Cathy Carroll's Blog
April 16, 2025
Swinging to Extremes? Don’t Find the Midpoint. Seek the Both/And.
November 5, 2024
Two Polarities this Election Season
Today is Election Day in the US. I find it an enormous privilege to live in a democracy, (ok, a democratic republic), and I am grateful for the privilege to vote.
Actually, privilege is the wrong word. It feels like a privilege, but in truth, it’s a civic responsibility. It’s my responsibility to vote for the better future.
But what criteria determine better? Do I vote for the candidate who is better for me? The candidate who is better for our country? Well, that’s quite a polarity, isn’t it? Do right by me and do right by us.
This Me::We tension is a polarity that family leaders face regularly. As leaders, they must manage the tension between what’s right for themselves, and what’s right for their family. The answers are not always the same – what’s right for themselves may not be what’s right for their family business and vice versa.
How do they choose between the needs of the individual and the needs of the collective? Polarity thinking would invite a different question: How might they capture both the upsides of meeting their own needs and the upsides of meeting the needs of the family? That question sparks creativity, innovation and can lead to a better outcome for all.
Returning to the US election... how do we harmonize this Me::We polarity when we are faced with a binary, either/or choice? Do I choose the candidate that’s better for me, or do I choose the candidate that’s better for us?
Which leads to an interesting question: Who constitutes “us?” Our family and friends? Our neighbors? Everyone in the state? Country? Humanity? The Earth? It gets complex quickly, making it tempting to simplify and just vote for what’s right for me. But we in the US have a cultural bias in favor of the individual over the collective.

Culturally (on average) in the West, the needs of the individual are celebrated over the needs of the collective. To sacrifice oneself for the “greater good of society” is … what’s the word?... Naïve? Foolish? I can see incredible upsides and painful overuses of Individualism.
In contrast, in the East, (culturally, on average) the needs of the collective take priority over the needs of the individual. To sacrifice the greater good for oneself is culturally wrong. I can see incredible upsides and painful overuses of Collectivism.
Are we in the overuse of Individualism in the US? I fear so. Sprinkling a more collectivist ethos into our culture could pull us out of that overuse of Individualism.
But embracing WE over ME isn’t easy in today’s polarized political environment. It asks us to really listen to the other side…listen empathically to the political TV channel that makes our skin crawl. That is a path to regaining a sense of WE; a feeling I miss greatly.
I’ll close by blending the two polarities this election season: Privileges::Responsibilities and Me::We. If you live in the US, I hope you exercise both your privilege and responsibility to vote, and as you select your candidate, I hope you mark the ballot of the candidate who meets more of the needs of both yourself and all your fellow citizens. That may bring us one step closer to feeling like a WE again.
To learn more about managing polarities, join my mailing list and/or read my new book, Hug of War: How to Lead a Family Business With both Love and Logic. Chapter 5 is dedicated to privileges and responsibilities in family businesses.
August 12, 2024
What I Learned About Truly Listening
Last week, I witnessed a demonstration of the Speaker-Listener Technique that became the standout highlight of the conference I attended.
Jokingly, the emcee introduced the three presenters as follows: “A Christian, a Sikh and a Latter-Day Saint walked into a bar. One was from the north, one from the south and one from the middle of the US. One identified conservative, one liberal and one moderate.” Everything was true, except for the walking into the bar part.
Three presenters then walked onto the stage, facing an audience of over 200 people. The southern, Christian, conservative then sat across from the northern, Sikh, liberal and they began demonstrating the Speaker-Listener technique. The Speaker shared how frustrated he was for being judged for his beliefs, and the Listener listened actively, following the Speaker-Listener instructions as best he could.
Speaker-Listener Instructions
Speaker has the floor while Listener actively listens until Speaker is finished speaking. When Speaker is finished, Listener can become Speaker as roles are reversed. The Speaker-Listener roles can change back and forth as desired.
Speaker
Speak for yourself; Use “I” statements.
Keep statements brief.
Pause to let the Listener paraphrase.
Listener
Paraphrase what you hear.
Focus on understanding Speaker’s message. Don’t rebut. Understanding doesn't necessitate agreement.
Speaker keeps the floor until Speaker is finished.
