The Special Issues of Career Transition for Senior Executives–Raymond P. Harrison, Ph.D.

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Senior executives don’t get to their positions of leadership by accident. Unless they have inherited a company, senior executives are not like the rest of us. The fact that they have ascended to the highest levels in their organization is a testament in itself that they have passed numerous hurdles and filters to become a member of a very limited and elite group of people.

Although there are exceptions to every rule, certain characteristics show up again and again among the senior elite:

  • A large part of their personal identity is tied to the job
  • Their reputation is important to them
  • As a group, they have higher than average levels of energy and work long hours
  • They are proactive, not reactive to events
  • They like to direct things
  • They like to direct others
  • They are ruthless in their choice of subordinates based on performance
  • They are competitive and keep score by comparing themselves to others in terms of compensation, scope of responsibility, title, career progression, etc.
  • Their families, particularly spouses, often bask in the glow of their status and success
  • They are usually well networked and well known in the industry in which they work
  • They “put their stamp” on a business while they run it
  • They exert a profound influence on the culture of their immediate team and often the larger organization
  • They are concerned about their legacy after they leave a business
  • For many their financial pressures may not be as great, but the professional pressure to continue to do something of significance will be important
  • They have a wider array of career options than others
  • A wider array of career options also translates into more complex career decision making
  • The “fit” between the executive and the culture of an organization is even more critical than usual for that executive’s success.

Any review of senior leaders will find a spectrum of other psychological characteristics. One will find introverts, extroverts, detail-oriented managers, “big picture” managers, tacticians, strategists, the brilliant and the not-so brilliant. But unless someone inherits a business the bullet points above are shared characteristics of most seniors.

It’s those bullet points that make career transition especially complex and the nature of a job search different for senior executives than it would for mid-level executives. Regardless of whether a senior executive is leaving a position because they have been fired, retired, become redundant through a merger or acquisition, or just decided they want to do something else with their life, certain features of the job search are different for senior level people.


One could argue that assessment is critical for anyone engaged in career transition. But because of the elements listed above, assessment is even more critical for seniors. And within the assessment process, certain dimensions are more important for them than mid-level executives.

All job requirements boil down to three issues: “can do,” “will do,” and “fit.”  Can do means can the person do the job? Does he or she have the requisite knowledge, intelligence, experience, competencies to do the job.  Ironically, most of the time in senior level jobs, can-do is of less importance. This is because seniors are not expected to do much if any hands-on work. In fact, sometimes being too knowledgeable or hands-on can be a hindrance. Their primary task is to provide leadership and to build a highly effective senior team that can do the work. All other things being equal, it’s nice to have a dynamic, visionary leader of an organization, but the truth is there are many successful organizations with leaders of only modest abilities. What is more important is that he or she can assemble a group of qualified and diverse individuals, build them into a team and then foster a team culture that fully leverages the collective intellectual horsepower of that team. There is actually a good deal of research evidence that suggests that organizations led by charismatic, heroic style leaders do not do as well over the long run than organizations run in a less flamboyant way.

Will do is the dimension of motivation. Does the executive really want to do the job? Given the large expenditure of energy a senior job entails, particularly in the first several months, the executive needs to be enthusiastic about the position. What will motivate a particular executive is a function of their underlying value structure. And values change over time and situation. Things that motivate a person in the early stages of their career may be quite different at later stages. While compensation typically is an important consideration at all stages of a career, often for senior executives, it can become less important than factors like recognition, challenge, legacy-building, becoming a mentor to others, being a statesman for your industry, creativity or altruistic contributions.

Fortunately, there are very good methodologies available today to tease out the motivational factor. A well tested method is to engage an exercise called “Motivated Abilities.” This is a simple process of systematically looking at those achievements in an executive’s career where they felt they were best utilizing their skills, and which they either enjoyed doing or felt a sense of gratification when completed.  There are many people in jobs today who are good at what they do and yet if you get them to open up about their true feelings they will privately admit that they are burned out at what they do.

Psychometric science has also progressed at this date to provide some additional insights into an individual’s motivational makeup. There are several good instruments available such as the Leadership Motives, Values and Preferences Inventory that can profile motivational structure in a very precise and comprehensive way.

