It Depends - How to Make the Right Strategic Decisions

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Ever wonder if the quick-fire answers to your big business questions are right for you? 

Ever wish someone would dig a little deeper before telling you what to do next?

Are you making the right decisions to support your business vision, or are you making fast choices that create long-term complexity?

One of the most common questions I get from clients is: “What should I do here?” And while it might be tempting to offer a quick yes or no, the truth is, strategic decisions rarely have a one-size-fits-all answer. That’s why my favorite answer is often the one that frustrates people the most: it depends.

The fastest way to stall your growth is to jump on one-size-fits-all advice without stopping to look at what you’re really trying to achieve. 

Taking a step back and asking better questions can save you a lot of time, money, and unnecessary work down the line. 

Sometimes the best answer isn’t the fastest one. There’s so much value in taking the time to get clear before you get started. For improved decision-making, it is important to learn the following:

  • Why context shapes every strategic answer
  • How quick decisions create longer-term headaches
  • Questions to consider before making important decisions
  • What goes wrong when you skip the “it depends” step
  • Setting your business up for long-term scalability

If you want to build a business that’s aligned with your vision and capable of evolving with you, this post is for you.

In episode 225 of the Simplify to Scale Show, I also break down how to make smarter decisions using the "it depends" approach and share what questions you need to be asking (or getting asked) every time you’re at a crossroads.

Tune into Episode 225 of the Simplify to Scale Show or keep reading below.


Why Quick Answers Often Lead to Misalignment

It can feel productive to get fast answers and move forward. But without pausing to ask the right questions, you risk choosing what looks right in the moment over what actually supports your long-term goals.

Every decision exists within a larger context:

  • What’s your goal for this offer or change?

  • How does this align with where you want to take your business?

  • What is already working that you don’t want to disrupt?

  • What are the actual problems you’re solving for?

Answering these questions takes more time.

However, skipping them almost always leads to disjointed decisions that create more work later.

 

Context Creates Clarity

Let’s take a real client example: She was adjusting her offer suite and reached out to ask what I thought of a new price for a downsell. Instead of a yes or no, I asked a series of questions.

Is this truly a downsell, or is it a lower-tier entry point into your funnel?

Are you offering it as an either-or at the start, or introducing it only after someone opts out of your core program?

Those questions completely change how you price, position, and deliver the offer.

When you answer without asking these kinds of questions, you make decisions that might work tactically in the short term but miss the bigger picture.

When you take time to understand the context, you create offers, systems, and structures that are aligned and scalable.

 

The Real Role of Strategic Support

If you’re leading a business or you’re supporting clients in growing theirs, your role isn’t to hand out answers. It’s to create clarity.

Another client came to me wanting to upgrade her CRM.

She was taking more sales calls and needed a better way to manage her leads. She thought it was a simple tool decision. 

However, we spent hours walking through her goals, how her leads enter and flow through her system, and how she wanted to nurture them.

The right CRM depends on how you sell, the experience you want your leads to have, and how your team works best.

You can’t make the right choice without knowing that first.

The same goes for any decision you’re making in your business.

The more complex the business becomes, the more critical it is that every decision fits together.

 

Simplify by Design, Not by Cleanup

Many businesses come to me because things have become too complex.

Their offers feel disconnected. Systems don’t talk to each other. Teams are unclear on priorities.

These businesses didn’t set out to create complexity. They just made fast decisions in the moment.

What’s missing is intentional design.

Instead of building with your vision in mind, you make choices based on today’s needs.

The result is a patchwork of solutions that don’t scale well together.

Here’s what to do instead:

  • Start with your long-term vision

  • Build the structure and team that supports that vision

  • Then choose your tools and tactics

Doing this doesn’t just simplify your business. It prevents unnecessary complexity before it starts.

 

Confidence Comes from Context

When someone says, “Just tell me what to do,” they usually feel overwhelmed.

But what they really need is confidence, and confidence doesn’t come from someone else’s answer.

It comes from knowing that the answer is right for you.

That’s why I always take the time to ask the deeper questions, because the right answer today might not be the right answer six months from now.

If your context shifts, your decisions should too.

You can’t create scalable solutions without thinking holistically.

Every shortcut leads to something that has to be reworked later.

 

Making the Right Decisions for Sustainable Growth

To make decisions that support where you’re going, not just where you are, start here:

  • Don’t settle for surface-level answers. Ask better questions first.

  • Align each decision with your long-term goals and vision.

  • Consider the ripple effects of each choice across your entire business.

  • Build with intentionality so you simplify by design.

The more aligned your decisions are, the more sustainable your growth becomes.


Do you need help applying this in your business?

Join me for the Scale Smarter, Not Harder interactive workshop. You’ll gain clarity on what’s keeping you stuck, explore how to build a more scalable structure, and ask me your questions live.
Register at strategicopsinstitute.com/scalesmarter

by Crista Grasso

Crista Grasso is the go-to strategic planning expert for leading global businesses and online entrepreneurs when they want to scale.  Known as the "Business Optimizer", Crista has the ability to quickly cut through noise and focus on optimizing the core things that will make the biggest impact to scale a business simply and sustainably. She specializes in helping businesses gain clarity on the most important things that will drive maximum value for their clients and maximum profits for their business.  She is the creator of the Lean Out Method, 90 Day Lean Out Planner, and host of the Lean Out Your Business Podcast

WORK WITH CRISTA

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