The purpose of the demonstration was to show how to “communicate respectfully across differences” in an “increasingly diverse and interconnected world” by demonstrating empathy and active listening.
To be honest, it was clunky. They didn’t demonstrate it well at first, but the audience learned from their attempts regardless, and soon the presenters invited the audience to pair up and try it out. That’s when we had all the feels.
I paired up with a total stranger, Sarah, whose close friend from age four had taken the opposite political turn that Sarah had taken. Sarah was so distressed by her friend’s politics that she had stopped accepting her friend’s phone calls.
“Perfect,” I said. “Should we practice the Speaker-Listener technique with this scenario? I can role play your friend.” Sarah was game.
As Speaker, I started spouting about how offended I was by the other party’s beliefs (and boy I had fun playing it up!) When I paused to let Sarah paraphrase, she did ok at first, but couldn’t sustain the active listening. She started defending her beliefs. Vehemently. So I switched to Listener and shortly, the session leaders paused us for questions before inviting us to reverse roles.

Truly Listening
We decided to try again with Sarah as Listener. I resumed full bore with another political rant, and this time, Sarah truly listened. She paraphrased. She acknowledged how hard it was for me. I felt truly heard. Then she leaned forward, her face sad, and said, “I miss you.” We both teared up and hugged from our chairs. She took a deep breath and said, “Thank you so much. I have to go call my friend.”
That experience was powerful. It opened a place in Sarah’s heart to reconnect with her childhood friend as a human being, not as an ideologue. I’ll never forget it.
I’ve started to practice truly listening with my family members whose political beliefs differ from my own. I’m not good at it. With family, I’m far quicker to defend, get angry, or simply switch topics. But I’m getting better.
I've learned that when I truly listen, when a speaker feels truly heard, their strident attempts to convince me that I'm wrong, abate. We can disagree without being disagreeable.
It helps that I now hold liberal-conservative as a polarity. As with any polarity, one ideology is not more correct than the other, despite my fierce desire to cling to one. As I’ve forced myself to acknowledge the problems that arise when my preferred politics are overused, and I’ve recognized the genuine need for the opposite party’s ideology to keep the ongoing tension healthy for our country, I’ve been able to engage in political conversations with my family members with more ease, grace, acceptance, and love.
I’m going to need these Speaker-Listener skills over the next three months leading up to the US election, and beyond. We all need these skills. Regardless of the election outcome, we are one country, we are the United States. We can do this.
To learn more about managing polarities in family conversations, join my mailing list and/or read my new book, Hug of War: How to Lead a Family Business With both Love and Logic which launched on July 12th!
July 16, 2024
"Hug of War" has launched!
I've been a little quiet lately while focused on the launch of Hug of War: How to Lead a Family Business With both Love and Logic. I'm happy to say that the launch went very well, and below, you can watch a 30-minute video that provides some insights into what you'll find in the book.
Spoiler Alert: In Hug of War, you'll find:
Stories filled with drama, anguish, and joy;
An understanding why family business leadership is harder than elsewhere;
Three unique power dynamics that exist only in family business;
An understanding of the unsolvable dilemmas unique to family business;
A hidden reason for pervasive conflict in family business;
And best of all, a straight-forward path through the muck so you find greater harmony in your family, clarity in your mind, and peace in your heart.
Hug of War is about the realities of leadership in a family business, and filled with Pro Tips, it is written with the leader in mind. Listen to the video to learn more, and/or visit www.legacyonward.com/hug-of-war.
Enjoy!
Cathy
June 13, 2024
Family Business Succession – Why is it so hard to let go?
I know too many rising generation leaders whose parents can’t let go of leadership. Seems to happen often in father-son relationships, and I’ve noticed a disproportionate number of examples in real estate families. What gives?
Here are two recent examples, each with different outcomes.
Family Business Succession - Example 1
Juan and his 72-year-old father scheduled the date for their leadership transition three years ago, but as the date approached, Juan seriously doubted whether his father would follow through. Juan grew more and more anxious as he watched his father deftly dodge any succession conversations.
As the transition date drew close, Juan firmed up his backup plan in case succession fell through. His father had the power to decide, and Juan was prepared to walk away if his dad refused to honor the transition date. They had been dancing this dance for too long, and it was hurting Juan’s health, his marriage, and destroying any affection he felt for his father.
