WET CIGARS, POLYESTER SUITS AND POINTED-TOE SHOES — EXECUTIVES SHARE THEIR (BEST) WORST INTERVIEW STORIES

At The Alexander Group and Alex & Red, we have collectively conducted thousands (and thousands) of interviews in our three-plus decades in executive search. We’ve seen the good, the bad and the ugly, and we have shared a few of our less impressive interview experiences here—partly as cautionary tale, partly for our readers’ amusement.

This time around, we asked clients, candidates and friends of the firm to share their (best) worst interview stories. Here are the ones that left us shaking our heads, laughing out loud and nodding in empathy. Who doesn’t have a story like these?

The air up there

“As a second-year law student at the University of Chicago, I was going through the law firm interview process for the first time in my life,” shares one legal executive. “I found myself in an interview with a posh and somewhat patronizing partner from an L.A.-based firm. About five minutes into the interview, he asked me whether I was in the top 5 percent of my class. I promptly assured him that I almost certainly did not breathe such rarefied air. He then informed me that his firm’s policy was to only hire students in the top 5 percent of their class.

“Flippantly, I responded, ‘Every firm says that, but the top 5 percent of students can only be spread so thin.’ He assured me that his firm has always managed to fill its needs fishing in such a tiny pond. We then silently stared at each other for what seemed like hours, at which point I thanked him for his time, excused myself, and slunk out of the interview with 20 minutes to go.”

Right on time?

A former trial attorney turned leadership coach recalls this story: “In the days before digital calendars, I showed up for my interview to clerk for a well-known Federal Court Judge only to find that his administrative assistant had written the appointment down for a week later. She was mortified and apologized profusely. I graciously put her at ease and said I’d be happy to come back in a week. She and the judge both felt so bad, they insisted I stay and the hour passed pleasantly with repeated apologies from them and kind demurs by me.

“When I returned home, I double-checked my desk calendar—and realized that I had in fact showed up a week early!”

When HR falls over backwards for you… literally

An executive in the energy industry learned early in his career to keep his ego in check: “I interviewed with Boeing while a student at MIT Sloan (the business school of the Massachusetts Institute of Technology). I walked into the room to find to my great disappointment not a senior corporate executive but a junior HR associate. He leaned back in his chair and fell over backwards on the floor. He then proceeded to ask me some rather basic math questions, which I found insulting. I said I was not interested in any further discussions with him, and I left.” That was wrong, he admits. “I should have kept my ego in check and used the opportunity to impress him with my skills. I never repeated the mistake.”

At the wrong end of a wet cigar

“Years ago,” shares one law firm executive, “I spent a day with a firm in Chicago. I had five good interviews and one awful one—and the awful one was with the Managing Partner. He spent most of the interview pointing the wet end of a cigar at me and was highly agitated. Every time I thought I nailed a question, he just seemed more upset. I tried harder with every question to show him I had what it took to do the job. I tried to connect with him on a personal level. Nothing seemed to work. The cigar kept coming.

“I was hugely relieved when the HR representative arrived to escort me to the next meeting. The managing partner didn’t shake my hand or even say good bye; he just said good luck and turned back to his computer and piles and piles of paper.

“Just like in sports,” he advises, “you can’t let one bad play turn into a string of bad plays. You have to focus, play your game and not get shaken. If you can’t turn it around, you can walk away confident that it isn’t a good fit.”

What’s wrong with you?

An executive seeking a new position, before she landed her current position at JPMorgan Chase, spoke to the head of a contingency search firm. She relayed this conversation: “The consultant opened with, ‘Here’s the problem with you: You don’t make enough money for your level. People are going to think there’s something wrong with you.’

“I looked at the consultant from the contingency firm, knowing full well that this would be the last conversation we had, and said, ‘here’s my concern with you representing me as a candidate: If you can’t present my skills and experience (and tenure) as ‘the deal of the century, even if we all we do is bring her up to market’, then I am not sure we have anything else to talk about.’

“Needless to say, that was the last time I entertained a cold call from that firm.”

You can be too prepared

A legal executive with a multibillion-dollar corporation was interviewing with an international consumer packaged goods company for a Deputy General Counsel position. “I was so convinced that the role was right for me that, at the interview, I became deeply engaged in a conversation with my interviewers about their business issues and the legal risks associated with them. I thought we had engaged in a concrete and practical business discussion. The feedback from the recruiter, however, was that I hadn’t let my interviewers get a word—or question in—edgewise! When I returned for the second round, I was conscious of the number of questions I asked. It was a lesson to me to pay attention to the dynamic of the interview and let the interviewer guide the conversation.”

What are you implying?

