10 Challenges Senior Executives Face in the Job Search

By Ford R. Myers
President, Career Potential, LLC

Over the course of my consulting career, I have worked with thousands of key executives – CEOs, Partners, COOs, Presidents, Senior Vice Presidents, Directors and so on. Top business professionals like these present special challenges to the Career Coach, because these clients face unique challenges in their own career transitions! As someone who specializes in working with this clientele, I have identified 10 distinct issues that senior executives usually confront when conducting a job search – and I have developed some practical, effective suggestions for each of those issues:

#1 – EGO


  • Loss of self-esteem, identity, self-worth, and self-concept
  • Embarrassment, shame, and “tarnished image”
  • Loss of control; feeling “out of control”
  • Used to making BIG decisions and having MAJOR impact
  • It can be VERY lonely at the top


  • Keep your “usual life” going (family activities, volunteer, fitness, hobbies, etc.)
  • Develop/recognize your worth OUTSIDE of the job
  • Be open to learning new things and taking small risks
  • Recognize the value and power of “baby steps” (doing the right things over and over)
  • Connect and share the experience with other top executives in transition (not isolated)
  • Ask for support!



  • Not accustomed to doing all the day-to-day administrative tasks yourself
  • Lack some basic habits/skills for details and logistics; organization of tasks, etc.
  • May be “technology impaired”
  • Must think of everything/burdened with time-consuming planning and activities that used to be handled by support personnel


  • Get over it and get busy
  • Learn new behaviors and organizational skills
  • Leverage technology and basic productivity tools
  • Respect and value the small tasks that support the whole process
  • Possibly hire someone to assist part-time, or get a volunteer to help with some tasks (friend, family member, etc.)



  • Search takes longer, and frustration can be greater
  • Simply less opportunities at this level; sometimes only a few appropriate positions open in the entire region/country


  • Expand your scope, consider being more flexible, and possibly relocate
  • Consider taking a short-term step back in order to eventually move forward
  • Explore consulting or starting/buying a business
  • Be more creative in developing your Target Company List and personal marketing plan



  • Difficult to command large salary, especially tough in a bad economy
  • May be a threat to other senior employees
  • Hiring someone at this salary level often requires many “sign-offs;” the approval process can take a lot of time
  • Bigger lifestyle and bigger bills, so pressure to earn “top dollar” is greater


  • Be prepared (create a top-notch Job-Seekers’ Toolkit)
  • Be sure you talk to the right people, i.e., the ultimate decision makers
  • Focus relentlessly on tangible results that can me measured in financial terms
  • Research the target company and talk to contacts for compensation information
  • Collect data on actual salary ranges for the type of position you are seeking (salary web sites, industry journals, etc.)
  • Do financial planning, including diversifying and developing other income streams
  • Seek flexible financial arrangements, such as an equity position, bonus income, or employment contract with bigger upside
  • Get career coaching to “practice” salary negotiation and maximize the outcome
  • Assume a “partnering” attitude rather than a “take control” attitude
  • Be realistic about what you NEED vs. what you WANT
  • Downshift your lifestyle to take the pressure off



  • Higher barrier of entry; difficult to get through senior executives’ gatekeepers
  • Human Resources is of little or no help in this regard
  • Only appropriate to speak with C-level leaders, who may feel competitive/threatened


  • Talk to hiring managers about ways you can help them reach THEIR business goals; positions are often created at this level
  • Join and participate in executive networking programs, boards of directors, and venture capital groups
  • Leverage relationships with search firms and other professional contacts
  • Use your senior-level references and referrals
  • Focus on solutions and the added value you offer
  • Call-in favors and get help from senior-level friends and colleagues
  • Develop a “Work Proposal” and quantify the real value of your contributions



  • Staff members have been “paying dues” for years at the company, and are already in line to get top jobs
  • Company does not want to take a risk bringing an outsider into such an important position
  • Employer does not want to spend the money to conduct a search for an outside senior executive, so they may favor internal candidates


  • Explain how being from the outside can be a strength; you can “broaden the gene pool” and bring a new perspective
  • Focus on companies that are open to bringing-in outside management, and that have done it successfully before
  • Target troubled companies that might need your fresh view and specialized skills
  • Leverage your professional referrals and contacts
  • Research the internal structure of a company to determine how to best position yourself



