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The executive midlife crisis

executive midlife crisis

I recently had a conversation with a Sr Dir of HR at Medtronic. She has a lot of admiration for her employer. I do too. So, when she told me that some of the internal coaching she does is with executives who are questioning what they are doing with their careers, it gave me pause.

Consider this a long-haul symptom of the pandemic. The time away from the office and a break in a years-long routine had led to employees breaking free from habit and into self-reflection. The result has been a tsunami of executive midlife crises.

I wrote about the Great Resignation just last month. Part of it is a function of demographics. As Boomers reached an age where retirement became an attractive option, they were bound to leave the job market. Part of it is a result of healthy 401-Ks, as stocks have rocketed in the past year.

But there are other things going on. Employees between 30 and 45 years old have seen a 20% increase in resignations year on year. Women in this age range are more likely to be leaving. Their work experiences tend to be less satisfying than men’s. They are often in the front-line jobs of healthcare and education that saw stress accelerate the most during COVID. And they felt the joys and obligations of family life most acutely, with their children at home.

Now, add factors like reaching the midpoint of your working career, working from the echo chamber of a home office, an organizational pyramid that narrows career options with your current employer and a glimpse of your own mortality, as the COVID death toll approaches 800K Americans. You have the building blocks for a midlife crisis. And it is touching a large number of corporate executives.

Somehow, this feels different from what we traditionally think of as a midlife crisis. There is far less of the typical selfishness, maybe because selfish outlets were closed down for so long. You can’t get a facelift if clinics are not accepting elective surgery. Having an affair is far less exciting via Zoom. Instead, we are reacting to racial tensions, income inequality, polarizing politics and threats to our way of life from human-induced acts of God. Freud is taking a back seat to Frankl.

In the New Yorker, Lizzie Widdicombe interviewed some marketing executives: “We’re reconsidering who we are, what we care about, what we want to do with our time. I’m sitting here writing pitches for big-box retailers on how they can sell more products that people don’t need.”

Having identified this crisis, what can we do about it? I’m going to stop short of suggesting a radical change, whether it is in your career or your whole life. There are four things you can do that can make a difference in how you feel, how you feel about yourself, your work and your relationships. They may shed light on a way out of your crisis, or they might show just how needed a fundamental change is.
  • Keep a journal. This is advice that I give to all of Executive Springboard’s mentees. At a minimum, journaling helps you reflect on what is happening to yourself and to those around you. It can also be an outlet for identifying emotions that you have suppressed.
  • Reconnect with a higher purpose. Are there things you are passionate about but stopped devoting time to them? Re-engage! Are there aspects of your work that link with your personal mission? Dive in! Is your career getting in the way of what you find important? Find a way to contribute, either outside of work or through a more satisfying job.
  • Embrace discovery. Try new things. Find joy in learning. Open yourself to knowledge that can come from unexpected places. Maybe it is being mentored by somebody junior than yourself. Maybe it is taking a new route to a familiar destination, trying as new recipe, listening to new music or vacationing someplace you’ve never been before. Enjoy experimentation, especially when it fails.
  • Take care of your physical health. A critical part to ensuring that a crisis becomes a positive turning point is to make improvements in your physical wellbeing. Whether it’s getting enough quality sleep, exercise, diet.
Suppose you are not in the throes of a midcareer crisis, but you are responsible for people experiencing this. You don’t want to lose valuable people by having them become additional Great Resignation data points. And you don’t want them in limbo, limping through their crises, working at less than full speed, bringing down co-workers. What can you do about it?
  • Get a pulse on how your people are feeling. I’m not talking about employee engagement surveys, though they certainly have their place. Instead of aggregate metrics, it’s important to get to an individual level. Start with the assumption that, over the past year, everybody has been dealing with significant emotional difficulties. Probe on where there may be issues, which if not addressed, can be unhealthy for the individual and the company.
  • Find ways to offer individualized support. The needs are different, and so are the solutions. Some people would benefit from a coach or mentor. Common issues might be addressed through a sense of community, within your organization or associated with outside groups. Others need to develop their own individual plans for resolution. Some organizations have succeeded by providing people with sabbaticals.
  • Operationalize your mission. Hopefully, you have a reason for being that goes beyond providing shareholder value. If your business has articulated a mission or purpose that can motivate employees to get out of bed in the morning, create ways for your people to get involved. This connects them to a higher purpose. It connects them to their colleagues and the community. And it enhances their connection to the company.
  • Be prepared to lose people. Some managers will find a new career opportunity the inevitable result of the crisis they face. It feels like a failure when valuable people leave. In truth it is part of growth, for them and for you. The respect and compassion you show employees struggling through a critical personal and professional time pays dividends. It enhances your brand, builds respect and loyalty among remaining employees and may add intentionality to your succession plans.
When it comes to addressing a career crisis, there is no such thing as benign neglect. Ignoring the problem doesn’t make it go away. Tackle it head-on. Provide time for reflection. Recognize that changes, though not inevitable, might be for the best.