An experienced HR consultant recollects one interview with the head of the legal department who also managed the HR function (always a red flag, says this consultant). “He rambled on without focus about the HR team being relatively junior, etc. etc. He then simply stopped speaking. I paused a moment and then asked, ‘Is there a question for me?’ His smug response to me was, ‘It’s implied.’

“I just stared at him and went on to discuss my approach to mentoring. I did not elect to proceed with the ‘process.’”

More best of the worst:

• A successful journalist once applied for a job with Investor’s Business Daily as a writer. The interviewer asked him if he knew what an investment banker was. He misunderstood and replied, “An investment anchor is someone that anchors all the transactions together.” It was a short interview.
• “As he entered the room,” Abby Buchold, Research Associate for The Alexander Group, recalls, “my interviewer yelled ‘just do your job!’ at a maintenance worker in the hall outside his office. I finished the interview, but politely declined to return for round two.”
• One HR consultant discloses an interview with a Vice President of HR, during which “he never turned around to look at me. I talked to the back of his chair the entire hour. He did hire me though—my first HR job!”
• Another executive was asked if she was going to work when she had kids. “I was 25 and single.”
• Our Founder and Managing Director Jane Howze remembers this early interview: “I flew into town to for an interview. Ted, the hiring manager, wasn’t there. His staff was obviously embarrassed; as one person frantically tried to find him, another tried to make up for it by saying ‘this is Ted’s office; here is where Ted has coffee every morning; here is where Ted sits in the law library.’ After two hours, I flew back home, never having met Ted. I learned later that Ted was a bit of a problem.”

Polyester and pointed-toe shoes

“When you grow up in Mount Pleasant, Michigan, your fashion choices are limited,” laughs one investor who began his career in law. “In my first year of law school, I interviewed with the big-three Detroit firms. I show up on interview day in a medium gray polyester suit, peach-colored tie, and $8 Bally loafers with pointed toes—sadly they were navy and not black or brown. On this fateful day, I’m watching my classmates in dark gray and navy wool suits, and I look like my grandpa Hanson at a funeral! I later learned from a classmate of mine who joined that law firm and saw my application, that the interviewing partner had written a big “NO” across the entire page of my evaluation form.

“I was making great grades at law school, defying the odds, but I wasn’t getting any job offers. The next year, I got smart. I went to Sears in Ann Arbor—I still remember standing at the cashier’s counter—and bought a navy-blue pinstriped “King’s Road” suit for $89 and a lawyer-like pair of tasseled loafers. That year, I got the first permanent associate offer out of Dickinson Wright. And the difference was an $89 suit.”

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Questions, we get questions. “What should I do?” “Who should our company hire?” “How should our company structure this position?”

The most important question of the week is not any of the above. Not surprisingly the question is “How can I help my son or daughter who is a recent college graduate get a job?” One recent report indicates that only 22% of college graduates have secured jobs this year. Although this is not our focus, much of the expertise that we use to recruit outstanding executive management is applicable to your son/daughter’s search. The following are a few brief recommendations.

1. The Mind Set. Finding a job is a full time job, especially in these tough times. Merely sending out three or four resumes a day will not suffice. You must act as if you have a job and you have to report to work at 8 am. The job’s location can be at a library or home office. The important thing is that you are not distracted by personal phone calls, household activities or friends. This is why the outplacement firms do well-not because they find you a job-but because they instill a discipline of going to an office where you devote eight hours a day to getting a job.

2. Have a good resume. I am always amazed at how many resumes we get that have spelling errors-and this happens with even with senior executives. Ask friends and your parent’s friends who are in the workforce for feedback on your resume.

3. Ask yourself these important questions: What do you want to do? What companies offer positions that would allow you to do this? What size company do you want to work for? What industry? What geographical location? Remember that many positions are not advertised and are found by word of mouth.

4. Once you have answered these questions, start researching. Look at business periodicals. I find the Houston Business Journal’s Book of Lists is an amazing resource because it lists a number of different types of companies-those that are growing the fastest, pay the most, are the nicest places to work etc. Most other major cities have these books. They are a good investment. Fortune, Forbes, Business Week and local papers also have articles that talk about notable companies.

5. Once you have found companies you would want to work for, write or email them a concise letter along with your resume. In writing the letter, do not address it to “Dear Sir or Madam” or “to head of Human Resources”. Do your research and find out the name of the President of the company, the head of human resources or the department in which you would want to work. Always use a middle initial and his or her exact title. That shows that you are detailed and resourceful.

6. The most important part of any job search for a college graduate or anyone looking for a job for that matter: Network, network, network. Do not be afraid to ask for help. If you went to a certain college, get lists of alums that may be working at companies you are interested in. If you are a member of a certain fraternity or sorority, see if you can find alums at those companies. People are usually happy to do a favor for someone they have something in common with. Use sites like LinkedIn to add your own contacts. The more contacts you have, you are connected to the contacts of those contacts. Remember also to return the favor. It is the law of karma….what you give comes back to you again and again.