If you are a mid-level executive, lacking gratification from your job is not fun, but it’s not disastrous. You can seek other sources of fulfillment. You can join a non-profit board, you can volunteer for charitable work, take up a hobby or join a church group. But senior executives, because of the demands on their time and energy rarely have these kind of options. Values are particularly important for senior leaders because of the wider range of career options they have available. If you are at a stage in your career where mentoring others or giving advice will be gratifying, then a follow-up career in consulting is likely to be rewarding. But if you still have a need to direct and control the actions of others, consulting or board membership is not likely to be as gratifying. And, if you join another company, what is important to you in terms of your values will inevitably be transmitted to your executive team and from there cascade through the whole organization.

The last dimension, Fit, is the most difficult to define but, like pornography, we know it when we see it. As human beings we all have to figure out how to get along with others. Senior executives have done more than that; they have figured out how to get ahead of others. Often the way one gets ahead is by being different, by standing out from the crowd in some way. Senior executives have stood out from the crowd in a way that was different but not so different that the organization could not appreciate their uniqueness. But there is an obvious danger in standing out as well and this danger increases when a senior has to look at new, unfamiliar organizations.

Even within the same industry, companies can vary widely in terms of corporate culture. What might be tolerated or even encouraged in one organization might be considered a major transgression in another. The business periodicals are filled in any given year with examples of executives who started in new leadership positions with great fanfare and then failed often spectacularly, quickly and publicly.

The fit equation has two components: (1) What is in your repertoire of executive behaviors that you prefer to exercise that have made you successful? and (2) What is the range of acceptable behavior the organization  will tolerate? Often organizations will lure a senior executive to them by explicitly saying the want to recruit someone “different” or someone who will “shake things up.” They have usually convinced themselves of this, but often the reality is that unless you really have a blank check there will be a limited range of things you can do.

Solving the Fit equation begins by fully understanding your own leadership style-what is unique or at least unusual about the way you lead and manage things that has worked for you in the past to get you where you are today. Then one has to conduct an objective, unemotional, systematic study of the culture of the organization to determine the size of the gap between your leadership style and the prevailing culture you would be entering. There is almost never a perfect fit between these two factors but some gaps are surmountable and some are not.

Fortunately, there are again some systematic assessment devices to help determine the size of the gap. For the individual executive there are several instruments like the Leadership Potential Inventory and the Challenge Inventory or the Life Styles Inventory. These assessment devices yield quantifiable and precise data about aspects of a leader’s style of which even he or she might not be aware. Assessing another organization’s culture is slightly more challenging but there are good instruments available such as the Organizational Culture Inventory that can assist in this.

The Network

Senior executives almost always have large networks in place. Often their jobs have required them to reach out far beyond their immediate organization in a variety of ways. The issue with seniors is not so much creating a network as it is how to fully exploit it. Since the 1970s networking has been systematically studied by sociologists and information theorists and there is a huge body of research that concludes:

  • The higher status the job is, the more likely it will come through the network
  • The better compensated the job, the more likely it will come from networking
  • Networking is most effective when the individual can clearly articulate who they are, what they want to do career-wise, and how the network contact may be of help
  • Network interviews are most effective when there is an element of mutuality. Mutuality occurs when both parties come away feeling as if they derived some benefit from the meeting
  • The best opportunities come, not from one’s “strong network,” but from the “weak network”

This last point is especially important for senior executives. The “strong” network is comprised of people the executive already knows reasonably well and they know him or her. Perhaps they have worked together in the past. The “weak” network is comprised of people the executive doesn’t know or knows very slightly. The overwhelming body of evidence is that the best, higher status, more desirable jobs are likely to come from the weak network.

Information theorists say that this makes perfect sense. Individuals in one’s strong network know you, you know them and you each know most of the same people. There is little new information that penetrates that closed system. The weak network represents links to new people, situations and opportunities of which you would not otherwise be aware.

What makes these new links particularly important is that at the senior level, jobs often don’t exist, but they may be created if the right person comes along. Again, this is a distinctly different aspect of a senior level job search. If you are a mid-level accountant you will probably look for something else quite similar to your current job, but at a different company. But if you are a senior executive, particularly if your former company is well known, many organizations will consider creating a job uniquely designed for you. You may even be able to participate in its design.

