I Saved My Career by Killing Half My Projects (Here's How AI Showed Me Which Ones)
AI-driven portfolio management showed me which projects were bleeding resources and which deserved attention—turning me from overwhelmed to a strategic project master.
I grew up in the grunge era, and nothing captured that wild energy quite like the Jim Rose Circus—a traveling freak show of fire-eaters, sword-swallowers, and barely contained mayhem. Honestly, it feels a lot like how most project managers juggle portfolios today. Every day’s a new act, every meeting a surprise performance, and you’re somehow expected to keep the whole thing moving without it collapsing under its own weight.
But hold on, AI gives you the chance to go from barely holding it together to running the show like a true pro. It doesn’t just help you track tasks—it gives you visibility, foresight, and control over the full spectrum of the actual project.
Going back to the circus analogy—Let’s say you’re the ringmaster managing seven projects simultaneously, each pulling you in different directions like wild, prancing ponies. Your execs want status updates on when the show is going to start every five minutes. Your teams need resources (send in the clowns!) that you can’t give them. Your stakeholders change priorities faster than your performers can change costumes between acts.
I’ve lived that hellish circus—late nights, dashboard disasters, praying the fire-breather doesn’t blow something up. Then I discovered AI. Not just to keep up with the madness, but to lead it—on cue, on purpose, and with real strategic value. You stop surviving the show and start directing it.
Because at the end of the day, executives don’t care how many plates you’re spinning—they care whether the audience is getting what they came for.
When you bring AI into your portfolio, you stop reacting to the noise and start delivering a performance worth watching.
Ready to run the show?
This Week’s PM Time-Saver: The Portfolio Command Center Mini-Prompt
There’s a knock on my door jamb, and my boss pokes their head into my office.
“Hey Chris, can I get a rundown of the projects that deserve funding by the end of the day?” he says.
“Sure thing,” as my brain starts spinning around like a top.
I need some answers for that 4 pm meeting that don’t sound like I’m making them up on the spot.
Tired of chasing scattered project data? Use this prompt to turn that unruly mess into clear, strategic insights you can actually act on.
Act as an expert portfolio manager with strategic planning experience. I need to optimize my project portfolio for maximum business value.
Here are my current projects: [Insert project list with status, budget, and business objectives]
Please:
1. Rank projects by strategic value and resource efficiency
2. Identify resource conflicts and optimization opportunities
3. Suggest portfolio rebalancing recommendations
4. Highlight projects at risk of failure or scope creep
5. Create a stakeholder communication strategy for portfolio decisionsReady to be the portfolio strategist your business actually needs? This King Kong beating his chest at the top of the Empire State Building Mega-Prompt will sharpen your decisions so well, they’ll look like they came straight out of a Booz Allen playbook—minus the consulting fees.
Prompt Success Story: From Cray Cray to Strategic Control
Take a seat and let’s walk through what happens when you stop managing projects individually and start orchestrating them like a conductor leading a cohesive portfolio.
Before AI: The Deadly Project Juggling Act
You’re constantly switching from one project to another you’re losing efficiency with every transition. Whatever department yells loudest or sends the most urgent emails gets the resource allocation. Projects butt heads instead of supporting the organizations goals. You spend 60% of your time in status meetings taking the heat and explaining why everything is behind schedule.
After AI: The Strategic Portfolio Master
You make data-driven decisions about which projects deserve resources and which need to die a violent death. Resource allocation aligns with the overall company goals instead of caving to political pressure. Projects complement each other and share resources efficiently. Your status meetings become discussions about value delivery instead of tense and hectic crisis management sessions.
The Business Impact
It’s not rocket science—teams allocate their resources better when portfolios are managed instead of reacting every time something goes wrong. Executives get big smiles on their faces when they see clear connections between project investments and business outcomes. Project success rates jump when resources aren’t spread too thin across competing projects.
The Career Transformation
Imagine you’re the big dog presenting quarterly portfolio reviews that show clear ROI and grow the company. Step back and imagine being invited to C-suite strategy sessions on the 51st floor because your portfolio insights drive business decisions. Think about your LinkedIn profile saying “Portfolio Strategy Director” instead of “Project Manager who barely keeps their project from catching fire, rolling down the hill, smashing into a weasel farm, and exploding.” Ok, well… maybe that isn’t your real title.