7. If you are a parent, do not micromanage the process. Be supportive without asking “how many resumes did you send out today?”

In summary, getting a job is a numbers game. Do you have to make ten calls, or ten thousand calls? Assuming it is 10,000 calls, the faster and more disciplined you are, the faster you will get a job.

June 12, 2009
Follow Up to “The Most Asked Question of the Week”
Wrapping up last week’s blog by answering a few of the many questions we got to help the children of our clients who are graduating from college and who do not have jobs Thanks so much for your response to our first blog.

Hi, thank you very much for the suggestions you posted last week. They were suggestions that I was able to pass along to my daughter. How can my daughter find a headhunter to help her?

Posted by: Paula Finlay June 11, 2009

First, it is helpful to understand how headhunters are paid. They typically earn a percentage of the first year’s salary (usually 20-30%) of the candidate they place. There are not many headhunters that will find a new college graduate a job because the fee would be so low. As one of our bloggers mentioned in an earlier post, graduating engineers can sometimes find a headhunter to help them. But aside from that, I’m not a big fan of using headhunters to find you a job. I think it builds character when someone can go out and determine who they want to work for and try to get an introduction. Secondly, many corporations simply cannot afford to pay fees these days and given the huge number of people competing for the same jobs, they don’t have to. Thirdly, if you don’t know the headhunter well, you really don’t know how he or she is regarded by some companies. Better to represent yourself.

How much should I be willing to help my college graduate in his job search?

Posted by: Matt Conroy, June 11, 2009

Parents can help by looking at a resume and offering suggestions, if asked. In this economy, if the parent has contacts that will open doors, he or she should use them. Just don’t fall into the trap of being responsible for all of your child’s job leads. People who really do the work to find exciting companies that are hiring, get interviews and eventually jobs, will build a sense of self esteem that is important as one enters the business world. If your child does meet with your professional friends, make sure he or she writes thank you notes.

Loved reading your ideas last week but my son wants to know what else he can do.

Posted by: John Hurwitz, June 11, 2009

1. The government is spending a lot of money now. Search the internet to see if there are entry level jobs there.

2. Take some courses this summer at a local college to beef up your resume. For example, accounting is always good, in addition to marketing and computer science.

3. There are companies in remote parts of the country that are hiring, if you have any wanderlust, apply to them. One that comes to mind is Wal-Mart. Now Bentonville, Arkansas may not satisfy your need for wanderlust, but they are hiring. Some of the large credit card companies have operations in South Dakota.

4. Research the type of company you want to work for…forget saying “I just have to get a job”.

5. While you have the time, dare to dream about what would be the perfect company. Go to the library and research. Which are the best companies in Houston, Texas, and the US to work for? Do those companies resonate with you? If so, see if you have contacts there through alums, parents etc.

6. Volunteer a few hours a week. It will make you realize how lucky you are, allow you to meet new people, and provide a beneficial diversion to your job search challenges.

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In my 35 years of recruiting, I can’t remember a happy ending to a case where an individual resigned and then accepted a counter offer to stay at his or her current employer. Why is that? Counter offers usually don’t address the underlying reasons why people want to leave their current positions.

Individuals change jobs for a variety of reasons. Their current role may lack intellectual stimulation, career development or progression opportunities. He or she may lack a cultural fit with the manager or organization. Or the executive may be tired of a long commute or an intense travel schedule and want a better work-life balance. Compensation is usually the last reason people leave their current positions or not even a factor at all.

Compensation is usually the last reason people leave their current positions or not even a factor at all.

Ironically, counter offers are almost always only about money. Companies may match or even go beyond the new offer to try to convince the person to stay. However, most other “promises” to address the driving force behind the decision to leave are simply “false promises,” and the reasons the employee had for searching for new employment in the first place do not go away.

If the reason was cultural fit, the company will rarely change its organizational structure or culture for one person. Even if management sincerely wanted to, effecting organizational change is a challenge that takes a great deal of time and effort. If the reason was lack of intellectual stimulation or professional development opportunities, the company would have promoted the person before he or she resigned and on its own terms.

According to one 2018 survey, 58 percent of managers make counteroffers to retain employees who receive job offers from other employers. How long do employees who accept a counter offer stay with the company? “Less than two years,” was the average response, according to the same survey. Counter offers are nothing more than a quick fix—a band-aid that gives a company time to assess the situation and determine the best action to take. Ultimately, the end result is often the same: the person is replaced or leaves.

Counter offers are nothing more than a quick fix—a band-aid that gives a company time to assess the situation and determine the best action to take.

