Category: Leadership

Dear Strategy Consultants: Stop Annoying Your Clients with Irrelevant Questions

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My dissertation explored the questions organizations ask when setting strategy. I wanted to develop an approach to strategic thinking that produced better insights and more options. Ironically, while I scrutinized the influence of leaders’ mental models on the strategy questions they ask, I failed to notice the mental model driving my own research. Why should there be a generic approach to strategic thinking?

Not every chess player analyzes the board the same way. Doctors don’t recommend a one-size-fits-all strategy for an individual’s health. As I age, I want to continue running for exercise, but I’m also happy to take “run a marathon” off the table.

Organizations want to thrive and grow, but they don’t all share the same appetite for growth. Organizations are also constrained by their situations and choices, but not to the same degree. Strategy questions should match the logic of how a given organization actually makes choices. To help me continue running as I age, my doctor shouldn’t focus on shaving time off my pace, she should help me think about stretching.

Contrasting what an organization wants to do with what an organization won’t consider doing creates a simple, powerful, and customized approach to planning.

Appetite for Growth versus Degrees of Freedom

Understanding how an organization’s appetite for growth intersects with its degrees of freedom creates four distinct strategy settings. I’ve labeled each quadrant with a persona that captures the motivations and constraints shaping that organization’s strategic logic.

The Surfer: High degrees of freedom and low appetite for growth

Surfers value agility, mission, and meaningful work over aggressive growth. They read the environment carefully, pursue opportunities that align with their purpose, and adapt quickly without getting locked into rigid structures. Like a chef-run restaurant with a seasonal menu or a nonprofit that shifts programs as community needs evolve, Surfer organizations maintain a high degree of freedom so they can do the work they believe in. Their strategy is sensing, choosing, responding, and releasing—not scaling.

Strategy question for Surfers:

What useful lessons have you harvested about the work that lights you up?

The Watchmaker: Low degrees of freedom and low appetite for growth

Watchmakers value reliability, precision, and consistency. They prioritize longevity and mastery over growth. Some Watchmaker organizations are constrained by regulation and risk, think hospitals or nuclear plants. Others are constrained by self-imposed ideals like heritage and craftsmanship, luxury brands or artisan workshops. Rather than catching the next wave, Watchmakers want to perfect what is already in motion. Reliability comes from doing fewer things exceptionally well.

Strategy question for Watchmakers:

How will you ensure that the next generation of stakeholders continues to experience the ideal value of your offering?

The Industrialist: Low degrees of freedom and high appetite for growth

Industrialists value volume, standardization, and leverage. They prefer optimizing what already exists to inventing what doesn’t. They scale by acquiring undervalued assets and extracting hidden value. Private equity firms and conglomerates are classic Industrialists. Sometimes their constraints come from regulation, other times they impose constraints through strict acquisition and divestiture criteria. Industrialist organizations create power through accumulation, not invention.

Strategy question for Industrialists:

How will you sense and respond to emerging environmental trends that could alter the calculus of your growth strategy?

The Inventor: High degrees of freedom and high appetite for growth

Inventors value innovation and discovery. Because they combine creativity with the resources to scale big ideas, Inventor organizations don’t spend time trying to predict the future, they cultivate it. Inventors take risks with prototypes and minimally viable products. They release solutions quickly, learn from users, and iterate. Thomas Edison personifies the Inventor mindset, Henry Ford personifies the Industrialist.

Strategy question for Inventors:

What unarticulated human needs are hiding behind the world’s status-quo assumptions about constraints?

The sooner we stop insisting that every organization needs the same strategy process, the sooner strategy will feel less like ritual and more like relevance. When leaders understand their authentic strategic posture, they give themselves permission to work in ways that feel natural, energizing, and aligned. Strategy becomes less about chasing someone else’s version of success and more about manifesting the conditions under which the organization, and the people in it, will flourish.

Leadership Begins with Managing Performance and Matures into Manifesting Purpose

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For decades, organizations have defined “good leadership” through the language of competencies. They build models that specify what leaders should know, say, and do – how to give feedback, how to manage conflict, how to make decisions. These models create consistency and a sense of fairness. They make it possible to assess, promote, and design training programs.

