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10 Challenges and Helpful Tips for Senior Executives in the Job Search

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Over the years, I have worked with hundreds of key executives – CEOs, Partners, COOs, Presidents, Senior Vice Presidents, and so on. Top business professionals like these present 10 Challenges and Helpful Tips for Senior Executives in the Job Searchunique challenges to the Career Consultant, because they face unique challenges in their own transitions! Specializing in working with this clientele, I have identified 10 distinct issues that senior executives usually confront with when conducting a job search – and I have developed practical solutions for each one of them:

#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


  • Keep your “usual life” going (family activities, volunteer, sports, 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)
  • Ask for support!


  • Not accustomed to doing all the day-to-day administrative tasks yourself
  • Lack some basic habits for details and logistics; organization of tasks, etc.
  • 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 technical skills
  • Leverage technology and basic organizational 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 one or two appropriate positions open in the entire country


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


  • Difficult at all times, but especially tough in a bad economy
  • May be a threat to other senior employees


  • Be prepared (job-seekers’ toolkit!)
  • Be sure you talk to the right people, i.e., the ultimate decision makers
  • 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, directories, 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
  • 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


  • Join and participate in executive networking programs, boards of directors, and venture capital groups
  • Leverage relationships with search firms and other career 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
  • Talk to hiring managers about ways you can help them reach THEIR business goals; positions are often created at this level
  • Develop a “Proposal for Service” 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 the top job
  • Company does not want to take a risk bringing an outsider into such an important position
  • Company does not want to spend the money to conduct a search for an outside senior executive


  • Explain how being from the outside can be a strength; you can “broaden the gene pool”
  • 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 perspective 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.)
  • Leverage your professional referrals and contacts
  • 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
  • Be totally prepared. Sell yourself HARDER (job-seekers’ toolkit, accomplishment stories, etc.)
  • Do more networking with your “centers of influence”
  • Learn how to “rise above the crowd” and get an edge

#8 – AGE!

  • Perceived as being too old, “washed-up” or “over the hill”
  • This concern can be expressed in many ways (i.e., “you’re overqualified”). Listen and watch carefully for the clues!


  • Refocus the employer on your 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 40, don’t try to get hired at 64!
  • Target smaller companies that might appreciate your experience, contacts and credibility
  • Maintain/demonstrate your health, vitality, energy, and enthusiasm
  • Avoid “the R word” (retirement)
  • Be “tech-savvy,” up-to-date and informed about your industry
  • Convey your intention and commitment to stay at the company long-term

#9 – LOCKED IN 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” and get busy
  • Do market testing to assess the real worth of your qualifications
  • Engage the services of a professional Career Consultant 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
  • Others are in denial, 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 the 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 all landed wonderful, new jobs!

About Ford Myers

Career Success and Job Search Expert, Ford R. Myers

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 have appeared in thousands of publications and web sites, and he has been interviewed on every major television and radio network. Ford has also conducted presentations at hundreds of companies, associations and universities. Learn more at

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