If you are the recipient of a counter offer, be aware and follow your gut. If your instinct is to leave for another opportunity, stick to your decision and go. Be excited to look ahead. Of course, resign with grace and always keep the door open, as we’ve written about before. Sideline any objections with a clear and confident explanation that covers where, when and why you are leaving. Once you make the announcement, you are basically past tense in the eyes of the organization, but you will always be remembered for how you left. Keep all bridges intact. Times have changed over the years; and it is now acceptable to return to a former employer in a more senior role after having gained additional experience elsewhere.

If you are the employer contemplating extending a counter offer, be sure to think through the long-term implications. If you really desire to retain the individual for the long term, how will a restructured role or compensation package effect the organization? Will it positively or negatively impact your succession planning process? Will it upset internal parity? Can you sincerely address the fundamental reasons that caused the person to resign in the first place? If not, then congratulate the individual and keep the lines of communication open. This way, if an opportunity presents itself at some point in the future for the person to be invited to come back, he or she may do just that.

Article updated September 30, 2019

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Our firm has just completed a two-year stint as a columnist for CIO.com (the online newspaper for information technology professionals). For our column, “The Hiring Manager,” we interviewed top Chief Information Officers from companies large and small: Starbucks and the U.S. Golf Association; new and old: Facebook and The Harvard Business School; fun and not fun: Harrah’s Casino and MD Anderson; flying high and digging out from a low: US Air and AIG. Collectively, these executives have hired thousands of managers. We asked them, “What have you learned about hiring?” “Can you teach someone how to make good hiring decisions?” “What can you share that would help a job seeker in today’s market?” And, “What was the worst interview you ever had?”

For those looking for the one piece of advice that may land you that coveted job, these may work:

• Every CIO commented that he or she is impressed by candidates who not only do research on the position and employer, but also show they care about the position. “I want someone who realizes that it is important to understand our company so that person can maximize the interview time for himself or herself and me,” said one CIO. Another instructed candidates, “Come prepared with good questions: ‘How do you measure success?’ ‘How do you like to manage?’ ‘What are your priorities?'”
• Prepare for questions you may be asked. For example, if you have had a number of job changes in the past several years, expect to be asked about it and have a concise, well thought out answer. If there are projects or departments you have managed, be prepared with numbers to back up your accomplishments without being boring. The goal is to strike a balance between offering substantive facts and not inundating your interviewer with number overload.
• Dress appropriately. While this seems like a no-brainer, many CIOs counseled that showing up overdressed can be as bad as dressing too casual. One CIO commented that his software company is a business casual environment, and if a candidate arrived in a suit, he would conclude that the candidate had not done appropriate research on the culture of the company. Bottom line: do not be afraid to call and ask what is appropriate.
• Read your audience. In addition to being prepared, read the body language of the interviewer and observe the details. Some interviewers like to make small talk as a way of getting to know you. Is the interviewer’s office filled with pictures and memorabilia? Most people put pictures on their walls as a statement about who they are, where they have been, what they do. Don’t be afraid to comment on them, especially if it allows you to establish a common ground. The second part of reading your audience is to let them direct the conversation. Some interviewers are comfortable spending 15 minutes discussing your mutual love of golf and their golf trophies, while others would see that as excessive. Good interviewees follow the lead of their interviewers.
• Use your interview time wisely. One of the biggest mistakes interviewees make is to take too long to explain accomplishments or answer questions. One CIO always asks candidates to give her some context to their resume. She says how candidates answer this question tells her how they budget their time, what is important to them and how they communicate. She advises candidates to ask, “Will you tell me if I’m giving you too much or too little detail?”
• Ask for feedback. Several executives commented that they are impressed by the candidate who, at the end of the interview, asks, “How do you assess my background in light of the requirements of the position?” If you do ask for feedback, do it in a confident, yet non-threatening manner.
• Thank you notes and follow up. While most executives conceded that a thank you note will not alone get someone a position, all agreed that it did not hurt. One executive recounted an instance where the candidate was not qualified for a position but wrote such a gracious thank you note that the CIO kept it, and when a different position arose, contacted the candidate for the position.
• If you do not get a position, ask for feedback on your interview from the HR department or the search firm. Interviewing is an art and a skill. Use each interview as a learning experience. The interview that did not go well can be a great lesson for the next interview.

Last week, we covered five tips for first-time board members who are preparing for their first board meeting. There is a lot to learn—both about the company and its culture, as well as the board and its culture. Continuing last week’s column, here are more suggestions on how to be an effective, productive part of a company’s board.

