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Published on January 28, 2020

How to Ace an Interview: Nailing the 10 Most Tricky Questions

How to Ace an Interview: Nailing the 10 Most Tricky Questions

As someone who has been in recruiting for over 10 years I can tell you the interview is vitally important to getting that new job you really want. During the interview process, there will most likely be at least 2 interviews, a phone interview and an in person interview. Both are important.

Companies can of course have different interviewing processes but in general, there is at least one phone interview, also known as a phone screen, and a live, in-person interview. The in-person interview can be with one person or it might be with a variety of people. While they are both important, the live interview is typically the one that will make or break you as a candidate for the position you are interviewing for.

Many of the interview questions we will review here will more likely come up during the live interview. But it’s a good idea to be prepared for them on the phone interview as well.

To illustrate how important the live interview is, I’ll tell you about my search that happened a year ago. I’d decided it was time to move on from the role I’d been in for a little over 6 years. As I started researching and looking for a new opportunity, I began down the path with 2 companies. With the one I landed with, I’d had 3 separate phone screens, each one an hour long. They must have thought they went well because I was asked to fly to the city where the corporate office is at and do an in-person interview. — with 8 people.

Yeah, it was a long day. The good news is I rocked the interviews across the board. I flew home that evening and the following day, I received a call with the job offer. That was less than 24 hours after I’d had the in person interview. This is how important the live interview is.

So how to ace an interview? We can dive right in to helping you nail the 10 most tricky interview questions:

1. What’s Your Biggest Weakness?

This is a personal favorite of mine. The primary reason for this question is not to actually find out what your biggest weakness is. Unless of course, you say something like “showing up to work on a regular basis,” then it’s probably going to get you kicked out of consideration for the role.

The main reason for someone asking you this question is to see if you are self-aware. That is if you know your weaknesses and are smart enough to account for them.

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The smart play here is to answer in a modest way. You want to be able to show that your biggest weakness actually has an upside. For instance, I usually say that mine is impatience. Which is true, I like to get things done. But what I ensure what I point out is that even though I am impatient, it’s because I like to crank and get a lot of work done.

2. Why Do You Want to Work Here?

Interestingly enough, a lot of people don’t have an answer to this question. It’s designed to find out if you’ve actually done research on the company and if you are excited about this position.

When I ask this question, many people have told me something like “because it looks like a good opportunity”. I mean, can you be any more generic?

The key to answering this is to show you’ve done research on the company and that you are enthusiastic about the actual position. Companies want people that are excited to work there, not just someone that shows up for a paycheck.

3. Where Do You See Yourself in 5 Years?

Employers are asking you this question to see if you have somewhat of a plan for your career. It doesn’t have to be completely mapped out in a step by step manner but, a general overall plan is good to see. It means you are goal oriented and are working towards something.

Don’t worry about answering in a way that states you are planning on sticking with the company until you retire. Rather, focus more on how it’s important to you to continue to learn and get better and better at what you do. Companies like to hire self-motivated people.

4. Tell Me About a Time You Messed Up

Or tell me about a time something didn’t work out the way you planned. Similar in concept. The key here is to show that you take accountability for your actions and how you react to things going wrong.

Companies like to see that you are willing to accept responsibility for the things you oversee and own up when you are wrong. People that always find a way to blame their missteps on other people or circumstances typically don’t make good team mates.

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The other component here is things don’t always go as planned, how good are you at adapting and thinking on your feet.

5. Why Are You Looking to Leave Your Current Job?

This may seem like a place to launch into all the things you don’t like about your current job. Or to talk about what a terrible person your boss is. Don’t do it. That’s the path you do not want to go down. And that’s really what this question tends to prod out of many people.

If I am interviewing you and ask this question and you tell me all the ways your boss doesn’t appreciate you and your company has terrible leadership, I’m thinking what you’re going to be saying about me in a year when you are interviewing somewhere else.

Make sure you are framing your answer in a way that doesn’t shed bad light on your current or most recent employer. You want to focus on things like you’ve enjoyed working for the company but your growth options are limited there so you are exploring outside opportunities.

6. How Would Your Current Manager Describe You?

This question gives you the opportunity to show off your strengths and what your boss appreciates about what you bring to the table. You want to focus on the positive traits that your boss likes and how it helps you in your role.

What you do not want to do is sprinkle in the things your boss doesn’t think as highly of. Don’t say something like my boss would describe me as a focused worker, at least on the days I make it into the office.

