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In an ideal world, every CEO would be gifted with a C-suite of people who are terrific by any measure—a team that consistently drives performance, delivers results, and contributes positively to a culture that wins by bringing out the best in its people. However, sometimes even highly accomplished C-suite leaders, individuals who were carefully selected, exhaustively recruited, and even have an impressive previous track record, really struggle in their roles.

When you find yourself in a situation in which one of your most senior executives is not quite hitting the mark, what do you do? How do you, as the leader who is ultimately accountable for the person’s performance and results, maneuver the reality in a way that is eyes-wide-open, responsive, and courageous, yet also decent and kind?

I’m an optimist by nature, so I believe that most senior business executives want to do right by their fellow humans. It is an optimism that’s well-supported by what I see daily as an executive coach and teamwork facilitator. Because most senior executives are good humans at their core, the situation I describe above can be exceedingly painful for the big boss who must decide what to do about a fellow overachiever who is now struggling. Yet there is an imperative to push through the reluctance, deal with the matter head-on, and take constructive action.

No matter how much it hurts the heart of the top leader, for a business to achieve and sustain competitive advantage, strugglers, poor fits, and underperformers—particularly highly paid ones—must be proactively supported back to success or, in the worst-case scenario, replaced.

Go All In

When one of your senior leaders is struggling, failing to hit their goals, or causing disruptive problems with other valuable people in the organization, the first thing to do is simply to acknowledge it to yourself. It can be tempting to ignore signs of struggle in the hope that things will resolve on their own, or in telling yourself it’s not a big deal. The temptation is even stronger if you really like the person, or conversely if you really dislike the idea of a confrontation. Yet if you ignore what you see, you risk negative downstream implications like missed business goals, disengaged fellow leaders, and even lost talent.

Once you resolve to believe your own eyes, then it’s time for a thoughtful and heartfelt yet very direct conversation, one in which you seek to do what renowned self-help author Steven R. Covey argues across his body of work: “Seek first to understand then to be understood.” Prepare for a conversation in which there is a low risk that you come off as condescending or bossy. You don’t want to convey that you have passed judgment or that you’re put off or disappointed.

You want to convey genuine, empathetic interest. The idea is to bring your objective curiosity to the conversation. Seek to discover what is going on with the individual on as deep a level as possible. Are they concerned about the business’s direction? Is an element of strategy gnawing at them? Are they bored? Are they experiencing difficulties on the home front?

Get Curious

The way to get an honest take on topics like these is to get into a neutral frame of mind, one that assumes positive intent, and then gently ask open-ended questions like these:

  • What’s something going well for you right now, both at work and at home?
  • What are some areas where you feel you’re struggling?
  • How are you doing relative to what you’ve committed to do/signed up to deliver?
  • If you could wave a magic wand and alter one thing about your work right now, what would it be?
  • What’s keeping you up at night?

Notice the absence of the word “why” in these questions. Questions that begin with why certainly have their place in the leadership lexicon, but in these moments, they land like cross-examination and have a way of activating defenses.

For the record, asking such questions is not manipulation. Newer clients of mine often ask me if utilizing these kinds of questions risks coming off to others as playing head games. Yet with practice, my clients inevitably discover that, if posed with genuine curiosity and neutral intent, such questions cultivate connection and produce understanding. They honor the fact that the leader is not only an accomplished professional with pride, aspirations, and a sense of conscientiousness but also a human with blind spots, limitations, down periods, and fears—and undoubtedly a complicated life happening outside of work.

“When one of your senior leaders is struggling, failing to hit their goals, or causing disruptive problems with other valuable people in the organization, the first thing to do is simply to acknowledge it to yourself. ”

Shane Kinkennon

– Shane Kinkennon


Formulate a Plan

Once the truth is uncovered, and the individual has owned that they are in fact struggling, then you can facilitate clarity and candor on the gap that you see between the business’s expectations and the reality of the person’s current contributions. A simple table can help. Here’s one I have seen used to great effect:

Observed leadership performance or behavioral challengeDesired replacement behavior or resultSigns of incremental effort the business expects to see between today and future sustained successTarget date for change to be firmly established

Filling out this form collaboratively with the leader in question and getting it to a state that you both can agree to and accept may take time and multiple conversations. Stay with it. Once you’ve done so, what you will have created is a mutually agreed-to plan of attack, a roadmap that signals that the business believes in the rich potential and capacity of its top leaders, and the people who work for it can count on both the support they need and the unfettered accountability that a performance culture requires.

