in the marketing campaign where the client didn’t agree with something. So, there could be conflict there. 

Another example would be, tell me about a time that a project shifted direction last minute or it didn’t go as planned. No marketing campaign goes smoothly from end to end, so there’s bound to be one situation from a marketing management campaign perspective where it didn’t go as planned. So, you’ll use that bullet point in terms of managing a marketing campaign and talk about that as well. 

Another final example would be, tell me about a time that the results were not ideal and weren’t as projected as we thought. How did you resolve the client’s concerns? Right? So, that could be talking about like a learning lesson in that marketing campaign. 

So, that’s what I mean by, like, taking a bullet point in your resume and pivoting it in multiple angles based off the job ad because no story is from A to B. There’s multiple angels that you can utilize because we do so much in our jobs. There are multiple parts in it, and we want to take specific parts and integrate them into specific bullet points.

Mac Prichard:

How do you help your clients, Max, anticipate what some of those different questions might be? So, they’ve got the story, they’ve managed this marketing campaign, it had a lot of different parts and elements to it. But you don’t want to make this up on the spot. How do you help people anticipate what the different variations of the behavioral interview question might be? 

Max Chan:

Yes, so it goes back to what we discussed earlier in terms of there’s two ways an interviewer will ask you a question. Behavioral, which is tell me about a time when, and the hypothetical walk me through the process. 

So, for example, if one of the bullet points was about managing vendor relationships, there’s, again, two ways to ask it. Behavioral would be, tell me about a time that you had a conflict with a vendor, or tell me about a time that you had to juggle multiple vendors for a project. So, that’s on the behavioral side. On the hypothetical side, they could ask you walk me through how you would build a good relationship with a vendor to decrease costs. 

So, even though the bullet point says must have experience in vendor relationship management, as an example, they could ask one of two ways. How did you manage the vendor relationship? And how would you build a new vendor relationship? 

So, when you look at bullet points in a job ad, you always want to think about in the past and think about the future. About the time you’ve had experience in it and then how you would do it again. 

Mac Prichard:

Well, let’s talk about that second set of questions, the approach. Give us some more tips about how to prepare for those questions and answer them. 

Max Chan:

Yeah, so, even though they’re talking hypothetical, you can still use an example because you’re providing context of your methodology from past experiences. So, if they say, tell me about a time that you had to juggle multiple priorities, you could introduce the answer by saying, yes, I have juggled multiple projects throughout my career as a marketing manager. 

So, for example, in my last role at ABC company, I had this quarter that I had to juggle multiple new client projects because we got a lot of new clients signed on, and this is my methodology on how to balance everything, so I still ensure that all of the literals would still be delivered on the agreed-upon timelines. 

And then you would just, again, go through the STAR format, go through your action steps, and then what was the result. So, even though they’re asking in a hypothetical way of how you would do something, you’re still spinning it back to an example of how you’ve done it before to ease the concerns of the interviewer because the main thing the interviewer wants to know is that you have experience in what you’re doing. 

So, because, again, hiring is a big risk. So, if they bring in the wrong person, it could cost them a lot of money in the long run. So, that’s why they’re so adamant on finding someone that has the qualifications. So, by bringing in an example, even if they’re asking a hypothetical way, it does put them at ease. That, okay, this person has done this job before. I have confidence that he can do it again. 

Mac Prichard:

Well, it’s been a great conversation, Max. Now, tell us, what’s next for you? 

Max Chan:

Yes, so, thanks again for having me, Mac. In terms of what’s next for me, I, again, am building my podcast right now. It’s over a hundred episodes. It’s about helping professionals with obstacles and providing them with actual steps to overcome those obstacles to get their career to the next level. 

I also have a resume writing and interview preparation services. If you feel stuck in your career and you need some guidance to push you past those obstacles that you’re currently facing in your job search, I have those services available to strategize and help you get to the next level. 

Mac Prichard:

Well, I know listeners can learn more about your resume and interview services by visiting your website, and they can also find past episodes of your podcast there as well. And congratulations, Max, on breaking the hundred podcast episode barrier recently. That’s a big milestone. 

Now, Max, given all the great advice you’ve shared today, what’s the one thing you want a listener to remember about how to predict job interview questions and answer them.  

Max Chan:

So, the main thing that I’ve seen when it comes to whether a professional is going to be successful or not in an interview is how well they’ve prepared. The more you prepare for an interview, the more confident you’re gonna be. 

So, the tips and strategies that I shared with you today, if you take, let’s say, a few hours and just practice what I’ve given you guidance on, you’ll be way better off. What tends to happen is a lot of professionals they’ll just Google the top popular questions and then have answers for those, but my methodology, you’re gonna have customized answers based off customized questions for that specific job, and it’s really gonna help you stand out. But you do have to put in the hours to utilize the methodology properly, so you can be the standout candidate that they’re looking for. 

Mac Prichard:

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Next week, our guest will be Matthew Sorensen. 

He’s the founder of Candidate Club and the host of The Job Interview Experience Podcast. 

When you talk to an employer about a job, you’re exploring a new and important relationship. 

And as with a personal relationship, you want to make sure it’s a good fit for both parties. 

Join us next Wednesday when Matthew Sorensen and I talk about what dating mistakes can teach you about job interviews.

Until next time, thanks for letting us help you find your dream job.

This show is produced by Mac’s List. 

Susan Thornton-Hough schedules our guests and writes our newsletter. Lisa Kislingbury Anderson manages our social media.

Our sound engineer is Matt Fiorillo.  Ryan Morrison at Podfly Productions edits the show. Dawn Mole creates our transcripts. And our music is by Freddy Trujillo.

This is Mac Prichard. See you next week.