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Why your tools are costing more than they're worth, and how to fix it without starting over

How to avoid the trap of thinking technology can solve human collaboration problems

The Kenzie Note

Last year during budget season, we discovered a tool graveyard.

Not duplicate subscriptions exactly. Worse. We found tools that had been deemed "absolutely necessary" when approved, championed by someone who promised they'd transform our workflow, now sitting unused with auto-renewing subscriptions nobody had bothered to cancel.

A social media scheduling tool we'd committed to for a year? Used for two months, then abandoned when the champion left the team. A graphic design platform that was going to "finally speed up assets"? Everyone went back to Canva and Figma within three weeks. An analytics dashboard that cost $400/month? Last login: 8 months ago.

Each one made perfect sense in the moment. Each pitch was compelling. Each approval felt justified. But nobody had checked whether we were actually using them. We were just paying for tools we'd forgotten we bought.

The embarrassing part? I teach workshops about this exact problem. It's like being a personal trainer who gets winded walking up stairs. Or a financial advisor whose credit cards are maxed out. Except somehow worse, because I literally have a slide deck about this exact problem.

When I ask small businesses "how many tools are you paying for that you don't really use?", they get uncomfortable. Then they start counting. Turns out we weren’t consistently following our own advice.

The Hidden Time and Money Drain

"How many hours did you waste last week looking for files, transferring data between tools, or doing the same task twice?"

When I ask this question to small businesses the silence is telling. Then the numbers start coming out.

Five hours a week on manual data entry between systems that don't talk to each other. Three hours searching for files scattered across different platforms. Two hours on duplicate communications because information lives in silos. When we add it up, some teams are spending 20% of their time just managing their technology stack.

The financial impact gets worse. Businesses regularly discover they're paying $200-500 per month for duplicate subscriptions they forgot about. Lost billable hours from inefficient processes cost thousands monthly. But the hidden costs hurt more: staff frustration leading to turnover, inconsistent client experiences damaging referrals, delayed projects hurting reputation.

One founder in a Hello Alice Boost Camp listed her tools out loud. She started confident: "Seven." Then kept counting. "Wait, nine. No, eleven if you count the automation tools connecting everything."

By the time she finished, we were at seventeen.

"How many do you actually need?" I asked.

Long pause. "Probably four. Maybe five."

"So what would happen if you cut the other twelve?"

"Honestly? We'd probably be more productive."

This conversation happens a lot. The numbers change, but the pattern doesn't.

Tool Creep Happens Innocently

You add Slack for communication. That works great, so you add Asana for project management. Then you add Zapier to connect them. Then you're adding AI assistants to summarize Slack conversations, automation to create Asana tasks from emails, and webhooks to update dashboards based on task completion.

Each connection makes logical sense in isolation. It's like that drawer everyone has in their kitchen - started with useful things, now it won't close and you're not sure what half the stuff does anymore.

But what actually happens is that people start spending enormous chunks of their time keeping the technology stack running. Troubleshooting integrations that break. Updating configurations when something changes. Training new people on how all the tools work together. Working around automation that doesn't quite fit what you're trying to do right now.

The bigger problem isn't the time drain. It's what happens to human connection.

When tools handle coordination automatically, people talk to each other less. Those quick conversations where you actually understand why someone made a decision? They disappear. Important context gets trapped in automated workflows instead of being shared and discussed.

What you end up with are teams that work beautifully when everything goes according to plan, but fall apart the moment they need to adapt quickly or handle something their automation wasn't designed for.

Focus On Tools That Amplify

The difference between helpful and harmful technology comes down to understanding what should be amplified versus what should be replaced.

  • Tools that amplify make information more accessible, coordination more efficient, and communication clearer while preserving human agency. Motion helps you schedule tasks more efficiently, but you still set the priorities and can override its suggestions when circumstances change. Notion makes information accessible across teams without forcing rigid workflows.

  • Tools that replace appropriately handle repetitive, low-level tasks that free humans to focus on higher-value work. Automating data entry, scheduling routine tasks, generating standard reports. These replacements eliminate tedious work without removing human judgment from important decisions.

  • Tools that replace problematically attempt to eliminate human involvement in strategic thinking, nuanced decision-making, and meaningful collaboration. An AI system that automatically assigns complex projects, sets strategic priorities, or escalates sensitive issues without human oversight removes people from decisions that require context, judgment, and relationship understanding.

Consider two teams coordinating a project across multiple departments:

Team A uses tools to make information visible and communication easier, but humans still make the coordination decisions. A shared dashboard shows everyone's progress. A group chat facilitates quick questions. Regular check-ins ensure alignment.

Team B automates the coordination through sophisticated rules and AI. Tasks get assigned algorithmically. Updates flow automatically between systems. Escalations trigger based on predetermined criteria. Humans become operators of the system rather than collaborators with each other.

Both approaches can deliver results when everything goes according to plan. But when priorities shift, unexpected obstacles arise, or new information changes the context, Team A adapts quickly. Team B has to reconfigure the automation.

Automating Decisions Isn't the Same as Improving Them

This pattern is probably familiar to you.

A company implements AI-powered ticket routing. For three months, every metric improves. Response times drop. Throughput increases. The dashboards glow green. Everyone celebrates the successful "digital transformation."

Then customers start quietly leaving.

Here's what happens: The AI optimizes for what it can measure—response time, resolution speed, ticket volume. But it can't see what actually matters: relationship history, strategic importance, context that lives in human heads, not databases.

