“Our tech stack is a mess.”

This is one of the most common complaints mid-sized companies make during a strategy or operations reset.

The instinct is to start by reviewing the tools. Which ones are redundant? Which ones aren’t being used? Which ones should be replaced?

But that’s the wrong starting point.

In this week’s newsletter, we’ll break down:

• Why technology problems are usually process problems in disguise
• How to spot the real sources of friction inside your systems
• What to do before adding or replacing a single tool

Let’s dive in.

Start with the process, not the platform

Most companies add tools to solve surface-level symptoms.

For example:

• Response times are lagging, so they add a chat tool.
• Reports aren’t being generated, so they add a dashboard product.
• Deadlines are slipping, so they add a project management platform.

But none of these tools fix the underlying reasons:

• Why are response times lagging?
• Why don’t team members have the data they need?
• Why are deadlines getting missed?

Technology can’t fix a broken workflow. It can only make the broken workflow more expensive and more complicated.

Map how work actually gets done

Before evaluating software, map the current reality:

• How are tasks initiated and tracked?
• What tools are used for which parts of the process?
• Where are things breaking down or getting delayed?

In most companies, this review reveals a few consistent issues:

• Teams are using different tools for the same function
• Multiple people enter the same data in different systems
• Manual workarounds (like spreadsheets or Slack messages) are common
• Handoffs between departments lack structure or clarity

This mapping doesn’t just show what’s not working, it surfaces why.

Ask the right diagnostic questions

Once the process is visible, it’s easier to evaluate the tech. Start with these 4 questions:

1. What’s actually being used, and by whom?
   Most companies pay for dozens of tools, but only a handful are core to daily work.
2. Where is friction happening most often?
   Look for repeated bottlenecks, missed handoffs, or complaints from specific teams.
3. What workarounds have become permanent?
   If people are defaulting to manual steps outside of the system, it’s a signal.
4. Are systems integrated or siloed?
   Tools that don’t talk to each other create duplicative work and data inconsistency.

The most common tech stack issues we see

Here are the patterns we see most often when auditing operations and systems:

• Unused licenses and overlapping tools: Teams using Slack, Teams, Asana, and email—simultaneously. The result? Chaos.
• Manual processes built to work around the software: CRMs with messy data. Spreadsheets copied and pasted weekly. Long email chains confirming things already “in the system.”
• Shadow systems that leadership doesn’t know exist: One department using Airtable. Another using Trello. A third tracking it all in Notion.
• Lack of clarity around ownership and training: Software rolled out without enablement leads to inconsistent usage and frustration.

So what’s the solution?

The answer isn’t always a new platform. In fact, most of the time, you don’t need more software → you need clarity.

That can take a few forms:

• Streamlining tools to reduce overlap and simplify workflows
• Training teams on how to use the systems already in place
• Redesigning workflows so tools support how people actually work
• Improving handoffs and responsibilities across functions
• Eliminating subscriptions that aren’t aligned with core operations

The right tools, layered on top of clear processes, work.

The wrong tools, forced into messy workflows, don’t.

Try this before investing in another tool

If you feel your tech stack is underperforming, here’s a quick 3-step diagnostic exercise:

Step 1: Have each department list their top 5 most-used tools

Step 2: For each tool, write down:

• Who uses it
• What it’s used for
• Where it creates friction

Step 3: Circle any tool that has:

• Overlap with other tools
• No clear owner
• Frequent complaints
• Manual workarounds

This simple exercise surfaces issues in 30 minutes, and gives you a place to start.

Whenever you’re ready, there are three ways we can help your team…

1. Strategy & Growth Blueprint: A market-grounded strategy, annual planning, and 90-day execution framework the whole team owns.

2. Operations & Tech Reset: Bottlenecks mapped, future-state processes designed, and a phased tech roadmap ready to launch.

3. Manager+ Accelerator: Build core skills in delegation, feedback, goal-setting, and develop a plan to lead a stronger team.