Why a Weak Technology Strategy Could Be Your Biggest Business Risk. 

Introduction

Everything about the situation and the CEO in front of him told Terry, a Technology Solutions professional, that he wasn’t getting the whole story. The business owner and CEO sharing breakfast with Terry was clearly stressed. This was their fourth breakfast meeting. Terry had answered countless questions. Terry tried to ask follow-up questions to better understand the context of the questions. The CEO gave little to no clarity. Terry knew that the root concerns were still hidden. He was unsure of the CEO’s objectives or what really motivated their early morning meals every other week. Finally, during their 4th breakfast, Terry leaned in and asked the CEO, “What is really going on here? Why do we keep meeting? What are you trying to accomplish?”

The CEO paused, became emotional, and then replied, “Terry, I’m going to lose my business.”

Effective leadership sometimes requires vulnerability and it always requires strategic insight. It often requires the ability to pivot when challenges arise. This real-life case study examines how a CEO facing existential threats to his business found clarity, direction, and success by engaging with the right technology professional to address systemic failures and to create and deliver a Technology Strategy. The partnership grew, and Terry became the CEO’s Fractional CTO. Their partnership ignited the transformation needed to save the company and uncover new growth opportunities.

The Situation

A business owner and CEO struggling with declining performance and competitive pressures began by reaching out to a trusted and proven technology professional for advice over some informal breakfast meetings. Initially, the CEO asked broad, exploratory questions about technology and business alignment. The technologist responded thoughtfully but lacked a clear understanding of the CEO’s deeper concerns. 

By the fourth meeting, the technologist sensed underlying issues and asked a pivotal question: “What is really going on here? What are you trying to accomplish?” In a moment of vulnerability, the CEO revealed the gravity of the situation:  “My technology is inadequate, boxing us in, outdated, and completely ineffective. My operational systems are dysfunctional, and they are crippling us. My adversaries are conspiring against me, and direct attacks are imminent.”

The Turning Point

With the CEO’s admission, Terry had a clear problem to address. Within days, Terry distilled the issues and reached a clarity of thought. He quickly developed a complete technology strategy with a multi-phase plan for implementation. He helped the CEO prepare to present the plan and alleviate the pressure. 

The plan created a unifying vision. It built positive energy and momentum. Enemies became collaborators. Anxiety was dispelled. The plan’s implementation revitalized the business and led to an extended season of growth and prosperity.

The Solution

The technologist implemented a structured process to address the CEO’s concerns systematically:

1. Clarity of Thought  

• Conducted a detailed analysis of existing technology systems and business operations  
• Identified critical pain points and inefficiencies
• Established clear goals to align technology with business objectives

2. Technology Strategy  

• Created a roadmap that prioritized the technology path forward
• Recommended tools and platforms to improve scalability, efficiency, and security  
• Ensured the strategy aligned with long-term business goals

3. Implementation Plan  

• Developed a phased approach to minimize disruption during the transition
• Assigned clear responsibilities and timelines for internal teams and external vendors

4. Communication Strategy  

• Created a unified vision to share with stakeholders, ensuring buy-in across the organization  
• Simplified technical jargon into relatable business benefits to foster understanding and collaboration

The Results

The implementation of this technology strategy brought transformative results:  

• Unified Vision: The entire organization rallied around shared technological and operational excellence goals
• Positive Energy and Momentum: Teams became energized by clear direction and visible progress
• Collaborative Relationships: Internal and external adversaries became collaborators through improved communication and alignment  
• Anxiety Alleviated: The CEO and employees felt reassured by the actionable plan and steady execution  
• Business Turnaround: Operational efficiency improved, competitive threats diminished, and the company returned to growth and sustained profitability

Key Takeaways

1. Open, Vulnerable, and Transparent Dialogue is Crucial:

• The CEO’s willingness to be open, vulnerable, and fully transparent allowed the technologist to accurately understand the true scope of the problems and opportunities  

2. Technology is a Strategic Asset: 

• Thoughtful integration of technology can transform businesses and overcome significant challenges  

3. Technology Leadership Requires Vision and the ability to DELIVER results

• A clear and well-communicated strategy aligns teams and creates momentum toward success  

4. Expertise Matters:

• A skilled technologist who understands both business and technology will bridge the gap between operational challenges and strategic solutions.

