7 Common Challenges and Tips for Executives in Transition


By Camille Block, Executive Career Coach

You are not alone. As an executive, you have made it to the peak of your career and thus, have climbed high on the professional mountain. It’s been hard work, but you’ve enjoyed building a team, a product or a skillset, and you’ve most likely enjoyed the thrill of making an impact in your daily work life.

So, what happens when you find yourself out of work due to a layoff, merger, acquisition, dismissal or even a personal choice?  Your world changes drastically, of course, and you find yourself having to navigate unfamiliar territory and learn new skills, without a clear road map. Some skills are tangible (like revising an outdated resume) and others, intangible (like building emotional resilience to ride the unknown journey ahead). For many years now, I have worked with executives – either by hunting them down as a retained executive recruiter, by coaching them as a career consultant, or by interacting socially with them as my friends, family and network. Through these experiences, I have discovered seven common challenges often faced by executives in transition, and developed some thoughts on tackling them.

1. Your ego took a blow and you are experiencing some grief.

If you have lived most of your life thinking that your job and professional title were your identity, you may now be in for a shock. Defining ourselves by our job, while common, can be disheartening when we no longer have a job. It’s often the first question asked when you meet someone new: “So, what do you DO?” And, while it may be unintentional, our egos do get wrapped up in our titles, functions, and paycheck. Without the security of a job title, our self-worth can suffer a hit. And, don’t forget it is a loss and with that, often a grieving process. Don’t dismiss this as an unacceptable type of grief.

TIP:  Remind yourself that you are NOT your job title. Your identity and life’s purpose run deeper, and grasping this is critical to keeping your confidence in check. But, also allow yourself some time to grieve the array of emotions that come with any loss, which may include shock, anger and depression before you arrive at solutions. Just don’t get stuck in the grief. You may need a short vacation, or some time to vent and process it with a good friend or career coach. Ideally, see this time as an opportunity to do some soul-searching about who you are apart from your work. For example:

  • What are you good at AND what do you really enjoy doing?
  • What problem keeps you up at night that you may want to address?
  • What makes you unique?
  • What you are most proud of?
  • Where can you make a difference that aligns with your values?
  • What do people naturally seek your advice for?
  • What regrets do you have and how can this season in your life serve as a catalyst to make some changes?

With a little time off the corporate treadmill, you may discover dreams that have been pushed aside or gain a fresh perspective shedding light on new passions. This could be a time to learn new skills, seek a healthier work environment, consult, serve on the board of a nonprofit, or own a franchise – all while figuring out next steps. Reconnect with your network and friends from the past, but also expand your connections into new industries and functions. Remind yourself that you are more than “just a job.” As recently shared by the former CEO of Intuit during his transition, make time to “Discover your why” – the purpose, cause or belief that inspires you. This soul-searching may just be what is needed to propel you into your greater purpose.

2.  Senior jobs are difficult to land.

Obviously, there is often only one C-suite or senior level job in each function at each company. But also, remember it took you a lot of hard work to get where you are, so you shouldn’t expect it to be easy to walk into a new position quickly. The vetting process is time-consuming. Additionally, your price tag is higher, there is more competition, and often you are at the stage in your life that you have a family and may be unwilling or unable to relocate. 

TIP:  Acknowledge that it is tougher and longer for an executive to land and prepare yourself for a marathon, not a sprint. A typical executive job search is six to twelve months or more, and it can feel like a marathon. So, how do marathon runners prepare themselves? I have heard from friends (because I certainly wouldn’t know) that they do at least the following: get the right equipment to go the distance; train daily as if it was their job, but intentionally integrate rest days for recovery; and take care of themselves physically and mentally to stay fit. So, how does this translate into a marathon job search? 

  • Get the right equipment – Update and optimize your marketing materials, including your executive resume, LinkedIn profile, communication strategies, and marketing plan. However, your best equipment is your personal network, which must be cultivated and grown wider and deeper.
  • Train daily but make time to rest  Think about looking for a job AS a job.  Commit to spending at least four to five hours each workday on your job search. Set realistic goals, such as making five networking calls each day, or researching three target companies each week. Yet, don’t forget to rest and recover – make some space for days that have nothing to do with your job search, to allow your mind to recuperate from the stress.
  • Take care of yourself – Eat right, exercise, be social, and keep your mind and skills sharp. Consider taking an online course, volunteer, and/or consult for friends or charity to stay engaged and current in your field.

3.  You have to become a salesperson (of yourself). 

For some, aggressively selling oneself won’t be hard – salespeople may have an edge over most engineers (yes, stereotype noted); however, it is fairly tough for just about everyone to sell themselves. Creating and delivering your own “elevator pitch” – a concise summary of your extended career, along with your strengths, skills and uniqueness in one minute – is hard for most, at least at first.

TIP:  While you do not have to be pushy or "salesy" (please don’t), you do need to get comfortable with a little humble self-promotion. There is some low-hanging fruit for everyone, especially you introverts, so don’t sweat too much. Start with your personal network and their connections/referrals. Let them know you are in the job market and the type of role and organization that would make a good fit for you and ask for the referral to someone they know at a target company for an informational interview/discussion. Also, use LinkedIn to connect authentically with others, join a networking group, and practice getting comfortable with your elevator pitch, but never let it sound scripted. Be natural. Confidently, yet humbly, with genuine enthusiasm, show others how you can make someone’s life or company better. Just remember that your authenticity is tantamount to a hiring manager’s ultimate decision. So, be yourself.