Illustration of a collaborative C-suite executive leadership

Executive Springboard mentor John Keppeler shared an anecdote from his first time leading a company’s sales function. It was at CNS, the company that made Breathe Right nasal strips. Its CEO, Marti Morfitt, told John, “You are a really good sales guy. Learn what it takes to contribute to a cross-functional management team. Don’t be afraid of getting out of your lane.”

It happens all the time in the work we do with executives. A mentor is selected on the basis of shared experience, functional and otherwise. The mentor and mentee speak the same language. The mentor’s experience is relevant to the situations the executive faces. But the conversations are seldom about being a better CFO or CIO; they are about becoming a valued member of a leadership team.

Gaurav Lahiri, Jeff Schwartz, and Erica Volini of Deloitte wrote about the symphonic C-suite in 2018. Their notion was that the future of C-suites would be “specialized experts playing in harmony – instead of a cacophony of experts who sound great alone, but not together.” At the time, it seemed like an aspirational model; egos and turf protection were defining characteristics of many leadership teams that collaborated in crises but were often dysfunctional.

Our hopes for a symphonic C-suite were that it could better serve the expanding, increasingly complicated goals of organizations. The marketplace has become a driver of social progress. Employees increasingly seek meaning in their work. Large companies are looking for how they can address global challenges like decarbonization. These new social purposes require cross-functional collaboration. Sometimes this involves the whole C-suite; other times it might require the heads of marketing, supply chain and IT to work on digital solutions or the CHRO and CFO to work through equity issues.

COVID’s impact on symphonic progress was inconsistent. Some teams pulled together, using technology to work better remotely. Others reverted to individual survival strategies, and teamwork suffered.

Now, we begin to glimpse a post-COVID world. We’ve learned just how much a motivated workforce can adapt in real time. There is optimism that demand will be take a leap forward, and we will function less in survival mode. The big issues beyond shareholder value that we want to tackle are still ahead of us. We are heading towards a hybrid office that offers the best of both worlds of independent work at home and the return of face-to-face collaboration. What happens now?
  • 1. Leaders have to get whole. Mental health issues have hit the C-suite harder than the rest of the employee base. Their ability work collectively will suffer if they are still suffering as individuals.
  • 2. Members of the C-suite need to follow Ms. Morfitt’s advice and learn to get out of their own lane. This might be working closely in subgroups or contributing to the function of the larger C-suite.
  • 3. C-suite members have the opportunity to provide situational leadership with the peers, when their expertise is valuable to the entire team. For instance, Chief Sales Officers have been able to leverage their experience leading a distributed work force, to the benefit of their peers during COVID.
  • 4. The CEO and CHRO should assume conductor roles, enabling their colleagues to form bonds of collaboration. Interpersonal tension never goes away, but people need to establish positive working relationships to common goals.
  • 4. The leadership team needs to create its own micro-culture of how members will interact. Values like assumption of positive intent and cabinet responsibility should be established to facilitate teamwork.
  • 5. Incentive systems should cascade from common corporate objectives, so functional leaders don’t find themselves at cross-purposes with their colleagues.
  • 6. Senior execs can create capacity by nurturing their reports’ development in functional leadership. In the process, they groom the C-suite’s next generation.
Corporations are redefining their place in society, and with it the dynamics of the C-suite. Functional expertise might lead to an exec joining the leadership team, but collaboration skills will determine their success in the role.

the supply side of mentoring

“Do you do mentoring outside of onboarding?“

I received the same question four times in the past two months, from companies facing eerily similar situations. The companies each had a VP of Sales with 15-20 years of experience in the company, elevated to the VP level 2-4 years ago. The VPs were hitting their numbers and their customers loved them, so the requests for help were not couched as remedial. Instead, there was interest in expanding their skill set, exploring different aspects and technology of selling, ensuring that these successful salespeople were becoming strong sales leaders and becoming more vocal participants within the leadership team.

My answer to these questions was, “Sure. You know we have intellectual property in the area of executive onboarding. But we have a network of highly accomplished executives as mentors, who are quite capable of helping to develop your Vice President.”

