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.”

ALL ARTICLES

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.”

We’ve had numerous opportunities over the years to conduct searches for executives who will be replacing a retiree, or soon-to-be retiree. The process of retiring can be awkward for both the retiree and the company. As is true with most things in life, there are no absolutes, and every organization must determine the best plan for everyone involved.

Not surprisingly, when exiting executives can’t wait to hit the door—whatever their reasons—it makes for a crisp transition. Conversely, when retiring executives don’t have a plan for their new life in retirement, or worse, they don’t want to retire, the change of control can be difficult for everyone, at both a professional and a very personal, emotional level.

Timing

No two clients handle the setting of an executive’s retirement timetable in the same way, and we hear strong opinions about timing formed through experience in the trenches.

Two weeks? Too fast. Executives tell us that there simply is not enough time to even learn what questions to ask, much less absorb the knowledge dump in that amount of time, even when those leaving remain available.

An extended transition, while seemingly well-intended, creates more problems than solutions.

Two quarters to two years? Too slow. Many times, an extended transition, while seemingly well-intended, creates more problems than solutions. For one, the retiring executives must continue to find ways to remain relevant to the organization and validate themselves and their (usually large) paychecks. Perhaps more critical is the impact such delays have on the troops who are uncertain about to whom to look for directives and leadership. Despite everyone’s best intentions, employees will most often pursue familiar routes of problem solving and communications until forced to do otherwise.

That said, a longer transition can help, especially when the outgoing executive is able to manage certain matters while the new executive deals with bigger issues, like getting up to speed on the organization, its business strategy, its people, and its potential needs.

Worst case? Undefined transition schedules that leave the organization in a state of limbo. A mandate for change can be made especially difficult when the creator of those policies and procedures is still around. If the trains are running on time, installing a new leader doesn’t imply wholesale change. Either way, the ambiguity creates a tightrope upon which the entire organization is perched, trying to balance potentially competing loyalties, questions about authority and chain of command, and employees’ uncertainty about their own future vis-à-vis the organization and their new manager.

Undefined transition schedules leave the organization in a state of limbo.

Just right. We have found some consensus indicating that a one- to two-month transition period is just right. This seems to allow for both the outgoing and incoming executives, and the people on their teams, to implement an effective, efficient, and respectful change of control that honors the contributions of those leaving while conferring credibility on the new leader.

Announcing the transition

How an organization handles the messaging of retiring executives and their replacements seems to play a significant role in how smoothly the transition occurs. One major corporate client begins planning at the highest levels six months before the selected retirement date, makes a formal announcement two months out, and then the retiree is gone. Some organizations prefer to ease the executive into retirement, being careful to not offend anyone or intimate anything less than a stellar performance by the retiree, and a longer overlap is often viewed as more appreciative of their contribution.

So much seems tied to the frequency with which an organization may deal with these situations. Generally speaking, larger organizations have standardized procedures and smaller organizations almost have to reinvent the wheel each time.

Consider the future

Interestingly, a couple of themes consistently surface as we speak to both outgoing and incoming executives: (1) treat people with respect, and (2) remember that this is just one piece of a continuing story.

They express it in various ways: what goes around comes around, karma, the Golden Rule. Call it what you will, the message is clear: We would be wise to remember that we will all be the retiree someday.

The company culture conversation isn’t anything new, but as employment rates stay low and the remote versus in-office debate volleys back and forth, it’s a discussion here to stay.

Intentionality is at the core of building company culture; sometimes, the strongest advocates for culture come from inside the building. Often, the best response leadership can give its employees is to listen and empower employees to suggest and implement plans. This approach isn’t just about the warm fuzzies; Gallup reports an eighty-five percent net profit increase over five years within companies that build a strong culture.

So, what does this look like in a real-time, tangible way? With offices and time zones spread across the country, The Alexander Group, like many other professional services firms, asked the same question, with leadership actively listening and welcoming ideas.

The results?

Well, for one, you will find most of us gathered or in front of our computers the third Thursday of every month for happy hour, a 60-minute opportunity to chat, laugh and discover new things about each other. The Alexander Group’s Anthony Ott spearheads the monthly event, drawing from experiences at a former employer.