But competency models also do something else, something unintended. They imply there’s a single, correct way to lead. They teach people to manage leadership rather than to manifest it.

Early in a leader’s journey, managing is essential. New leaders need guidance, structure, and standards. They need to understand how to set expectations, how to hold people accountable, how to ensure that work gets done safely and ethically. Managing performance is the foundation of effective leadership.

As leaders mature, they discover that management alone doesn’t inspire excellence or adaptation. When environments change, when uncertainty rises, when teams face complex and ambiguous challenges, leaders can’t rely on checklists. The competencies that once provided confidence start to feel confining.

This is the turning point where leadership matures, when it shifts from managing performance to manifesting purpose. When early-career leaders focus on managing performance, they tend to emulate their role models. When leaders mature, they need to connect who they are to how they lead, that might mean reframing competencies as foundational, not aspirational.

From Competencies to Conditions

Manifesting purpose means creating the conditions in which people and organizations can thrive. It’s not about whether leaders have mastered the right behaviors; it’s about whether their leadership is producing the right organizational climate.

Think of leadership outcomes not as what leaders do, but as what people experience when leadership is working as intended.

  • Do people understand how their work connects to a larger purpose?
  • Do they feel safe to raise concerns, take risks, and innovate?
  • Do they see decisions being made transparently and collaboratively?
  • Do they believe their contributions matter?

If those conditions exist, leadership is functioning. If they don’t, it isn’t – regardless of how well a leader performs against a competency checklist.

And who is best positioned to determine whether those conditions exist? Not the leader’s manager. Not an HR algorithm. The people being led. The most direct way to know whether leadership outcomes are being achieved is to ask the people impacted by them.

There’s No One Right Way to Lead

Every organization’s strategy calls for different conditions. Every team’s context is unique. And every leader’s personality, history, and strengths shape how they bring those conditions to life.

Organizations exert control by establishing structures. Yet when it comes to professional development, there’s no one right way to lead. If we’re not careful, we can end up treating leaders like widgets on an assembly line. Competency models turn into quality assurance standards, and facilitating leadership workshops feels like teaching to the test.

What organizations really need are leaders who can translate purpose into experience. Some will do that through storytelling and inspiration. Others will do it through systems and structure. Still others through empathy, inquiry, or relentless problem-solving. What matters isn’t the method, it’s what the method manifests.

Rethinking Leadership Development

If organizations want leaders who manifest purpose rather than just manage performance, their development practices need to evolve. That means shifting from competency-based instruction to outcome-based reflection.

Instead of asking:

“Has this leader demonstrated effective communication?”

Ask:

“Do people on this leader’s team feel informed, heard, and aligned?”

Instead of designing programs to improve discrete skills, design experiences that help leaders experiment with new ways of creating the conditions their teams need. Replace competency assessments with outcome conversations. Replace one-size-fits-all workshops with real-time reflection, feedback, and coaching tied to strategic outcomes.

The question isn’t whether leaders know what good leadership looks like. It’s whether people around them can feel it.

Lane Changes

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My wife and I moved to Dallas from Los Angeles. Among the many stark contrasts, we were most struck by the difference in driving habits. In Los Angeles, driving is a cultural phenomenon. In Dallas, driving feels competitive. When meeting friends and colleagues in L.A., you talk about freeways. In Dallas, you talk about sports.

When I lead workshops that cover topics like the Ladder of Inference or confirmation bias, I often use driving behavior to illustrate how our beliefs shape what we notice. I’ll claim that Dallas drivers don’t use their turn signals. And because of that belief, I see endless “evidence” that I’m right: cars weaving across lanes without signaling. My daughters, aware of my bias, like to call out counterexamples: “Look, Dad, that green car just signaled.” They see what I filter out. I’ll even reinterpret their evidence to fit my belief: “That driver must not be from Dallas.”

Our brains love shortcuts. We cling to assumptions because they feel efficient. But those shortcuts can blind us to signals and to each other.

