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The CRM System Disaster: When Leadership Checks Out and Chaos Takes Over

Writer: Ryan Redmond Ryan Redmond
A CRM system represented as a ship tilting on turbulent ocean waves under stormy skies, symbolizing risk and instability.


If denial were an Olympic sport, this CRM project’s steering committee would have taken home the gold.


Six months into their Microsoft Dynamics 365 Sales implementation, the company expected to see real progress—streamlined processes, better data visibility, and a more efficient sales pipeline. Instead, progress had stalled, deadlines were slipping, and red flags were practically waving themselves.


Yet when the executive steering committee finally met, excitement had faded—and so had momentum. Instead of tackling real issues, the meeting quickly became a masterclass in polite avoidance.


The Key Players:

  • Michael (Owner): Calling in from his car, half-listening while navigating traffic.

  • Valerie (VP of Sales, and Michael’s sister): Eyes glued to emails, barely registering the discussion.

  • Monica (Project Manager): The only one actually taking the meeting seriously—maybe too seriously.


The meeting ended without debate, without tough questions—and without anyone fully grasping how much trouble the project was in. But in reality, it was veering off course—fast.


And that’s the problem. A steering committee is supposed to…steer!


Catching risks early, making strategic decisions, and ensuring the project stays on track. Instead, this one had set the corporate equivalent of cruise control and hoped for the best.


Welcome to Blog #5 in our CRM Horror Stories series, featuring a family-owned business that learned the hard way what happens when leadership assumes a CRM system will run itself.



Why Steering Committees Matter More Than You Think


A steering committee isn’t just a formality – it’s the guiding force that keeps a CRM implementation from spiraling into chaos.


But when a committee is disengaged, like Michael and Valerie’s team, here’s what happens:

  • Critical risks go unnoticed. Minor issues snowball into major roadblocks.

  • Decisions get delayed – or worse, ignored. No one takes ownership, so problems linger.

  • The project loses direction. Without leadership, teams waste time on the wrong priorities.


The committee’s silence wasn’t neutrality – it was neglect. And the longer they coasted, the harder it became to course correct.


Even with a powerful solution like Microsoft Dynamics 365 CRM, leadership must stay engaged to ensure adoption and success. Otherwise, even the best CRM system becomes an expensive, underutilized tool.


So how do you fix a steering committee that’s asleep at the wheel?


 

A False Sense of Progress: When a CRM System Runs on Optimism 


Monica knew the project was already two months behind schedule – but saying that out loud wouldn’t do anyone any favors. Everyone attends the steering committee meetings and understands reality … at least, that’s what she told herself.


So instead of waving (more) red flags, she framed the delays as minor hiccups, minimizing their severity, and instead pointing to burn-down charts and timelines that looked promising – on paper. She assured the steering committee that everything was still “on track” and, for good measure, suggested adding a CRM resource to “make up time.”


Someone paying attention would have caught the obvious contradiction… “If the project is on-track, why do we need more resources”. Monica, wanting to avoid confrontation, failed to mention the extra cost, the scope creep, and the fact that piling more people onto a delayed project rarely speeds things up.


Michael muttered an occasional “uh-huh” while dodging traffic. Valerie, drowning in emails, barely glanced at the report. No one pushed back. No one questioned a thing.


The meeting wrapped up with nods and muted agreement—no debate, no discussion, and no grasp of how much trouble the project was in.


They had one job: ask a single tough question. Instead, they went with willful oblivion.


What they didn’t realize? That "green" status was actually “bright red” and would come with a hefty price tag– so high that Monica was afraid to bring attention too.


 

The Hidden Risks No One Saw Coming 


On paper, everything still looked fine. The steering committee walked away confident that minor delays were under control, but beneath the surface, those “minor” issues were quietly snowballing.

  • Budget risks – Monica’s proposed “catch-up resource” was approved without discussion, but no one accounted for where that extra $125,000 annual budget would come from.

  • Scope creep – With no pushback, small adjustments were made to accommodate delays, quietly expanding the project’s scope (and timeline).

  • Lack of accountability – With the steering committee disengaged, Monica was left making unchecked decisions, turning temporary workarounds into permanent problems.


By the time leadership saw the full picture, fixing the damage would take more than a few “catch-up” resources.


A steering committee that doesn’t challenge assumptions, ask the hard questions, or demand full transparency isn’t just ineffective – it’s actively making things worse.



Warning Signs Everyone Missed

 

The signs were there from the beginning—small signals that something was off—but no one was paying close enough attention.

