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Four Simple Questions for When You Know Something Needs to Change

Businessman In A Suit Standing By A Window At Dusk, Thinking With A Pen To His Chin; Notebook And Coffee Cup On The Sill Nearby

You feel it before you can name it. The team is busy but the momentum is gone. The numbers are fine but they’ve been “fine” for a while now. You catch yourself running the same plays out of habit, not conviction. Nothing is on fire — and honestly, that’s part of the problem. There’s no crisis to force your hand. Just a quiet, nagging sense that it might be time to shake things up.

Here’s what I’ve noticed over the years: leaders are great at reacting to emergencies and terrible at responding to that quieter signal. When the building is burning, everybody moves. But when things are merely stuck — coasting, plateaued, running on yesterday’s plan — we tend to do nothing. We tell ourselves we’ll deal with it later. And later, we run the same plays again, a little more tired, wondering why the results won’t budge.

There’s an old saying that the definition of insanity is doing the same thing over and over but expecting different results. Cute line. Painful truth. Because that’s exactly what happens when you sense a shift is needed and keep hitting the copy button anyway — same effort, same patterns, same stubborn hope that this time the outcome will magically be different.

So let me offer you a different move. Not a reorg. Not a 40-page strategic overhaul. Just four questions. They’re simple enough to answer over a cup of coffee, and honest enough to break whatever cycle has quietly been working against you. Pull them out anytime you feel that itch — a new quarter, a stalled project, a team that needs fresh energy, or just a Tuesday when you know deep down that “more of the same” isn’t the answer.

The Four Questions

Grab a notepad. Here they are:

  1. What is working, and how do I do more of it?
  2. What is not working, and how do I get rid of it or make it work?
  3. What do I want to do that is new?
  4. What do I want to do that is big?

That’s it. Four questions. But don’t let the simplicity fool you. These aren’t small questions — they’re just clearly worded ones. And clear beats clever every single time.

Think about a doctor at a checkup. She doesn’t hand you a hundred-page diagnostic manual. She asks a handful of pointed questions — how you’re sleeping, what hurts, what’s changed — and those answers tell her where to look. Simple questions, asked with intention, cut straight to what matters. These four do the same thing for your business, your team, and your leadership.

Let me walk you through each one.

What’s Working — And How Do I Do More of It?

We’re strangely bad at this one. When something is going well, we take it for granted and move on. We spend ninety percent of our energy chasing the broken thing and almost none of it protecting and multiplying the thing that’s actually driving results.

Think about a gardener deciding what to do with a plot of land. Before she plants anything new, she looks at what thrived — which corner got the right light, which plants took off — and she leans into it. She plants more of what already works in the soil that already works. That’s not laziness. That’s Wisdom.

So look hard at your wins. That client relationship that keeps paying off. The morning routine that keeps your team focused. The one product line quietly carrying the whole business. Name them. Then ask the follow-up that most people skip: how do I do more of it? Not just “keep it going” — actively pour more fuel on the fire that’s already burning. A lot of the momentum you’re chasing is already sitting right there, underfunded.

What’s Not Working — And How Do I Fix It or Kill It?

Now for the honest part. Every one of us is hauling around something that isn’t working. A process that eats hours and produces nothing. A meeting nobody needs. A commitment we said yes to out of guilt. We know it’s not working. We just keep dragging it along because stopping feels like admitting we were wrong.

Here’s the thing: you have two clean options with anything that’s broken. You fix it, or you get rid of it. What you can’t keep doing is the third thing — tolerating it. Limping along, half-committed, hoping it sorts itself out. It won’t. And that dead weight is a big part of why things feel stuck.

It’s like keeping a car with a slow oil leak. You can take it to the shop and fix it, or you can decide it’s not worth the trouble and let it go. What you can’t do is keep driving it, topping off the oil every few days, pretending that’s a plan. That’s not maintenance. That’s denial with extra steps.