Turn signals are a form of communication. A signal might be a polite, “May I move over?” or a warning, “Heads up!” Most often, it’s simply, “Here’s what I’m about to do.” At its core, signaling is an acknowledgment that other people’s needs matter.

At its core, signaling is an acknowledgment that other people’s needs matter.

Cars obscure the body language we rely on to interpret intentions. And life is full of invisible “vehicles”—schedules, inboxes, calendars—that make it hard for others to see where we’re headed. Without signals, people are left guessing.

We travel through the world in these bodies, much like cars: enclosed, private, and easy to forget there’s someone else behind every windshield. We work across distances and time zones. We make plans, change plans, and often assume others will just “figure it out.” When we fail to signal, it’s not always selfishness, it’s often habit, distraction, or the illusion that others can see what we see.

Compassion starts with simply acknowledging that other people exist and have needs too. Compassion isn’t just empathy; it’s action. To communicate compassionately is to anticipate others’ need for clarity before they’re left reacting to unexpected changes.

Travel compassionately by signaling your intentions:

  • A quick update. Send the “I might be late” text before someone starts worrying.
  • A small heads-up. Share a draft early so your colleague doesn’t feel ambushed later.
  • A sign of respect. Tell a teammate when you’ve changed course instead of assuming they’ll notice.
  • A kindness. Ask, “Is this still a good time?” before diving into a heavy topic.

Signals don’t need to be elaborate. A quick message, a note in a shared calendar, a sentence of context—these are all turn signals for life.

Signaling helps you, too. When we pause to share our intentions, we slow down, reflect, and notice others. We interrupt autopilot. We shift from competition to cooperation. We strengthen our attention agility, the ability to quickly and easily shift one’s focus in response to dynamic conditions.

The habit of signaling reminds us we’re not driving alone. We’re part of a complex flow of people, each carrying their own invisible cargo of worries, hopes, and deadlines.

So, when you feel rushed, overwhelmed, or ready to change lanes in life, ask yourself: Who needs to know what I’m about to do? Then, use your indicator.

Work Awake!

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Is taking leaders away from their work and putting them in a classroom really the best way to help them improve?

Classroom training has its benefits, but often not the ones we advertise. It promotes social connection and peer learning through shared experience. At a time when social isolation and loneliness are being described as a public health crisis, any opportunity to bring people together feels important. Sometimes, we ask leaders to attend a training session simply to signal that a topic warrants their full attention.

The classroom is an artificial environment. We simulate reality with case studies, role-plays, and structured activities. But what if we flipped the script? Instead of making the classroom feel more like the real world, what if we made the real world feel more like a classroom? Learning opportunities are everywhere—we just need to help leaders notice them and extract the relevant lessons.

Instead of making the classroom feel more like the real world, what if we made the real world feel more like a classroom? Learning opportunities are everywhere—we just need to help leaders notice them and extract the relevant lessons.

Learning in Context

The good news: readily available artificial intelligence (AI) tools make learning in the flow of work more accessible than ever. Leaders no longer have to wait for a weekly coaching session to process a challenging situation. They don’t have to flip through a long-forgotten participant manual to recall a useful framework.

That’s why we created Work Awake—a systematic approach to in-the-moment development for leaders.

Working awake means maintaining real-time awareness of your mindsets, behaviors, and impacts so that skill development becomes a deliberate part of your leadership practice.

Meet Your Work-Awake Coach

At the center of our strategy is a customized AI coach: the Work-Awake Coach. You can interact with our prototype here. We’d love to hear what you think.

Unlike general-purpose tools like ChatGPT, Claude, or Gemini, the Work-Awake Coach is purpose-built. It’s trained on your organization’s leadership philosophy, values, and frameworks. Whether you want to reinforce concepts like emotional intelligence, growth mindset, or navigating adaptive challenges, the coach helps leaders become fluent in your organization’s leadership language.

Want your leaders to use the GROW model to coach others? The Work-Awake Coach helps them prepare coaching conversations using that very model.

This is what we mean by a learning integration strategy—embedding what you teach into how your leaders think and act every day.