Conclusion

This case study demonstrates the power of strategic thinking, delivery, collaboration, and clarity. The CEO and technology leader partnership transformed the organization from a struggling enterprise into a thriving business by engaging the right expertise and fostering open communication. Terry’s systematic approach saved the company and positioned it for sustained growth in a competitive landscape.

The Message to business leaders: LEAD OUT with the right technology leader partnership!

You are smart–brilliant, in fact. Your education, business acumen, and industry-specific savvy qualify you for your leadership role. You trust your team, and you don’t want to micro-manage them. 

For most executives, this is especially true with their technology teams. Their tech people are smart in ways the other business executives are not. Oh, many leaders are pretty good with technology; they grew up in a tech world. The use of technology is their native air. Still, tech innovations are invading business at a rate and with a level of complexity that most business leaders simply can’t keep up. The speed and complexity of technology innovation are frequently beyond the comfort zone of most business leaders. Increasingly, executives leave the tech decisions to someone else, and they just pay the bill with little ability to control or lead. 

The research demonstrates that this is true. Fully 85% of mid-sized companies (businesses with revenue over $50 million but less than $1 billion) do NOT have a technology strategy (Association for Information Managers).

Business executives operating without a technology strategy in which they are intimately involved–creation, implementation, and maintenance–should be petrified. And by petrified, I don’t mean paralyzed or frozen. I mean, they should be scared to death. The very survival of the business you lead is dependent on the technology that permeates every aspect of your company. 

Executives without an intentional technology plan are working a high-wire act without a net. At the very least, they are complicit in creating inefficiency, waste, and incompetence. At most, they are putting organizational survivability at risk. 

This ebook is the executive’s guide to technology leadership redemption.

Are you thinking about your technology strategy? You should be!

If you saw her on the street or in a shopping mall, you might not recognize this petite bundle of optimism as the tough-minded CEO of a technology services company. Sitting in her downtown Salt Lake City office with the snow-capped Rocky Mountains behind her, Crystal Peterson, CEO of STG, speaks boldly and confidently about the technology-related risks facing business leaders today.

Despite the rapid-fire listing of iconic failures related to poor technology strategies, like the data breaches experienced by Equifax and Target or the failure to innovate and inability to scale by Blackberry, Blockbuster, and Kodak, Crystal is a purveyor of optimism and hope. She quickly points to the way Crumbl Cookies and Domino’s Pizza are using technology to create a competitive advantage and drive revenue and profits. 

When asked what she wants executives to know about business technology and the associated risks, she is unequivocal,

“Every business executive should recognize that they don’t have to feel lost or afraid.”

“Proper investments in technology provide big returns.”

“It’s not their technology that fails them; it is their strategy that fails them.”

Crystal acknowledges that there are risks, and they are real. She points out that it is not uncommon for business leaders to feel burned by some technology-related experience. Maybe they fell victim to unscrupulous offers to develop their business app for $50,000! The promise of big results with low investment is often followed by poor design, unclear expectations, and inability to implement. Failed or frustrating software development experiences are as common as skin blemishes in a teenager. 

With her army of Software Solutions Architects, Engineers, and IT Professionals, Crystal roots out inefficiency and waste in technology spending. STG frequently starts an engagement by cutting between 30% and 40% on software licenses. Her team often asks, “Are you really still paying retail for your software licenses?”

The war on waste in technology goes beyond bait and switch technology offers. It includes failed or inefficient IT Projects, never-negotiated contracts, underused or unnecessary Cloud and SaaS spending, non-performing cybersecurity contracts, and misconfigured systems. 

Often overlooked are the issues of Technical Debt, the maintenance of legacy systems, and employee productivity losses due to inefficient technology. These examples point to the real issues and risks that face business executives as they wrestle with their organizational technology strategy. Data breaches and cybersecurity are very real concerns. Inefficiency and waste are common. Unscrupulous bait-and-switch providers can leave businesses with inoperable systems and software programs. Technical debt erodes profits and retards growth, and misconfigured systems slow down productivity.

Founder of O’Reilly Media, Tim O’Reilly declared, “Technology is neither good nor bad; it’s what we do with it that makes the difference.” Business executives need not fear if they will be intentional. Each executive should remember that proper investments in technology can provide big returns. And as Crystal pointed out, “It’s not their technology that fails them; it is their strategy that fails them.”

