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The Stoic Coach: Stop talking. Start listening.

Coaching, within a stoic framework, is a journey of personal transformation.

At the core, both Stoicism and coaching thrive on introspection, self-improvement, and resilience. They foster a deep sense of understanding, empowering individuals to navigate their paths with wisdom. Both respect the boundary of control, focusing on self-development and facilitating others to do the same.

The Stoic’s pursuit of virtue aligns seamlessly with the coach’s commitment to unlocking potential, making them two sides of the same transformational coin.

In my journey, the principles of Stoicism and coaching harmoniously intertwined, creating a profound impact. Early in my career, each problem presented itself as a puzzle, which I, in my well-intentioned desire to control, felt compelled to solve. However, my perspective shifted under the guidance of mentors Aneesh Bhanot (Read this first), Ambar MehrotraEtinder Pal Singh and many more, including ðŸ“š Michael Bungay Stanier‘s books, who embodied the stoic virtue of wisdom and the coach-like approach of questioning.

Understanding the Stoic Challenge

The challenge, borrowing from Stoic principles, lies in understanding that our role as a coach is not to control the outcomes of others but to guide them towards finding their own solutions. We must temper our “Advice Monster,” the internal force that pushes us to affirm our value through advice-giving, which is essentially a form of attempting to control the uncontrollable.

The Coaching Habit: Embracing Stoic Wisdom through Questions

“The Coaching Habit” introduces a series of transformative conversation techniques that echo Stoic wisdom. The seven key questions foster deeper engagement and self-discovery, much like a Stoic encourages introspection and self-improvement.

By asking questions such as “What’s the real challenge here for you?” or “If you say yes to this task, what are you saying no to?” we emulate the Stoic practice of inviting introspection and promoting self-discovery.

Here are all seven questions:

  1. The Kickstart Question: “What’s on your mind?” This invites your coachee to bring forward their pressing concerns.
  2. The AWE Question: “And what else?” This question encourages a deeper exploration of the topic.
  3. The Focus Question: “What’s the real challenge here for you?” This narrows the scope, pinpointing the critical issues.
  4. The Foundation Question: “What do you want?” This query clarifies the desired outcomes and goals.
  5. The Lazy Question: “How can I help?” This question facilitates a direct request for help, reducing assumptions.
  6. The Strategic Question: “If you say yes to this, what are you saying no to?” This question illuminates the trade-offs of every decision.
  7. The Learning Question: “What was most useful for you?” This question allows reflection and reinforces learning.

Consider a scenario where a team member struggles with workload management. Traditional advice-giving might involve dictating a new schedule. However, utilizing the Coaching Habit framework, you might ask, “What’s the real challenge here for you?” or “If you say yes to this task, what are you saying no to?” This facilitates self-realization and helps your coachee arrive at their own solutions.

The Advice Trap: Taming the Stoic’s Advice Monster

“The Advice Trap” resonates with the stoic concept of understanding what is within our control. Bungay Stanier identifies three types of Advice Monsters that we need to tame to become effective Stoic coaches:

  • Tell It: Always offering unsolicited advice.
  • Save It: Seeking to shield others from challenges.
  • Control It: Striving for constant control over situations and outcomes.

These Advice Monsters embody our misguided attempts to control what is not within our control, disrupting our effectiveness as Stoic coaches.

As a leader, if you find yourself jumping into problem-solving mode the moment a challenge arises, you might be dealing with a “Tell It” Advice Monster. Identifying this helps you recalibrate your approach and nurture a more facilitative role.

Building Your Stoic Coaching Habit: Actionable Steps

To cultivate an effective Stoic coaching habit, consider the following steps, each resonating with Stoic principles:

  1. Identify Your Advice Monster: Reflect on when and why you resort to giving advice.
  2. Practice Active Listening: Focus on understanding, mirroring the Stoic emphasis on perception overreaction.
  3. Incorporate the Seven Key Questions: Habitually use these questions in your conversations, embodying the Stoic practice of introspection.
  4. Allocate Time for Reflection: Post-conversation, assess what worked and what can be improved, in line with the Stoic practice of evening reflection.
  5. Extend Your Curiosity: Resist the immediate urge to advise, reflecting the Stoic principle of maintaining control over your impulses.
  6. Embrace Mindfulness: Develop self-awareness around your triggers and responses, a fundamental tenet in Stoicism.
  7. Solicit Feedback: Seek feedback actively, mirroring the Stoic focus on continuous self-improvement.

