How to handle uncomfortable questions in an interview

April 27, 2010 at 2:37 am 2 comments

It’s a job candidate’s nightmare-come-true: All is going well, you seem to be developing a good rapport with the interviewer, and then wham, seemingly out of nowhere they toss out an uncomfortable question that you didn’t see coming. What to do? Obviously, covering your ears like a three-year-old and refusing to answer, or ducking under the desk will end your candidacy pretty quickly. But how can you answer an uncomfortable question (especially a surprise one) in a direct and honest way without making yourself look bad?

Because you can’t wave away such questions, much as you’d like to, the best strategy is to prepare for them. Then, if they’re asked, you’re ready, and if they’re not, well, at least you prepared well. Often these type of questions have to do with personnel matters — people you may have worked with in the past who may not have seen you in the best light; so-called reputational issues. (Remember what a small town Washington can be.) Someone may be spreading unflattering stories about you and you need to address them, especially because if you don’t, you’ll look weak. Or, sometimes, an interviewer may have legitimate concerns about some aspect of your candidacy that could make you uncomfortable.

Hiring experts say that in such situations you should, above all, remain calm. Don’t act defensive but don’t go on the offensive either. The interviewer may be testing you a bit, to see how you react under pressure. Or they may be baiting you. Or they may be asking a similar question of all candidates. In any case, here are some tips on how to handle potentially awkward or uncomfortable questions in an interview:

*Don’t assume the worst. An interview situation is inherently stressful and awkward in any case. If the hiring manager lobs an uncomfortable question your way, you may presume that you’re out of luck and your candidacy is sunk. That may be very far from the truth — if you react calmly and with poise. Take the question at face value. If, for instance, the hiring manager says, “Many of us have had jobs for which we were ill-suited. What jobs have you had where you weren’t a good fit?” (An email correspondent was asked a question like this in a recent interview, by the way!) You don’t have to answer affirmatively — you can say that you actually have found most of your jobs to be a good fit, because you’ve sought positions that you carefully researched to make sure they would be right for your skills.  Don’t presume they’ve dug up some dirt on you. And remember, you’re not on the witness stand — answer to the best of your knowledge and move on.

*Don’t take the bait. Sometimes interviewers are trying to see how you react under pressure and will ask a question to try to get a rise out of you. Don’t rise to that occasion. Instead, say something like, “I’m not sure exactly what you’re getting at. Could you try to be more specific?” Or “I’d really like to answer your question, but I’m having trouble trying to figure out just what you mean.” Without being confrontational (which you never want to do in an interview situation, see Dec. 28 post, “How to make the most of a job interview”) you want to try to deflect a question intended to make you uncomfortable — yet in a polite way. If the recruiter persists, try to answer as honestly as you can. And you can always do what many politicians do when asked a question they don’t like in a debate or public forum — remark on what an interesting question that is, and then go ahead and give an answer that isn’t exactly on-point, but allows you to highlight some skills you wanted to mention anyway. It may work; if not, it buys you some time to try to figure out what the interviewer is up to.

*Never say anything negative in an interview about someone in your past. An interviewer may have determined that someone you worked with — it may have been years ago! — isn’t your biggest fan and may have said a few things that don’t exactly make you sound like a great fit for this position. It happens all the time. The question often comes up like this: “So, I understand you worked with Jane at XYZ Media. What was that like?” The problem with a question like this is you don’t know what the interviewer is getting at, and most times, you don’t know what their relationship is with the person in your past. Above all, be careful. (A former colleague of mine once said something mildly negative about a person mentioned in such a question, and the interviewer turned out to be married to that person! Needless to say, things did not go well from that point on.) If you can, try to find out what they know and what they’re getting at — might the person have said negative things about you? Or is the interviewer merely fishing? You can say something noncommittal, like “Oh, I didn’t realize you know Jane. We worked together at XYZ years ago; I believe she’s still there. How do you know each other?” And if the interviewer indicates that Jane may have said some unfavorable things about you, don’t assume a defensive posture. Instead, try to deal with the concern the interviewer is expressing and don’t make it personal. (And a good interviewer will try to avoid personal accusations as well.) For instance, if the question is about how you handled a management situation, you might say, “I was a new manager then, and not nearly as adept at delegating as I am now. I expect I would handle things a lot differently today.” And then you can give an example of a tricky management situation you recently handled well — try to turn lemons into lemonade whenever possible in an interview.

