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How Do You Know When It’s Not Working at Work? (The Project, The Job, The Hire, or Anything)

How Do You Know If It's Not Working at Work _ Red Cape Revolution

“How do you know when it’s not working, really?”

I was sharing a bottle of wine one evening with team leaders who are struggling through a complicated change management project. The leader who spoke continued on.

“I don’t get it. I’ve been part of these changes  before, but somehow, this one’s different.

Another colleague waved her off, jumping in with, “Well, we’ll know when we know.”

That’s when I ordered more wine.

Because the old-fashioned “you’ll know when you know” couldn’t be farther from the truth. 

It’s true. Often, when something’s not working at work–whether it’s a project, a role, or even a person–we know much sooner than we’ve been taught to admit.

But we’ve been taught we shouldn’t give up. We’ve been taught not to quit.

That’s not working.

As author Seth Godin teaches in his classic book The Dip: A Little Book That Teaches You When to Quit and When to Stick (affliate link), the only way to focus on the right things long-term is to quit many of the wrong things along the way.

So how do we know when it’s not working, especially inside the complicated world of work?

What if we could speed that process up, and spend less time in the squirrely swirly space of confusion?

How do you know when it’s not working at work? Here are three surprising tests.

1. You Can No Longer Explain Why It Matters

Nothing in our workplaces gets started without a story. The story might be spoken, or it might be subtle. But there’s no forward motion without some kind of story:

  • “This project will help us get answers to our customers faster, with more accuracy.”
  • “Buying and implementing this new technology will make sure we don’t get left behind.”
  • “Hiring that senior editor from our competitor will allow us to launch the new publication.”

The story typically includes the answer to one key factor: WHY.

  • Why does it matter?
  • Why do we care?
  • Why is it worth time, energy, money?

When I begin coaching leaders who are trying to decide why a particular project, initiative, or even person isn’t working in the way they’d hoped, I always push them to tell me why it mattered in the first place.

If they can explain the why, we then test whether that why is still relevant.

  • What assumptions did we make then that may no longer be true?
  • What did we believe was important that isn’t anymore?
  • What else has happened since we started that changes our reasons why?

Reviewing the relevance helps you see whether the effort is still worth doing, and allows you to now tweek or even overhaul the process accordingly.

On the other hand, if they can’t explain the why, it’s a good sign that you’re wasting your time.

2. Nobody’s Learning Anything New

The concept of “lifetime learner” isn’t just a cliche you use on your LinkedIn profile.

It’s actually a success requirement in the 21st century workplace.


Learning is not just about facts and data. More importantly–and of higher value today–it’s about personal interactions, including the ones with ourselves where we learn who & how we want to be in our world of work.

Where’s the new learning coming from in this situation?

It’s not enough that you’re relearning things you already know (like change is complicated, or people are messy, etc.).

If nobody’s learning anything new and of value, it’s a good reason to take a hard look at whether the situation should continue.

3. Your Gut Says It’s Not Working

Somewhere deep inside you, you’re getting a signal from your brain and body.

It may just be a whisper late at night, or in a quiet moment on the drive home.

Or your signal may be actual physical signs–aches, injuries, skin breakouts, etc.

It’s the signal that made you start asking the question to begin with.

Don’t ignore these signals.

Too often, we’re told to just “muscle through” a tough situation. But when we really listen to the signals our brain and body are sending, we can find the truth.

Even just admitting the truth when it’s really not working can be a relief, and send a signal back to your body that you’ve noticed, and are getting into action.

Your brain and body are smart, and are biologically programmed to notice and react to things well beyond what you can do consciously.

Give them a listen, trust what they’re saying, and you’ll make the right decision.

Hey—want more help?

No matter what’s happening in your life at work, a 30-minute chat with me can help you get unstuck and move forward, fast. 

Just hit the button below, and pick a date and time that’s available. Answer a few short questions, and then I’ll call you at the time you picked. There’s nothing to prepare–just show up right where you are. If, after we talk, it sounds like one of my coaching programs or courses will help you going forward, I’ll share details after our call. There’s no pressure -my goal is to be helpful immediately.

Spots fill up fast, though, so schedule yours now and start getting the support you deserve.

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