Coloring Within the Lines

What Coloring books, Questions, and Structure Teach Us About Sturdy Leadership

I’ve been thinking a lot about leadership—how to direct and guide, how to hold space, and how good structure can feel. There’s a balance between being flexible and open while also providing scaffolding and support.

This might sound odd, but I love to color. I have enjoyed coloring since I was a kid. But more than just coloring, I love coloring books. Don’t give me a blank sheet of paper and tell me to just color—I’d freeze. I’d overthink it. And I can’t draw to save my life. But hand me a coloring book, and my imagination lights up. The lines, shapes, and designs give just enough structure to set me free to use whatever colors I want, how I want. I get to focus on the thing I love most: the coloring.

Photo by Jess Bailey on Unsplash

In the same way, I think great leadership, great parenting, great hosting, and great advising all follow a similar pattern. This article explores how structure can enhance these roles, and why, especially in financial planning, it matters.

The Cold Open: A Classroom with No Teacher

In The Art of Gathering, Priya Parker (2018) shares a story about Ronald Heifetz, a professor at the Harvard Kennedy School and a well-known authority on leadership. On the first day of his adaptive leadership class, Heifetz walks to the front of the room, takes a seat… and says nothing. He doesn’t take attendance. He doesn’t lecture. He just sits there—expressionless, silent, unmoving.

His students fidget. Then comes the whispering. Nervous laughter. My students would behave the same way. Eventually, someone speaks up; soon, the group begins to spiral. They debate what’s happening, what they’re supposed to be learning, and who’s in charge. Heifetz is demonstrating how “creating freedom” can—and often does—create chaos.

“By doing nothing,” Parker writes, “he is abdicating his command of the classroom… [He was] not easing their way or setting them free. [He was] pumping them full of confusion and anxiety” (Parker 2018, 53).

Parker uses the story to illustrate the danger of being a “chill host,” someone who withholds structure in the name of flexibility. It’s a dynamic that might seem unrelated to financial planning, but the parallels are surprisingly close. Financial advisors aren’t professors, and client meetings aren’t lecture halls. But the dynamic is familiar. An advisor who opens a first meeting with, “So… what would you like to talk about today?” may believe they’re being respectful, open-minded, and even client-centered.

But for a new client—especially one navigating uncertainty or anxiety—that kind of freedom can feel like fog. Even for experienced clients, walking into a new advisor relationship with unclear expectations can be unnerving. A lack of structure can make the room feel heavier than it should. Well-intentioned openness may actually generate stress and reduce creativity, openness, and sharing.

Clients don’t need chill; they need generous leadership.

Generous Authority: A Better Kind of Leadership

There’s a common misunderstanding in modern leadership that being client-centered means being hands-off. That real service comes from stepping back. That the less you steer, the more respected your client will feel.

Although well-intentioned, this just isn’t true.

Real service doesn’t come from disappearing. It comes from showing up. Clients need clarity, care, and enough structure to feel steady. That’s what Priya Parker calls generous authority: the act of confidently shaping space in service of others—not to control them, but to support them.

“Generous authority is about using power for good,” Parker writes. “It’s not about being the boss. It’s about being the host” (2018, 65).

This idea resonates deeply with how many financial advisors want to show up: not as gatekeepers, but as guides, a term we like to use at Shaping Wealth. Still, it can be hard to strike the balance. Some advisors hesitate to impose structure, fearing it might feel rigid or overly formal. Others worry it might stifle openness or engagement. But in reality, structure creates safety. It signals that someone is in charge—and that they’re not in charge of the client, but of the container: the meeting, the tone, the pace.

Dr. Becky Kennedy, author of Good Inside (2022) and well known for her parenting work, calls this kind of presence “sturdy leadership.” In her framework, a parent’s job is to be the calm, confident captain of the ship. When a child is melting down, they don’t need a parent who melts with them—or disappears into passivity. They need someone who can weather the storm and model how to move through it.

“Our kids don’t need us to have all the answers,” she often says, “but they do need us to show them that we can handle the moment.”