Follow Up and Follow Through

As a next step, you can facilitate the person’s commitment to the plan while simultaneously showing them that you believe in them and are in their corner. Once again, open-ended questions are a simple but effective tool. Consider ones along these lines:

  • What will commitment to these changes look like for you in daily action?
  • How will you go about making this change journey a primary focus?
  • How might you talk about this with others?
  • What allies would be happy to support you?
  • To whom will you be accountable?
  • What role can I play as a supporter, accountability partner, and/or cheerleader?

Don’t leave the interaction without a high level of confidence that your fellow executive understands exactly what you expect of them going forward and is committed to putting in the effort that will be necessary to achieve or return to a high level of contribution.

Of course, it’s possible that the struggling fellow executive simply won’t, or can’t, admit that something is afoot. Or they might place blame elsewhere rather than accept accountability. Or perhaps in their heart of hearts, they simply don’t or no longer have it in them. In such a situation, if you’ve really done all that you can to communicate that you believe in them and are on their side, then it may be a sign that the employment arrangement simply is no longer the right one for the business or the individual.

When Separation Is the Answer, Don’t Delay

Even if you take all the right steps to engage and support an executive leader who is undershooting expectations, the sad fact is that sometimes people simply don’t work out. Or they stop working out as well as they once did. It happens, even with very accomplished people.

When it has become clear that a fellow leader is not working out, and every option to support and encourage their improvement has been exhausted, it is essential that you decide to make a change. And importantly, that you act swiftly and surely.

There are a couple of compelling reasons for urgency. The first is captured in this quote by author Perry Belcher: “Nothing will kill a great employee faster than watching you tolerate a bad one.” If you can see that one of your executives is underperforming or otherwise is not a fit, you can be certain that others can see it as well. Your people watching what the leader “gets away with,” in their view, reflects poorly on you as the supervisor who tolerates it.

Most top performers are loathe to share space with mediocrity on a sustained basis. The longer you let an underperformer or mismatch get by, the greater the risk that their peers and the people who work for them will start to phone it in. By contrast, when you deal with missing the mark head-on, the people in your organization see that you are dead serious about situating the team and the business to win.

The second reason is about treating the separated individual in a manner that is distinctly humane. If you know someone is not or no longer a match, yet you keep them around anyway in a situation that does not bring out their best, you effectively deny them access to other opportunities for which they may be a better fit. You think you’re doing them a favor by saving them from income disruption, yet you may be denying them a different kind of riches. In the end, you do your fellow leader no favors by joining them to pretend there is no problem.

If you’ve decided that the leader’s separation is inevitable, then deal with it. Act now. Free them to go be inspired and find success and fulfillment elsewhere.

In the early days of the pandemic, empathy and empathetic leadership emerged as the premier topics of conversation in corporate America. As businesses shut their doors and employees began working from home, leaders understandably searched for answers to the big question: How do I keep my business operational while taking into account the unique and deeply personal challenges employees are facing?

As an organizational psychologist and empathy researcher, I was excited to see the term make its way into the mainstream workplace vocabulary, but there was still a learning curve as business leaders began to incorporate empathy into their organizations. In my work with executives across the country, I’ve encountered the same four myths about empathetic leadership that, if left unchecked, have the potential to seriously harm a business. Here are a few ways to mitigate that risk.

1.  ‘Empathetic Leadership Results in a Lack of Leadership.’

This myth is probably the most damaging of the four we’ll cover because it can limit how much empathy a leader ultimately shows their team. Typically, those who hold this belief fundamentally misunderstand empathetic leadership. They assume that leading with empathy means there is no clear structure within an organization and that everyone is so busy talking about their feelings all the time that hardly any work gets done—but this couldn’t be further from the truth. In fact, a recent survey found the exact opposite: empathetic leadership is actually linked with higher levels of productivity.