6. Be prepared

Study and assimilate each meeting’s materials that the company has sent you, and do so before the meeting. Don’t use meeting time to read materials you had received in advance. It will be embarrassing for you and annoying to others if you appear inattentive and disinterested, or if you ask a question that was answered in the board materials. Be attentive during meetings—listen, observe and think.

7. Observe and use your wisdom and instincts.

Directors should exercise their wisdom. Being wise involves more than intelligence and good instincts: it requires knowledge, experience, observation, and assessment. This combination of skills and talents produces judgment that, over sufficient time, can lead to wisdom. You have already developed business acumen, but to become a wise director, you must learn how to hone your observation skills.

A wise person once said that you have two eyes and ears, but only one mouth; use them accordingly. Listen and observe at least twice as much as you talk. This is particularly applicable for your first few board meetings, when you are learning not only about the company, but about how the board works in practice—the personalities, the dynamics, and how the directors interact with each other and with the executive team.

Observe the board’s social culture, that is, the relationships and interactions among directors, themselves, and with the company’s management. What are the board’s unwritten rules and traditions? Does it have a developed “style” or way of conducting its business? Just how formal or informal, courtly or direct, are these interactions? A board’s social culture can vary greatly by industry, geography, and the company’s age. A Silicon Valley tech company’s board may operate and interact much more informally than a hundred-year-old northeastern industrial company’s board.

Do directors seek consensus, or do they move rapidly to a vote? Are there factions on the board? There can be, particularly when various constituencies like unions or large shareholders have won representation. If the board is consensus-driven, think about how you can use your facilitation skills in helping arrive at consensus; if it is decision-driven, think about how you can help sharpen the issue and state the question.

Remain observant before you enter and after you leave the boardroom. Many boards have a directors’ dinner prior to the board meeting. Do they use the time to discuss business or is it more about building relationships? One new director of a manufacturing company got off on the wrong foot by monopolizing dinner conversation talking about his gun hobby when the board typically used the board dinner to continue discussing company matters. He should have listened before “pulling the trigger.”

8. Understand your role, the board’s role, and management’s role.

A common mistake that new directors make is not knowing the difference between management’s role and the board’s role. We all know that officers manage a company and run its operations, and that directors oversee management on behalf of the shareholders and authorize and approve certain actions as law or stock exchange rules may require. Your questions and comments should reflect that you are performing this oversight role.

Directors are elected by the shareholders to represent the shareholders’ collective interests—not the interests of the CEO and not the interests of any particular shareholder or group of shareholders, with some rare exceptions. Again, your questions and comments should reflect that you are performing your oversight role on behalf of all shareholders, and not any particular faction or constituency.

While we are on this subject, one gripe we hear from senior management is that some board members try to foist their friends who are consultants or attorneys on the company when not requested. One CEO complained about a board member who asked management to meet with management consultants to whom he owed favors. These special favors waste management’s time and are not needed and inappropriate. Similarly, don’t recommend friends, contacts, or family for positions with the company unless asked.

9. Don’t point out every inconsequential error.

As a board member, you will be bombarded with information, data, and reports. Inevitably, you will find a few typos or numbers that don’t match up. Avoid wasting time by bringing up every mistake that you encounter. “Senior management is under a tremendous time pressure to get these board packages out, and they’re usually voluminous,” an experienced board director told us. “There are going to be inconsistencies in the data between when the CFO put his page together and the COO put his page together.” Focus on what is material, and don’t dwell on the inconsequential.

10. Ask for a mentor.

Many boards offer a formal on-boarding program and orientation for new board members. If your board does not have one, ask the Chairman, Lead Director or Chairman of the Nominating & Governance Committee for a mentor to help you assimilate quickly into the board.

11. The company’s employees are not your employees.

When you ask management for something—especially when it is for you—be cognizant of what you are asking for. Is it important to you performing your role as a director? Is it time-sensitive? Realize that management drops everything when directors ask for something. Be sensitive to their time.

12. Be available, and be of service.

One of the most common complaints we hear about board directors is that getting them together outside of scheduled board meetings can be like “herding cats.” Many board members are retired and serve on other boards, while others are still working. Everyone has demands on his or her time, but to be a successful board director, you must be available and responsive outside of meetings. Your responsibilities to the company shareholders and the board do not end when you walk out of the boardroom.

Likewise, don’t be afraid to go above and beyond the call of duty. One CEO raved about his new director because the director had asked if he could visit stores with the CEO after the board meeting. Another new board member of a company that was making a major acquisition told the CEO that if it would be helpful, she would be pleased to meet with the management team to share her experience with a similar type of transaction. As a board director, seek out ways to demonstrate that you are engaged and committed.

Continue reading for more expert advice on effectively communicating as a board director.