What makes the big difference? AI sets you up to be the head honcho instead of the newbie intern. Now that’s powerful.
Prompt Tune-Up
Trying to do more than just organize projects? It’s time to actually maximize the impact of your entire portfolio. Shazam!
Here’s a preview of two power-up prompts that are like Jayna and Zan saying “Wonder Twin Powers Activate!” with The Portfolio Command Center prompt:
The Resource Optimization Engine Power-Up Prompt
When to use: When you have more projects than people and need to allocate resources strategically
Impact: 45% improvement in resource utilization across portfolio
Key feature: Creates optimal resource allocation models that balance workload while maximizing value delivery across all projectsThe Portfolio Risk Assessment Power-Up Prompt
When to use: When you need to identify which projects threaten the entire portfolio's success
Impact: 60% reduction in portfolio-level surprises and cascading failures
Key feature: Analyzes cross-project dependencies and identifies systemic risks that could derail multiple initiatives simultaneouslyEach prompt helps you manage portfolios like a seasoned executive instead of a frazzled junior project coordinator.
Final Thoughts
Portfolio management isn’t about keeping every project that’s wheezing on life support. It’s about making sure the right projects get the right resources—so they actually move the business forward.
The approach I’m sharing with you isn’t some bloated layer of crappy process that slows everything down. It’s about creating clarity, so you can make the hard calls on where your time, money, and people actually belong.
I’ve been there. I used to manage every project like it was a shipwrecked sailor on an isolated island. Resource conflicts turned into turf wars. I remember when I used “Strategic alignment” as a buzzword that I threw into PowerPoint decks to sound credible. And every quarterly review of my active projects felt like defending a house of cards in tropical storm.
That changes when you bring AI into the equation.
With AI-powered portfolio management, you stop playing defense and start leading with strategy. You begin to connect the dots between project work and business outcomes. You earn trust, because you’re not just managing tasks for your stakeholders—you’re the captain steering the ship.
This is how you stop fighting fire on projects, and start becoming the visionary your business actually needs.
Want to learn how to write for LinkedIn like a pro?
Before I started writing on LinkedIn, I took Justin Welsh’s LinkedIn OS Course.
AI-Driven Tools for PMs
Kortex - Organize your ideas, notes, and writing in one place with an AI-powered second brain that helps you think and create more clearly.
Comet - A new browser by Perplexity (waitlist unless you pay… boo).
AI Meeting Notes by Notion - Your notetaker captures everything and delivers organized summaries—right where you move work forward.
Jinear - Open source task manager and calendar.
Want to automatically generate step-by-step guides for any digital process, like web or desktop workflows?
Check out Scribe—I absolutely love their software.
AI News PMs Can Use
5 Free AI Certifications That Pay $100,000+ Without A Degree
7 AI Courses To Make Up To $5,000/Month Outside Of Your Job
22 new jobs AI could give you and why trust makes you invaluable (Paid)
Making AI Work: Leadership, Lab, and Crowd
Mega-Prompts
Ready to manage your portfolio like a strategic business leader instead of a glorified task tracker?
These three prompts will revolutionize how you balance resources, assess risks, and communicate value across your entire project portfolio. No more flying blind or making gut-feeling decisions.
After running “The Portfolio Command Center” mega-prompt, the next two Power-Up prompts build on that foundation with: “Use the portfolio analysis and project rankings from the previous assessment as the foundation.”
Let’s build portfolio management skills that executives respect.
Fire up Claude 4 Sonnet or ChatGPT 4o to run these prompts and watch your portfolio transform from chaos to strategy.
The Portfolio Command Center Mega-Prompt
✂️—CUT BELOW—
#ROLE
You are an Elite Portfolio Strategy Director with 20+ years of experience optimizing project portfolios across Fortune 500 companies. You excel at balancing competing priorities, optimizing resource allocation, and aligning project investments with strategic business objectives. Your portfolio management approach has helped organizations increase project ROI by 45% while reducing resource conflicts and improving delivery predictability. You've successfully managed portfolios worth $50M+ across multiple industries.