The Hidden Agenda of Working Awake

Yes, the Work-Awake Coach is practical. It offers just-in-time support for tricky conversations and complex decisions.

But it also nurtures something more profound: attention agility.

Attention agility is the ability to shift your focus and perspective when conditions change. It’s what helps us spot insights and generate options we would have missed by relying on our usual habits of thought and familiar social connections.

Sleepwalking through your day—mindlessly following routines—limits what you notice. Working awake means reclaiming your attention. And that changes everything.

In a volatile and uncertain world, adaptation is non-negotiable. But we can’t adapt unless we notice we’re stuck. And when we’re stuck, we need someone to ask provocative, perspective-shifting questions.

Even better if that “someone” understands your communication style, never forgets a conversation, is always available, and puts your growth first.

Listen for Underlying Influences; Helping Your Colleagues Get Unstuck

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Be present, get curious, listen with empathy, listen actively, set aside your own opinions and reactions. All good advice for developing your listening skills.

For over 30 years, I’ve been teaching listening skills workshops to organizational leaders. A few workshop participants get a lot better. Most improve in the classroom and then revert to their familiar communication habits when they get back to work – some are hopeless.

I’ll let you in on a secret. Those of us who teach leaders how to listen, secretly want to use the skill as a trojan horse for creating more humane workplaces. These noble intentions, however, can undermine the effectiveness of listening skills training. We place too much emphasis on behavior and mindset: how to be a better listener. We don’t place enough emphasis on what to listen for, becoming a more strategic listener.

Those of us who teach leaders how to listen, secretly want to use the skill as a trojan horse for creating more humane workplaces.

I can anticipate the reaction of purists who would warn against polluting one’s mind with listening filters. You wouldn’t choose bait without knowing what’s swimming below. When training therapists, coaches, or social workers I stand with the purists. Empty your mind, open your heart. When training leaders – busy, time-starved, results-oriented leaders – we need easy-to-adopt guidance so they can experience a noticeable improvement.

Got a Minute?

Some conversations are about career development, some are about establishing and maintaining relationship. Let’s focus on how to strategically listen when someone with a problem to share approaches a leader with the deceptively casual, “Hi, got a minute?”

As David Straus, the founder of Interaction Associates, pointed out in “How to Make Collaboration Work,” a problem is a situation someone wants to change.

Most problems brought to leaders at work are situations that the person raising the issue wants to change. The key to being a better strategic listener is to explore the nature of the situation and the nature of the change.

When a person feels stuck, it is likely that there are underlying or hidden influences missing from their thinking. The SCAN model from Unstuck Minds can help reveal what we might be missing when trying to make sense of the situations we want to change. Here’s a quick explainer video about SCAN.

When interacting with someone feeling stuck, a leader should listen for information from each of the SCAN dimensions:

  • Ask about structures: What existing systems, routines, or processes are resisting the change you want to make?
  • Ask about context: What environmental factors outside your control pose threats or opportunities?
  • Ask about assumptions: Name underlying beliefs you hold about the situation? What underlying organizational beliefs maintain the status quo?
  • Ask about needs: Who matters to the situation, what do they each care about? Whose perspective is missing from your understanding of the situation?

Without a framework like SCAN, we are all tempted to seek the kind of information we like best. Our favorite sources of information are like our preset music stations or playlists. We get a steady diet of what the channel provides, but a breakthrough might require a conscious effort to hear something unexpected.

If you’d like to learn which of the SCAN dimensions you’re most attracted to, you can take a free assessment and download a report.

Five Cut-and-Paste Chatbot Hacks for Overwhelmed Decision Makers

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Imagine having a whip-smart, creative summer intern who only fetches coffee while managers solve all the problems. That’s how many organizations employ AI assistants today.

To help you get more from this underutilized resource literally at your fingertips, here are five hacks to elevate your chatbot responses.

1. Ask Me Questions

Chatbots can do much more than provide responses to your queries. At the end of a chatbot prompt, include a sentence like this: “Feel free to ask me questions to clarify this request and ensure your response is not constrained by the way I framed my question.”