Advisors aren’t “parents” to their clients, of course—but the emotional logic is the same. When money is on the table, fear, stress, intolerance, and other big emotions are often close by. Clients don’t need perfection; they need presence. Clients want to feel held—not in a controlling way, but in a confident one. They want to know that someone is prepared, focused, and ready to guide the conversation, especially when it veers into uncertainty.

Dr. Kennedy also reminds us of something just as essential: it’s not just about holding the moment. It’s about believing in the other person’s ability to get through it. A sturdy leader doesn’t just show up calm and collected; they also trust the other person in the conversation, and the moment itself, to rise to the challenge. A parent believes their kid can tie their shoes. An advisor believes their client can weather a volatile moment. Generous authority becomes a form of care. It’s an offering: Let me take responsibility for the process, so you can focus on what matters to you.

It’s like my coloring. I don’t want to think about creating a picture; I just want to scribble and play with the color. Structure frees me to enjoy the part I love most.

Likewise, when advisors step in with a meeting agenda, talking points, or a list of considerations, they’re not taking away anything away from the client. Instead, they’re doing the opposite: They’re giving something to the client: the structure, safety, and space to show up more confidently, to grow, to try new things.

And when you think about it that way… structure isn’t something to apologize for. It’s something to lean into.

Reducing Client Fear and Anxiety Through Structure

For many prospective clients, the first meeting with a financial advisor is as emotionally loaded as it is logistically uncertain. It’s not just about discussing investments or taxes—it’s about exposing fears, flaws, and long-held financial habits to a stranger. The emotional stakes are high, and the smallest unknowns can become barriers to showing up fully.

Research supports this. Financial Advisor Anxiety (FAA)—a term first defined by Paul Gerrans and Douglas Hershey (2016)—describes the specific, often paralyzing discomfort people feel when disclosing personal financial details to an advisor. It combines two powerful fears: the fear of disclosure and the fear of evaluation. Unlike medical patients, whose anxieties often fall into one category or the other, individuals experiencing FAA tend to face both simultaneously: I’ll have to share everything, and I’ll be judged for all of it. This anxiety can be so intense that many never reach out—not because they don’t want help, but because asking for it feels too vulnerable (Lurtz 2021).

Carl Richards, co-host of the Kitces & Carl podcast, describes this vividly in a recent conversation about reducing fear for new clients (Kitces and Richards 2025). Drawing from Jonathan Pope’s work on performance training, Richards talks about the anxiety people feel when entering unfamiliar spaces—like a gym, or a financial planning office. Even basic logistics—where to park, how formal the meeting will be, or whether documents are needed—can create stress that clouds the conversation.

As Richards suggests, “What are the things you can do to lower that fear? Give them a description—a clear outline of what to expect before the session” (Kitces and Richards 2025, 00:45).

He suggests treating advisory firms like high-end hospitality environments—reducing uncertainty at every turn, not to impress, but to invite. This framing resonates with me and brings us back to the idea of being a host. Financial planning, after all, isn’t just a service—it’s also an experience.

Which raises the question: What if financial planning were embraced as part of the experience economy?

Coined by Joseph Pine and James Gilmore (1999), the term “experience economy” describes a business model where value is created by staging memorable and engaging experiences, rather than simply delivering goods or services. So what would it change if advisors begin to see their meetings, services, and client interactions as acts of hosting?

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Go with me for a moment: Imagine “hosting” a financial planning meeting and inviting me into a conversation with you. A week before our first meeting—I’m your new prospective client—I receive an email outlining what to expect. It includes three reflection prompts and invites me to respond however I’m most comfortable: by replying to the email or jotting down notes to bring with me.

Two attachments are included. The first is a link to a short video you’ve recorded, introducing yourself, sharing why you love financial planning, and offering a few personal details. Now you’re no longer a total stranger—I’ve begun to form a small sense of who you are.