A lack of leadership often goes hand-in-hand with a lack of accountability across a team—from the executive board to entry-level associates. So how do you solve this? Ironically enough, by empathizing with employees and taking on a holistic approach to problem-solving. When people know their needs will be met with compassion and understanding, they’re much more likely to ask clarifying questions or take ownership of their part in an unsuccessful venture. If you’re concerned about a lack of clear, strong leadership in your organization, start by incorporating more empathy, not less.

2. ‘We Have to Have Similar Experiences to Empathize.’

Many people assume, both inside and outside of the workplace, that we can’t empathize with others unless we’ve experienced similar circumstances ourselves. However, empathy is about understanding the emotional experience of a situation, not necessarily relating to the situation itself. In her 2018 book, Dare to Lead, Brené Brown summarizes it perfectly: “Empathy is not connecting to an experience. Empathy is connecting to the emotions that underpin the experience.” When confronted with a situation you think you can’t relate to, pause and ask yourself, “Have I ever experienced the emotion this situation is evoking for this other person?”

Let’s use conversations around DEI as a real-world example. These conversations can be polarizing, but they don’t need to be. When someone feels uncomfortable hearing about another person’s lived experience that’s different from their own, they might respond with, “Well that’s not my experience.” Responding this way can be hurtful to the individual, who will likely feel dismissed and unheard. This can translate to feeling largely unsupported by the organization itself, which could elicit a number of consequences such as disconnected teams and interpersonal conflicts.

I’ll say it again: Relatability doesn’t matter when it comes to empathizing. So let’s go back to our DEI example. Let’s assume during a company-wide training, someone is brave enough to share that they’ve been the target of microaggressions on several occasions since joining the organization. Even if you’ve never experienced microaggressions yourself, you can still understand why it would be traumatic for someone. Ask yourself: Have you ever felt belittled, condescended to or stereotyped based on certain aspects of your identity? If the answer is yes, then you can empathize.

“In my work with executives across the country, I’ve encountered the same four myths about empathetic leadership that, if left unchecked, have the potential to seriously harm a business.”

Payal Beri

– Payal Beri


3. ‘Empathy Isn’t a Teachable Skill.’

Considering empathy is a “soft skill,” it’s understandable why some might assume that we either feel empathy or we don’t, as if there’s nothing we can do to change our intrinsic emotional response. But like any skill, it’s possible to get better with practice.

But how exactly do you “practice” empathy? You ask questions until you understand. If one of your employees tells you about a problem that’s impacting them and/or their ability to carry out their duties, start by asking questions such as, “Can you tell me more about that?” or, “How does this make you feel?” or “Is there anything I can do to support you?” From there, you can begin working on a solution.

It’s important to train ourselves to open up when we’re in uncomfortable situations instead of shutting down. If we give ourselves time to ask difficult questions, we can improve our empathy skills one issue at a time. But don’t get me wrong—there will be some growing pains. You will probably never fully understand every single situation, but over time, as you connect with a variety of emotional experiences, you’ll find it gets easier and easier.

4. ‘Empathy is Empathy—There’s Only One Type.’ 

This last myth is pretty easy to debunk considering the amount of research available on the three distinct types of empathy, but let’s dig into these distinctions and consider how each type of empathy can be useful in different professional situations.

The first type of empathy is cognitive empathy, or intellectually understanding what someone is going through but not experiencing those feelings yourself. Cognitive empathy is an excellent tool when you need to keep some emotional distance from a situation, such as when entering a negotiation. In these situations, you might hear someone say something like, “I understand you feel this way.” Granted, it’s not the warmest or fuzziest type of empathy but there’s definitely a time and place for it in your business.

The next is emotional empathy, sometimes known as parallel empathy, or when we sense and take on someone else’s emotions. Imagine for a moment that you’re a mentor to an up-and-comer in your field. You support them as they prepare to pitch a potential client, but ultimately, your mentee doesn’t close the deal. Afterward, your mentee is upset and a little embarrassed to have lost such a monumental opportunity, and although their loss doesn’t impact your business or career, you feel the same sadness and embarrassment your mentee is feeling. Emotional empathy can be an excellent tool when it comes to things like team building, but make sure you have firm boundaries in place or you might end up carrying every emotion as your own, which can leave you feeling exhausted and unproductive. 

