20. You’re Not Indecisive. You’re in the Wrong Conversation.
In this episode, Michelle Kay Anderson challenges the idea of indecision as a personal flaw:
Why we mislabel indecision: It often signals lack of clarity on goals, values, risks, or roles—not lack of confidence.
The “indecision myth”: Hesitation isn’t weakness. It’s a cue to ask better questions about what matters, what’s at stake, and who’s involved.
What happens when you leap: A personal story about buying her dream house—how fear overshadowed joy—and what she wishes she’d done differently.
Decision styles & the Enneagram: How Type 9 Peacemakers tend to stall, avoid conflict, and how naming your instincts can shift momentum.
Michelle’s 5-step decision-making framework for conscious leaders.
The research: Structured decision frameworks boost success and financial performance, and increase trust and engagement.
Key takeaways:
Indecision is often situational—not a character flaw.
Clarity comes from aligning values, context, and action.
Leadership means listening to head, heart, and gut in concert.
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Transcript
Introduction: Overcoming Indecision and Building Leadership Clarity
Have you ever noticed that when you’re unsure how to decide, it’s easy to assume it’s a confidence problem—that you just need to be more decisive? But what if it’s not actually about you, and instead, it’s more about the situation or conversation you’re in? Could it be that indecision is less a personal shortcoming and more a signal to get curious about the questions you’re asking, or the context shaping your choices?
Welcome to Upleveling Work. I’m Michelle Kay Anderson, executive coach, here with real strategies for navigating growth, uncertainty, and leadership with humanity. Whether you’re stepping into a new role or trying to stay sane in chaos, this podcast helps you build habits and mindsets for lasting impact.
Today, we’re exploring the real story behind indecision. What if your so-called “indecisiveness” was actually a signpost, not a personal failing? Let’s dive into how conscious leaders make aligned decisions, even when the path isn’t clear.
Here’s a trap I see: a lot of leaders think they have a “decision problem.” They blame themselves for being slow or uncertain, and hustle harder—gathering advice, polling the team, pushing just to “get it done.”
But that rush actually leads to more confusion and even regret. Why? Because the real problem isn’t indecisiveness. It’s unclear criteria. Unnamed expectations. Roles, boundaries, or risks that haven’t been spoken.
Quick story: I recently facilitated a team retreat where the leader thought the problem was decision making. Turns out, they didn’t need training in decisiveness—they needed tools to create the conditions for clarity. They needed the right map.
This isn’t rare: what looks like indecision is often the signal that you’re missing the structures or conversations that make natural alignment possible. It can be a sign that you are operating in complexity and may be dealing with something that is non-linear or incomprehensible.
Debunking the Indecision Myth: Why You’re Not Really Indecisive
Let’s bust the myth that “good leaders” are always quick and certain. Or that hesitation is weakness. In real life, indecision is rarely about not being smart or driven enough. More often, it signals something deeper:
The “what” isn’t clear,
The “why” isn’t shared,
The risk feels unspoken,
Or, the decision is touching on values or emotions left unnamed.
Reflective Question:
Have you ever felt stuck—not because you didn’t know what to do, but because none of the options felt quite right?
Facing Uncertainty: How to Act When You Don’t Like Your Options
Sometimes, indecision isn’t because you lack information. It’s because you don’t like your current options. You hope something better will magically appear—so you wait, and that waiting transforms into rigidity, anxiety, and tunnel vision.
I see this all the time with clients: staying in a role you’ve outgrown, not because you’re confused, but because every exit ramp feels risky or incomplete. While resisting the imperfect choices, we miss new doors opening, simply because they don’t look like what we expected.
Reflective Question:
Is there a decision in your life right now where you’re waiting for a “perfect” choice—and is that keeping you stuck?
Often, the path only reveals itself after you start walking. In uncertainty, acting to gather more data is key—clarity emerges from engagement, not from endless contemplation.
Let’s talk about what happens when you do finally leap—when you say yes to that big, scary move.
Managing Stress and Fear After Big Decisions: The Dream House
Recently, my husband and I bought our dream house—a beautiful place on the water. It looked like a fairy-tale ending, but the reality? It was a massive financial stretch for us. Both our kids were in college, tuition was due, and suddenly we found ourselves “house poor” for the first time in 20 years. The first few months weren’t spent celebrating. Instead, we worried—what if this doesn’t work? What if we made a terrible mistake? All we could see were flaws, risks, and unanswerable “what-ifs.”
