Most job interviews will have some version of the question: Whats the biggest challenge you faced in your current position?
Your instinct might be to scream, "Nothing as challenging as this question!" It really can feel like a doozy. You want to answer the question honestly, but also not show too much weakness, or give away too many negative feelings about something (or someone) that might have been problematic at work, and at the same time, you want to show that you will be up for any challenge in this potential new role without being too cocky about your skills.
Skilled interviewers can also tell who has prepared for this question and who hasn't. We don't share that with you to add to your stress, but rather to reinforce the deep need to prepare. By preparing, you're also showing that you're the sort of person who takes yourself and your work seriously and that you're conscientious.
The first step to preparing an answer for this question is to consider why it's being asked. There are three main qualities that your interviewer is trying to assess here:
1. How well do you handle difficult or high-pressure situations?
2. Will the responsibilities of the position you’re applying for be too far out of your comfort zone?
3. Can you speak about your current (or most recent) position with poise and professionalism?
The second step is to figure out an anecdote that you can share. This is important for all interview questions, but especially here. The interviewer really wants you to be specific, so saying, "Well, we often had a lot of tight turnarounds on set, so that was challenging, but I made sure to work with the AD to keep everything on schedule" isn't going to cut it.
The anecdote should be a situation that sounds legitimately challenging and doesn't give away personal information about your current employer or proprietary information about a project. For example, maybe the following is true: "I worked on SHOW X, and our budgets were only $150K an episode, and the producers above me were insisting I book CELEBRITY A whose going rate is $80K, and there was no way to get it done with the rest of the show budget, so I had to come up with 50 other pitches of affordable celebrities while my boss screamed at me for being an incompetent fool." But you don't want to say all that, as it includes protected information and a lot of bitterness, and your interviewer might know the producer you're talking about directly -- this isn't the time for gossip or therapy. See if you can figure out a way to share that story without the details or bitterness, or pick a different story that's challenging for reasons that have less to do with mismanagement.
The story should offer an opportunity for you to show how you work through problems, what you learned, and what skills you developed as a result. For example, let’s say your company received an RFP from a coveted client, but your boss was on her honeymoon and you had to fill in to lead the team at the last minute, knowing that you needed to land this contract or your boss would come back upset, and that you absolutely couldn't bother her during her time away. You can talk through your ability to learn quickly, how you used your client services skills to cover for your boss so the potential client wouldn't think they were getting the short end of the stick, how you tapped into leadership skills by rallying junior members of the team to brainstorm awesome ideas, and leaned into your creative problem-solving and intuition to use the bones of a deck your boss had approved for a previous project for this one so you knew it would be to her liking, and ultimately landed the client. This story would also work if you didn't land the client -- you can showcase what you learned in the process and explain how it informed your approach moving forward.
One thing to note: if your actual biggest challenge is something you’re still struggling with, and you have yet to come up with a solution to your problem, find a different challenge. This questions is very much about what you've learned and how you solve problems. It's okay not to be 100% literal here with the "toughest" or "biggest" challenge, but rather just a memorable, illustrative one. If you choose a current challenge, you run the risk of getting mired in whatever is driving you out of your current role, rather than focusing on how the skills you've used over the course of your career will impact your next role.
Overall, keep this answer short and sweet. Don't give every detail of the challenge, but just enough to set the stage. Focus on what your personal role was in responding to the challenge -- not the team's role, but yours. Explain how your perspective has shifted because of this, and why you think your approach will be beneficial to the new employer.
-- Angela Silak & Cindy Kaplan
What's the deal with LinkedIn messaging?
We get a lot of questions about the LinkedIn messaging feature – when is it ok to send a message, who is it worthwhile to message over LinkedIn, or why does no one respond to my messages? In our experience, to use the LinkedIn messaging feature effectively, you have to be strategic with your outreach -- and sometimes, that means not using the feature at all.