Finally, there’s compassionate empathy, also known as reactive empathy, which I consider to be the highest level of empathy. Compassionate empathy makes you want to spring into action and provide tangible solutions to the problem at hand. Of course, if you lack boundaries and start trying to solve everyone’s problems, this type of empathy could present some issues. But in most cases, this is the kind of empathy you should strive for in your organization.

When one of your team members is faced with an issue, you’ll want to go beyond simply acknowledging their experience (cognitive empathy) in order to embrace those emotions as your own (emotional empathy) and actually provide tangible support as best you can (compassionate empathy). Your organization will almost certainly be better for it.

It can be tempting to keep doing the things that we know we do well, even if it means neglecting the responsibilities we know we should be tending to instead. There’s comfort in playing to our strengths and, let’s be honest, it’s fun to be good at something. When we practice our skills in woodworking, knitting or the local pickleball league, we gain relaxation, satisfaction and fulfillment. We enjoy ourselves, level up and feel rewarded. But when it comes to work, this tendency gets trickier.

Rarely does an executive-level job need us to keep doing the specific technical thing—the accounting, sales management, finance, lawyering or whatever else—that we did with excellence for most of our careers. What the business needs from us instead is to shift our focus to the inspiration and persuasion parts of leadership, despite any discomfort we may harbor in that realm.

Executive leaders can be deeply resistant to taking their hands off the operational wheel. I see it regularly in my executive coaching practice with C-level leaders. Out of a desire to bring our best, we immerse ourselves in the day-to-day, tackling challenges, sounding off on routine matters and dispensing wisdom. We go particularly deep in areas in which we believe we’re the resident expert. What we fail to realize is that when we do all of that, in effect, we are telling others what to do. We shrink our teams’ accountability for results. We create the conditions in which our business fails to get the most out of its human capital.

Stepping Into Your Executive Role

When I worked in the C-suite, I couldn’t resist dispensing wisdom in the one area that happened to be my legacy career domain. I could see that I annoyed my direct report who led that area, yet I thought I was doing my job. When I finally shut up and got out of their way, they did things more strategically, creatively and effectively than I could have imagined.

“Well, being an expert is the very definition of my role,” you might respond. “Of course, my business needs me to use what I know!” 

Yes, but not in the way that you think. In their book, What Happens Now? Reinvent Yourself as a Leader Before Your Business Outruns You, John Hillen and Mark Nevins argue that when C-suite leaders stick with what they know technically, their focus is inevitably trained on “problems of complexity,” the tactical, operational and organizational challenges of the business. They stay in the thick of things, calling the shots. This almost inevitably means they’re doing other peoples’ jobs while doing too little of that which only they, as executives, can do (i.e., make sense of the future, iron out alignment wrinkles and cultivate other leaders).

Meanwhile, wiser, more skillful executive leaders, despite whatever level of technical competency they possess, focus their energy on “problems of sophistication,” those challenges that exist in the interpersonal and political realms. Companies that achieve and sustain competitive advantage are led by executives who place most of their focus here. In the words of Eleanor Roosevelt, “A good leader inspires people to have confidence in the leader. A great leader inspires people to have confidence in themselves.”

“Ask your team how you can provide strategic guidance and direction while keeping agency and decision rights firmly in their court. And then hold yourself accountable for what they ask you to do.”

Shane Kinkennon

– Shane Kinkennon


Breaking the Cycle

Ask your direct reports if you provide them with the type of executive leadership that they need. It could be that you’re showing up for them exactly as they want, clearing brush when they ask but otherwise giving them space. Good for you! Or you might learn that you’re smothering them, particularly in the areas you specialized in. Be humble. Ask your team how you can provide strategic guidance and direction while keeping agency and decision rights firmly in their court. And then hold yourself accountable for what they ask you to do.

Ask yourself: Are you more hands-on in functional areas that you have experience in? Are you more socially at ease with coworkers who share your career background? Do you have the nagging sense that your teams wait for you to tell them what to do rather than assert themselves or take positive initiative? All are clues that you’ve inadvertently trained your team that your expertise matters more than their contributions. You can say all the right things about valuing your team’s perspective, but the reality is they have figured out that their opinions rarely shape your decisions.