The second attachment is a Client Engagement Standards document (originally created by George Kinder). It outlines what you expect from me—come prepared to share, be open to new ways of making financial decisions, and know at least the ballpark of my financial situation. It also clarifies what I can expect from you—you’ll ask thoughtful questions (some I’ve likely never been asked before), you care about values as much as financial data, and you’re genuinely here to get to know me.

On the day of our meeting, I arrive and I’m greeted by name. The person at the front desk smiles warmly and invites me in. In the lobby, I see my name—Welcome, Meghaan!—displayed on a screen. I know without a doubt that I’m in the right place, and someone thought enough about me to plan the moment of my arrival.

Soon after, I’m ushered to a living-room style office and asked about my beverage preference and offered something to drink. I’m told it’s a delight to have me, and that you’ll be in shortly. When you arrive, you greet me by name with a handshake, thank me for the notes I sent, and let me know that you’re delighted to be hosting me today. You’re already so curious about me and what I shared.

In that moment, I feel safe, comfortable, prepared, and open. I’m eager to begin.

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This subtle but powerful shift opens the door to so many small, but memorable opportunities to reduce fear and build trust. A simple pre-meeting email—one that includes directions, what to expect, what to bring (if anything), and even the dress code—does more than provide information. It offers reassurance. It removes friction. It says, You’re safe here. We’ve thought about what you need.

It’s no longer just a meeting. It’s an invite-only experience.

These elements may seem like “small touches,” but their cumulative effect is significant. As Kitces notes in the same episode, reducing a client’s cognitive load doesn’t just help them arrive on time—it helps them arrive emotionally ready to engage. It frees up energy that would otherwise be spent navigating uncertainty and allows it to be invested in the conversation at hand.

This kind of intentional setup aligns perfectly with sturdy leadership. It’s leadership that anticipates, prepares, and eliminates friction in service of deeper connection.

To turn this philosophy into practice, advisors can rely on a set of tools—like engagement standards documents, meeting agendas, and brainwriting techniques—that lower the emotional stakes and make this kind of leadership not just possible, but repeatable.

Four Tools Financial Advisors Can Use to Practice Sturdy Leadership

Sturdy leadership isn’t just a mindset—it’s a practice. And like any practice, it becomes more consistent when supported with the right tools. For financial advisors, the goal isn’t to script every meeting or enforce rigidity. It’s to offer structure that builds trust and frees the client to focus on what really matters.

Here are four simple but powerful tools that bring generous authority to life.

Tool #1: The Client Engagement Standards Document

One of the clearest ways to set expectations is to put them in writing. A Client Engagement Standards document—originally designed by George Kinder—does just that. It outlines what the advisor will provide, what the client is expected to contribute, and how the relationship will be managed over time.

Unlike a legal contract, this document is conversational. Collaborative. Clear.

A strong engagement standards document might include:

• The philosophy of the planning firm

• What’s included in the relationship

• How and when communication happens

• Any preparation expected from the client

• How to handle concerns or reevaluate fit

Used well, this isn’t just a reference—it’s a relationship tool. It can be shared before the first meeting, reviewed together during onboarding, or returned to when difficult conversations arise. It signals that the advisor has a system, and the client has a seat at the table.

As Brené Brown (2018) puts it: “Clear is kind.” And a document like this is an act of kindness.

Tool #2: Meeting Agendas

Agendas don’t make a meeting less human. They make it more humane.

When clients receive a meeting agenda in advance—whether as a full outline or just a short note in the confirmation email—they walk in prepared. They know what to expect. They’re not burning mental energy wondering what kind of conversation they’re about to enter.

When I work with financial planning firms, I always recommend including both a pre-meeting and post-meeting email.

• The pre-meeting email can include sample questions or discussion points to help clients arrive prepared and ready to engage.

• The post-meeting email can reuse those same prompts, but now with responses filled in. It offers a chance to summarize key takeaways, reflect what was heard, and outline next steps. It can also serve as a helpful prompt for anything still needed, such as documents or signatures.