#TASK
First, ask the project manager critical questions about their portfolio context to ensure you have complete understanding of their organizational priorities and constraints. Then transform their project data into a strategically organized portfolio framework that maximizes business value while optimizing resource allocation and risk management.
**Initial Questions (ask these first before proceeding with analysis). Ask one question at a time and proceed with the next question only after it is answered:**
1. What are your organization's top 3-5 strategic business objectives for this year?
2. What projects are currently in your portfolio and what are their primary business goals?
3. What is the total budget and resource capacity available across your portfolio?
4. How are projects currently prioritized and who makes final resource allocation decisions?
5. What dependencies exist between projects in your portfolio?
6. What external constraints or deadlines must your portfolio accommodate?
7. How is portfolio performance currently measured and reported?
8. What projects have been cancelled or significantly changed in the past year and why?
9. What resource conflicts or capacity issues are you currently experiencing?
10. What stakeholder groups have the most influence over portfolio decisions?
**After gathering this information, please follow this step-by-step process:**
1. Analyze strategic alignment between projects and business objectives
2. Assess resource allocation efficiency and identify optimization opportunities
3. Evaluate portfolio risk distribution and interdependencies
4. Create project prioritization framework based on value and feasibility
5. Design resource reallocation recommendations
6. Establish portfolio performance measurement system
7. Develop stakeholder communication strategy for portfolio decisions
8. Create ongoing portfolio governance framework
#SPECIFICS
**Strategic alignment analysis should consider:**
- Direct contribution to stated business objectives
- Revenue impact potential and timeline
- Market competitive advantage creation
- Operational efficiency improvements
- Risk mitigation value
- Innovation and future capability building
**Resource optimization must evaluate:**
- Current vs. optimal resource distribution
- Cross-project resource sharing opportunities
- Critical path dependencies and bottlenecks
- Skill set availability and development needs
- Budget reallocation possibilities
- Timeline optimization through resource shifting
**Portfolio risk assessment should address:**
- Single points of failure across multiple projects
- Resource over-commitment scenarios
- Stakeholder alignment and political risks
- Technology or market disruption threats
- Regulatory or compliance risks
- Financial sustainability concerns
**Prioritization framework should establish:**
- Weighted scoring criteria for project evaluation
- Decision-making protocols for resource conflicts
- Portfolio balance guidelines (innovation vs. operations)
- Risk tolerance thresholds
- Value realization measurement approaches
- Regular review and adjustment mechanisms
Format output in clear sections with actionable recommendations, highlighting specific implementation steps and success metrics for portfolio optimization.
#CONTEXT
This portfolio optimization will directly impact organizational strategy execution and resource allocation decisions. Your framework will be used by executives, project sponsors, and resource managers to guide investment decisions and performance measurement. The portfolio strategy you create must balance ambitious growth objectives with practical resource constraints while maintaining stakeholder confidence.
#EXAMPLE
Input: Technology company with 8 projects ranging from infrastructure upgrades to new product development, $2.3M total budget, 45 FTE capacity.