And then I had conversations with several of my mentors who come from the sales function. They were as excited about the opportunity to develop an established leader as they have been in working with those new to their position.

It might seem that the benefit of mentorship is accrued mainly by the mentee. They are receiving wisdom. They are getting support in situations where they are vulnerable. They are learning from their mentors’ mistakes, which is less painful than learning from their own. But, in working with professional mentors, I think they might enjoy these relationships at least as much as their mentees.

Many successful professionals reach the point in their lives when they are no longer motivated by position or additional wealth. At Executive Springboard, the majority of our mentors are out of corporate life, either retired or consulting. But they are not done with the contribution they can make. They have legacies that they are intent on building.

When I vet mentors for Executive Springboard, I am seeking four qualities.
  • 1. Does somebody have a history of accomplishment and experience that would be valuable to current executives? When I recommend a mentor to an executive, that executive has to recognize how they can learn from the mentor. On top of strength of resume, I seek a diversity of experiences across our portfolio of mentors. That helps us find a mentor who has faced similar situations to those an executive might encounter.
  • 2. Does the person exhibit active listening? The work we do is often an alternative to more traditional executive coaching. Part of a coach’s credentials will be tied to their active listening skills, the ability to follow a conversation, consider what maybe underlying the executive’s answers or tone and the skill to respond accordingly. A mentor often has an advantage over a coach in terms of relevant experience. I want to make sure a mentor is not significantly disadvantaged as a listener.
  • 3. Can the mentor bury their own ego, demonstrate humility and make the work about the mentee? The mentee’s success is the ultimate measure of a mentor’s success. It is a waste of time for a mentor to regale an executive with stories of their triumphs, unless they address the mentee’s question of “How do I do this?” Many current or former CEOs cannot get over themselves, continuing to seek affirmation on their careers. They have not bought into legacy building, and they don’t make it as mentors.The best mentors own up to their own mistakes and talk openly about what they have learned from them.
  • 4. Does the mentor show a passion for the work? The best mentors find that they can learn as much from their relationship as the mentee can. They often have been touched by mentors themselves, people who have left indelible marks on their careers and on their lives, even if those relationships were not long-term. I had three mentors, Sig Yaffe, Bonnie McCafferty and Fred LeDrew, who left their marks on me. They not only inspired me to want to pay it forward with others, but they instructed me on what it takes to play that role. All are gone but remain in my heart.
Penny Loretto described characteristics of good mentors that go beyond Executive Springboard’s vetting.



​We try to address these in training, the process of matching mentors and mentees or through coaching during mentoring engagements.

Executive Springboard began as a mentored-delivered vehicle to onboard leaders in new roles. We still have this at our core. But we’ve responded to clients who see how this broad team of incredibly talented and committed mentors can impact leaders in other ways:
  • Helping to develop leaders reach their potential. This can involve filling knowledge gaps, either directly by the mentor or through introductions to people with greater expertise. This might also include developing strategies for how women and people of color can gain acceptance and alignment while remaining true to who they are.
  • Serving as a sounding board. Mentors create a safe place for managers to explore courageous actions, to think through potential consequences and to pressure-test assumptions.
  • Holding a mirror up, so people see how others view them. Sometimes, this can be reassuring and supportive. Sometimes, this is a needed reset on an exec’s perception of themselves.
  • Being a confidante. Companies often having mentoring programs in place to develop and retain junior and middle managers. The results are significant: people with mentors are five times more likely to get promoted than those without (Chronus), and 77% of companies report that their mentoring programs boosted retention and performance (WeSpire). At senior levels in organizations, internal mentoring breaks down. There is too much at stake for the leader to make themselves vulnerable or transparent with colleagues, their boss or board members. But the need to confide in others, to get support and to be challenged remains. This is the role we try to play at Executive Springboard. The need may be keenest when somebody is getting their footing in a new situation. But it never goes away.

I want to thank the incredibly talented mentors at Executive Springboard for their work to support and develop leaders, for their passion towards passing on a legacy and for spurring me on to make our business bigger than its initial vision.

Empowering the Moral Courage

In July, Bruno Dey, at the age of 93, was found guilty of 5230 counts of accessory to murder. Dey had served as a guard at the Stutthof concentration camp for 9 months, until April 1945. He was tried in juvenile court, because he was 17 years old at the time his crimes began.

As Dey stood in his guard tower, he heard the screams of people in the gas chambers. He watched as corpses were removed to be burned. But he said nothing. He stayed at his post.



