Why Do Some Organisations Keep Failing at Change?

You’re not alone. Most people who’ve worked in development know that feeling. That moment when you believe this time will be different, only to watch it follow the same old pattern. All that’s left is fatigue and frustration.

But what if the issue isn’t with that one project? What if the failure wasn’t a fluke, but a sign of something deeper that affects how your whole organization approaches change?

When history repeats itself: the cycle of failed change

Heli Häyrynen, change management expert at Greenstep, talks about the vicious cycle of change.

According to her, when an organization fails at change, it doesn’t just leave behind one failed project - it leaves behind a scar. A cultural one.

“If an organization fails at change and the same people are still working there, the next change will be twice as hard.”

This impacts everything. New initiatives spark doubt. Commitment stays surface-level. People start expecting change to just blow over again.

Where there used to be curiosity, there’s now fatigue. Where ideas used to flow, silence creeps in: “It won’t lead anywhere anyway.”

What’s it like to lead a change-wary organization?

Imagine the CEO unveils a bold new strategy. The goals are clear, the plan ambitious. But you still catch yourself thinking: “How am I going to get people excited about this?”

In an organization worn down by failed changes, people protect themselves. They don’t resist out loud - they just wait it out in silence. Leadership shifts its focus to new priorities, and the old familiar routines quietly return. You know this pattern, and that’s what makes it so exhausting.

Heli reminds us that successful change delivers more than just results:

“In successful organizations, every individual becomes more confident and capable. People commit in a completely different way.”

When trust erodes, you don’t just lose a project. You lose innovation. You lose engagement. You lose your top talent. At worst, you pay for it in skyrocketing recruitment costs, onboarding, and lost productivity.

Signs of change fatigue: do these sound familiar?

Often, the signs are more visible than we’re willing to admit:

At the coffee machine:

• “We’ve seen this before.”

• “Don’t waste too much time on this.”

• “Let’s just wait it out.”

In meetings:

• People show up physically, but not mentally.

• Questions go unasked, even when things are unclear.

• Nods all around, but no real commitment.

As a leader:

• You’re already tired before the project starts.

• You’re frustrated when no one follows through.

• You feel alone in carrying the responsibility for change.

If any of this hits home, know that you’re not alone. And more importantly: it’s not permanent.

The cycle can be broken

Heli describes a client case where a new CRM system could have easily triggered resistance. But it didn’t.

“Instead, people felt heard, their input was respected, and they received the support they needed. When results started showing, people got excited: ‘This actually works.’”

A successful change isn’t just one victory. It lays the groundwork for the next one. An organization that succeeds starts expecting change - not fearing it.

So how do you break the pattern?

If your organization is carrying the weight of past failures, don’t start with a new strategy or tool. Start by pausing. And ask yourself (and your team) honestly:

• When was the last time we really listened to our people?

• Were past changes based on genuine needs, or just hype?

• Have we supported people throughout the journey, or left someone behind?

• Do we have the courage to admit when something didn’t work?

Heli puts it simply:

“Every change should begin with listening. That’s what we tend to forget when we get excited about the change itself.”

Maybe that’s the key. When listening becomes part of the culture, hope returns. A new kind of expectation emerges: maybe this time really will be different.

And that’s how the journey out of the vicious cycle begins, toward a culture where people no longer fear change… but look forward to it.