4.  Your resume is outdated, and you are skeptical about LinkedIn

At least half of my executive clients have recently left a job they held for 15-25 years. For them, arriving in the job search modern world is a bit like being dropped into another planet; the hiring processes and climate, use of robots as HR screeners, and social media tools are all brand new, and thus foreign to them. When they last looked for a job the Internet was just gaining traction, job opportunities were found in newspaper ads, and resumes were printed on cardstock paper. Often, these same executives proudly tell me, “I don’t do social media” as a reason they don’t have a LinkedIn profile. Understandably, they don’t grasp the powerful professional tool it can be.

TIP:  Get some help in creating a fresh, modern-looking and functional executive resume. While it seems straightforward, there are nuances that turn it from “it will do” to being “a real standout.” It should be accomplishment-focused, able to get past scanning machines to a human being, and contain a short summary highlighting your “professional brand.” Recruiters use LinkedIn about 97% of the time to find their perfect candidate, so it cannot be skipped. It should represent not only your past experiences, but also your overall professional brand and unique skillsets, sprinkled with a personal narrative, which is a different flavor from a resume. These days, LinkedIn is often the hook that leads the recruiter to the resume.

5.  You are worried about the perception of others.

It’s emotionally exhausting to come up with a good answer to “What do you do?” and “Why did you leave your company?” every time you meet someone. You know it is important to come off positive and confident, but it can be draining and perhaps feel embarrassing, especially if you left your job some time ago. You may worry about how you are being perceived, or even worse, feel like people don’t really understand the personal and financial crisis you are in.

TIP:  While we can’t control how others think, we certainly can work on controlling our thought life. Brené Brown, well known Ted Talk speaker, author and researcher on shame and vulnerability, teaches about the “stories we tell ourselves” that are not based in reality. Often, we waste mental energy on these contrived thoughts, zapping our confidence at a time we need it the most. However, it is still wise to address these POSSIBLE perceptions head-on to increase your confidence and remove these mind-gripping worries as potential barriers. A well-articulated and authentic “Exit Statement” – why you left your last job – is an example of how to do this. Keep it short, positive and real with a quick pivot towards what you are looking for now and how you can benefit your next employer. This quickly addresses the “elephant in the room” (i.e.  Why were you laid off – were you fired for cause?) and allows you to clear the way to focus on the more important task of networking for your next role.

6.  Ageism: you believe it’s happening

Let’s face it – you may be right that your age may be a factor in the recruiting process, although it will never be stated or truly known. Playing the victim to this theory will only make matters worse and reinforce stereotypes. While it can be an unstated detriment to be more senior for many jobs, qualified executives can often bypass this concern.

TIP:  You cannot control or hide your age (you can try, but good luck -- recruiters can sniff this out so no need for keeping that 15-year old wrinkle-free picture online). So, what CAN you control?  For starters:  your energy level, attitude, messaging, curiosity, agility, innovative forward-thinking mindset, as well as your up-to-date knowledge of technology and emerging markets. These are the skills that often counter any unstated age concerns. However, to be wise, remove any areas that scream “I’m old and past my prime” such as dates on resumes past 15-20 years; poor resolution and outdated pictures with old hairstyles and large shoulder pads; resume formats with an “objective” statement, and any words like “retired” or “seasoned.” 

7.  Your spouse/partner questions your progress.

I’ve been on both sides of this one. Many of my clients confess one of their biggest sources of stress is having to answer the daily questions from their spouse/partner about “How many people did you talk to today?” or “How many jobs did you apply to?” or “Have you heard from the recruiter yet after your phone interview?” Not only are the jobseekers stressed, themselves, but now they also feel the need to manage their spouse’s anxiety and expectations.

TIP:  While it’s tough being the one in a job transition, it is also not easy to be the spouse/partner of the jobseeker, as they often share your anxiety, yet may feel frustrated with being unable to help. It may be no surprise, but spouses/partners are usually not the best people to hold you accountable for staying on the job search task as it can invite unwanted tension. Setting some friendly ground rules about family conversations may be helpful to reduce this stress. For example, consider limiting daily questions with the understanding that you agree to update your spouse with anything significant. This will increase trust, reduce anxiety, and ensure some normalcy at home. Additionally, I suggest you find a peer/friend/business mentor – perhaps someone in a similar situation, or who has been through it before – to be your peer accountability partner. Two executives I know set up weekly Monday morning coffees to discuss networking goals and search progress, and it proved to be motivating and effective. 

Similarly, joining a networking group can be a great forum to give you outside input, referrals, new connections, and also provide you opportunities to help others -- all productive uses of your time and inadvertently, takes the pressure off of your spouse/partner.

In sum, being an executive in a job transition is not easy, yet it can also be a transformative time both personally and professionally. The key is to manage the challenges with stride, remember who you are at your core, keep your perspective, and invest in the tools you need to bridge the gap from where you are to where you want to be.

Camille Block is an executive career advisor and coach who helps clients in a transition to simplify and accelerate their job search, both at Lee Hecht Harrison and her own personal consulting business, Connectivity. With a background in executive recruiting and sales, she is known for her high touch, concierge-style consulting approach to all aspects of the career search process including personal brand marketing, resumes, working with recruiters, LinkedIn profile makeovers, and strategic networking and interviewing to land the job. For more information, see www.connectivity.cc or contact Camille at Camille@connectivity.cc.