This simple invitation transforms a one-way interaction into a collaborative dialogue. Instead of accepting a potentially limited response, you’re opening the door to deeper, more nuanced insights.

2. Play Devil’s Advocate

Chatbots are unfailingly polite and supportive. But sometimes, you need a thought partner to pressure test your thinking or identify potential pitfalls.

Instead of posing a straightforward question, try this approach: Enter your conclusion or plan of action, then invite opposition. Use a prompt like: “Please play ‘devil’s advocate’ in response to what I’ve shared. I’m interested in what I might be missing and what flaws you detect in my reasoning.”

3. What Would (Insert Expert Here) Do?

Chatbots can adopt personas based on their extensive training data about well-known experts. Want to brainstorm with Thomas Edison or get Indra Nooyi’s take on a thorny investment option? Here’s a powerful prompt:

“I’m trying to figure out X. I would like you to coach and advise me as if you were [expert]. Please use what you know about [expert] to inform the questions you ask and the perspectives you share.”

4. Role-Play a Difficult Conversation

Remember those awkward role-play exercises in training workshops? Now you can practice challenging interactions in private. Start by providing the chatbot with relevant information about the person and situation. Include any anticipated challenging behaviors.

You can even explain your goals and have the chatbot ask you questions to help realistically portray the other person. It’s like having a personal communication coach available 24/7.

5. Get the Image You Want

AI image generation can be frustratingly hit-or-miss. While it feels magical to create images with a few words, getting exactly what you want can be challenging.

If you’re unhappy with the initial image, get the chatbot to help you craft a better prompt. Try this approach: “Looking at the image you’ve generated, here are a few things I want to change. Before regenerating an image, I’ll list the changes. Then, I want you to provide a complete prompt that will generate a new, improved image.”

These hacks aren’t about replacing human creativity and decision-making. They’re about amplifying your capabilities, providing new perspectives, and helping you work smarter, not harder.

How Leaders Turn Thinking Into Action: Lessons From Five Years of Data

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Organizations develop unique patterns in how they navigate complexity and uncertainty. After five years of assessing how leaders approach challenging situations, we’ve discovered that different organizational cultures rely on markedly different information sources to make decisions – insights that challenge our traditional one-size-fits-all approach to leadership development.

I don’t think anyone would be surprised to learn that a group of leaders in a government auditing function would process information differently than a group of technology company sales leaders. Why then, do we offer both groups the same advice about aligning stakeholders, influencing senior leaders, and managing change?

The SCAN Framework

To help leaders identify hidden influences and unseen barriers in complex environments, we developed the SCAN framework. This tool assesses four critical data sources that inform leadership thinking: Structures (organizational systems and norms), Context (environmental factors), Assumptions (underlying beliefs), and Needs (stakeholder motivations and desires). SCAN scores allow us to visualize how different leaders prioritize these information sources when moving from thinking to action.

Our analysis reveals that functional groups and organizations develop distinct thinking-to-action cultures – consistent patterns in how they process information when setting direction, making decisions, or solving problems under uncertainty.

Three Distinct Thinking-to-Action Cultures

The bar graph compares three different groups of leaders from three different organizations and functions. Bar heights represent percentile scores for each dimension of the SCAN framework. The black dashed line represents the average score for each dimension based on total database responses from groups working in the same functions and organizations (n=1528).

Leading Change

Let’s consider what the SCAN profiles in the above graph suggest about how each group of leaders might design a large-scale change effort and the pitfalls they might encounter during implementation.

Government Audit Managers

These leaders demonstrate a strong focus on existing systems and norms, scoring notably higher than average in the Structures dimension. Their systematic approach brings stability and consistency, but also creates specific challenges in change management. They tend to overlook environmental factors outside their direct control (low Context) and rarely question established systems (low Assumptions).

When leading change initiatives, these leaders excel at working within established frameworks but need to strengthen their ability to:

  • Connect change efforts to broader strategic objectives
  • Respond to shifting external factors
  • Challenge procedures that no longer serve their purpose

Technology Company Sales Leaders

These leaders excel at reading market signals and external trends, with significantly higher Context scores than average. This market sensitivity creates agility but can lead to implementation challenges. Their attention to market dynamics often comes at the expense of understanding internal systems and processes (low Structures), while established organizational beliefs remain largely unexamined (low Assumptions).