*Be prepared. The Boy Scout motto is one of the best ways to approach uncomfortable questions that may arise in an interview. Do some research on the interviewer (especially where they have worked — that will give you a sense of who they know that you may know), their questioning style and what their concerns may be about your candidacy. Practice answering uncomfortable questions with someone else or in front of a mirror — and carefully note your reaction. If you are prepared for how to deal with these type of questions, you’ll be much more poised when they come up in an interview.

*More grim circulation news from the newspaper world, via this link to a piece. Yet at least things have leveled off a bit and the declines are not nearly as bad as those reported last October:

Latest Newspaper Circulation Numbers Less Bad, But Still Bad

*As always, some good leads to pursue or pass along to others:

*The U.S. Chamber of Commerce in D.C. has an opening for a special assistant (this is a mid-level position for someone with experience; not an entry-level position):
Special Assistant
U.S. Chamber of Commerce – Washington, DC
handle meeting and travel logistics; assist with training for lobbyists; prepare lobbying reports and help… verbal and written communication skills; strong…
From U.S. Chamber of Commerce

*The Sierra Club has an opening in D.C. for a national press secretary; could be a good fit for a transitioning journalist:

Sierra Club, America’s oldest national environmental organization, seeks an experienced National Press Secretary.  This position will be based in Washington, DC and  is responsible for planning and executing media strategies for several campaigns including Federal and International Climate Change and Energy policy, serving as liaison and spokesperson with media, writing/researching messaging, op-eds, reports, press releases, talking points and other materials, coordinating media events and supervising staff..  Requires five years prior experience as a journalist, media specialist or other position involving media/press relations, and a Bachelor’s in communications, journalism, or a closely related field, or the equivalent combination of education and experience.  Knowledge of and/or experience with environmental issues and/or national politics strongly desired.  To apply please email your resume with a cover letter (specifying “National Press Secretary– SCDC41910” in the subject line) to: <>

*A D.C.-area company is looking for a technical writer/editor; details follow:

My company is looking for a technical writer/editor.  The position is full time and will require significant editing and formatting as well as actual writing.  The project primarily involves project management documents but may include some material in the energy arena.  It will not involve public relations or proposal material.

Please note, this is not a Federal position although you will be working on a Recovery Act (ARRA) related government project.  Work location is TBD.

If you know of anyone interested or are interested yourself, please send a resume to erica.kolatch at

*With a hat tip to (for these next few leads), the Chronicle of Philanthropy in D.C. has an opening for a staff writer:

About The Chronicle of Philanthropy

The Chronicle of Philanthropy is an independent news source that has covered the nonprofit world since 1988. Published by The Chronicle of Higher Education, it has a strong reputation for its mix of news, opinion, and trend articles. The Chronicle of Philanthropy has a print readership of over 100,000 and Web traffic of more than 1.2 million pages per month. The biweekly newspaper and The Chronicle’s daily newsletter Philanthropy Today is widely read by major philanthropists, government official….more info

View all our jobs

Job Description

The Chronicle of Philanthropy is seeking an experienced journalist to join its Washington, D.C. staff. The reporter will cover one of The Chronicle’s most prominent areas of coverage – trends and innovations in nonprofit fundraising (especially through increasingly sophisticated new techniques like text messaging and social media). As an integral part of a small news staff, the reporter will also have the opportunity to explore emerging trends and organizations in philanthropy as we seek to enhance coverage of larger organizations like Doctors Without Borders and Teach for America, and newer organizations like



We are seeking a versatile writer and reporter with at least 5-10 years of journalism experience. The ideal candidate will have a sharp and clear writing style and experience writing a mix of trend stories, hard news and service pieces. Applicants who demonstrate proficiency in Web storytelling skills, including audio and video pieces are especially preferred. Candidates with experience writing about technology or business issues are also ideal. Applicants with a strong background in any of the areas that are a key part of the nonprofit world — like education, arts, and health care — are encouraged to apply.

The Chronicle offers excellent benefits and competitive salaries.

How to Apply:

Interested candidates should send a cover letter, resume, salary requirements and 3-5 story clips or Web links that the candidate has written to or by mail to Stacy Palmer, Editor, The Chronicle of Philanthropy, 1255 Twenty-Third Street, N.W., Suite 700, Washington, D.C. 20037. For more information about this job opportunity and a password to the Web site, please write to No phone calls, please.