With no reason to delay and no transition plan in place three weeks before the scheduled transition date, Juan called his father and made it clear that he would resign if succession didn’t happen. Juan was reluctant to make an ultimatum, but this was his life. His career and his family’s future were at stake.
His father was furious. He stopped speaking with Juan and instead, turned to Juan’s mother to complain. She ended up being the lynch pin to save the transition. At the 11th hour, a few days before the final deadline and to Juan’s surprise, Juan’s father agreed to transition the business to Juan. Juan has his mom to thank for it.
Family Business Succession - Example 2
Sebastian’s experience was different. He spent five years successfully growing his 78-year-old father’s business, and for the last two years, he and his father worked with a succession consultant to establish a succession plan. As succession drew near, Sebastian’s father suddenly fired both Sebastian and the consultant, turning to Sebastian and declaring, “This business is no longer a family business, and I never promised you a job.” Despite clear intentions, in the end, his father couldn’t follow through.
Both Juan’s and Sebastian’s succession plans had rational roots. Yet both were hijacked by emotion. Hmm. Emotion and reason – quite a powerful polarity in family business succession.

Why it's So Hard to Let Go
Family business leaders are notoriously famous for struggling to let go. Why is it so hard?
I don’t know because the leading generation rarely seeks coaching (from me at least) to address the complex emotions involved in succession. So, I can only guess.
But I have some clues. I know one entrepreneur who recently transitioned his business to the next generation. This man consults with family business owners regarding succession strategies, so he knows how hard this transition is. Nevertheless, he was surprised by the anguish he felt at losing the decision authority that once was his.
Now he sees a new generation of leaders, impatiently seizing the authority to change all the things that need changing. I bet every change feels like a repudiation of his prior leadership. That’s got to burn.
Although he serves on the board, he's cautious; unclear about when he can chime in and what he can say. He’s trying to respect the new decision-making processes, but people still come to him expecting him to make the calls.
I think that is the hardest part. People come to him, and he doesn’t have the power to help any more. He loves to help people. He’s great at it too. It’s one of the many reasons he’s so beloved.
I bet it’s hard to intentionally give up power, especially power that fulfills your soul.
Yeah. No wonder it’s hard to let go. Now that I’ve put myself empathically in the leader’s shoes, I can feel the anguish too.
Rational and emotional. Patient and impatient. Control and trust. Tradition and innovation. These are just some of the polarities of succession in a family business. Tough tensions to manage between generations.
To learn more about how to manage the tensions of succession in a family business, join my mailing list and pre-order my forthcoming book, Hug of War: How to Lead a Family Business With both Love and Logic. Official launch is July 12th!
May 28, 2024
Harmonizing both Focus and Fun
45 seconds on how I harmonized both FOCUS and FUN this long weekend. To get what you want in life and leadership, what do you need more of? Focus or fun?
May 14, 2024
Strengths Overused
Nathan, is trying too hard to be the opposite of his father (who is also his boss.)
Nathan came to coaching because he struggled to make decisions. A gifted excel modeler, he grew concerned that if he looked up "analysis paralysis" on Wikipedia, he’d find his picture. He built brilliant models to analyze the marketplace, but when it came down to making a decision, he would kick the can by identifying more data to collect and better models to build.
Over time, Nathan realized that his obsession with analysis was due to an aversion to “just winging it,” which is how he described his father’s leadership. Liam, his dad, used gut instinct to lead their family business. There was no planning, no data; he shot from the hip using pure intuition when recognizing an opportunity. “That’s just who I am,” says Liam.
That scares Nathan. As a kid, he watched Liam hit some home runs and some duds, but mostly, Liam landed somewhere in between. Neither a success nor failure; the business mostly broke even.
Nathan knew he could add value to the family business by bringing structured analysis to decision making. But it’s not working. Not only is Nathan indecisive, his relationship with his dad is rancorous because Liam won’t engage in strategic planning conversations with Nathan. Liam’s lack of patience or interest in strategy infuriates Nathan.

Strengths Overused
Although Nathan and Liam prefer opposite poles of an Analysis :: Intuition polarity, both men are in the overuse of their preferred pole.