So make the call. For each thing that’s not working, write “fix” or “drop” next to it. No middle column. Clearing that weight is often what frees up the energy to change direction in the first place.

What Do I Want to Do That’s New?

The first two questions clean up what you’ve got. This one opens up the future.

We are creatures of habit, and habit has a gravitational pull. Left alone, we’ll repeat this quarter on autopilot, then the next one, then the one after that. That’s exactly why you have to consciously ask what’s new — because new almost never happens by default. It happens on purpose.

New doesn’t have to mean enormous. Maybe it’s a skill you’ve been meaning to build. A market you’ve been circling. A way of running your one-on-ones that you’ve been curious about. A conversation you’ve been avoiding. New is simply the thing that wasn’t on the old page — the deliberate step outside the routine that’s had you feeling stuck.

So give yourself permission to write something down that scares you a little. If nothing on your list feels new, you haven’t finished answering the question yet.

What Do I Want to Do That’s Big?

And finally, the fun one. What’s the big swing?

New and big aren’t the same thing. New is about direction. Big is about scale and ambition. This is the goal that makes you sit up a little straighter — the one you’d be a little embarrassed to say out loud because part of you isn’t sure you can pull it off. If you’re looking to build real momentum, this is where it comes from. Small tweaks rarely wake a team up. A bold, worthy goal does.

Every big thing worth doing starts as a slightly uncomfortable sentence on a notepad. The founder who built the company, the leader who grew the team, the person who changed careers at fifty — every one of them wrote down something that felt too big at the time. You don’t have to know how yet. You just have to be brave enough to name the what.

Do This Twice — At Work and At Home

Here’s a step most people miss. Run these four questions through both sides of your life, not just one.

Make one list for your professional world and a completely separate list for your personal world. The version of you that leads a team and the version of you that shows up at the dinner table both deserve an honest look. What’s working in your Marriage? What’s not working with your Health? What’s new you want to try with your Family? What’s the big personal goal you keep shelving?

We spend so much energy on the work list that we quietly let the home list run on autopilot indefinitely. Don’t do that. The whole point is work-life-faith balance, and you can’t balance something you’ve never actually looked at.

Then Share Your Answers

Once you’ve built your lists, don’t keep them locked in a drawer. Answers written down are helpful. Answers shared out loud are powerful.

At home, walk through yours with your spouse or the significant people in your life. You’ll be amazed how often “what’s not working” is something they’ve been quietly noticing too — and how much lighter it feels to say it together.

At work, share yours with your manager or your team. Use your answers as the foundation for where you go next instead of starting from a blank page. And if you lead a team, hand them these same four questions. Have each person answer for themselves, then pull it all together into one master set for the group. You’ll walk out of that room with a clearer picture of your team — and a shared sense of the shift you’re about to make — than any survey could ever give you.

The Real Point

None of this is complicated. That’s the whole idea. The best leadership tools aren’t the ones with the most moving parts — they’re the ones simple enough that you’ll actually use them, again and again, every time you sense it’s time for a change.

Four questions. A cup of coffee. A notepad. That’s all it takes to stop coasting on the old plan and start deliberately building the next chapter.

So here’s the question worth sitting with the next time you feel that itch: are you actually changing direction — or just running the same plays a little harder and hoping?

Grab the notepad. Answer the four. And give yourself a real shot at something different this time.


What’s the shift you’ve been sensing but haven’t named yet? Drop a comment — I’d Love to hear your take.

The post Four Simple Questions for When You Know Something Needs to Change first appeared on Servant Leadership Coaching | Practical Leadership Development | Doug Thorpe.

Small business owners will hit an invisible wall that can stall the growth of the company. The key reason there is a wall is that owners need to shift from manager to leader. The question is, how to do that?

Doug is a coach for CEOs and Senior Leadership Teams with 30 years of leadership experience. He is the president & CEO of Doug Thorpe Group. Doug is also a podcast host.

He helps owners understand the ways they need to reshape their thinking and attitude to make a successful break through the wall.

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