Their change initiatives benefit from strong market alignment but require additional focus on:

  • Analyzing how new priorities interact with existing systems
  • Building sustainable processes amid market volatility
  • Balancing quick responses with structural considerations

Software Engineering Leaders

This group stands out for their strategic and innovative mindset, showing exceptionally high scores in both Context and Assumptions. They readily embrace new trends and willingly challenge status quo operations. However, their significantly lower Needs scores suggest that they do not seek inspiration for innovation by attending to the desires and motivations of people.

Their change leadership strengths lie in driving innovation, but success requires:

  • Balancing innovation with operational stability
  • Maintaining quality standards while pursuing new ideas
  • Increasing focus on stakeholder impact and adoption

Implications for influencing, aligning, and deciding

Identifying distinct thinking-to-action patterns help us support rather than overwhelm decision makers when they deal with multiple complex, uncertain, and high-stakes situations. We can start by supplying information that’s easy to digest given a leadership team’s SCAN preferences. Next, we can make information from overlooked sources easier to digest so that leaders don’t run the risk of missing something important.

Understanding your organization’s thinking-to-action culture provides a foundation for more effective leadership development and organizational change. It allows you to leverage your cultural strengths while systematically addressing potential blind spots.

The Emotional Mismatch in Organizational Change

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If you’re exhausted, overwhelmed, and uncertain about what might be changing at work next week, take comfort: you’re not alone. The scale of organizational change is staggering. Consider this: in 2023, the management consulting industry in the U.S. grew at 7.7% — more than twice the overall U.S. GDP growth of 3%. When consulting firms generate more change strategies, leaders and employees face even more upheaval in the years ahead.

The Messy Middle of Change

Given this trend, we at Unstuck Minds aren’t surprised by the recent requests for workshops about dealing with change. While most organizations want help preparing for change, many reach out when they’re already stuck in the middle of it.

While developing a change workshop, I found unexpected insight from an emergency room physician. In an October 5th New York Times opinion piece titled “I’m a Doctor. ChatGPT’s Bedside Manner is Better Than Mine,” Jonathan Reisman wrote about his training in delivering bad news to patients and families. He was initially skeptical about using scripts and techniques, believing that “compassion and empathy couldn’t be choreographed like dance steps.”

As an ER physician, Reisman regularly delivers versions of this “bad news” script. He noted, “For patients and their families, these conversations can be life-changing, yet for me it is just another day at work – a colossal mismatch in emotion.”

This concept of emotional mismatch perfectly captures a crucial challenge in organizational change.

The Change-Emotion Gap

When leaders discuss change with their teams, they face a similar emotional disconnect. While not as devastating as delivering life-altering medical news, this mismatch creates tension that can derail productive dialogue about change.

William Bridges’ famous Transitions model emphasizes that while change is situational, transition is psychological. It involves three stages:

1. Ending: People let go of the old way

2. The Neutral Zone: A period of uncertainty and confusion

3. New Beginning: Individuals embrace new identities and ways of working

The greatest emotional mismatch occurs in the “neutral zone.” Leaders, eager for results, grow impatient while their teams still mourn the loss of familiar routines.

Bridging the Gap: A Better Approach

Just as physicians learn scripts for delivering difficult news, leaders can use specific prompts when change efforts stall. Instead of selling the benefits of change, try these questions — and resist the urge to solve, fix, or judge:

– “What’s making this change hard for you?”

– “Here’s what I’m still getting used to ________. What about you?”

– “Does it feel like something you value is going away? Like what?”

When you sense the emotional gap narrowing, explore possibilities:

– “Not everything is set in stone yet. What might we be able to influence now that things are changing?”

Remember: You can’t force emotional alignment. If people don’t feel safe expressing their true feelings, they’ll find others who share their emotional state — often colleagues who reinforce resistance to change.

The key to successful change management isn’t pushing harder; it’s creating space for honest dialogue about the emotional journey.

