🦋 The #1 Mistake That Kills Change Before It Starts

I was 22. My first job. I was frustrated. My boss seemed to micromanage every decision I made. "He just doesn't trust me," I thought. My solutions? Work harder to prove myself, or find a new job. But when I dug deeper, I discovered my boss was under pressure from leadership to hit aggressive targets. The real problem wasn't trust—it was fear. This reframing opened up completely different solutions: offering to take ownership of specific metrics and having regular check-ins to reduce overall anxiety.

Here's what most people miss: how you frame the problem determines what solutions you can see.

Same situation. Different problem frames. Different solutions. The frame is everything!

Last week, we discussed Resistance to Change. This week, let's examine the first step in leading change: framing the problem 👇

Step 1: What Kind of Challenge Are You Dealing With?

When leading change, first identify what type of challenge you're facing. I like to categorize challenges into 4 types that differ in the challenge complexity and the amount of uncertainty they produce.

🧩 Simple Challenges

Involving minimal uncertainty and complexity, these are straightforward issues with known solutions - "recipe-following" problems. Anyone can handle them using existing knowledge or established guidelines. Example: a customer service rep processing a refund simply follows standard company procedure.

But even simple challenges become problematic when solutions aren't properly documented or easily accessible.

🔧 Technical Challenges

These challenges require specialized expertise to solve effectively. They are more complex than simple ones, involving multiple interacting factors.

Example: Upgrading cybersecurity requires more than installing software—it needs careful planning and expert knowledge.

To solve these challenges, you typically need specialists or personal expertise. This creates an authority exchange: when sick, you authorize a doctor to direct your treatment.

🧠 Adaptive Challenges

These are messy, unclear, and deeply personal challenges.

Often, you don't even know what the real problem is, making solutions and responsibilities unclear. This creates uncertainty, stress, conflict, confusion.

Adaptive challenges demand behavioral change, difficult choices, and cultural shifts. They trigger fear of loss, requiring leadership rather than management.

🌐 Systemic Challenges

Systemic challenges are multiple adaptive challenges caused not only by people but also by systems. They span across much longer timeframes and require an intergenerational approach. These challenges demand paradigm shifts, careful prioritization, and long-term thinking (like climate change).

Key indicators you're facing an adaptive or systemic challenge:

• Does it require people to change their values, beliefs, or priorities?

• Is this challenge creating high anxiety in the system?

• Are you seeing ongoing resistance or recurring setbacks?

Step 2: Resist Quick Fixes

Once you recognize something as adaptive ot systemic, slow down. Spend more time with the challenge before jumping to solutions.

Most people fail at change because they treat adaptive/systemic challenges like technical problems. They want the quick fix, the silver bullet, the simple answer.

There isn't one.

Step 3: Don't Fall for Your First Interpretation

Your first interpretation is usually based on your biases and puts you on the moral high ground. It feels good, but it's rarely accurate.

Instead, ask yourself:

• What else could explain this situation? (Generate multiple interpretations)

• What data do I have for these interpretations? What am I actually observing? What did I hear in that meeting? What behaviors am I seeing? (Feelings aren't data—they're interpretations of data - important, but not sufficient)

• What might I be missing? What other factors or people are affecting this situation?

• What habits, norms, beliefs, culture, mindset, or structures might explain what's happening?

Step 4: Learn More (You Need Other Perspectives)

Your perspective alone isn't enough. You need other angles to see the fuller picture.

How to gather intelligence:

1. Talk to 2-3 trusted colleagues or friends about what you're observing. This is your reality check. Maybe you're completely off. Maybe you sensed something, but it's a different problem.

2. Talk to people who see the situation differently from you. This helps you understand potential resistance and learn their perspective.

3. Keep these conversations 1-on-1. It's much safer for everyone to be honest.

4. Stay curious. Ask questions. Don't persuade—listen to understand.

Step 5: Identify the Scope of the Problem

Being precise about how often, when, where, with whom the challenge appears will give you more clarity on why it appears at all.

For example: When I was quitting smoking, I identified that I only smoked when drinking coffee and going out. Similarly, in my early 20s, I noticed my boss was harsh with me only when his boss attended our meetings—and he treated everyone this way. So it wasn't personal! It was about his relationship with his boss. Not judging or justifying, just understanding.

Ask yourself:

• How often is this happening? Is it a pattern?

• Does this challenge occur only with particular people, or within particular parts of the organization, or in particular situations?

• Is it affecting only me, or others too? How?

Step 6: Map Your Stakeholders

You can also start with this, but it's an iterative process of understanding all the sides affected by the challenge you're trying to understand.

For organizational challenges:

• Who are the 3-6 key stakeholders affected by this challenge?

• What are their interests? How do they understand this situation?

• What might they perceive as loss or gain?

• Who are they loyal to? Whose interests do they represent/protect?

• What relationships do they need to manage, and how does that affect their thinking?

For personal challenges:

• Who are the 2-5 people or groups that might have opinions or are affected by your challenge?

• Whose opinions actually matter because they care about your well-being?

• Whose opinions are more about impressing others or avoiding judgment?

Step 7: Create Alliances

Just like it's easier to start running if you join a running group, it's more effective to lead change when you have allies.

Never lead change alone.

The best change efforts look like mini movement-building projects inside your team or organization.

Ask yourself:

• Who sees the challenge similarly to how you do?

• Who do you trust?

• How can you organize to lead change together? (Formal team, informal meetings, group chat)

• How can you create a strategy and expand your influence together?

🔄 Remember: This Is an Iterative Process

You need to observe, act, reflect, and restrategize. Your understanding of the problem might change as you learn more, and the ultimate tool for learning is action!

The world needs more people who can see what others miss, ask the questions that matter, and bring people together around what's actually true. Every time you choose depth over convenience, understanding over assumptions, you're not just solving a problem—you're modeling a different way of thinking for everyone around you. That's how real change spreads: one person willing to go deeper at a time. ✊

PS: 🦋 If you know someone who could benefit from this article, please share it with them to support their leadership journey!

💡 Support our free newsletter by checking out our sponsor for this issue 👇

Fact-based news without bias awaits. Make 1440 your choice today.

Overwhelmed by biased news? Cut through the clutter and get straight facts with your daily 1440 digest. From politics to sports, join millions who start their day informed.

Sign up now!