Liam’s shoot-from-the-hip style of leadership has some upsides. It’s nimble and low-cost in the near term. But he has some blind spots about the value of intuition. Sprinkling even a little analysis could help him make better investment choices and safeguard against his over-focus on possibilities.
Nathan’s preference for analysis has some upsides too. It’s data-driven and theoretically less emotional. But Nathan has some blind spots about the value of analysis. Accessing even a little gut instinct could help him shift out of paralysis and safeguard against his over-focus on risk.
These generational swings in leadership styles are common in family businesses. When children witness the overuse of a parent’s value or style, they naturally swing the opposite direction, but they often over-correct.
I sure did.
When I worked for my father, all I could see were the overuses of his disruptive, controlling, bold leadership. It’s no wonder I strove for stability, collaboration, and humility. “It’s just who I am,” I thought. I identified with these traits, as if they defined me. In fact, they are the same traits I’d use to describe my grandfather. Hmm.
I didn’t realize that stability :: disruption, collaborate :: control, and humble :: bold were leadership polarities. I just knew I was right, and my dad was wrong. (Nathan believes the same thing about his dad.)
At the time, my preference for stability, collaboration and humility served the business well because it balanced my father’s overuse of disruption, controlling and bold. However, it didn’t serve my relationship with my father well because we each believed the other to be wrong. Very wrong.
Had I understood leadership polarities back then, I might have appreciated and acknowledged the value of my father’s leadership preferences. And maybe he’d have respected mine.
But that was over a decade ago. Now, I understand how polarities operate, and I am careful not to fall into the overuse of stability, collaboration, and humility.
For example, I’m disrupting my cozy life by publishing a book about polarities. Hug of War comes out July 12th, and my calendar is filled with speaking on podcasts, activating my book launch team, and building author pages on Amazon, Facebook and LinkedIn. When the book opened for pre-sales last week, I activated my launch team: “Order my book now!” That felt uncomfortably controlling. (Fortunately, they are all volunteers.) I’ve even found the courage to ask people for book endorsements. Bold! Awkward for me! And oddly humbling because the quotes have been so touching.
Expanding Identity
Although I’ll always prefer stability, collaboration, and humility, I’m expanding my identity to include disruption, commanding and bold. This helps me operate in the world with greater effectiveness.
As for Nathan, he’s learning about polarities now too. He has zoomed out and can see how he and his father complement each other; how their individual preferences can enhance their effectiveness. Plus, he’s sharing what he’s learning with his father, which helps them both expand their identities.
While Nathan is recognizing the value of intuition, Liam is recognizing the value of analysis. They are learning how to learn from each other and leverage their respective strengths. It’s a slow process because both men are reactive and defensive when the other reveals their blind spots. After all, one’s identity can be an awfully tender topic.
To learn more about leadership polarities and strengths overused in a family business, join my mailing list. That should tide you over until Hug of War: Leading a Family Business With both Love and Logic is released in July. (Pre-sales are open on Amazon and Barnes & Noble!)
April 9, 2024
What is Entitlement, Anyway?
Defining “entitlement” is kinda like defining porn. It’s hard to describe, but you know it when you see it. Or do you?
I may or may not know an 18-year-old (who will remain anonymous to protect the guilty) who I think demonstrates entitled behavior. Last spring, he forgot to apply for a Senior Parking Pass, and his high school sold out of them. So, he used his stellar graphic arts skills to replicate the parking pass, and he parks illegally in the Senior parking lot using that fake pass every day. He just decided he could jump ahead of the other classmates who responsibly applied for, earned and paid for a parking pass. Because he thinks he can.
Is this egregious entitlement? Probably not. To a rule follower like me, it’s just wrong, wrong, wrong. But my developmental journey has been discerning when it’s ok to break the rules. So part of me admires him.
What gigs me the most is that he did it last year too, when as a Junior, he wasn’t even eligible for the Senior parking lot. He got caught. The principal punished him. And he just did it again this year.
I’m wrapped around the axle about what’s fair and not fair. (Cheating is not fair, and he’s cheating!) To me, it’s classic entitlement behavior. He thinks he can get away with it, and that’s justification enough even though he knows “it’s wrong.”