  • High-level job openings often get national exposure
  • The more desirable the position, the more people are fighting for it
  • There is only ONE President or CEO (and perhaps only FIVE Senior VPs, etc.) at each company
  • In a tough economy, top people “stay put,” so turnover is slower


  • Research a company’s culture and weaknesses; understand BOTH and sell to the company’s needs
  • Do or say something extraordinary to stand apart from other candidates; get and edge and be memorable
  • Be totally prepared. Sell yourself HARDER and demonstrate tangible business results (Job-Seekers’ Toolkit, Accomplishment Stories, etc.)
  • Do more networking with your “centers of influence”
  • Learn how to “rise above the crowd” and differentiate yourself

#8 – AGE!


  • Perceived as being too old, “washed-up” or “over the hill”
  • Fear that you won’t last long at the company, and concern about investing in you
  • This concern can be expressed in many ways (i.e., “you’re overqualified”). Listen and watch carefully for the clues!
  • Employer fears a cultural mis-match (not fit-in)
  • Many don’t have technology skills necessary to thrive in today’s work environment
  • Concern that you might not be able to keep-up with a fast pace
  • Belief that you may be “too expensive”


  • Refocus the employer on your exceptional qualifications, proven results, industry contacts, and experience – not age
  • Identify REAL issue underneath the age concern
  • Know the culture of the company: if no one there is over 35, don’t try to get hired at 64!
  • Target smaller companies that might appreciate your experience, contacts and credibility (“adult supervision”)
  • Focus on and enhance your appearance, wardrobe, physical fitness, etc. to look your best
  • Maintain/demonstrate your health, vitality, energy, and enthusiasm
  • Avoid “the R word” (retirement) in conversation
  • Be “tech-savvy,” up-to-date and informed about your industry
  • Convey your intention and commitment to stay at the company long-term
  • Provide examples of other mature employees who have made big contributions to their companies

#9 – LOCKED IN A PARADIGM (of being The Boss)


  • Losing a job at this level can be devastating (“the bigger they are, the harder they fall”)
  • Feeling “invulnerable” on the job (“layoffs won’t affect me; I am IN CHARGE!”)
  • Don’t feel comfortable asking for help
  • Have been isolated and “cocooned” or “coddled” for too long
  • Hidden fear that maybe you really CAN’T hack it on the outside (been at same company/job so long)


  • Get over the DENIAL, “roll up your sleeves,” get humble, and get busy
  • Do market testing to assess the real worth of your qualifications
  • Engage the services of an Executive Career Coach to get you on track and keep you accountable
  • Prepare a great portfolio of job-seeking tools
  • Pull your head “out of the sand” and deal with the reality of the situation
  • Rely on the ability and intelligence that got you to the top in the first place
  • Seek-out support as needed



  • Your failure seems greater – because you were higher up on the corporate ladder
  • Not being taken seriously as a job candidate (“she doesn’t really need to work”)
  • Others project their own fears onto you, so they feel threatened
  • Some people will try to shame you
  • Others are in denial or act dismissive, not believing that your crisis is real
  • People act like you’re “contagious” (if YOU lost YOUR job, then NO ONE is safe!)


  • Tell the story about your departure from the company (get comfortable with it)
  • Let everyone know that you’re OK with the situation
  • Gently “straighten people out” regarding your real situation (push back)
  • Be genuine, humble, relaxed, and real
  • Demonstrate positive attitude, faith, and perseverance in your search
  • Tell friends and family how their reactions affect you (positively or negatively)

By gaining a better understanding of the special challenges they face, and implementing the solutions outlined above, my senior-level clients have dramatically improved their job search results – and significantly decreased their levels of anxiety and frustration. More importantly, they have consistently landed wonderful, new jobs!

About the Author:
Ford R. Myers is an award-winning career coach and President of Career Potential, LLC. He is author of the best-seller, Get The Job You Want, Even When No One’s Hiring. Ford’s firm helps clients take charge of their careers, create the work they love, and earn what they deserve! He has held senior consulting positions at three of the nation’s largest career service firms. Ford’s articles and interviews have appeared in hundreds of magazines, newspapers, television and radio networks. He has also conducted presentations at many companies, associations and universities. Learn more at www.CareerPotential.com or contact Ford directly at 1-800-972-6588.

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