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Over the years, we have definitely seen our fair share of wacky interview questions here at The Alexander Group (TAG). Some, like the client who asked business continuity candidates how they would keep their lawyers in the building following the recent East Coast earthquake, are spot-on and give real-life examples of how the candidate deals with stress. Others like, “If you were shrunk to the size of a pencil and put in a blender, how would you get out?” (reportedly from Deloitte), seem just a little less relevant.

We believe by asking the right interview questions, an employer can avoid some of these hiring mistakes by getting a picture of who the candidate is at their core and how well they will be able to become an integral part of your organization. Here are a few of the basic questions we often ask and we recommend to our clients in order to avoid one of those dreaded hiring mistakes.

1. What three adjectives best describe you? This simple question can provide speedy insight into how a candidate operates (or how they would like to operate). Not only will someone list whatever they believe are their most impressive attributes, you’ll also get the ones that come to mind first. Did they say they are inclusive? Decisive? Purposeful? As a firm, TAG has been asking this question for twenty years, and no one ever responds with the same three adjectives.

Depending on what kind of leader you’re looking for, this question gives quick insight into what the candidate thinks of themselves in a business setting. Watch out for the candidate who can’t come up with three words, however. We remember a candidate for CFO position with a highly entrepreneurial, rapidly growing company who sat in total silence for an entire two minutes before responding with “thoughtful” and “methodical” (well no kidding!). He then asked if he could email us later with a third adjective. Given the fast-paced atmosphere at the company, it should come as no surprise that we did not move forward with him for this role.

2. In just five minutes, tell us about yourself (and start at the beginning). We like to begin an interview with this question. It allows the candidate to hit the highlights, but if you’ve read their resume, you already know those. What the answer really tells the interviewer is how good the candidate is at listening and following direction. A candidate who actually followed your instruction within the five minute time frame is a rare gem. After all, you don’t want to be sitting there 40 minutes later, while the candidate still prattles on about their high school marching band. Having them start with their childhood may also help you understand what their lifelong passions are. We recently had a candidate whose loss of his father to a brain tumor at a young age inspired him to pursue a career in neuroscience. Understand what makes your candidate tick at a personal level, and you can get a feel for what will be important once they are making decisions for your company.

3. What is your management style? And how do you like to be managed? One of the most challenging aspects of bringing a new executive into your organization can be meshing their (new) leadership style with the existing philosophy. For example, some of my colleagues once interviewed a candidate who responded that he was not a micro-manager; in fact, he liked to spend as little time dealing with his direct reports as possible. Unfortunately for the candidate, the client’s company culture was particularly collaborative and they were looking for someone who was willing to get down in the trenches with his team. Needless to say, he didn’t get the position.

4. What has been the hardest time in your career? This is a great question to see how the candidate has been able to handle sticky situations or overcome difficult hurdles. Do they describe it with humility and tell you how they solved the issue, or do they pass the blame to others or chalk it up to circumstances “beyond their control”? A great candidate will also be able to tell you how it made them a better person and strengthened their career.

Of course, the answers to questions like these may make that hiring decision more paralyzing than ever if you aren’t quite sure what kind of person you’re looking for. While measurable skills and past career successes may be exactly what you’re looking for on paper, you’ll be back at that interview table again in a year if you can’t articulate what personality traits will be most effective in your organization.

To identify these characteristics, ask the questions above of your own organization. What are three adjectives that describe your culture? Is the structure highly matrixed or does management have more of a top-down approach? What has been the greatest challenge in recent years, and how did your organization approach it?

By recognizing how the company operates from a motivation and community standpoint, you’ll be able to identify your front-runner candidate who will want to put their whole heart into the position.

All of us have friends, family or co-workers who just seem unable to find that next position. Although The Alexander Group is not on that side of the placement business, we have counseled untold numbers of executives seeking positions. Here are six tips you can offer your friends that will make you seem like the guru of career counseling.

1. Re-evaluate your resume.

Ask friends, especially those who are in human resources or any type of writing field to critique your resume. It is very difficult to prepare your own resume. Remember that a resume should show how you made your company a better place. Hiring managers are interested in a resume that outlines not just responsibilities, but quantifiable achievements. If you have a broad background, you may need more than one resume depending on the position for which you are being considered

2. Get fit.

Once you get your resume into shape, it’s time to get yourself into shape. Use the extra time you always wished you’d had to get to the gym, the tennis court, the yoga studio, or just outside for a long walk. The benefits of a workout regimen while you are job searching are numerous. First of all, it can lend some structure to your day that you might be missing without a full time job. By marking it on the calendar, you’ll know you have something you can plan your day around. Secondly, getting those endorphins going will reduce your stress and provide a boost to your mood. Last but not least, the physical benefits of getting in shape will make you feel strong, confident, and increase your self-esteem during a challenging time. Working out and making sure you have a strong body is one thing you can control when other parts of your life are unpredictable.

