How to Design Systems That Work With You, Not Against You

If you’ve ever felt like your systems were running you instead of supporting you — this one’s for you.

Here’s what I see most often: people try to fix their systems by tweaking what’s already there. “This part’s not working so well. That part’s not working so well.” Then they pivot, patch, and plug in a few new tools — hoping that’ll solve it.

But it rarely does.

Because the problem usually isn’t the tool. It’s the way the system was built in the first place.

Most people start with someone else’s setup but don’t customize, or chase a shiny new app that promises to make life easier. The result? A process that doesn’t actually match the way they work or the outcome they want. They buy software with tons of cool features and end up using three of them. The rest just sit there — costing you time, money, and energy. Even more so if their trying to find creative ways to use the extra features.

And when the system doesn’t do what they expect, they scrap it completely and start over. But starting over doesn’t fix the root problem.

The truth is, great systems aren’t built around tools. They’re built around experience.

Start with the Experience

When I design a system, the very first question I ask is:

What experience do I want people to have?

That includes both sides — the customer experience and the internal experience.

For customers, it’s about how you want them to feel, think, and interact with your business at every step. For your team (or yourself), it’s about how you want things to look, flow, and function day to day.

I always start with the customer experience first because that’s where clarity begins. If I want my client to feel guided, supported, and confident — that tells me how the system needs to operate.

Once you know what the experience should feel like on both ends, then you can start mapping out what needs to happen to make that experience real.

Map the Steps Before You Touch the Tools

This part is critical — and the step most people skip.

Before thinking about software or automations, outline every key step that needs to happen. Draw it out. Seeing it visually helps you catch things you’d normally miss.

Be specific. What needs to happen first? What triggers the next step? Who’s responsible?

When you see the full picture, ask:

How can we make this happen with the least amount of effort — for us and for our clients?

That’s the golden question. It reveals what to automate, what to delegate, and what to simplify.

Choose Tools Last — Not First

Only once you’ve mapped the system should you start thinking about tools.

Too often, people pick software first and then build their workflow around it. That’s backwards.

The right tools support your system. They don’t define it.

If you just need project management, pick something that does that — not a complex all-in-one app that turns into another full-time job to manage.

More features don’t equal better systems. They often mean more friction, more decisions, and more noise. Choose tools because they help you do exactly what you need — nothing more.

Build Feedback Into the System

Feedback is how your system evolves. Without it, you’re flying blind.

Create a simple way to gather it — from both clients and your team. Ask:

• What feels clunky or confusing?
• What’s taking too long?
• What do you find yourself skipping or bypassing — and why?

Those bypasses are your biggest clues. They show you where your system needs refinement.

Then evaluate feedback based on two things:

1. Is this within my control to fix?
2. What’s the impact if I do?

Not all feedback needs action, but all of it deserves consideration.

Keep It Adaptable

Here’s the truth: when you design a system around experience, adaptability is built in.

The what — the outcome you’re delivering — stays the same.

The how — the tools, processes, and workflows — can evolve.

Do an annual review. Ask yourself:

• Are the tools still helping us deliver the best experience?
• Are there steps that feel outdated or redundant?

Adaptability doesn’t mean reinventing everything. It means continuously improving what already works.

Define What Success Looks Like

A successful system should:

1. Deliver the experience you designed for — inside and out.
2. Be easy and efficient to use.
3. Hit the milestones you’ve set (emails sent, calls booked, etc.).
4. Include a clear way to measure success — through metrics or feedback.
5. Stay simple enough that anyone can use it confidently.

When someone says, “Wow, that was so easy,” — that’s success.

Quick Win: Design Your Experience in 15 Minutes

1. Write two lists: “Customer Experience” and “Team Experience.”
2. Note what each should think, feel, and do.
3. Map 5–7 key steps that make those experiences possible.
4. Circle what can be automated or delegated.
5. Only after that — pick the minimal tool stack that gets it done.

Before You Close This Tab…

If your systems feel clunky, don’t toss them. Start with the experience you want. Map the steps. Simplify the flow. Then find tools that support what matters most.

You don’t need to rebuild everything. You just need to realign it.

Reflection: Where are you working for the tool instead of letting the tool work for you?