Remember, transitioning from an advice-giver to a Stoic coach is a journey of learning and unlearning. It requires patience, practice, and a deep commitment to helping others find their own path. As we embrace Stoic principles in our coaching journey, we become facilitators of discovery, growth, and empowerment, truly embodying the Stoic virtues of wisdom, justice, courage, and moderation.

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Buyer Experience Design SYNG

Selling is not helping. Helping is selling.

Though its origin remains a mystery, this nugget of wisdom is the crux of our discourse today. But first, a bit of context. During my tenure at a creative agency, my primary role was to bring in new business and strategize. The question that often arose was, “How do you land such big accounts?” Well, let’s unravel that mystery.

The Great Divide: Doing the Work vs. Selling the Work

There’s a common misconception that talent and the ability to do the work is all it takes. But here’s a secret, the secret sauce that has been the cornerstone of my business strategy for years. It’s not about my skillset, the hard sell, pushy tactics, or the relentless pursuit of a signed contract. Instead, it’s about something far more potent yet often overlooked: curiosity.

Yes, you heard it right, curiosity. But before you scoff at the simplicity of it, let’s delve into why curiosity is the secret ingredient to successful early conversations with prospective clients.

The Cardinal Sin of Selling: Being Self-Serving

In the initial stages of client interaction, we often fall into the trap of being self-serving. We’re so eager to sell our product or service that we forget to listen. We talk more than we should, push our agenda, and truly miss the opportunity to understand our client’s needs. We’re so focused on selling that we forget to help.

But here’s the twist: selling is not helping. Helping is selling. Take a moment to let that sink in.

The Power of Curiosity: A Page from Malcolm Gladwell’s Book

In his infinite wisdom, Malcolm Gladwell often talks about the power of curiosity. He suggests that curiosity leads to understanding, and understanding leads to empathy. And empathy, my friends, is the key to helping. It also builds trust and gives your client reassurance — subtext they are not verbalizing.

The best salespeople do precisely that. They aren’t the ones who can talk the fastest or pitch the hardest. They’re the ones who can listen the best — including the conversation subtext. They’re the ones who are genuinely curious about their clients. They’re the ones who understand that selling isn’t about pushing a product; it’s about solving a problem. And to solve a problem, you first need to understand it.

The Shift from Selling to Helping: Insights from “The Coaching Habit”

“But how do I do that? How do I shift from selling to helping?” I hear you ask. To answer that, let’s borrow some wisdom from Michael Bungay Stanier’s book “The Coaching Habit.” Stanier suggests that the key to effective coaching (or selling, in our case) is to stay curious a little longer and rush to advice-giving a little slower. He suggests asking questions like, “What’s the real challenge here for you?” and “What do you want?” These questions not only show that you’re genuinely interested in helping, but they also encourage the client to open up and share more about their needs and goals.

The Art of Listening: Cultivating Curiosity

When we approach a conversation with genuine curiosity, we shift our focus from selling to understanding. We ask questions, listen, and learn about our client’s needs, challenges, and goals. This understanding allows us to offer solutions that truly help our clients rather than pushing a product or service that may not be the right fit.

And here’s the beautiful part: when we help, we sell. When we provide a solution that truly meets our client’s needs, the sale naturally follows. Here’s how to cultivate this curiosity and shift your focus from selling to helping.

1. Listen more than you talk 

This might sound simple, but it’s more complicated than you think. It requires you to put your agenda aside and focus on your client.

2. Ask open-ended questions 

These questions invite conversation and encourage our clients to share their thoughts and feelings.

Examples:

  • Can you tell me more about the challenges you’re currently facing in your business?
  • What are your long-term goals for your company, and how do you plan to achieve them?
  • What do you think is the most important factor in choosing a product or service in your industry?
  • How have your needs or expectations changed over the past year?
  • What would an ideal solution look like for you and your team?

3. Be genuinely interested in your client

This isn’t about pretending to care; it’s about genuinely wanting to understand and help our clients. Don’t just nod along. Be genuinely interested. 

So, the next time you find yourself in an early conversation with a prospective client, remember the power of curiosity. Remember that selling is not helping, but helping is selling. And most importantly, remember to listen, ask, and care.

And now, in the spirit of Neil French, I’ll leave you with this: “The best salespeople are not those who talk the most, but those who listen the most.” So, let’s all strive to be the best listeners we can be.

Remember, curiosity didn’t kill the cat; it made the sale.

So, go ahead, be that inquisitive person. It’s not just approved. It’s encouraged. After all, curiosity is not just about being nosy; it’s about being interested, engaged, and, most importantly, helpful. 

Now, shoo!Â