Use LinkedIn.

LinkedIn is a tremendously important tool for many career-related purposes: getting new business, checking references, following particular companies, locating people from your past. Many believe that it is enough to be registered on LinkedIn. Not so. As we’ve written about before, anyone seeking a new position should have a picture, a fully completed profile and should be aggressively adding contacts.

We recommend spending a minimum of 30 minutes to an hour of each day reaching out to potential contacts such as search firm professionals, past and present business contacts, former managers, classmates, friends, etc. Additionally, add a couple of recommendations from past managers or co-workers and join academic and/or corporate alumni groups. Spend time examining the connections of your contacts. Do any of your current contacts have friends who could possibly help you? Use Google to find articles on how to use LinkedIn in your job search. If your job seeking friend cannot do all of the things mentioned above, then they are running a race blindfolded.

Understand what recruiters can and cannot do.

Most people misunderstand what recruiters and executive search professionals can and cannot do for them; this is especially the case for retained executive search firms. We often hear complaints from job seekers that Korn Ferry, Russell Reynolds—and any other retained firms you can name—refused to meet with them. But please understand that there is a distinction between recruiters and headhunters. Headhunters represent candidates. Recruiters represent the hiring organization and—in the case of a retained search firm—are retained to identify and recruit talent for a specific position. Given a choice between meeting the needs of an existing client, meeting with a prospective client, or advising a job seeker, most of the time, job seekers come last.

There is an exception to this rule: If you or your company had a relationship with a search firm before you were unemployed, then the above should not apply. Search firms are interested in relationships, and if you have given a search firm business, don’t hesitate to ask them for help reviewing your resume and introducing you to other partners in their firm. They owe you. And if a retained search firm has helped you, don’t thank them by referring all of your other out-of-work friends to them. Thank them by telling them that, once you get a new position, they will get your first search.

Be your own headhunter.

Encourage your friends to embrace introspection, research and responsibility. If you could design your own position, where and what would it look like? Can you think of specific companies that attract you? Do you know anyone at these companies? Some will say “I just want to get back to work again”. But, if you are not working, why not spend time thinking about and researching what type of company would be a fit for you. After all, who knows what makes you happier better than you? Job seekers must assume responsibility for their job search, at least in terms of being clear on what they want. Don’t assume a new position will fall into your lap. Do not be afraid to send your resume directly to the president or board member of the company. It may be better received coming from you rather than a recruiter.

Don’t get discouraged.

It is hard not to get discouraged, believe that your networking efforts are not working or, worse, take the rejection personally. As an old friend said to me, “There have never been two winters in a row.” Nothing lasts forever—including your current job (or unemployment) stress. Approach your search for a new position as a gardener approaches planting flowers. Not all flowers or leads may bloom. With bad weather conditions (i.e. the economy), maybe only one flower or lead will bloom. But, this should not stop you from continuing to plant the seeds or reaching out to new contacts because it only takes one for a new opportunity. The next contact you make may be the one.

Ask for help—both personally and professionally. Many find it hard to reach out and say “I’m struggling and feeling despondent.” They think it denotes weakness. Force yourself to reach out to friends for reinforcement and encouragement and vow to yourself that you will give the same support to others. You cannot get what you don’t give.

Strategist. Gatekeeper. Advisor. These aren’t just buzzwords for resumes or LinkedIn profiles. They are the critical duties of a role becoming prevalent in the C-Suite.

TV shows like “West Wing” and recent turnover at the Presidential level have attracted national attention to the role of Chief of Staff. Once primarily a government or military role, Chiefs of Staff (COS, for short) are beginning to appear on the rosters of non-government organizations. The trend began in the tech industry about five years ago as many former government officials left D.C. to join Silicon Valley startups.

“I first saw the role emerge more than 10 years ago in the financial services space,” says Jane Howze, Managing Director at The Alexander Group. “Larry Green held the title at Tudor Pickering Holt & Co. for six years, working side by side with President and Founder Dan Pickering.”

Today, the role has spread into banking, arts, professional services firms, and media. Warren Buffett has a Chief of Staff, as do Amazon’s Jeff Bezos and Merck CEO Kenneth Frazier. Venture capitalist Peter Thiel’s COS famously went on to become Chief Technology Officer of the United States.

Demand for transparency, corporate accountability and the rise of social media mean that many chief executives are becoming more like politicians or public personalities, spending more time connecting with the public and media. Chief executives need a way to offload the work that isn’t getting done. Enter the Chief of Staff.