Think about what this actually means in practice:

  • A longtime customer with a small problem gets routed to the slow queue because the dollar amount is low

  • A complaint that signals a product-wide issue gets classified as "isolated incident" because the AI doesn't recognize the pattern

  • A VIP having a bad day gets the same treatment as someone complaining for sport

The AI doesn't know that this customer championed you internally for years. It doesn't know their contract is up for renewal. It doesn't know they're about to speak at a conference where they could praise or bury your product.

Any human would spot these nuances instantly. Would make the judgment call. Would break the rules when breaking the rules is exactly the right thing to do.

But here's the part that actually costs money: Once teams realize the AI is making costly mistakes, they don't remove it (too much invested). Instead, they add human oversight. Now you're paying for artificial intelligence AND human intelligence to do the same job. The efficiency you wanted? Gone. The trust you need? Shattered.

I've seen teams add three full-time people just to "supervise" their automation. That's $300,000+ annually to babysit a system that was supposed to save money.

The worst part? These companies often know something's wrong but can't pinpoint it. The dashboards still show green. The metrics still look good. They just can't figure out why customers keep leaving.

How to Know If Your Tools Own You

After running workshops on this topic, I've started to notice something: Teams talk about their tools the way people talk about bad relationships they can't leave.

  • "We've invested too much to quit now." (Sunk cost fallacy, anyone?)

  • "It'll get better when we add the premium features." (It won't.)

  • "We just need to try harder to make it work." (No, the tool should work for you.)

  • "Everyone else uses it, so the problem must be us." (Maybe everyone else is struggling too.)

Here's how to spot the warning signs in your own team:

The Dependency Test If your main tools stopped working tomorrow, would your team be helpless or just less efficient?

This isn't hypothetical - outages happen. I've seen teams completely unable to function when their project management system went down. Not because they couldn't track tasks on paper or a whiteboard temporarily, but because they'd literally forgotten how to coordinate without the tool.

The Onboarding Reality Check How long before new team members can actually contribute? Not just get access to everything, but genuinely add value?

When new hires spend their first weeks just learning how to navigate your tool ecosystem, you've built a barrier to productivity, not an enabler. The complexity tax compounds - each new tool adds training time, context switching, and cognitive load.

The Adaptation Speed Test When something unexpected happens - rush request, key person out sick, priority shift - how quickly can your team adjust?

Watch what happens when you need to work differently for just one project. If it requires reconfiguring multiple automations, updating numerous workflows, or extensive workarounds, your tools are dictating your capabilities rather than enabling them.

The Decision Audit Where do real decisions happen in your organization? In human conversations with tools documenting outcomes? Or inside tools based on automated rules?

When Monday's meeting becomes "reviewing what the algorithm decided over the weekend," you're not leading anymore. You're just overseeing automation.

The uncomfortable truth: Every tool that makes you more efficient in perfect conditions often makes you more fragile in imperfect ones. And conditions are almost never perfect.

What I Tell Teams Now

When I run these workshops, I always end with the same recommendation: start with one tool. Get comfortable with it. Make sure it's integrated well into your environment. Then, and only then, consider adding another.

This is especially critical in the era of AI. The temptation is to add AI everywhere immediately. Summarize conversations. Generate tasks. Automate decisions. Connect everything.

Resist that temptation.

Pick one place where AI genuinely amplifies human capability without replacing human judgment. Use it well. Understand its limitations. Then decide if you need more.

The goal isn't to avoid technology. It's to choose technology that makes your team more capable, not more fragile.

When evaluating new tools, ask:

Does it fit how your team naturally works, or does it force artificial workflows? Great tools adapt to your collaboration patterns. Bad tools make you adapt to theirs.

Can people override it easily when circumstances change? Flexibility is more valuable than optimization. Tools that can be quickly adjusted or bypassed when needed support adaptation rather than constraining it.

Does it preserve context and reasoning, or just decisions? Information without context becomes data without wisdom.

Will your team maintain their core skills while using it? Tools that enhance capabilities without replacing them keep teams resilient and adaptable.

The best technology becomes nearly invisible. It supports excellent work without dominating the conversation. Your team becomes more capable and more adaptable because their tools amplify their strengths rather than replacing their thinking.

3 Ways To Build Better

I

Audit your current stack: List every tool your team uses. For each one, ask: "If this stopped working tomorrow, would we be helpless or just less efficient?" If "helpless" appears more than twice, you've crossed from useful to fragile.

II

Track where time actually goes: For one week, have team members note when they're using tools productively versus managing tools, troubleshooting integrations, or working around automation. If management time exceeds productive time, simplify.

II

Default to human coordination: When considering new automation or AI features, ask: "Would a quick conversation solve this faster and more flexibly?" If yes, keep it human. Save automation for truly repetitive tasks where human judgment adds no value.

2 Questions That Matter

I

Are we using tools to enhance collaboration or to avoid it?" This reveals whether technology is amplifying human capabilities or replacing human connection. The best tools make coordination easier, not unnecessary.

II

"If everything automated stopped working, could we still function?" This exposes dangerous dependencies. Effective teams have strong core collaboration skills that technology enhances, not sophisticated automation masking weak fundamentals.

1 Big Idea

Thriving with technology isn't about sophisticated tool stacks. It's understanding how to use technology to amplify human judgment, while having the discipline to choose less when more seems more impressive.