What is the path to technological confidence and competence?

“Companies that embrace digital transformation are 26% more profitable than their competitors.”

– MIT Sloan Management Review

So, how does an effective executive enter the business technology battle? A Business Technology Assessment is the cornerstone of a successful technology strategy. Each of these words is significant. This is a Business initiative. It is to be initiated and led at the C-Suite with significant participation from the CEO. 

Anything less is an abdication of the responsibility of the CEO for the overarching organizational strategy, which is their fundamental duty. Simply turning over the technology strategy to lower-level employees or the IT department is tantamount to CEO malpractice. 

While the responsibility to lead the technology strategy may seem overwhelming, remember it is not just a technology strategy; it is a fundamental business strategy. Operational excellence and ultimate performance depend upon the quality of the plan and its execution. 

Although the CEO and the C-suite must initiate and lead, they aren’t without resources to help. In the same way that advisors and consultants may be employed in any strategic planning effort, executives are well served to find and engage trustworthy technology talent with executive leadership skills. It is, after all, a Technology assessment. Establishing and following rigorous criteria for selecting a strategic technology partner is in the best interest of the organization.

The final word is Assessment. The kind of research and evaluation required must be thorough. It must reach every corner of the business touched by technology.

An essential component of the Business Technology Assessment should be a Risk and Readiness Review. When multiple dimensions of technology, its use, and impact are evaluated and scored for risk and readiness, it puts decision-making and action into the hands of those charged and trusted with these responsibilities–the CEO and other key executives.

A Chief Technology and Strategy Officer offers help to the C-Suite.

Grounded, pragmatic, and passionate best describe Mel Tingey, who is the Chief Technology and Strategy Officer at STG. Mel is a brilliant technology mind with loads of executive experience. Mel and STG have assembled an astonishing body of top technology executives. This group of professionals makes up as fine an assemblage of technology executives as can be found. These technology executives are part of the STG Chief Technology Officer Council. This body provides STG and its clients with an astonishing competitive advantage. 

For STG, the Business Technology Assessment is conducted by a small group of Chief Technology Officers drawn from this council. Because they are technologically experienced and sound, they have the ability to identify and understand both business and technology issues and pertinent remedies. Because of their executive experience, each council member possesses the leadership experience and skills to interface with C-suite executives and business leaders effectively. 

Each member of the CTO Council is independent of partnership entanglements with any technology provider. They are, therefore, free to recommend the solutions that are best for the client instead of best for themselves and their partners.

Furthermore, once the Business Technology Assessment is completed, their work is peer-reviewed by other members of the CTO Council. Peer review ensures that evaluations are appropriately conducted and scored, and more importantly, it adds balance and perspective to every assessment and the resulting recommendations.

One part of the Business Technology Assessment is the Technology Contracts Review.

The Technology Contract Review identifies waste and inefficiency. This single function often produces a remarkable return on investment right out of the gate. Mel explains that the savings generated from this activity often equates to 30% to 40% of the overall spend on software, IT infrastructure, services, and cybersecurity contracts. Here are some of the issues explored in the Technology Contract Review.

Here is one example of the power of the Technology Contracts Review

Case Study: “Are You Really Still Paying Retail for Your Software Licenses?”

Introduction

In the ever-evolving world of technology, many companies fall into the trap of reactionary purchasing. Someone in the organization declares, “We need a new sales commission tool,” or, “Let’s get AWS to run this new program,” or, “We must have an ERP, HRS, or CRM system.” Without a cohesive technology strategy, these companies hastily turn to the internet, make purchases, and hope for the best.

But hope is not a strategy.

Instead of fostering efficiency and innovation, these disjointed decisions often lead to a tangled web of competing and conflicting technology systems. The result? Slower workflows, frustrated employees, and wasted resources—all of which could have been avoided with a strategic approach to technology procurement.

The Problem

A mid-sized manufacturing company, Allied Manufacturing Solutions, found itself in this exact predicament. Over the years, the organization had accumulated a hodgepodge of technology systems:

• An outdated accounting program incompatible with their e-commerce platform.  
• A CRM that didn’t sync with their ERP.  
• A cloud hosting environment (AWS) that was both underutilized and overpriced.  