While the value of agendas and follow-ups often feels intuitive, it’s also backed by behavioral and workplace research—underscoring how structure improves both logistics and emotional readiness. Leach, Rogelberg, Warr, and Burnfield (2009) found that meeting design—including the use of agendas—significantly improves perceived effectiveness. Other sources note that agendas boost participation, clarify objectives, and reduce anxiety (MIT Human Resources n.d.; University of Minnesota Extension n.d.).

Even a brief outline is enough. For example:

Meeting Agenda

• Review progress on action items

• Discuss recent life changes or new goals

• Answer any open questions and confirm the next steps

In financial planning, an agenda is less about controlling the conversation; it’s about opening it wisely.

A brief follow-up might look like this:

• Review progress on action items

  • Meghaan has spoken to the estate planner; their meeting is set for next Thursday. A follow-up with the planner is scheduled for the week after to review materials.

• Discuss recent life changes or new goals

  • Meghaan has decided to officially begin saving for her future home in Spain! She’s opened a new account and set up automatic contributions.

• Answer any open questions and confirm next steps

  • The estate planning meeting is on the calendar.

  • The planner has agreed to connect Meghaan with another client who recently purchased a home abroad.

The post-meeting follow-up serves as a simple but powerful way to confirm progress and capture updates. Like the opening agenda, it reinforces expectations and helps everyone stay on the same page.

Tool #3: Brainwriting, Not Just Brainstorming

In group or couple meetings, the first person to speak (or the one who speaks the loudest) often sets the tone for the entire conversation. Traditional brainstorming tends to favor fast thinkers and dominant personalities, while quieter, more reflective clients may get edged out.

Brainwriting flips the script. It’s a simple technique where clients write down their thoughts or questions in advance. They might reflect on prompts, submit answers through a form, or bring pre-written notes to share during the meeting.

Imagine this integrated into the pre-meeting agenda above. After listing the agenda items, the advisor might include the following message to encourage brainwriting:

As you can see, we’ve kept the agenda short. This is on purpose. I want to make sure we have space to explore your goals in depth. Over the next week, I’d love for you to consider the following questions. If you’re willing, feel free to send your thoughts by email—or just jot them down somewhere easy to access during our meeting.

• What’s something new you’d like to do in the next six months?

• What’s something you’ve done before that you want to do again in the next three years?

• What’s a life change you’re looking forward to in the next five years?

This isn’t just anecdotal. Research consistently shows that brainwriting generates more—and better—ideas compared to traditional brainstorming (Thompson 2003; Paulus and Nijstad 2003). It reduces pressure to perform in real time and helps clients show up more fully, opening the door to richer, more thoughtful conversations.

This is why sharing questions ahead of time matters. Clients are more naturally thoughtful when they’ve had space to reflect. Instead of saying, “Hmm, that’s a great question; I’ve never thought about that before,” they’re able to arrive already grounded in their answers.

Brainwriting gives clients the scaffolding they need to engage deeply, and gives advisors a powerful tool for structuring conversations that matter.

Tool #4: Questions That Hold the Room

Finally, the most elegant tool of all: the well-timed question.

In financial advice, we often talk about asking better questions. But the real power of a good question isn’t just in curiosity or the insight it draws out—it’s in the safety and containment it creates. A thoughtfully framed question can shape the emotional space of the meeting, slowing the moment down and helping the client feel grounded and seen.

“A good question is like a good chair,” I have said. “It supports the conversation and helps the other person relax into themselves.”

These questions don’t need to be clever or complex, they just need to show care, offering a moment of permission to go deeper. The advisor doesn’t need to rush, redirect, or impress. Just asking, and holding the space.

That, too, is sturdy leadership.

While this tool is more art than science, even this practice echoes what the research tells us: thoughtful structure deepens engagement.

The Thoughtful Structure Behind Great Meetings

Together, these four tools create the conditions for clarity, care, and meaningful dialogue. They show clients that leadership doesn’t mean taking over—it means taking responsibility for the environment. And that can make all the difference.

This also gets much easier when advisors take just five minutes before a meeting to ask: “What is the purpose of this conversation?”

From that answer, the agenda unfolds, along with two or three questions that match the meeting’s goals. And that small moment of intention is what can turn a good meeting into a powerful one.