But to him, it’s not entitlement. To him, it’s a victimless crime. It’s simply a risk/reward tradeoff, and he’s decided that the risk is worth the reward. He’s not wrong. If he gets caught again, he’ll take his punishment, and it’ll be worth the months of sneaking in the Senior parking lot for free and ahead of everyone else who played by the rules.
What is Entitlement, Anyway?
This is what makes entitlement such a slippery topic. What’s entitlement to one person isn’t entitlement to another. Further, what looks like entitlement on the surface can be behavior motivated by something very different than “because I can.”
In my book Hug of War (coming in July!), I describe twin brothers, Maks and Peter, who enjoyed working together in their mother’s business, until Peter started to spend more time golfing than working. This went on for months, and Maks didn’t say anything for fear of violating their unwritten code that twins don’t judge each other.
Although Peter’s behavior bothered Maks, it really got to Maks’s wife, Lenore, who also worked in the business and refused to tolerate such flagrantly entitled behavior in Peter. Knowing her husband Maks wouldn’t say anything, Lenore raised a stink with Peter and insisted he show up at the office for a full workweek. Instead coming to the office more, however, Peter did the opposite – he showed up even less.
This pattern went on for a few more months – the more Lenore barked at Peter, the more Peter went golfing – until a consultant interviewed the family members, and eventually the truth came out.
Truth was, Peter couldn’t stand Lenore. He wanted out from under Lenore’s oppressive judgment, but he didn’t know how to escape. He couldn’t disappoint his mom by leaving, and he didn’t know how to tell his brother that he couldn’t tolerate Lenore. So he golfed. That’s not entitlement. That’s a coping strategy.
How I Define Entitlement
Because I hold privilege and responsibility as a polarity*, my definition of entitlement is the overuse of privilege. There’s nothing inherently wrong with privilege – everyone has some form of privilege in their lives. However, what keeps excess privilege from spilling over into entitlement is a healthy dose of responsibility. Privilege and responsibility pair well together, like dark chocolate and red wine.
(*By polarity I mean, a set of interdependent opposites, each of which represents one half of a whole. Think inhale and exhale, for example.)

What do you call the overuse of responsibility? Well, as you can guess by my Church Lady tut tut of this 18-year-old’s brazen use of a fraudulent parking pass, I tend to operate in the overuse of responsibility. (“Isn’t that special?”) There is nothing inherently wrong with responsibility, but when responsibility is overused, it looks like judgment and feels like a burden.
While my 18-year-old high schooler is learning how to sprinkle some responsibility into his privilege to stay out of its overuse, I’m learning how to sprinkle some privilege into my responsibility to do the same. And I’m not alone in feeling the pressure of responsibility. Countless family business leaders I interviewed for Hug of War feel heavily burdened by responsibility in their family business.
Speaking of Hug of War, to learn more about polarities, especially its privileges and responsibilities in a family businesses, join my mailing list. That should tide you over until Hug of War: Leading a Family Business With both Love and Logic is released in July 2024.
PS: I’m still beta testing the family business polarity assessment so leaders can see how well they are leveraging the most common tensions in family business leadership. To access the assessment, click here and check the box next to “Please send me the complementary family business assessment.”
March 26, 2024
How to Take Feedback
Feedback in a family business can be hard to take. Here's how I digested some recent feedback that I really didn't want to hear. Listen for a one minute tip on how to take feedback, which I discuss in my upcoming book, Hug of War: How to Lead a Family Business With both Love and Logic (coming in July 2024). Join my mailing list to learn more!
March 12, 2024
How to Have a Brave Conversation using PlayFAIR
“Help! I need to prepare for a brave conversation with my cousin Miranda tomorrow,” said Dillon, CEO of the manufacturing company his grandfather started. “Miranda has been with the company for 24 years – she joined the HR team right out of college – and she’s become a great asset as VP of HR, but now she wants to slow down and work part time.” His bright eyes began to furrow.
”Last year, she hired an impressive HR Director, Ezra, who’s been covering for Miranda while she spent February in Hawaii, and Ezra is taking HR to a whole new level,” continued Dillon, his eyes brightening back up. “But tomorrow, we’re discussing her request to work part time. We could use Miranda for a few months, but Ezra can do this job and more. We’re just not going to need Miranda in a few months.” He looked up. “How do I have this conversation? I want to do right by her, and I also want to do right by the shareholders.”
