Why Flexibility Matters More Than Objectivity
Outside perspectives aren’t magic.
Or, more accurately, they aren’t free magic. You have to earn their value.
I could use my coaching experience to tell the same old story: my value comes from distance.
But my outside insights are only valuable because they’re paired with insider perspectives. It may not be my company, but I know my clients and their work deeply, and we always collaborate in partnership.
When you ignore the view from within, outside perspectives fail in predictable ways. Either they lack the context to actually be wise. Or, if they are wise, they don’t sound like it because we’re not ready to hear them.
I once worked with a founder who asked me to be “purely objective” about a big decision. He wanted facts, not emotion.
But nothing I said landed.
He was still grieving a version of the business he loved. Until we acknowledged that grief, all of my insights felt cold or threatening. When we started with his internal experience—attachment and loss—my insights became usable.
Outside perspectives are most valuable when they respect inside wisdom.
That’s true when you bring in someone new. It’s even more true if you’re trying to cultivate a new perspective yourself.
Great leadership doesn’t mean escaping emotional investment or the weight of experience. It means learning how to move between immersion and distance.
Rather than trying to replace your insider view with an outsider one, imagine they worked like hats you could put on and take off. Sometimes you need one. Sometimes the other. Sometimes both at once.
The View from Within
External and internal perspectives are often pitted against each other.
The internal view is dismissed as old, boring, slow, and blind.
The external view is celebrated as new, fresh, powerful, and objective.
This story comes from the real difficulty of being embedded in the mess. Every founder knows the feeling of carrying the company, the team, the consequences, and the vision.
From inside that load, everything feels urgent and impossible. Of course you wish you could just breeze in unattached, drop some wisdom, and leave.
But being stuck on the inside is not the same as having an inside perspective.
Recognizing Value
The job of our internal perspective is essential. It protects both the order and the heart of the company.
Order
Imagine throwing someone who knows nothing about your company into your role. They might catch something important that you totally missed, but first full chaos would ensue.
The impulse to protect the company from that kind of chaos helps keep the business stable, functional, and alive.
Heart
People say that subjectivity and emotional investment blind you, but these are also the very things that make your company your company.
Your company is built on unique values that reflect you and your goals. Attachment to these values means you’re growing something you believe in.
The impulse to protect the heart of your company keeps it aligned with your vision.
When Closeness Becomes Blindness
Problems arise if we get stuck on the inside.
This happens when a healthy impulse toward safety and continuity mixes with our fear of failure or loss and turns rigid.
Protecting order becomes a stubborn attachment to the way things have always been done. Protecting heart becomes resistance to anything that feels challenging or destabilizing.
Getting stuck in this mode looks like:
constantly firefighting instead of pausing to think strategically
solutions feeling increasingly complex rather than elegant and simple
being anxious, controlling, or snappy with your team
skipping activities that normally bring you joy or clarity
I have one client who described spending days rehearsing hard conversations, before they happened, after they happened, over and over. The conversation really only took ten minutes, but the looping killed all her energy.
At that point, the view from within is no longer wisdom. And it’s our tendency to get stuck there that gives it a bad reputation.
But the solution can’t be rejection.
Getting Unstuck
We don’t get stuck because we care too much. We get stuck because we don’t know how to shift perspectives without threatening safety and identity.
When leaders ignore the value of their desire for security, that desire tightens. It creates a kind of dam, blocking new information from coming in and making it harder to step back.
To gain distance, or to let in something new, you have to face the need for safety instead of fighting it.
When you value the wisdom of the inside view, even when it’s distorted, you regain flexibility. Then you can see with the specificity of the insider and the breadth of the outsider.
Practice
Inside perspectives create security. Outside perspectives drive growth. Moving between them creates strong leadership and sustainable scaling.
These are three practices to build the muscles that let you move back and forth between perspectives.
1. Clarity
Knowing when you’re stuck.
Pay attention to moments when:
Everything feels harder instead of clearer
Solutions are multiplying instead of simplifying
You’re reacting quickly or emotionally to suggestions
You keep pushing for answers but feel more lost
These are signals that you’ve reached the limits of your current perspective. Getting unstuck means pausing when you want to push.
2. Value
Valuing your insider wisdom.
Notice when you’re frustrated with yourself for being “too close,” “too emotional,” or “too involved.” Instead of trying to override that feeling, acknowledge what it’s protecting:
What am I trying to keep safe right now?
What part of this actually matters to me?
What would it look like to respect this instinct instead of fighting it?
The insider perspective carries memory, context, values, and care. When you dismiss it, you become defensive.
I see this every time a founder stops shaming themselves for caring or being obsessive. The moment they acknowledge what they’re protecting—values, people, identity—their defensiveness softens.
3. Stretching
Taking in new information.
Stretching doesn’t mean forcing yourself to accept every new idea. It means creating low-stakes ways to expose yourself to alternative viewpoints.
This might look like:
Asking, “What am I not seeing?” and listening without responding
Generating multiple explanations for a problem, even ones you don’t like
Scheduling time for unrestrained “what if” thinking
Letting an idea sit for a few days before deciding what you think of it
When stretching becomes routine, outside perspectives stop feeling threatening and start becoming usable.
The founders who do this well don’t accept every idea, but they do let ideas sit—even when they feel defensive. That’s what allows them to move more easily into an outside view.
Putting It All Together
Here’s the simplest way to practice that movement.
When you’re making a decision, ask two questions:
Insider question: What am I protecting?
(Values, people, reputation, stability, identity, etc)
Outsider question: If I wasn’t protecting that, what would I do?
(This is just an experiment, its not your decision.)
The goal isn’t to become “objective”, its to become flexible.
The insider knows how to keep things running. They understand fragile dependencies, the history of decisions, and the reasons things are the way they are.
The outsider pushes growth. They capture patterns, question assumptions, and help you imagine what could exist beyond the current shape of things.
Great leadership comes from their combination.
See you next week! 👑
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