7. Tell Me About a Time You Overcame an Obstacle

Another one of my favorite questions. Interviewers ask this question to see if you are able to deal with roadblocks.

Things don’t always go smoothly, so having people on the team who are able to solve problems has huge upside.

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Being able to overcome obstacles is a great trait to have. Make sure you have a few stories about how something didn’t go as planned that caused a challenge and how you were involved in solving the problem. It’s a way of turning a bad situation into a good one.

8. Why Should We Hire You?

If you are at the point of a live interview, you should be highly interested in the position.

By this point, you should have a pretty clear picture of what the role is and how your skills and experience will help you succeed. The reason this question is being asked is to see if you are the right candidate for this role.

This gives you a great opportunity to tell your interviewer how your expertise will positively impact the role. Right now, you are in the spotlight to clearly show that your experience is the perfect fit for the position and why. Shine on!

9. What’s Your Greatest Achievement?

Employers tend to ask this question to gain an understanding of what your big wins were. What are the really impactful things that have happened during your career and how you were the reason why they happened.

This is another great opportunity for you to toot your own horn. What you want to be conscious of is how you tell the story about your biggest achievement. You want to make sure you say why it was such a big achievement.

If possible, it’s always good to include your team as part of the big win. Employers love to hire people who can make things happen but, it’s also important they understand the importance of team work.

10. Do You Have Any Questions for Me?

You might be asking yourself why this is a tricky question. Honestly, it’s not a tricky question if you are prepared for it.

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What the interviewer is looking for here is how interested and excited you are for the position. You’d be surprised at how many people answer this question with a blank stare or have no questions prepared.

Again, if you are at a live interview, you should be highly interested in a position and the company. You will convey how interested you are in the opportunity with some well thought out questions to ask.

You don’t want to just ask one question like “How often is payday”? Have at least 4 to 5 questions prepared but don’t overwhelm your interviewer with dozens and dozens of questions. Show that you’ve given some serious thought to this position by coming prepared with solid questions to ask.

The Bottom Line

There you go, insight to nailing the 10 most tricky questions during the interview process. There are, of course, many other questions you might get asked during the interview process but, these tend to be the ones that trip most people up.

Remember to take your time and thoroughly prepare for the interview. You don’t have to memorize your answers or anything but having a good idea of how you’d answer these questions will help you ace the next interview.

Here’s to being career advancement ready!

More Tips on Job Hunting

Featured photo credit: Romain V via unsplash.com

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Last Updated on August 10, 2020

How to Start a Small Business From the Ground Up That Thrives

How to Start a Small Business From the Ground Up That Thrives

How to start a small business?

For most of us, it starts with an idea.

The idea can either be to break free from the corporate world. Be our own boss. Stop feeling like a cog in a machine and actually make a difference.

Or it can be more specific. Build the first or the best widget in the world. Because I’ve used every other widget out there and they are all lacking in a specific way.

The idea is to start a small business. To build something brand new. Brick by brick.

I have worked with dozens and dozens of small businesses and startups over the years. I’ve seen the good, the bad, and the ugly. I’ve seen companies go public at valuations of more than $200M, and others crumble under the weight of their own mistakes.

So if you have an idea, the spark is there but then your heart skips a beat, and you think to yourself: How exactly do I start?

To avoid some of the missteps that others have made, to build a business that thrives; here’s how to start a small business that thrives from the ground up:

1. Know Your Why

Simon Sinek has one of the most popular Ted Talks of all time, and a best selling book as well, called Start With Why. In it, he talks about how important it is to know why you are motivated to do what you do; and that why shouldn’t include “to make a million dollars” or “make my mother proud.”

It is about understanding the way you want to make an impact on the world. And it’s different, and personal, to each person.

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I have found that having a solid foundation on why you want to start a small business makes all the difference. When things get rough (and they will get rough), you can return to this fundamental understanding and as a reminder of why you want to keep moving forward. As Sinek says:

Working hard for something we don’t care about is called stress; working hard for something we love is called passion.

So ask yourself, how do I start a small business that aligns with my Why?

2. Be a Consumate Learner

The most successful Founders and CEO that I’ve met are constantly asking questions. They are confident in what they know but are aware that they can always learn more. This can come up in a few key ways:

Before you even start your business, research your market.

Then research some more. Never think that you already know everything about people who buy widgets or all the other widgets on the market.

Ask questions. Then ask some more. Find people smarter than you or have way more experience, and listen to what they tell you.