These fragmented systems were causing more harm than good. Key issues included:  

1. Duplication of Efforts: Teams frequently entered the same data into multiple systems, increasing errors and wasting time.  

2. Inefficiencies: Employees spent hours troubleshooting integrations between software never designed to work together.  

3. High Costs: The company was paying retail prices for licenses, missing out on potential discounts through strategic vendor relationships.  

4. Slowed Productivity: Internal bottlenecks and system conflicts made the company’s workflow slower than navigating a federal regulatory process.

The Turning Point

The CEO of Allied Manufacturing Solutions reached out to a technology consultant after a critical system integration failure. During the initial conversation, the consultant asked a simple yet eye-opening question: “Are you really still paying retail for your software licenses?”

This question sparked a deeper examination of the company’s technology strategy—or lack thereof. The consultant identified the root of their problems: a reactive approach to technology procurement that ignored the bigger picture.

The Solution

The consultant proposed a comprehensive plan to address Allied Tech’s technology challenges strategically:  

1. Conduct a Business Technology Assessment  

• Evaluated all existing systems, identifying redundancies, inefficiencies, and compatibility issues.  
• Evaluated all existing systems, identifying redundancies, inefficiencies, and compatibility issues.  

2. Develop a Unified Technology Strategy  

• Defined business objectives to ensure future technology purchases aligned with company goals.  
• Prioritized systems that could integrate seamlessly with each other.  

3. Negotiate Smarter Purchases  

• Leveraged vendor relationships to secure volume discounts and avoid retail pricing.  
• Transitioned to flexible licensing models to better align costs with actual usage.  

4. Streamline and Integrate Systems  

• Consolidated redundant software into a single, integrated platform wherever possible.  
• Implemented middleware solutions to connect critical systems that couldn’t be replaced immediately.  

5. Create Governance Policies  

• Established a cross-functional technology committee to evaluate and approve future software purchases.  
• Instituted guidelines for assessing ROI, compatibility, and long-term value before committing to new systems.

The Results

Within six months of implementing this strategy, Allied Tech Solutions experienced dramatic improvements:  

• Cost Savings: Reduced spend across software, IT infrastructure, services, and cybersecurity expenses by 30% through better contract agreements and the elimination of unused tools.  
• Increased Efficiency: Integration of key systems eliminated duplicate data entry and reduced employee frustration.  
• Streamlined Operations: Unified platforms improved collaboration and sped up workflows, enabling faster decision-making.  
• Scalability: A strategic technology roadmap prepared the company for future growth, ensuring that new systems would complement existing infrastructure.

Key Takeaways

1. Reactive Buying is Expensive: Hasty technology purchases lead to inefficiencies, high costs, and slower operations.  

2. Strategy is Essential: A comprehensive technology plan ensures that software investments align with business objectives.  

3. Vendor Relationships Matter: Avoiding retail prices and negotiating smarter purchases can save significant resources.  

4. Integration is Key: Systems must work together seamlessly to avoid bottlenecks and inefficiencies.  

5. Governance Prevents Chaos: A structured approval process for software acquisitions prevents future fragmentation.

Conclusion

The next time someone in your organization says, “We need XYZ system,” ask yourself: Are we being strategic, or are we just reacting? A thoughtful approach to technology procurement can save money, streamline operations, and set your company up for long-term success. And perhaps most importantly, it will ensure you never have to pay retail for your software licenses again. 

This case study is a composite of real-life experiences. In this fact pattern, Mel was immediately able to reduce the costs for Cloud computing from $15,000 per month to $9,000 per month, an immediate cost savings of $72,000 per year. He also negotiated more favorable terms on 4 other IT contracts. In the case of a manufacturing firm with a technology and licensing cost of $2.1 million per year, Mel will save them $350,000 in the first year and $750,000 in year two and every year thereafter. 

This simple case study demonstrates both the efficacy and substantial return on investment that a Business Technology Assessment can provide–starting with the Technology Contract Review.

Your Business Technology Assessment is an essential part of every business strategy

Another important element of the Business Technology Assessment is a Risk and Readiness Review. The Risk and Readiness Review evaluates the business landscape based on a Framework of nine crucial dimensions of technology. One dimension of the Framework is Leadership and People. Two case studies illustrate the value of the Risk and Readiness Review from the People and Leadership perspective.