Cultivate Generous Connections

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At a pivotal moment in Victor Hugo’s Les Misérables, the police capture the book’s protagonist, Jean Valjean and bring him before Bishop Myriel. Valjean had spent 19 years in prison for stealing a loaf of bread. Prison turned Valjean into a hardened and bitter man, resentful of society. Upon his release he had no food, shelter, or anyone to turn to for help.

The bishop had welcomed Valjean, fed him, and provided a comfortable place to stay. Despite his hospitality, Valjean stole the bishop’s silverware and the silver basket containing the silverware, and then fled in the night.

When the police captured Valjean and took him to the bishop, rather than accuse Valjean of theft, the bishop explained to the police that the silverware was a gift. The bishop goes further, offering Valjean a pair of silver candlesticks, telling him that he must have forgotten them when he left.

Inspired by the bishop’s mercy and compassion, Valjean experiences a moral awakening. He adopts a new identity. He dedicates himself to helping others.

Transactional Interactions

When we treat others transactionally, we’re only thinking about a current and temporary exchange. We have a specific need or a preferred outcome. We evaluate each interaction in terms of whether we get what we want. When we connect transactionally, we keep score. When we connect transactionally, we give little thought to the ripple effects beyond the quid pro quo exchange.

Consider Valjean’s first theft in Les Misérables. The consequence for stealing the loaf of bread was a prison sentence. The justice system dealt with Valjean transactionally, a brutal punishment for a minor crime. As the effects of his punishment rippled out, Valjean became an aggrieved and desperate man.

When we engage transactionally, we don’t know what, if any ripple effects we’ve created. If all parties are satisfied, we’ve preserved a kind of status quo. But have we missed an opportunity? If we feel stuck in a situation involving others, could it be that we’re overly focused on getting our preferred outcome in the present? What future possibilities might we attract by being more attentive to the needs of others?

Generous Connections

By contrast, Valjean’s second theft of the bishop’s silver resulted in compassion and an opportunity to walk a different path. Of course, there was no guarantee that the bishop’s mercy would trigger transformative moral growth. Some interactions defy transactional interpretation. A generous connection is one in which a person gives freely without an expectation of getting something in return.

We connect generously when we sense an opportunity to improve someone’s life. It feels natural to connect generously with those we care most about. On the other hand, connecting generously when conducting business feels counterintuitive, maybe even subversive. How often do we hear, “what’s in it for me?” or “run a cost-benefit analysis.”

The examples from Les Misérables represent extreme ends of a spectrum. Every day we encounter and interact with people, sometimes transactionally, sometimes generously. When contracting work with others, we evaluate what we’re giving against what we’re getting. When we’re moved to make charitable contributions, we look beyond the transaction to future impacts without consideration of how those future impacts may benefit us.

Every interaction provides an opportunity to connect generously. Consider the simple act of ordering a cup of coffee. We could play our roles, stay in our lanes, and perform the expected exchange. Or we could make generous, wholehearted contact with another human being. We might smile, noticing something positive about them, or sincerely ask about their day.

Getting Unstuck with Generous Connections

Have you noticed that the traditional management playbook is outdated? Particularly when it comes to how we think about our stakeholders and networks. People expect more from their organizational life than a fair exchange of work for pay. Customers expect more than goods and services from the businesses they are loyal to.

Defining success based on transactions alone carries risk. First, you’re not prepared when needs change. Second, you haven’t built relationships you can count on when unanticipated opportunities arise.

Consider an example of how a focus on keeping score can play out. You are in a business development role, it’s the end of the quarter and your sales manager is pressuring you to meet your quota. During the next meeting with a client, your training and conditioning kicks in. The meeting turns into the playing field of a numbers game. To make the sale is to win, and each win gets you closer to meeting your quota.

When you feel stress and pressured to achieve a goal, it’s difficult to access generosity. A scarcity mindset breeds fear and anxiety which undermines the opportunity to deepen your relationship. Instead of listening for the client’s needs, you narrow your focus and listen only for what serves your needs. Instead of harmonizing with the client, the conversation feels like a tennis match in which you serve up offers and volley objections.