Acknowledge that you don’t know everything. This is another critical piece to running a successful business.

I have seen it so many times. A Founder asks to “pick the brain” of someone else who has gone before. They hire a brilliant person to be part of the team — an expert in marketing or finance, and then disregard what they say or tell them what to do instead of asking them the best way to do it.

The CEO is missing a critical opportunity by not leveraging the team members/ expertise and not acknowledging that this team member has a lot to teach the CEO. It’s disempowering to the team member too.

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3. Roll up Your Sleeves

You might have the fancy title – CEO, Founder or Head Honcho, but when you start a small business, you are also the receptionist and in charge of data entry.

At the beginning, you need to be willing to do all the nitty gritty work that goes into your business. You can’t be too good to do anything. The tasks might not be in your zone of genius. And sooner or later, you will be able to hire and/or delegate a lot of the smaller stuff.

But if you don’t understand all the little pieces that go into making your business great, you won’t understand how to scale your business and grow when the time is right.

4. Get in the Weeds

I have worked with many, many CEO’s, Founders, and Entrepreneurs, and most of them have one thing in common:

They are Big Picture Thinkers.

They are the ones with the dreams and the big ideas. Execution? Not so much.

So, if you are going to start a small business that thrives, you need to get in the weeds. Take a look at the details:

Why would blue be the best color for your widget? Who will take the orders that come in from outside the US? How, exactly, will you ship your products to the people that buy them?

Don’t avoid the details of your business because the big picture ideas are more fun.

Dreams and big ideas are critical when you start a business. But if you don’t have a handle on any of the details, you won’t be able to make those dreams a reality. And eventually, your business will crumble like a house of cards.

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5. Build a Plan That Includes Budget, Expenses, and Profit

When you’re in those weeds, you must put together some numbers — real, researched, well-informed numbers.

Don’t assume you’ll take 50% of the current market because your idea is great. You need to create a plan that outlines every single expense that you’ll expect in the next 6 months to a year. You need to create a realistic timeline to product launch and create estimates for how much revenue you will get from your product, and when.

Without a plan that includes numbers, you will spend most of your time reacting to what happens around you instead of moving forward with intention.

Dave Ramsey is one of the big gurus of small business and personal finance. In his best selling book, EntreLeaders, he keeps it simple. He says:

Business is not really that hard. You are, however, required to do the basics or you will not win. Budget and do the accounting, stay out of debt, don’t buy what is not needed what is not needed to make a profit, save cash, and always be generous.

And you need to have a good answer to the most important question of all – when will you make a profit?

6. Avoid Shiny Object Syndrome

You’ve put your plan together. You’ve researched your market. You know that you want to create 2 inch widgets in a gorgeous shade of blue. You will sell them for $1/widget. Bob the designer is signed up to build them. You’ll launch in June!

And then…

My neighbor Betsy told me she’d love a widget in green. Should we change the color to green? And Johnny’s teacher mentioned that she could use a widget that is 3 inches. Let’s change the size of the widget!

It’s so common. We have an idea but what if there is a better idea?

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Do your research. Make informed decisions. And then stay the course. You can always pivot later.

But if you keep turning your head toward every shiny object, you won’t reach the goal right in front of you. You’ll never launch that product by June.

7. Trust Your Team

A small business might have one founder, but people rarely start a small business all alone. There is often a consultant, a partner, a sounding board. And then, consultants, accountants, and marketing experts.

No one’s “zone of genius” covers every area. So one of the best ideas on how to start a small business is to find a great team to help get your idea off the ground. Spend critical time on the front end vetting and hiring great people. And then let them do their job.

In my years on Wall Street, I saw first-hand the impact on a business when the Founder didn’t trust their team. I had hundreds of small private companies pitch their businesses to me, with the hope that my investment bank would take their company public.

The companies that gave me the most pause, the ones that rarely succeeded were the ones where the CEO did all the talking, or when he or she cut off his team members when they tried to answer questions.

Because in my mind, if that happened, it meant one of these two things: 1) the CEO is not listening to all the other smart people in the room; or 2) the CEO does not trust his team.

Both options were a recipe for failure.

Believe In Yourself!

Trying to start a small business can be incredibly difficult. We dream of the possibilities but get overwhelmed by the realities.

Know your why and believe in your abilities. Don’t try to be the best in the world or execute flawlessly. Learn and grow and keep trying.

If you do all the above things, you will be a success in whatever way you choose to define that word.

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Featured photo credit: Vitaly Nikolenko via unsplash.com

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