Case Study: Unlocking Hidden Potential with a Technology Risk and Readiness Review

Introduction

In the fast-paced world of technology and operations, misaligned roles and underutilized staff can go unnoticed, resulting in inefficiencies and missed opportunities. A Technology Risk and Readiness Review can uncover these gaps, turning what seems like a liability into a significant asset. This case study highlights how a strategic review not only saved a job but transformed a staff member into a key contributor, delivering over $1,000,000 in value to the organization annually.

The Situation

A mid-sized company engaged a consultant to conduct a Technology Risk and Readiness Review. The objective was to evaluate the organization’s technology infrastructure, operational efficiency, and alignment of staff responsibilities with business goals.

During the review, the consultant discovered that a Systems Operations (SysOps) staff member’s assigned duties only accounted for about 10% of their workweek. This revelation surprised leadership, as the company had assumed this role was critical and fully utilized.

Initial Reaction

Upon learning of the underutilization, the CEO’s immediate reaction was to terminate the employee, citing inefficiency and cost concerns. With an $80,000 annual salary, the CEO viewed the staff member as a drain on resources.

However, the consultant recognized an opportunity. Instead of recommending termination, the consultant suggested re-evaluating and re-defining the staff member’s responsibilities to better align with the organization’s strategic goals.

The Solution

The consultant facilitated a structured process to reconfigure the role:  

1. Role Assessment and Skill Evaluation

• Conducted a detailed assessment of the SysOps staff member’s skills, experience, and interests.  
• Identified additional areas where the employee could contribute value, particularly in emerging operational needs and overlooked gaps.

2. Redefining Responsibilities

• Collaborated with the employee and management to design a more comprehensive role.  
• Assigned new responsibilities, including managing key technology initiatives and streamlining operational workflows.  

3. Memorializing Responsibilities in a Key Document

• Created a clear, documented job description that outlined expectations, deliverables, and performance metrics.  
• Ensured alignment between the employee’s redefined role and the company’s broader strategic objectives.

4. Ongoing Support and Monitoring

• Provided initial guidance and resources to help the staff member transition into their expanded role.  
• Established regular performance reviews to track progress and adjust responsibilities as needed.

The Results

The reconfiguration of the SysOps role delivered transformative results:  

• Employee Performance: The staff member thrived in the new role, leveraging their skills to take on critical initiatives and contribute significantly to the organization.  
• Organizational Value: The employee’s contributions now generate more than $1,000,000 in measurable annual value, a remarkable return on their $80,000 salary.  
• Employee Retention: Instead of losing a capable team member, the organization retained and cultivated talent, saving costs associated with recruiting and onboarding a new hire.  
• Cultural Impact: The success of this initiative fostered a culture of maximizing internal talent and aligning roles with strategic priorities.

Key Takeaways

1. Assess Before Acting: Snap decisions, such as terminating underutilized employees, can overlook potential. A structured evaluation can reveal hidden value.  

2. Role Reconfiguration Works: Redefining and aligning responsibilities with organizational needs can transform low-value roles into high-impact positions.  

3. Document for Success: Memorializing roles and expectations in a Key Document ensures clarity, accountability, and alignment.  

4. Win-Win Scenarios Build Success: By addressing inefficiencies strategically, both the business and the employee benefit, creating a stronger, more resilient organization.  

Conclusion

This case demonstrates the value of a Technology Risk and Readiness Review as a tool to identify inefficiencies and uncover hidden potential. By rethinking roles and responsibilities rather than reacting impulsively, the organization saved a job, enhanced operational effectiveness, and achieved a significant return on investment.  

A well-executed review doesn’t just mitigate risk; it prepares businesses for growth, ensuring that talent and technology align with strategic goals.

One more look at the ROI generated by the Business Risk and Readiness Review

Case Study: Unlocking Leadership Potential with a Technology Risk and Readiness Review

Introduction

The importance of leadership in driving technology strategy cannot be overstated. However, identifying the right candidate for a key technology role often requires looking beyond traditional hiring pools. This case study highlights how a Technology Risk and Readiness Review not only helped a company prepare for a new Vice President of Technology but also uncovered an unexpected internal candidate who became a transformative leader.