How to Cultivate Generous Connections

The less instinctive approach is one of generosity. You choose to hold lightly the short-term goal of the quarterly quota and attend to the long-term goal of cultivating an authentic connection based on care and compassion. Connecting with the client as a human being allows unknown possibilities to emerge from the relationship.

Here are some things to try when feeling stuck between competing priorities

  • Acknowledge and hold the tension created by wanting to achieve your goals while prioritizing what best serves the person you’re with.
  • Lead with compassionate curiosity, listen with an open mind and open heart.
  • Pay attention to the passion you experience from the other person and delve deeper into those areas.
  • Seek to understand what feels relevant and important for the other person, have fun in the messy middle of the conversation with no attachment to the desired outcome you might have come in with.
  • Explore possibilities that arise even if they feel impractical and share your thoughts and feelings with trust and vulnerability.

You can always come back to your short-term need in the end (if it even still feels relevant). It will land differently because now it can be contextualized as one small part of a generous connection.

The Practice is What Matters

Yes, it’s ironic to extol the virtues of cultivating generous connections by listing its transactional benefits. We believe that a habit of kindness and compassion will “pay off” in the long run. We also believe that a habit of kindness and compassion rewires the brain circuitry responsible for our mindsets. Becoming a generous connector turns you into a person who attracts more opportunities.

Treating people with kindness and compassion is its own reward, so there’s that. But also, treating people with kindness and compassion is contagious. What goes around, comes around.

If your taste in examples runs more towards popular culture than 19th century French literature, check out the ripple effects in this clip from the 1947 movie Miracle on 34th Street when Santa connects generously with young Peter and his mom.

Are your employees and business associates rooting for you? How about your customers? Rather than keeping score, perhaps you should consider connecting generously with them?

Notice What You Want to be True

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My sister Judi and I often argue about the purpose of higher education. She believes that college is for developing marketable skills. I believe college is for developing thinking skills. She sees college as a path toward employment. I see college as a path toward human flourishing. Judi majored in journalism and ran her own communications and public relations firm. I majored in philosophy and went into the restaurant business.

In 2022, the MIT Open Learning Website posted a story about a recently published white paper called “The Workforce Relevance of a Liberal Arts Education.” Given my beliefs about higher education, I was primed to uncritically accept its findings. Based solely on the title, I sent a ‘told-you-so’ link to Judi before I’d even read it.

When I clicked through to the white paper, I noticed that a series of roundtable discussions with senior campus leaders informed the paper’s point of view. At the end of the paper, the authors listed the roundtable participants. Of the eleven institutions represented, nine of them identified as liberal arts colleges.

Granted, a white paper takes a position and advocates for it. The report did not claim to be a research paper. Still, I could easily see myself using the report as evidence for a belief I want to be true.

Judi and I would probably characterize our views on higher education as polarized. In truth, if we ever bothered to explore each other’s perspectives, I’m confident we’d discover broad areas of agreement. But what fun would that be? We get a strange satisfaction from adopting our roles as combatants. Our relationship is not at risk over the disagreement.

A more consequential polarization grips our society. We are all primed to uncritically accept our tribe’s claims. We’ll happily buy whatever our side is selling while simultaneously parsing every sneer and soundbite coming from the other side.

Signs point to a particularly nasty US presidential campaign between now and November. We’re about to be thrown into the deep end of a pool of lies and disinformation. To prevent yourself from drowning, notice what you want to be true.

Noticing what you want to be true requires humility and honesty. Do you care more about truth than you do about power, winning, and looking good? Perhaps you believe that your preferred ends justify dishonest means. You don’t need your claims to be true as long as they’re popular. Of course, one wonders what kind of future you have in mind if honesty can be so easily cast aside on the path to achieving it.

There don’t appear to be any consequences for public figures who tell lies. It’s all upside. It’s possible to gain an advantage over your opponents by lying about them, and no harm will come to your standing as an authority. And, since political campaigns are high-stakes competitions, we can expect to hear a lot of lies between now and November. Notice what you want to be true.