*The Environmental Defense Fund (EDF) has an opening for a part-time development writer:

About Environmental Defense Fund

With world attention focused on both the environment and the economy, Environmental Defense Fund is where policymakers and business leaders turn for win-win solutions. This leading green group, founded in 1967 as the Environmental Defense Fund, has tripled in size over the past decade by focusing on strong science, uncommon partnerships and market-based approaches. You can be part of a vibrant workplace that welcomes diverse perspectives, talents and contributions, where innovation and a focus o….more info

View all our jobs

Job Description

Development Writer (Part-Time)
Environmental Defense Fund
New York, New York or Washington, DC

Job description:
The Environmental Defense Fund is looking for a part-time Development Writer. This person must be able to present complex scientific, economic, and policy ideas in clear, lively, and compelling prose for diverse donor audiences.  The Development Writer will also be responsible for preparing proposals, reports, donor communications, talking points, Power Point presentations, brochures, fact sheets, and other collateral materials for EDF’s Oceans Program as well as other assigned program areas.  S/he will work closely with program, development, and marketing and communications staff to create persuasive fundraising materials.

This part-time position will work approximately three days 20 hrs per week and will be based in either Washington, DC or New York City. S/he will report to the Director of Donor Communications within the Development department.

— Helping to shape and articulate program work and vision for different donor audiences
— Gathering information and graphics to inform and support donor communications
— Developing and maintaining productive working relationships across the organization
— Identifying needs for new or revised materials


Qualified applicants should submit their cover letter (including salary requirements), resume and a writing sample to

Due to the volume of employment applications and queries received, EDF is unable to respond to each application individually.  Applicants will be contacted directly if selected as a candidate.

Environmental Defense Fund is an Equal Opportunity Employer.

(April 2010)


— Bachelor’s degree, Master’s degree a plus; journalism background preferred
— 3-5 years professional writing experience
— Outstanding and versatile writing skills
— Demonstrated ability to conduct research and analyze complex information
— Experience creating persuasive or fundraising communications material a plus
— Experience at a fast-paced work environment —must be able to come up to speed quickly on stories and juggling multiple assignments on deadline
— Familiarity with environmental issues and fundraising both plusses
— Motivation to develop relationships and work collaboratively across the organization

*And to wrap up today’s leads, Audionewspaper is looking for journalists to contribute to this startup; unpaid (at first they say):

About Audionewspaper

Audionewspaper is a Silicon Valley news start-up developed at Stanford by a range of experienced professionals from journalism, computer science and business. It is led by the former managing editor and GM of the Observer, the Guardian’s Sunday newspaper.

View all our jobs

Job Description

A new medium awaits.  A project to implement the world’s largest personalized audio news platform developed in the past six months at Stanford University needs up to 10 writers to work flexibly over the summer on the live daily prototypes. This is a great chance for journalists eager to explore new opportunities in an exciting but largely untapped space.

The work is unpaid, for now, but if the project gets funded by September this could be a great way to earn a reasonable living from your home wherever that may be.

The work is flexible and can be done from a home office at a variety of times.  We especially encourage currently employed journalists who are looking for their next opportunity to get in touch. We are happy to talk to you if you want to work as little as an hour a day or as much as five hours..

Your work will be credited and bylined on a website as well as providing a script for a team of newsreaders to generate content.

NOTES: 5 openings. Telecommuting is allowed. International Candidates Will Be Considered


In this early stage we are looking for quickthinking web-savvy journalists or journalism students who can…

* Make judgements about interesting stories in their area of interest.

* Find the story in multiple forms on the web.

* Summarize the coverage of the story in 250 words in an engaging distinctive style suitable for audio broadcast on our service.

* Propose and experiment with different ways of presenting audio news on the service.

* Help shape the future of the service.

Happy hunting!



Entry filed under: Uncategorized.

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2 Comments Add your own

  • 1. Maryann  |  April 27, 2010 at 6:21 am

    Oh, my. I wish people had ever asked me the “uncomfortable” question. It would SO cut out some bad things. My “ill-suited” job was incredibly ill-suited–it was night shift. I really don’t do night shift well AT ALL. And the reputation things? I haven’t dealt with any questions yet. but I suspect I know what they might be. And I would welcome questions. (Yes, I’m a less-then-cuddly b—-. Concerned? Here are refs from my reporters, rather than my bosses. It turns out they really liked me…)

  • 2. Alexis Grant  |  April 27, 2010 at 1:07 pm

    Your posts and job listings are fabulous! Saw one here today that I’m interested in that I hadn’t heard about. Thanks for your hard work!


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