The Situation

A mid-sized company was at a crossroads, preparing to hire a Vice President of Technology to lead its growing technology needs. The CEO engaged a technology consulting firm to conduct a Risk and Readiness Review to ensure the best candidate fit. The review aimed to assess the organization’s current technology landscape, identify gaps, and define the qualities needed in the new VP role.

At the conclusion of the review, the consultants presented an unexpected recommendation: move the company’s $32,000-per-year office manager into the tech role.

The CEO’s Reaction

The CEO was initially taken aback. The office manager wasn’t someone they had ever considered for such a senior role. However, the consultants presented compelling reasons why she was the ideal candidate:  

1. Trust and Credibility: She had built strong relationships with both internal staff and external customers, earning their trust and respect.  

2. Functional Knowledge: She had taken the initiative to learn and master the organization’s technologies and systems, demonstrating a deep understanding of the company’s needs.  

3. Leadership Potential: Her ability to navigate challenges, communicate effectively, and inspire confidence indicated she was ready for a leadership track.  

The Recommended Approach

Rather than immediately promoting the office manager to Vice President, the consultants proposed a step-wise plan:  

1. Intermediate Role as Director of IT

   – Recommended promoting her to Director of IT as a transitional role.  

   – Allowed her to gain executive-level experience and grow into the VP position.  

2. Training and Development

• Consultants provided targeted training to strengthen her technical expertise, strategic thinking, and leadership skills.  
• Focused on preparing her to succeed in an executive role.

3. Fair Compensation

• Advised the CEO to align her salary with her new responsibilities to reflect her value and prevent her from being poached by competitors.  

4. Ongoing Support

• Continued mentorship and evaluation by the consulting firm to ensure her success and identify areas for further growth.

The Results

Within a year, the office manager-turned-director of IT had fully transitioned into the role of Vice President of Technology. The results exceeded expectations:  

• High-Performing Leadership: She became a key driver of the company’s technology strategy, improving systems and fostering innovation.  
• Cultural Alignment: Her existing relationships and trust with staff ensured a smooth transition, uniting the team under her leadership.  
• Cost-Effective Succession: The company avoided the high costs of recruiting an external candidate while gaining a leader with intimate knowledge of the organization.  
• Enhanced Retention: By recognizing and rewarding her potential, the company solidified her loyalty and long-term commitment.

Key Takeaways

1. Internal Talent Can Be Hidden Gold: A thorough review can uncover high-potential employees who might be overlooked for leadership roles.  

2. Trust and Credibility Matter: Leadership isn’t just about technical skills—it’s about relationships, communication, and earning respect.  

3. A Step-Wise Approach Mitigates Risk: Transitioning an internal candidate through intermediate roles ensures they are well-prepared for executive responsibilities.  

4. Fair Compensation is Critical: Aligning pay with responsibility not only reflects the employee’s value but also protects against external offers.  

5. Training and Mentorship Yield Results: Investing in leadership development maximizes the potential of internal candidates.  

Conclusion

This case demonstrates the transformative power of a Technology Risk and Readiness Review. The organization gained a high-performing Vice President of Technology by uncovering the hidden potential of a trusted office manager and strategically preparing her for an executive role. This success story is a testament to the value of looking within, developing talent, and aligning strategy with individual potential.

A final look at the Business Technology Assessment

A Business Technology Assessment is a great way to initiate a digital transformation. Essential elements of the assessment include a Technology Contracts Review and a Technology Risk and Readiness Review. 

Important considerations when launching a Business Technology Assessment include the critical role of C-suite executives and business leaders and securing the assistance of competent and independent technology professionals. When a technology Framework guides external technology professionals and internal leaders and staff, the work can go forward competently and confidently. When the conclusions are peer-reviewed by other experienced CTOs, the organization stacks the odds of success in its favor. 

Throughout this document, there are links to additional educational assets and free resources to help you along your path to technology safety and strategic excellence. Links to those resources are duplicated here.

• Blog outlining, discussing, and diagnosing some of the iconic technology failures
• Blog discussing some principles to help avoid failure on a software development project
• Blog outlining criteria for selecting a technology partner for your strategic planning and execution process
• Self-diagnostic survey regarding your strategic technology readiness
• Presentation of the 9 elements in the Strategic Framework used by STG

When you are ready, schedule a meeting to discuss your questions, your goals, and your priorities.