A springboard to the C-suite

As a researcher for an executive search firm, I often identify Chiefs of Staff as potential C-suite candidates: Chiefs of Staff learn first-hand what it takes to run and grow a business, and the experience can accelerate their careers. They have valuable operations, financial or human resources experience—or all of the above—and make excellent candidates for Chief Operations Officer, Chief Strategy Officer and many other C-Suite roles, depending on the search.

Chief of Staffs are also highly influential: This influence has helped women and people of color in the role forge their own unique career paths. “They are being positioned as the next wave of C-Suite executives themselves which is really exciting,” says Caroline Pugh, COS to President of CareJourney. “The chief of staff role could be the very role that finally evens out the gender disparity in boardrooms.”

Karen van Bergen, former CEO of Omnicom Public Relations Group, spent three years as Chief of Staff to the President of McDonald’s Europe before she advanced to the CEO role. Today, she serves as Dean of Omnicom University, the holding company’s long-standing management development program. Kathleen Lynch joined UBS Group Americas as Chief of Staff and a strategic advisor to senior management; today she serves as Chief Operating Officer.

”It’s the best leadership course you could potentially take,” said Nate Jenkins, Chief of Staff to Founder and Chief Executive of Sidewalk Labs, Daniel L. Doctoroff. “I am expanding how I both take in information and make decisions.”

What are typical responsibilities?

Beyond being the chief executive’s right hand, a COS will likely take on a specific focus while acting as a trusted partner for the chief. Sound ambiguous? “No Chief of Staff is the same,” according to Scott Amenta, another Chief of Staff profiled in a recent New York Times article. Dennis Yu, Chief of Staff at Chime, described the role as a “foil to the principal”. Like a weird kind of work twin? “Yes,” he replied.

Maggie Hsu, former Chief of Staff to the Zappos CEO, describes the variety of responsibilities a Chief of Staff may take on:

• Administrative. These could include scheduling and planning meetings, attending along with the executive to take notes, and later following up on post-meeting action items. They may coordinate the executive’s calendar, keep critical contact information updated, and help them prioritize their tasks. It is important that a COS be organized, efficient and flexible.
• Project management, such as tracking important initiatives, keeping stakeholders updated on a project’s status, and managing project teams. An ability to build relationships between business units is an important skill for a COS focused on project management. It is also important to be able to track the full lifecycle of a project from start to finish while keeping an eye on the big picture.
• Financial. This could include running the budgeting cycle, conducting quarterly business reviews, preparing for board meetings, tracking financial metrics, or evaluating investment opportunities. This blend of administrative and strategic duties is a common task for a COS.
• Strategic initiatives. It’s an ambiguous role and is custom-designed to fit the needs of a specific executive. As a result, the COS may take on projects that do not fit within any one business unit or function, such as developing new ideas and business opportunities, building out new functions or business units, designing function strategies, or providing decision support for stakeholders. Problem-solving skills are a must.
• Human resources. Some Chiefs of Staff have human resources backgrounds: They may evaluate the organizational structure to identify gaps, update the recruitment process, carry out diversity & inclusion initiatives, or work with the Chief Human Resources Officer to streamline HR processes. They can play a part in the people operations of a company, influencing the community culture. Being people-oriented is important no matter what duties are assigned; it is especially helpful in this case.
• Gatekeeping. Excellent communication skills are critical for this, as the COS represents the chief executive to his contacts and the public. The COS may spend much of their time fielding internal and external communications for the executive, vetting media requests, attending meetings on their behalf, and maintaining critical relationships. Excellent verbal and written communication skills are essential.

An effective Chief of Staff must be absolutely trustworthy.

Regardless of the blend of functional responsibilities, one quality trumps all others: Trust. An effective Chief of Staff serves as a trusted advisor who will represent and protect his or her executive’s reputation and serve as a trusted sounding board for politically sensitive and confidential matters. “The executive is constantly getting requests for their time, money, advice or other resources, and they need someone who can vet and respond to these requests appropriately,” says Hsu. “This requires a high degree of understanding and trust between the COS and the executive.”

Need more firepower in your C-suite?

“The main purpose of a chief of staff is to add firepower to the person he or she has been hired to support,” according to Chris Hutchins, the founder and CEO of Grove. Need that firepower in your C-suite? Hutchins suggests an organizational audit to discover what tasks are eating up too much of your chiefs’ time and what a COS could take on for her or him.

Ultimately, a Chief of Staff role will mean different things to different chief executives, and be an extension of that executive. No two are alike.

Brian Rumao, Chief of Staff to Jeff Weiner, LinkedIn’s CEO, said that while he has program management and strategic responsibilities, the role “has no boundaries or preconceived notions of how to measure success.” When discussing the details of his core responsibilities, Weiner said “The core part of the role is clearly defined. Above that, the role is ultimately what you make of it.”

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