Even Socrates Had a Structure: What Philosophy Teaches Advisors

Before wrapping up, it’s worth stepping back to ask: Why does structure matter so much, even beyond the practical?

We tend to think of great conversations as free-flowing, organic, and unstructured. But even in the history of philosophy, one of the most enduring and iconic conversations—Plato’s Symposium—didn’t just happen. It was hosted.

In Symposium, a foundational dialogue about love and meaning in the Western canon, the scene unfolds at a dinner party with a clearly defined structure: each guest is asked to give a speech in praise of love. There’s food. There’s pacing. There’s even a speaking order.

Socrates, one of the invited guests, didn’t arrive to a blank canvas. As the archetype of the open-ended questioner, he showed up in a space that had been intentionally shaped. The structure wasn’t restrictive—it was liberating. It gave each participant a clear role, which allowed them to think deeply and speak freely. Without that scaffolding, the conversation might have been splintered—or never started at all.

Feminist philosophers, too, have long recognized that structure can be a form of care. Carol Gilligan (1982) argues that ethics isn’t just about rules and justice, but about attentiveness and response. In this view, setting expectations isn’t about power—it’s about honoring the relationship.

It’s a way of saying: I’m here for you. I’ve thought about your experience. I want to make this easier.

To lead generously is to host well. And to host well is to shape the room, the moment, the meeting, and the conversation—not with rigidity, but with intention.

A financial planning meeting isn’t a Greek symposium or a moral debate, but it is a sacred space for reflection. And sacred spaces deserve thoughtfulness, structure, ritual.

What the Research Says About Better Client Meetings

So far, we’ve explored the philosophy and practice of sturdy leadership—how structure creates safety, how clarity reduces anxiety, and how intentional tools build trust. But these ideas aren’t just intuitive. They’re backed by a growing body of research.

Agendas Make Meetings Better

Well-designed agendas are widely recognized as a hallmark of effective meetings. Leach et al.(2009) found that participants rated meetings as significantly more effective when supported by clear structure, defined goals, and a sense of time management. Other sources reinforce this, noting that pre-meeting agendas create focus and direction, improve preparation, reduce frustration, and lead to more satisfying, goal-oriented meetings (MIT HR n.d.; University of Minnesota Extension n.d.; Scontrino-Powell n.d.).

For financial advisors, the implication is clear: Agendas reduce cognitive load for clients. They demystify the meeting, signal professionalism and care, and help clients show up more fully to the conversation—especially in moments where anxiety or vulnerability might otherwise hold them back.

Brainwriting > Brainstorming

In group settings, traditional brainstorming tends to favor fast thinkers and dominant personalities, while quieter or more reflective individuals may hesitate to contribute. Brainwriting offers a simple but powerful alternative. Rather than speaking first, clients reflect and write privately, reducing pressure and increasing originality.

Studies show that brainwriting groups generate more ideas—and significantly more novel ones (Thompson 2003). Paulus and Nijstad (2003) found it also facilitates deeper creativity and greater inclusion by reducing both production blocks and evaluation apprehension.

The implications are profound in financial planning. Giving clients time—and permission—to reflect in advance can transform the meeting from reactive to reflective, empowering every voice at the table.

The Science Is Clear: Structure Supports Human Flourishing

Taken together, these findings make a compelling case: structure doesn’t stifle connection—it strengthens it.

Sturdy leadership tools—from written agendas to pre-meeting prompts—don’t replace the human side of advice; they enhance it. In short, the science agrees with the sentiment: A little structure goes a long way.

Closing Reflection: Leadership with Clarity, Not Control

Structure doesn’t have to be the opposite of warmth, and boundaries aren’t the opposite of care. Leadership doesn’t mean having all the answers—it means knowing how to hold the room while others search for theirs.

In client relationships, as in parenting, as in hosting, what matters most is how we show up. Not with scripts, but with steadiness. Not with control, but with clarity.