Moving Forward

So, step back. Let go of the idea that what is needed from you is more of your domain expertise. Your more lasting impact will come from convincingly, even passionately, unlocking what is possible within others. In practice, that means less telling your fellow leaders what you would do in their shoes. Instead, ask them what they would do on consequential matters, be genuinely interested in what they come up with and let them run with their own solutions without shaping them into your own. Try it for a month. You might be surprised at what you learn.

Nothing shakes up a company quite like the departure of one of its top executives, and these days, it’s happening more and more. In the first quarter of 2022 alone, CEO exits were up 29% compared to the same quarter in the previous year, and a recent Deloitte survey found that nearly 70% of C-suite executives are “seriously considering quitting,” and it’s easy to understand why. 

As leaders burn out in the face of unprecedented pressures, rapid change and a looming recession, chief people officers and HR directors can attest to how costly replacing a top executive can be—according to one analysis by the Harvard Business Review, “the amount of market value wiped out by badly managed CEO and C-suite transitions in the S&P 1500 is close to $1 trillion a year.”

Instead of searching for your next CEO, you’d be wise to search for remedies that keep top-performing leaders from departing too quickly. If you’re a board director, shareholder or a decision maker of another stripe, consider these three tips to salvage what’s left of your executive team.

1. Allow for (or Mandate) Remote Work

There’s been a lot of hemming and hawing about the pros and cons of remote work, especially among CEOs. You might recall last spring when WeWork’s CEO Sandeep Mathrani quipped that only the “least engaged employees” didn’t want to return to the office. Ultimately, Mathrani apologized after his comments sparked outrage and others were quick to point out WeWork’s financial interests in employees returning to a physical office.

While there might be some instances where getting a group of employees together in person would be more conducive than a video call, on the whole, remote work can’t be beat. The flexibility and balance it brings simply do not compare to commuting to and working from an office for eight hours a day. According to a recent report by McKinsey & Co., “87% of workers offered at least some remote work embrace the opportunity and spend an average of three days a week working from home.”

Although they might not always seem like it, since they’re technically “the boss,” CEOs are workers, too, and they’re not immune from burnout and work-life imbalances. While remote work doesn’t miraculously cure these issues, the flexibility that remote work provides is unmatched and is key to improving executive retention.

“Instead of searching for your next CEO, you’d be wise to search for remedies that keep top-performing leaders from departing too quickly.”

Scott Poniewaz

– Scott Poniewaz


2. Require Vacations

It’s been pretty well established that most executives aren’t the greatest at taking planned vacations. In 2015, it was reported that Whole Foods’ then-CEO had accrued over a year’s worth of paid time off or 2,703 hours. In 2022, this toxic trait has seeped into the rest of the workforce, mostly as a reaction to the pandemic, and some companies are responding by making vacations mandatory.

The physical and mental health benefits of taking a vacation are well-documented. Not to mention, it can bring a renewed sense of purpose and determination to complete the job at hand. But if these aren’t reasons enough to convince your CEO to book a flight and fully disconnect, consider implementing a mandatory vacation policy that goes all the way to the top.

Now, I know what you’re thinking: It’s one thing to require employees to take a vacation, but how exactly do you mandate vacations to the folks ostensibly in charge of enforcing policies? A few ways. You could consider setting aside a week once a year for the entire company to check out—something that’s becoming increasingly popular these days—or you might consider folding in a travel stipend to the executive’s benefits package.

If they still won’t budge, you can always send them on a bleisure trip—that way, they might accidentally relax in between meetings.

3. Surprise and Delight

I’ve said it once, and I’ll say it again: CEOs are workers, too, and everyone likes to feel appreciated for their efforts every once in a while. When it comes to gifts, think outside the box of floral arrangements and “World’s Best Boss” mugs. Instead, consider how you can surprise and delight your executives, both inside and outside the office.

Think exclusive experiences, such as surf lessons or wine tastings, that encourage them to unplug and connect with loved ones, or health and wellness subscriptions, such as meal kits or spa memberships, to give them a chance to focus on themselves. And if you are able to convince them to take that vacation, consider upgrading their accommodations or gifting them a lounge pass for their preferred airline to make traveling less stressful—perhaps increasing the chance they’ll take another vacation in the future.

Executive Retention Starts Now

Whether you’re convinced your executives would never dream of leaving the company or you suspect some might already be interviewing elsewhere, there’s no sense in waiting. In order to retain your C-suite—or, worst case, attract their successors—you must act now. Implement an executive retention plan today, or begin the costly search for their replacement tomorrow.