During his trial, Dey’s attorney Stefan Waterkamp argued for acquittal, claiming it wasn’t his choice to be a guard and to have resisted duty would have been a threat to his own safety. He asked, “How could an 18-year-old step out of line in a situation like that?” The judge was not sympathetic to the argument, declaring that Dey’s duty was to honor human dignity at all costs, even at the cost of his own safety.

When George Floyd was killed by a knee to his neck, two of the police officers who restrained him were new to the force, having completed their probationary period just four days before. Alexander Kueng and Thomas Lane were charged with aiding and abetting. Lane’s lawyer said, “What was my client supposed to do but to follow his training officer’s orders? He was doing everything he thought he was supposed to do.” When interviewed by investigators, Lane remarked, “Once he kind of stopped fighting us, I think I had said again, ‘I think we should roll him over on his side.’” Lane recognized things had gone wrong, and he may have spoken out. But his strength of his convictions would not let him disobey his training officer.

Anybody who has studied psychology is familiar with the Milgram experiment, where a subject (the teacher) administered a test to an accomplice (the learner). When the learner got an answer wrong, the teacher subjected them to what they believed was an electric shock, increasing the voltage to dangerous levels and hearing the acting learner’s painful reaction. Quickly, the teacher reached a point where they are uncomfortable administering the shocks. But an authority figure (the experimenter) told them to continue with the shocks. And they did.

We see the subservience to authority as part of human nature. Even when faced with an obvious moral wrong, many will submit to the direction of authority. Particularly when that authority is “on our team.” To quote Albus Dumbledore in Harry Potter and the Sorcerer’s Stone, “It takes a great deal of bravery to stand up to our enemies, but just as much to stand up to our friends.” How can you empower your employees to act with moral courage and to do the right thing even if it means disobeying, disappointing, and risking ostracism or job status?

It comes from establishing a culture that values courageous acts, celebrates them and rewards them. Not just including COURAGE in a list of corporate values, but showing employees that acting with conviction, even if unpopular, need not penalize you. (“Ten points to Gryffindor!”) At a minimum, you need a robust whistleblower policy. But what I am talking about is at the heart of an organization’s diversity and inclusion effort; it is the recognition that you are enriched by other points of view. It comes with a realization that pointing out shortcomings or saying, “This is wrong” is good for the company. And, as an act of courage in itself, it might require leaders to admit to being wrong or to not seeing the full picture, when confronted with an act of defiance with moral underpinnings.

Before assuming it’s too much to ask that a German guard or a Minneapolis cop should have acted differently when facing a moral wrong, consider what our military and progressive police organizations have in place. Article 92 of the Uniform Code of Military Justice states that it is a dereliction of duty to disobey any lawful general order or regulation. If it’s determined that an order is unlawful, the UCMJ provides a moral and legal obligation to the Constitution, rather than to obey unlawful orders and the people who issue them. The Department of Defense also spells out what violations to submit in a whistleblower complaint. The New Orleans Police Department has developed a program called Ethical Policing is Courageous (EPIC), which defines teamwork as the inclusion of intervention to stop a harmful action. Recruits are taught it’s their duty to prevent another officer from engaging in misconduct, even a more senior officer.

Yes, an immoral order might be legal. But my point is that even in an organization dependent on discipline, there is room for moral courage. Building the desired values into training is a critical part of acculturation. If organizations that routinely deal with stress and authority like the military or police can value courageous behavior, so can your company.

Corporate cultures that embrace moral courage might find that other forms of courage will flourish, as well. I am unaware of studies backing up a correlation, but it is not too much to expect that the company that celebrates people standing up for what’s right will empower them to be courageous in innovation, in selling and in leadership positions. After all, being a leader means making unpopular decisions at times, doing what is right when it’s not easy. And part of leadership may be making it easier for others to act with moral courage.

P.S. On Aug 26, 2020 the Milwaukee Bucks chose to boycott their playoff game, in response to another episode of an unarmed Black man being shot by a police officer, this time in Kenosha, WI. Soon, the players on the other five teams involved in playoff games that night chose not to play. WNBA players followed suit, as did the Milwaukee Brewers baseball team. This was a peaceful, potent way to say, “This is wrong.” You can argue that it is the power NBA players hold to impact ratings that allowed this response. They are in a more privileged spot than a cop on his fourth day. I think it is more involved than this. Team ownership and management have repeatedly expressed support for social justice issues. Many of the same people own the WNBA franchises, whose TV ratings don’t make a ripple. This seems more like an effort at solidarity around organizational culture than a reversal in the traditional balance of power.

​What do you think?

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