It took months for our nervous systems to settle so we could actually enjoy being there. Looking back, I’m struck by how much joy we lost—how the fear of risk eclipsed the delight of our new chapter. There are no perfect decisions, only the ones we commit to and make meaningful through action and attitude.
Reflective Question:
Think of a big decision you made. Did the self-judgment and worry afterwards steal some of the joy or growth from that choice? What would it look like to focus on enjoying the experience, even before you “know” it’s right?
Leadership isn’t about making perfect choices—it’s about making choices right by how we show up and what meaning we create.
Understanding Decision Styles: Insights from the Enneagram
Now, it’s important to remember we all have different decision-making styles based on personality. Let me share how this plays out with a client I work with—someone who identifies as an Enneagram Type 9, the Peacemaker.
My 9-type client is caring, thoughtful, and always wants to include everyone. But when a tough decision comes up, she freezes—not because she’s incapable, but because she’s trying to avoid conflict and keep the peace. If expectations or roles aren’t crystal clear, she’ll wait…sometimes hoping others step in with the answer. As deadlines loom, the stress mounts—then she’ll get stubborn, or even passive aggressive, not out of malice but because the internal tension is so loud.
Teaching Point:
For 9s, and for all of us, it’s easy to drown in data and opinions, hoping for clarity to arrive from the outside. But sometimes, deciding means tuning into your gut; naming out loud what you know to be true early, even if it risks friction. You can always gather more information, but don’t let that become a hiding place.
Reflective Question:
If you’re someone who avoids ruffling feathers, where might you be holding back your own wisdom or wants? How could you err on the side of action rather than endless gathering?
Michelle’s 5-Step Decision-Making Framework for Conscious Leaders
All of this brings us to the framework I use to help leaders move from stuck to aligned momentum:
1. Define Criteria
Ask: “What matters most here?” Don’t start by picking options—instead, name the handful of goals or values at play. (Example: equity, impact, sustainability, trust.)
2. Explore Options
Widen the lens. What choices are actually on the table? What are you not seeing, or assuming is impossible? At least 4 alternatives—get creative.
3. Evaluate Alternatives
Map each option to your criteria. How do your options fit what matters? What’s aligned? What risks or trade-offs are worth it? Avoid perfection; focus on wise discernment.
4. Resolve to Act (Or Not)
Make the call, or delay consciously. Document the what, why, and who. This is about owning your stance and communicating it.
5. Build Belief
After you decide, support yourself. Ask for backing, rewrite internal doubts, and check in periodically to recalibrate. Your follow-through is what turns decision into impact.
You can apply this to almost any context—career, money, parenting, or team strategy.
The Research: Why Structure Matters
Science backs this up: Teams with structured decision frameworks improve outcomes sixfold and halve failure rates (Cloverpop). Bain & Company links better decision effectiveness to better financial performance. And engagement? 50% comes down to how decisions are made.
Reframing Decision-Making: Moving from Force to Flow
So—what if “decisiveness” isn’t about forcing it, but about building clarity and flow?
The model I teach starts with alignment and ends with belief. It’s not about speed or being the loudest—it’s about making choices that feel congruent with your values and build momentum, especially when the path ahead is foggy.
Often, when leaders say “I don’t know what to do,” what they’re living is an internal tug-of-war. Part of you wants action, another wants safety, another wants more data. That’s not indecision. That’s fragmentation.
Leadership is the practice of listening to those parts, integrating gut, heart, and head, so action emerges naturally.
Reflection Questions to Clarify Your Leadership Decisions and Align Your Values so You Can Make Confident Choices
So, next time you face a tough choice, don’t just ask, “What should I do?”
Ask:
“What’s really important here?”
“Am I resisting an option, or just craving certainty?”
“In what ways can I honor my gut, heart, and head together?”
If the path still isn't clear, maybe the work isn’t to decide, but to clarify what matters or act to gather more learning.
If this resonates and you want to bring this decision-making framework into your organization or life, I’d love to help—let’s turn hard choices into aligned, grounded action.
Find me at my website or LinkedIn Michelle Kay Anderson. I’d love to hear from you: What’s the hardest decision on your plate right now? You can even leave me a voicemail at uplevelingwork.com and I’ll either answer you back directly or explore it in an upcoming episode. as always, thank you for being part of the Upleveling Work community.
Until next time… Trust your instincts, name what matters, and keep showing up for the work that matters most.
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