If you’ve recently received a connection request from an old friend or former colleague over LinkedIn, it’s fine to send a quick “Hi! Nice to hear from you!” note. This probably isn’t going to result in any further interaction, but there’s no harm in sending a friendly message to someone you know. However, if you are actually trying to conduct business with someone, it’s better to take the communication off-platform. The same goes for when you're initiating connections with people from your past -- if you like, you can swap out the generic message from LinkedIn for a custom one to be pleasant, but you may not get a response.
Unfortunately, a lot of LinkedIn messages get buried among a sea of messages from random people trying to connect or are lost in the social media tab of the recipient's gmail inbox, so you might get unintentionally ghosted, even by someone you know. Plenty of people have LinkedIn profiles but are not active on the site at all. If you're trying to initiate a conversation that leads to a call or meeting with someone you know, send an email, which will have a better chance of getting read.
If you are trying to connect with someone you don’t know, either to apply for a job, set up an informational interview, or establish a business partnership, LinkedIn is a great tool for identifying targets, but it's still better to get in touch via email, for the reasons outlined above. If possible, try to get someone you know who knows the person to refer you through an introductory email. You can also try a cold email -- it's pretty easy to find someone's work email address, as most companies have a standard format.
If LinkedIn messaging is the absolute only way you can find to get in touch with someone, you’ll want to craft a message carefully. Be really specific about who you are, why you are reaching out, and what you are hoping to get by connecting with this person. If there’s something you have in common with the person (i.e. you went to the same alma mater), call that out in your note. In an ideal world, the person will respond, and you will get a meeting. But don’t be offended or discouraged if you don’t hear back – many people won’t even see the message or are simply too busy to respond.
Also, keep in mind that having a completed profile (with a picture!) is going to encourage people to want to do business with you and may increase your chances of getting a response. So if you haven’t taken the time to build out your profile, now is a good opportunity
-- Angela Silak & Cindy Kaplan
How to tailor your resume to a job posting
If you're actively on the job hunt and have a good sense of the types of roles you're looking for, it’s smart to have a resume ready to send off at a moment’s notice. However, the most effective job applications are those that are specifically tailored to the role at hand, so if you have the time (and it might not take more than a few hours!), it’s worth it to tailor your resume to a job posting.
How does this work? First, take a look at the job posting and figure out the main qualifications the employer is looking for. These are usually listed near the top and are often paraphrased several times in the posting. Is it clear from a quick glance at your resume that you have these skills or desirable qualities? If not, is there a way to reframe your experience to call attention to them, either by reordering your bullet points, adding or removing entries in your experience section, or customizing your professional summary? Remember, your goal with your resume is to tell the story the hiring manager wants to hear: namely, that you are a great candidate for this specific role and are truly interested in the potential work. Hiring managers don't have a ton of time and won't do guesswork to figure out why you might be a great candidate if you don't spell it out for them. They will not assume you eagerly meant to apply for this specific role if your resume reflects a wildly different trajectory with no explanation; they'll instead assume that you were resume bombing every somewhat adjacent job ad in sight.
The second step is to look at specific keywords in the job posting and make sure you have described your experience similarly. In particular, look at the action verbs the job posting uses and see if you can tweak your bullet points to include those same words. For example, if your resume says “Interface with agents and managers to source IP,” and the job posting says “Liaise with representation to solicit pitches and writers,” you could make a simple tweak to the verbs in your bullet point to match theirs and explicitly show them you have the skills they are looking for. Furthermore, if there are any specialized skills or software called out in the posting as a “nice-to-have,” and you have those skills, feature them on your resume! Tweaking keywords in this way is helpful for hiring managers who are skimming, as well as for applicant tracking systems (ATS) that are literally designed to match specific keywords.
It might seem more time consuming to tailor your resume to every job, but you'll also get the right job faster, rather than getting stuck in an endless loop of submissions and silence. Plus, if you're conducting a targeted, strategic job search and only going for the jobs you are most excited about, you won't be applying for a ton of jobs each week anyway. Proving to the hiring manager that you really want this job is half the battle in the job application process, and tailoring your resume is the perfect way to start making the case for yourself
-- Angela Silak & Cindy Kaplan
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