  • Leadership on autopilot. The busy steering committee members assumed everything was on track instead of actively verifying progress.

  • Red flags dismissed as “normal.” Early project hiccups were framed as minor bumps rather than warning signs of deeper issues.

  • No accountability for decisions. With no clear expectations for the steering committee’s role, leadership defaulted to passive observers rather than active problem-solvers.


By the time the true scope of the issues became clear, fixing them would require extra costs, additional delays, and frustration across teams.


Risks don’t just disappear – they pile up, hidden beneath a surface of forced optimism, until they’re impossible to ignore.


 

Hard Lessons from a CRM Implementation Gone Wrong 


A CRM system is only as effective as the leadership guiding it.


This implementation didn’t fail because of bad technology – it failed because the people responsible for making it successful checked out.


Here’s what this experience made painfully clear:

  • Transparency is non-negotiable. A "green" project status is meaningless if risks are swept under the rug. Clearly define what “green” means.

  • Steering committees must steer. Showing up to meetings isn’t enough – leaders must engage, ask tough questions, and challenge assumptions.

  • Early intervention prevents bigger problems. Ignored risks don’t go away – they snowball into major roadblocks.

  • Sugarcoating reality backfires. Hiding delays may smooth over meetings, but it sets up leadership for bigger conflicts later.


A project derails when leadership operates on surface-level updates instead of reality.


And the worst part? It’s totally avoidable.


 

How to Avoid These Mistakes  


These mistakes weren’t inevitable – they were the result of unchecked assumptions, absent leadership, and a collective agreement to avoid asking uncomfortable questions.


The good news is that they’re entirely preventable.

Steering committees must do more than receive updates – they need to guide decision-making, address risks early, and ensure accountability.


Here’s how to ensure your CRM project doesn’t become the next horror story:

  • Define and enforce clear governance. A steering committee must have real responsibilities and decision-making authority. (Sitting in a meeting while answering emails doesn’t count.)

    • Set clear expectations

    • Identify roadblocks

    • Make timely decisions

  • Hold leadership accountable for engagement. If your executives are more invested in their coffee orders than the CRM initiative, that’s a problem.

    • Commit to proactive leadership

    • Don’t wait until problems escalate – course-correct early

    • Remember that disengaging today leads to expensive damage control tomorrow

  • Insist on full transparency. If the status is always “green,” but no one can explain why, you don’t have a CRM project – you have a house of cards.

    • Ask direct questions

    • Challenge assumptions

    • Dig deeper if things seem “too on track”

  • Foster a culture where concerns are addressed – not avoided. If project managers feel like raising red flags is a career-ending move, they’ll just smile, nod, and hope for the best.

    • Encourage an open dialogue – a healthy discussion today prevents costly surprises later.

 

CRM implementations don’t typically fail because of software – they fail because leadership avoids hard conversations until it’s too late.

 

In the end, it wasn’t the CRM system that failed – it was leadership’s commitment to looking the other way.


This story is a cautionary tale of what happens when a steering committee forgets to steer, project updates get sugarcoated, and risks are quietly left to fester beneath the surface.


Leadership walked away from that first meeting feeling confident – but it was the kind of confidence that comes from not asking too many questions.


A steering committee exists to make tough calls, challenge assumptions, and keep the initiative from crashing and burning.


The bottom line: Prioritize transparency, accountability, and engagement from day one. Because when leadership runs on filtered updates instead of reality, small problems don’t just linger – they turn into expensive, full-scale project failures.


Of course, having the right technology makes a difference, and Microsoft Dynamics 365 CRM (aka Microsoft Dynamics 365 Sales) is a powerful choice for businesses looking to modernize their sales processes, improve customer insights, and enhance team collaboration.


Its seamless integration with Microsoft 365 and AI-driven automation helps companies operate more efficiently – but just remember, even the best technology requires leadership engagement to ensure success.


If you want expert guidance to ensure long-term CRM success, the Optrua team are Dynamics 365 CRM experts, offering tailored strategies, implementation expertise, and ongoing support through our Optrua Care Plans – so you’re covered long after go-live.


Let’s build your CRM the right way. Contact Optrua today.

 

 

 

About the Author

Photo of Ryan Redmond, the founder of Optrua, specializing in CRM

Ryan Redmond is the founder of Optrua, specializing in CRM and business process optimization. Ryan channeled his passion for efficiency from lessons learned in the Navy to his work today.

 

He helps businesses streamline technology to improve employee and customer experiences and empower teams to work smarter, not harder, without unnecessary overhead.

 

Connect with Ryan on LinkedIn.

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