I asked Dillon what values were in conflict. He shared that on one hand, he valued his cousin and her dedication to the company, and he wanted to show her respect for her good work and loyalty. On the other hand, he valued efficient operations and delivering adequate investment returns for shareholders, all of whom were also family.
“Hey, can you refresh my memory on how to have a brave conversation using that PlayFAIR model?” he asked. “I think this situation calls for it.”
PlayFAIR is a mnemonic which stands for:
· Permission
· Facts
· Assumptions
· Impact
· Request
How to Have a Brave Conversation
The PlayFAIR model offers a five-step framework to address a challenging topic. It flows like this:
1. Permission “Do you have some time to talk? This should take about X minutes.”
Make sure you have enough time for the conversation and that both parties are prepared to engage. The right conversation at the wrong time is the wrong conversation. It’s okay to share the topic if asked.
2. Facts “I noticed that . . .”
Start by stating the facts and only the indisputable facts. Starting with “I noticed . . .” implies a neutral observation. Be careful not to interpret the facts. For example, “You were short-tempered” is an assumption, not a fact. “Your voice grew louder, and your face reddened” is a fact.
3. Assumption “I’m telling myself that . . .” or “My story is . . .”
Share your interpretation of the facts. This is the story you are telling yourself about the facts. It’s important to “own” your story because it leaves room for other interpretations to coexist. Plus, if you state your story as “the truth,” you may trigger defensiveness. Your goal is to keep egos to a minimum and curiosity to a maximum.
4. Impact “The impact of this is . . .”
State the relevant impact on you, others, and/or the organization to put it into a broader context. State what makes this important to address and watch your tone. Don’t whine. Stay matter-of-fact to the extent appropriate.
5. Request “I’d like to resolve this . . .” or “I have a request . . .”
Express a desire to resolve the issue or make a request if you have one. Then listen with sincere curiosity to understand the other person’s perspective. Paraphrase what you hear and ask, “Is that right?” until the other person affirms, “That’s right.” Remember, you don’t have to agree with it to understand it.
“Right, thanks,” he said. “Let me rehearse a conversation with Miranda using PlayFAIR.” Here’s what he drafted:
1. Permission: The meeting was already scheduled so permission was implied.
2. Facts: “Dillon, while you were away last month, Ezra took the lead in HR, and he did well. In fact, I noticed that he proposed some innovative new programs that could uplevel the plant associates and enhance company culture. Ezra is a great asset to the team. Credit to you for bringing him on board to support your request to work at 75% of full time.”
3. Assumptions: “I’m assuming you already know how much I appreciate you personally and how valuable you’ve been to the company for over two decades.. I’m also assuming you would like to retain part-time employment indefinitely while retaining full-time benefits and a 25% reduction in salary.”
4. Impact: “Here’s my challenge. I want to honor your request to work part-time. I also believe we need a full-time HR leader, and Ezra can do the job. I’d like to promote him to VP. The impact of retaining you at 75% of your full-time salary is that we will have two highly paid HR leaders and not enough work to justify the compensation. I am torn between wanting to do right by you and wanting to do right by the shareholders.”
5. Resolution: “I’d like to talk about this openly. As VP of HR, I know you understand the budget constraints and the strategic issues in play from an organizational design perspective. How do you see this situation? Do you see it the same way I do, or do you see it differently?”

At our next coaching conversation, I could see relief in his smile. “It went better than my best hopes,” said Dillon. “Miranda appreciated my candor and understood the dilemma I faced as CEO. She asked for a few days to think about it, and last Friday she acknowledged that her extended time in Hawaii gave her time to reflect on her career goals. She wants to start her own coaching business serving family business leaders! She offered to stay part-time for three months to fully transition the VP role to Ezra before she starts training to be a coach. What a win for everyone!” he said, beaming.
And I’m happy to have another talented family business coach join the field.
To learn more about how to have a brave conversation in a family businesses, join my mailing list. That should tide you over until Hug of War: Leading a Family Business With both Love and Logic is released in July 2024!
PS: I’m still beta testing the family business polarity assessment so leaders can see how well they are leveraging the most common tensions in family business leadership. To access the assessment, join my mailing list and check the box next to “Please send me the complementary family business assessment.”