“We have our heads down, working so hard that it’s nice to take a breath and get to know each other better,” associate Anthony Ott said. “We talk about non-work things and that helps build camaraderie, empowerment and trust.”

Ott uses an app that randomly selects the various groups each month, making sure at least one member of leadership is included, supplying the teams with ice breakers, trivia, quizzes and other conversation starters should they be needed. The Alexander Group is a gregarious bunch, so while the trivia has largely gone untouched, the spirit behind happy hour is thriving. The four to six people per group allows for conversation in a small setting, which is also by design.

“Having a small group is more conducive to really talking with each other. It allows us to see another side of a co-worker they may not normally see because we’re in a work mindset,” Ott said. “We all have a common denominator, and this gives a chance to expand culture and team building.”

Sociologist Tracy Brower studies work-life happiness and fulfillment and calls this “Social Capital,” the ability to form fulfilling relationships, generate new ideas and ask advice for how to get things done within the organization.

“Strong cultures also have intricate webbing of social capital—the networks of people across the organization. To maintain positive cultures in hybrid/remote working situations, leaders need to be intentional about encouraging people to build their networks,” Brower said. “They can do this by connecting people across departments, providing for cross-functional learning opportunities and creating time for people to have virtual coffee or networking discussions with colleagues across the company.”

The happy hours are in addition to monthly catered lunches where staff is encouraged to catch up over a meal, group outings to play darts or Top Golf and annual company retreats. Many of The Alexander Group team members, including managing director John Lamar, are based in California, so the West Coast contingent makes it a priority to gather in person a few times a year.

“It’s so much fun to meet in person, give them a hug and spend that time together,” Ott said.

A by-product of leadership-supported gatherings is the framework of a safe space to exchange ideas and encourage mentorship. Employees who know they are seen and heard feel valued, and that means greater staff retention.

McKinsey & Company study authors Terra Allas and Brooke Weddle say connection building helps meet the psychological and emotional needs of employees. They suggest setting up regular/daily meetings at the beginning of each day, allowing time for socializing and creating regular events to build social connections. McKinsey research shows society is a key source of meaning for employees, along with company, customer, team, and individual.

Indeed, that is what Pax8 CEO John Street finds with his employees. Street prioritizes inclusivity within his company, connecting every day with someone on his staff in a meaningful way.

“Creating a feeling of belonging locally, regionally and globally is priceless, and sustaining that feeling requires an inclusive approach and active commitment from leaders. For example, I make it a practice to call one employee each day and ask, “What’s going on in your world? What are you thinking about?” These discussions help me signal to every employee that they belong and are valued,” Street said in a January 2023 Forbes Magazine article. “Embedding inclusion and belonging is a core tenet of employee recruitment and retention.”

Indeed, Ott, knowing he was heard and supported by leadership, was motivated to expand the social capital plans at The Alexander Group. Next steps include one-on-one exchanges where team members can dedicate time for business development, marketing and organizational ideas and a quarterly exchange of constructive firm-wide suggestions.
“Empowered employees feel like they have a voice. We all come from different places and have different ideas. We all have something to offer,” Ott said.

Street has also found an energized employee base by listening to his staff. They feel encouraged and see themselves rising within Street’s IT company.

“When employees know their voices are being heard, they not only feel engaged but are actually engaged. Innovations rise to the top, and the individuals who bring great ideas to the table often become future leaders in the organization. Because they deeply understand the importance of being heard, these new leaders will then continue to prioritize listening to team members. Leaders can encourage employees to speak up in a variety of ways, like physical or virtual suggestion boxes, surveys or simply asking them directly,” Street said.

Every company is different, so if happy hour and axe throwing aren’t exactly the social experiences your team would appreciate, human resources expert Renee Cocchi says what’s most important is choosing activities that will help teams get closer to each other, be happier and more comfortable in the workplace so they can produce their best work. Planning to get social? Cocchi offers these tips when adding events to the culture-building event calendar:

Clearly communicate the goals and purpose of the activity
Encourage participation and collaboration from all team members
Make the activity fun and enjoyable, but also challenging.
Follow up on the activity to discuss any lessons learned and how they can be applied in the workplace.