Project Risk Articles and Blog Posts https://transforming.com/tag/project-risk/ People. Process. Progress. Mon, 06 Apr 2026 16:12:00 +0000 en-US hourly 1 https://transforming.com/wp-content/uploads/2018/11/cropped-TSI-ICON-F-01-32x32.jpg Project Risk Articles and Blog Posts https://transforming.com/tag/project-risk/ 32 32 Is Your Project Keeping You Awake at Night? https://transforming.com/2026/04/06/is-your-project-keeping-you-awake-at-night/ Mon, 06 Apr 2026 16:11:58 +0000 https://transforming.com/?p=16969 9 Tips for Curing Project Induced Insomnia If you are like most business and technology leaders, you have probably lost a few hours of sleep over one or more critical projects during your career. Even when projects seem to be on track, your internal radar might be warning you that all might not be OK

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9 Tips for Curing Project Induced Insomnia

If you are like most business and technology leaders, you have probably lost a few hours of sleep over one or more critical projects during your career. Even when projects seem to be on track, your internal radar might be warning you that all might not be OK on the risk management front.

In my experience leading a $300 million IT portfolio for a Fortune 100 company, two things stood out during our transformation:

  1. Virtually all projects had “green” status reports, while feedback suggested the contrary.

  2. Daily fire drills indicated actual risk levels were much higher than those being reported.

Sound familiar? If so, where is a good place to start tackling the root causes of project risk? TSI has developed a Project Health-Check methodology to help you regain control.

Here are 9 key focal points for evaluating project risk in your organization today:

  1. Sponsorship Required Obtain the highest level of sponsorship possible (CXO Level). You are about to make some people uncomfortable; you’re going to need the support.
  2. Divide and Conquer Categorize your portfolio (e.g., tactical vs. strategic) and assign ownership to capable portfolio managers (PMs) responsible for mitigating risks.
  3. Prioritize Identify the top 20% of projects that are mission-critical. Prioritize these for quick “Fly-by” Health-checks and follow-up Deep Dives.
  4. Set Health-check Guidelines Assess potential risks across these four key dimensions:
    • Technology Risk: Scalability, user requirements, vendor support, and modern data/system security.
    • Business Risk (Includes people and process): Impact on operations, customer experience, and end-user buy-in.
    • Financial Risk: Failure to achieve the targeted ROI or budget overruns.
    • Legal Risk: Potential disputes or litigation with employees, vendors, or competitors.
  5. Integrate Embed the Health-check process into your Program Management Office (PMO) and align it with your phase gates.
  6. Develop Reporting Use easy-to-understand templates. Utilize stoplights and directional arrows to indicate risk on a summary page, supported by detailed action plans in the appendix.
  7. Pilot Phase Pilot this approach on a handful of projects to demonstrate immediate value and “proof of concept.”
  8. Govern the Initiative – Convene an empowered decision-making body to address urgent developments and manage escalations.
  9. Talent Utilize experienced IT and business risk assessment personnel to assure fast and effective results.

A proactive Health-check process makes a massive difference in project outcomes—and in your ability to get a more restful night’s sleep. At TSI, we continue to provide this assistance to a wide range of clients across many different types of projects.

Check out our Project Health Assessment and contact us today to learn more.

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Is Your Project Keeping You Awake at Night? https://transforming.com/2024/06/10/is-project-risk-keeping-you-awake-at-night/ Mon, 10 Jun 2024 22:12:13 +0000 https://transforming.com/?p=5669 9 Tips for Curing Project Induced Insomnia If you are like most business and technology leaders, you have probably lost a few hours of sleep over one or more critical projects during your career. Even when projects seem to be on track, your internal radar might be warning you that all might not be OK

The post Is Your Project Keeping You Awake at Night? appeared first on Transforming Solutions Inc..

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9 Tips for Curing Project Induced Insomnia

If you are like most business and technology leaders, you have probably lost a few hours of sleep over one or more critical projects during your career. Even when projects seem to be on track, your internal radar might be warning you that all might not be OK on the risk management front.

Earlier in my career, I assumed a sleep impacting IT leadership role at a Fortune 100 company where I was responsible for a major division with a $300 million IT spend, 20,000 users, 90 systems and hundreds of projects. The company was in the midst of a disruptive business transformation effort, and internal stakeholders were making major noise about on-going risks in the area of IT project delivery.

Looking over the vast and deep portfolio of projects, two things immediately stood out:

  • Virtually all projects had green status reports (indicating projects were on track to meet delivery expectations) while feedback would suggest the contrary.
  • Input from business stakeholders and daily fire drills indicated that actual project risk levels were much higher than those reported by underlying project managers.

Sound familiar?  If so, where is a good place to start tackling the root causes of your project risk induced insomnia?  TSI has developed methodology surrounding the Project Health-check process which will help you manage your project risk.

Here are 9 key focal points when addressing the need to evaluate on-going project risk management in your organization:

  1. Sponsorship Required Obtain the highest level of sponsorship possible in the organization (CXO Level). You are about to make some people uncomfortable, and you’re going to need the support.
  2. Divide and Conquer Divide your project portfolio into manageable categories (e.g., tactical vs. strategic, lines of business and/or products) and assign ownership of manageable categories to capable portfolio managers (PM’s). The PM’s will be responsible for tracking status and working with cross-functional teams to address and mitigate risks.
  3. Prioritize Collaborate with the business to identify the top 20% of projects that are mission critical and can’t afford to be off track. Prioritize these key projects for initial quick Health-check Assessments and follow-up Deep Dives if significant risks are identified.
  4. Set Health-check Guidelines Develop Health-check assessment templates and guidelines for two scenarios; 1. High-level or “Fly-by” Assessments and, 2. Deep Dive Assessments to address potential risks across the following example key dimensions:
    • Technology Risk
      • System won’t scale or perform.
      • System won’t meet user requirements.
      • Vendor will no longer support solution.
      • Information, data, and system security.
    • Business Risk (Includes people and process)
      • Major adverse impact on operations or customer experience.
      • Lack of involvement and buy-in from key end users and business customers.
      • Loss of productivity or efficiency and/or negative impact on morale.
      • Damage to reputation with public or credibility on Wall Street.
      • Missed opportunities to take competitive advantage in the marketplace.
    • Financial Risk
      • Failure to achieve targeted ROI or expected benefits.
      • Budget overruns and/or negative impact on on-going operating expenses.
    • Legal Risk
      • Potential disputes/litigation with employees, vendors, customers or competitors.
  5. IntegrateIntegrate the Health-check process into a Program Office and align required Health-check activities with key PMO phase gates.
  6. Develop Reporting– Develop easy to understand reporting templates
    1. Use stop lights and directional arrows to indicate risk on a summary page.
    2. Provide more detail in appendix.
    3. Include defined action plans and deadlines to remedy identified risks.
  7. Pilot PhasePilot the approach on a handful of projects to demonstrate value.
  8. Govern the Initiative- Convene an empowered decision-making body to be available on short notice to address sudden or urgent developments (include a defined escalation process for serious risks).
  9. TalentUtilize experienced IT and business risk assessment personnel to assure fast and effective results.

I am happy to report that the process made a huge positive difference in my former workplace as well as on my ability to get a more restful night’s sleep. At TSI, we continue to provide similar assistance to a wide range of clients across many different types of projects. Check out this Project Health Assessment Link and contact us today to learn more.

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