It’s time for a reality check on your data-gathering efforts. You’re probably monitoring basic workforce demographics, and you should feel good about the weekly “pulse” surveys you’ve implemented to broadly track employee satisfaction.

But what about specific departments? Do you see data that would reveal team-wide disengagement before it becomes a retention problem? Do you act on it?

Or even a specific worker, one of thousands of employees… working in a remote country? Is he happy? Does he have any lingering questions or concerns about employee benefits or company policies?

“The biggest handicap I see for HR individuals and HR executives is [not] having real-time data and metrics,” says Patricia Sharkey, senior director of human resources at IMI, a company that provides resources and software to automate distribution facilities across the globe. “That’s the way we’re going to be taken seriously.”

The company uses a homegrown, AI-driven HR platform called Rhonda to engage employees regularly, execute key HR functions such as performance reviews, and collect and analyze data to identify HR hotspots for leaders to act on. “What Rhonda does for HR, and what it brings to this company, is that our CEO has real-time metrics and data that he can make decisions based on,” Sharkey says. 

Senior Executive Media recently interviewed Sharkey about the company’s approach to employee communication and engagement. Read on for edited excerpts from our conversation.

“The biggest handicap I see for HR individuals and HR executives is [not] having real-time data and metrics. That’s the way we’re going to be taken seriously.”

Headshot of Patricia Sharkey

– Patricia Sharkey


Senior Executive Media: How is Rhonda regularly engaging employees and improving employee retention?

Patricia Sharkey: We have weekly surveys that go out, and employees rate, on a scale of one to five, how their week has gone… It’s a simple weekly, like, “Hey, please let us know how you’re doing.” And this goes out to the entire company. If an employee scores a three or lower, they’re going to get contacted by their manager, or by HR, and in some cases by the CEO directly, which is awesome.

I have employees that, every once in a while, I think they want to put a two because they want to talk to [CEO] Rudi [Asseer] because it turns out things are pretty good.

We run weekly reports that measure how many people are responding to us… I receive weekly reports of who’s engaging… If they’re not responding, or we’re getting a low response, we ask the manager, “Hey, how come your team isn’t responding?”

Senior Executive Media: What else does Rhonda do?

Patricia Sharkey: It’s a big part of the safety culture. We send out safety messages every Thursday. People can talk to us about any safety concerns.

We also have a weekly “hustle” that we send out via Rhonda, which is a newsletter, which reminds employees to respond to Rhonda and lists the employee of the week, by the way, too. So they’re engaged in the employee hustle because they may also see rewards.

Our employees can ask questions to Rhonda, like, “Hey, what’s up with my bank account?” … While we have an HR help desk and different areas where employees can contact us, the most successful is the AI application.

And with AI, it’s been much easier for us to get [performance] reviews back from the employees… This approach has increased accuracy, speed and employee satisfaction because it’s so easy for them to complete.

Senior Executive Media: During the actual conversations within the performance review process, how does the data you’ve collected come into play?

Patricia Sharkey: Managers… talk to their employees about their [self-evaluations] and how, say, for example, the employee gave themselves a three [in a certain area], but the manager scored a four for them.

Then I’m given all that information as well. Not only am I able to see the scores of each employee and what the managers are giving them, the AI also does the average of what the department’s overall score is, which is pretty interesting—great data for the CEO. Because it takes some of the subjectivity out and goes, “Alright, you’ve got your divisional lead, maybe saying he has the greatest department in the company. But look at these overall scores.”

Senior Executive Media: You’re gathering so much data. What are the most important or most interesting metrics that you specifically look out for?

Patricia Sharkey: What I’m looking for, as I’m doing a temperature gauge on my employees: Are they happy? Are they going to stay with us? Through data, you can see patterns of behavior, right? I can tell if someone’s not happy if I see that I’m getting a lot of twos, right? I have to not only do a one-time check in, but now I have to go and say what’s going on? What systemically is happening in this department if I see, you know, in one department, I’m getting lower scores, or people not responding? (People not responding is almost the same thing as giving a low score, in my opinion.) And the question is not about the employee, it becomes about the company and systemic practices. What are we doing well, and what aren’t we doing well?