One last point to make here is when senior leaders leave a position at a company, there is usually some provision for a non-compete agreement as part of their terms of severance. This may make it even more mandatory that the executive “think outside the box” about future career opportunities. The weak network can be very useful at uncovering opportunities that obviate non-compete conflicts.

Executive Recruiters

No discussion of senior executive career transition would be complete without mention of the executive search process. At the senior level retained-only executive recruiters obviously can play an important and helpful role. Seniors have usually used recruiters themselves or been placed in their last job by a recruiter, so they have much easier access to this group than the typical mid-level manager. Recruiters can be helpful in giving advice about the general job market, reacting to the individual’s resume, providing information about industry opportunities and often can give helpful interview tips.

But in any given year, recruiters account for only about 15-20% of the senior level jobs that are filled. Moreover, companies usually hire recruiters when they need a narrow set of job specs filled. Recruiters are not usually commissioned to be creative thinkers. For all the reasons mentioned in the above section, they may not be helpful in “thinking outside the box.” Senior executives who wants to think creatively about their next career opportunity or who want to expose themselves to the broadest swath of the job market would be well advised not to solely rely on recruiters and most recruiters would say the same.

Financial Considerations

As a group, senior level executives are usually but not always financially secure. When they leave an organization they often have generous severance or retirement agreements, stock options, deferred compensation packages and the like. In some instances these can lead to a lump sum distribution that can create tax or other financial planning issues. While this is a nice problem to have, it is still a problem. Traditional financial planning resources may not be sufficient to deal with these one-time events.

It is beyond the scope of this article to deal with such a complex set of issues which will be different for each individual, but one short example may suffice to demonstrate how financial considerations can play a role in career choice. As of this writing (2011) current IRS regulations allow private entrepreneurs to put away as much as $229,000 a year in a deferred compensation plan. This number is likely to go up in subsequent years. For an executive leaving an organization who may be encountering a larger than average financial boon in a given year, it may make sense to create an entrepreneurial option which allows for creation of a defined benefit plan. In the right set of circumstances this can create a huge financial benefit in the first year and in subsequent years.

Family Considerations

Thus far we have focused on the individual executive.  But individuals, even senior executives, do not live in a vacuum. Children in school at critical periods, spouses who may have a significant job themselves, parents or other relatives, style of life, and many other circumstances can affect the availability and choice of the next career option. Because seniors occupy the top end of the pyramid, there are consequently fewer positions in any one geographical area at that level. Although seniors have more options available to them, these options may be spread over a much wider geographical area than is common for mid-level managers.

A proper career transition program will acknowledge this and will not treat career counseling as something only offered to the individual. If the executive’s family is not happy, then ultimately that executive will not be happy and ultimately that will have an effect on performance.

There is no one correct formula to deal with the myriad of family circumstances that can come up. But there are more opportunities for creative problem solving of these issues when they come up. Technology today offers one such avenue. The growth and sophistication of the internet has made long distance management a more viable opportunity. Services like Skype, Halo and Go-To-Meeting allow executives to reach out to their people more effectively than teleconferencing and even teleconferencing has become much more reliable and inexpensive than several years ago.

Another avenue we have pursued with our senior clients in recent years is the creative use of work schedules. For executives who must work at geographically distant points, it can often be arranged for them to work a four day work week or even a schedule that allows them to work Mondays and Fridays from home. Senior executives will often have greater bargaining power and so often a company-paid apartment can be arranged for those days when presence in the office is required.

Perhaps the most important point to be made is that career transition doesn’t just impact the individual. It impacts the entire family often in unpredictable ways. A comprehensive career transition program needs to address familial needs as well as individual needs.


We began this review by stating that senior executives are not in their jobs by accident. They usually are different and that is why they are where they are. We have attempted to outline some of the distinct differences between traditional job search for mid-level managers and executives and those individuals who have reached the upper echelons of their organizations. Seniors have many distinct advantages in transitioning to their next opportunities, but they also have challenges and complexities to their transition that mandate special consideration. An effective career transition program should address these whether they be individual, situational, familial or some combination of those factors.