Sturdy leadership isn’t rigid. It’s reliable. And it doesn’t require reinventing your process—just re-centering it. On care. On preparation. On the belief that holding space well is a skill that can be practiced.

• “Clear is kind,” Brené Brown (2018) reminds us.

• “Our kids don’t need us to have all the answers,” says Dr. Becky Kennedy (2022).

• “Don’t be a chill host,” urges Priya Parker (2018).

All three point toward the same idea: Show up with structure. Offer it with heart.

Start small. Send a clearer agenda. Add a sentence to your scheduling emails. Introduce your next client meeting with a roadmap. And notice what changes—maybe not in what gets discussed, but in how safe it feels to discuss it.

That’s leadership. The generous kind.

Author’s Note: If “clear is kind,” as Brené Brown reminds us, then editing is one of the kindest acts we can offer our ideas—and our readers. This piece, like many others, became sturdier through thoughtful revision. I’m especially grateful to my editor, Erica Mito, for her generous editorial support and insight throughout this process. Good writing, like good leadership, benefits from someone who can hold space and shape it—gently, firmly, and with care.

References for the Nerds:

Brown, Brené. 2018. Dare to Lead: Brave Work. Tough Conversations. Whole Hearts. Random House.

Gerrans, Paul and Douglas A. Hershey. 2016. “Financial Adviser Anxiety, Financial Literacy, and Financial Advice Seeking.” Journal of Consumer Affairs. 51 (1): 54–90. http://dx.doi.org/10.1111/joca.12120.

Gilligan, Carol. 1982. In a Different Voice: Psychological Theory and Women’s Development. Harvard University Press.

Kennedy, Becky. 2022. Good Inside: A Guide to Becoming the Parent You Want to Be. Harper Wave.

Kitces, Michael and Carl Richards, hosts. Kitces & Carl. Podcast, Episode 157. “Reducing the Fears of Prospective Clients by Communicating Clear Expectations Before the First Meeting.” Kitces.com. February 6, 2025. https://www.kitces.com/blog/157-michael-kitces-carl-richards-fears-prospects-clients-communication-expectations/.

Leach, Desmond J., Steven G. Rogelberg, Peter B. Warr, and Jennifer L. Burnfield. 2009. “Perceived Meeting Effectiveness: the Role of Design Characteristics.” Journal of Business and Psychology. 24 (1): 65–76. https://doi.org/10.1007/s10869-009-9092-6.

Lurtz, Meghaan. “Addressing Financial Advisor Anxiety to Help Prospects Overcome Their Fear of Judgment.” Nerd’s Eye View (blog). Kitces.com. December 22, 2021. https://www.kitces.com/blog/financial-advisor-anxiety-faa-fear-of-disclosure-evaluation-terminology-attracting-prospects-gerrans-hershey/.

MIT Human Resources. n.d. “How and Why to Use a Meeting Agenda.” Massachusetts Institute of Technology. Accessed May 18, 2025. https://hr.mit.edu/learning-topics/meetings/articles/agendas.

Parker, Priya. 2018. The Art of Gathering: How We Meet and Why It Matters. Riverhead Books.

Paulus, Paul B. and Bernard A. Nijstad, eds. 2003. Group Creativity: Innovation Through Collaboration. Oxford University Press.

Pine, Joseph, II and James H. Gilmore. 1999. The Experience Economy: Work Is Theatre and Every Business a Stage. Harvard Business School Press.

Plato. Symposium. Translated by Alexander Nehamas and Paul Woodruff. Hackett Publishing Company, 1989.

Scontrino-Powell. n.d. “Research on Effective Meetings.” Accessed May 18, 2025. https://scontrino-powell.com/blog/research-on-effective-meetings.

Thompson, Leigh. 2003. “Improving the Creativity of Organizational Work Groups.” Academy of Management Perspectives, 17 (1): 96–109. http://dx.doi.org/10.5465/AME.2003.9474814.

University of Minnesota Extension. n.d. “Planning an Effective Meeting Agenda.” Accessed May 18, 2025. https://extension.umn.edu/leadership-development/planning-effective-meeting-agenda.