Inherited Systems: How to Turn Chaos into Opportunity

When you step into a new leadership role — especially as a CFO, COO, or CIO — it’s common to inherit systems and technology you didn’t choose. Whether it's a legacy ERP, an overly customized CRM, or a sprawl of disconnected tools, these systems often come with unclear ownership, hidden risks, and few clean handoffs.

Here’s the good news: chaos reveals where your business is resilient, fragile, and where smart investments can create value.

This guide will help you turn disorder into direction by showing you how to:

• Evaluate where you are
• Identify where you need to go
• Create a structured, scalable path forward

Evaluate Where You Are

It may be tempting to jump straight into problem-solving mode, especially when stakeholders are expecting fast results. But acting before understanding can lead to mismatched fixes and wasted effort.

Start by grounding yourself in the business context first. What drives this organization? Where is it headed? What constraints exist?

Understanding the Business

Start by gathering information. Ask stakeholders questions to understand how the business runs. This can help you build rapport with your new team while also giving you the foundational knowledge to understand your organization.

Here are a few questions to help you get started:

• What is your company’s core business model? Understanding this will guide your decisions and help align your work with revenue-generating activities.
• What are the top goals? Identify what leadership is focused on — e.g., growth, retention, expansion into new markets — and tailor your efforts accordingly.
• What are the biggest pain points? Being able to tie back to pain points will be helpful as you build business use cases.
• Who are your key stakeholders, and what motivates them? Know who the decision-makers are, what success looks like for them, and how they prefer to collaborate.
• What’s your geographic and regulatory footprint? Regional, national, and international organizations all have unique operational needs and compliance considerations.
• Who are your customers, and how do you acquire them? B2C vs B2B models will significantly shape system design.
• Do you work with contractors or partners? This will help you understand external influences in your processes, which can impact integrations that may be used or needed.
• What’s your current tech stack? Catalog the tools in use, who owns them, how they’re integrated (or not), and what historical context might affect adoption or replacement.

Once you have a holistic picture of the business, the next step is mapping out existing processes. Start simple: what’s happening today, and how? Document workflows across key areas — onboarding, deal flow, billing, customer support — and look for inconsistencies, bottlenecks, or manual workarounds.

Status Check: Review the Technology Landscape

Once you have the necessary high-level information on your new company, it's time to dig into the back end.

• Technical Debt: What workarounds or quick fixes have accumulated over time? What items are not used anymore? What is difficult to maintain or prone to breaking? What no longer meets the needs of the organization?
• Integrations: Which tools talk to each other, and which don’t? Lack of integration can result in manual data entry, reporting headaches, and misaligned teams. Identify where automation or connectors could save time and reduce risk.
• Data Health: Is your data accurate, consistent, and usable? Poor data creates reporting issues, weakens forecasting, and increases compliance risk.
• Security & Compliance: Does the current system meet your industry’s regulatory standards (e.g., HIPAA, SOX, GDPR)? Are there risks related to access controls, audit logs, or policy enforcement?
• Licensing & Contracts: What are your current vendor agreements? Are you locked into costly licenses, renewals, or shelfware? Understanding your total cost of ownership (TCO) and contract limitations will shape your options for upgrades or replacements.

This technical review will give you a better sense of what's salvageable, what needs rebuilding, and what should be retired altogether.

Identify Where You Need to Go

Now that you understand the current state, it’s time to prioritize and strategize.

Hold discovery sessions — whether through one-on-one interviews, workshops, or in groups — to get insight into current frustrations and future aspirations.

Start by asking system users:

• What’s working well today?
• What’s broken or inefficient?
• What do you anticipate needing as we scale?
• If you could build your ideal system from scratch, what would it look like?

The goal: identify urgent issues and long-term vision and avoid patchwork fixes and design systems that evolve with the business.

Consolidate and Prioritize

After intake, centralize all data in one repository to evaluate and prioritize requests and ideas.

Here’s an example:

As you input each item, be intentional about capturing the following:

• How important is this?
• Is it a must-have or a nice-to-have? Is it business-critical, or would it be a "quality of life" improvement?
• How big of a lift is this?
• Categorize by effort: Low-hanging fruit (1-2 hours), climb the tree (3-8 hours), need a ladder (1-5 days), or cut the tree down (1 week+).
• What’s the impact?
• Will this: Save time? Improve reporting accuracy? Reduce cost?

Before finalizing your priorities, share your high-level recommendations with your leadership/stakeholder team to align expectations and secure buy-in.

Create a Path Forward

You’ve prioritized what matters — now it’s time to deliver. Whether you're tackling a small workflow fix or a large-scale system overhaul, successful execution starts with a clear plan.

Projects without clear goals, ownership, or structure often lose momentum, extend timelines, or miss the mark entirely. Start by answering these key questions for each initiative:

• Why are we doing this? Does it align with company goals or address a critical pain point?
• What does success look like? Define measurable outcomes. Ensure all stakeholders agree on what success means and how it will be tracked.
• What’s the impact? Which teams, processes, or customers will be affected? Will communication, training, or change management be required?
• What are the risks? Identify potential blockers early and plan how to mitigate them.
• What resources are needed? Consider people, tools, budget, and time. Are there internal champions or subject matter experts who should be involved?

Break your initiatives into projects with clear scopes, owners, and timelines. Use a project management tool to track progress and communicate updates.

As you execute your plan, what matters most is clarity, accountability, and communication. Here are a few key execution tips:

• Maintain your project tracker. Keep status updates visible so stakeholders can self-serve. Avoid becoming the single source of truth.
• Communicate consistently. Share progress with leadership regularly, focusing on milestones, risks, blockers, and high-level outcomes — not just tasks.
• Clarify roles. Define who owns what. Daily stand-ups or weekly check-ins can help resolve blockers and maintain momentum.
• Document everything. Capture the what, why, and how for each project. This helps with future onboarding, audits, or handoffs.
• Prepare for go-live. Communicate upcoming changes clearly, provide training or enablement where needed, and celebrate the wins.

Transform Chaos into Clarity

Inheriting a complex system can feel daunting, but it is also an opportunity to drive lasting change. By taking the time to understand your business, engage stakeholders, prioritize needs, and execute with intention, you can turn disorder into a clear, scalable path forward.

At Eide Bailly, we help organizations make sense of complexity and drive meaningful change. Whether you're optimizing existing systems, aligning tools to business goals, or planning large-scale transformation, our team can help you move forward with confidence.