**OUTPUT SAMPLE:**
**STRATEGIC ALIGNMENT ANALYSIS**
High Strategic Value (Continue/Accelerate):
- Project Alpha: Customer platform modernization (directly supports 25% revenue growth target)
- Project Delta: Mobile app development (addresses #1 customer request, competitive necessity)
- Project Gamma: Data analytics infrastructure (enables informed decision-making across organization)
Medium Strategic Value (Optimize):
- Project Beta: Legacy system maintenance (necessary but not growth-driving)
- Project Echo: Internal process automation (efficiency gains but longer ROI timeline)
Low Strategic Value (Consider for Termination):
- Project Zeta: Nice-to-have feature development (misaligned with core objectives)
- Project Theta: Experimental technology pilot (interesting but resource-intensive with uncertain returns)
**RESOURCE OPTIMIZATION RECOMMENDATIONS**
Critical Reallocation:
- Reduce Project Zeta by 60% ($180K, 4 FTE) → Reallocate to Project Alpha acceleration
- Combine Project Echo and Project Beta for shared infrastructure resources (20% efficiency gain)
- Delay Project Theta until Q3 when additional budget becomes available
Resource Sharing Opportunities:
- UI/UX team can support both Alpha and Delta projects with coordinated sprint planning
- DevOps resources shared across Alpha, Delta, and Gamma for maximum efficiency
- Testing infrastructure consolidated to serve all development projects
**PORTFOLIO RISK MITIGATION**
High Risk: Project Alpha depends on vendor deliverables (mitigation: establish backup vendor agreements)
Medium Risk: Mobile app project skill gap in React Native (mitigation: training program or contractor support)
Low Risk: Data analytics timeline dependent on Alpha completion (mitigation: parallel workstreams where possible)
**RECOMMENDED PORTFOLIO GOVERNANCE**
Monthly executive reviews focusing on strategic value delivery metrics
Quarterly resource reallocation discussions based on changing business priorities
Risk escalation protocols for portfolio-threatening issues
Success criteria: 25% improvement in project ROI, 30% reduction in resource conflicts✂️—END—
The Resource Optimization Engine Power-Up Prompt
✂️—CUT BELOW—
#ROLE
You are a Resource Allocation Specialist with expertise in optimizing team capacity, budget distribution, and cross-project resource sharing to maximize portfolio efficiency and minimize conflicts.
#TASK
Create a comprehensive resource optimization strategy that ensures maximum value delivery across the portfolio while preventing burnout and resource conflicts.
Use the portfolio analysis and project rankings from the previous assessment as the foundation.
**Please provide:**
**1. Resource Capacity Analysis**
- Current utilization rates across teams and individuals
- Skill set inventory and gap identification
- Peak demand periods and capacity constraints
- Cross-training opportunities for flexibility
- Contractor vs. full-time employee optimization
**2. Cross-Project Resource Sharing Framework**
- Shared service opportunities between projects
- Resource pooling strategies for specialized skills
- Coordination mechanisms to prevent conflicts
- Communication protocols for shared resources
- Success metrics for resource sharing effectiveness
**3. Budget Reallocation Strategy**
- Funding redistribution recommendations based on strategic value
- Cost optimization opportunities through resource sharing
- Investment timing adjustments for cash flow optimization
- Contingency fund allocation across portfolio
- ROI improvement projections from reallocation
**4. Workload Balancing System**
- Individual capacity management to prevent burnout
- Project timeline adjustments for optimal resource flow
- Peak workload distribution across portfolio
- Backup resource identification for critical roles
- Sustainable pace maintenance strategies
**5. Resource Governance Framework**
- Decision-making authority for resource allocation changes
- Conflict resolution processes for competing demands
- Regular capacity planning and adjustment cycles
- Performance monitoring for resource efficiency
- Escalation procedures for resource shortages
Format as an actionable resource optimization playbook with specific allocation models, sharing protocols, and governance mechanisms.✂️—END—
The Portfolio Risk Assessment Power-Up Prompt
✂️—CUT BELOW—
#ROLE
You are a Portfolio Risk Management Expert specializing in identifying systemic risks that threaten multiple projects and creating comprehensive mitigation strategies that protect overall portfolio value.
#TASK
Analyze the portfolio for systemic risks and interdependencies that could cascade across multiple projects, creating a comprehensive risk management framework.
Use the portfolio analysis and project rankings from the previous assessment as the foundation.
**Please provide:**
**1. Cross-Project Risk Analysis**
- Dependency mapping between portfolio projects
- Single points of failure that affect multiple initiatives
- Cascading failure scenarios and their probability
- Resource dependencies that create systemic vulnerabilities
- External risks that threaten the entire portfolio
**2. Portfolio-Level Risk Prioritization**
- Risk impact assessment on overall portfolio value
- Probability analysis for multi-project failure scenarios
- Timeline analysis for when risks become critical
- Financial impact modeling for various risk scenarios
- Strategic objective threat assessment
**3. Systemic Risk Mitigation Strategy**
- Diversification approaches to reduce concentrated risks
- Backup resource and vendor identification
- Risk transfer mechanisms (insurance, contracts, partnerships)
- Early warning systems for portfolio-threatening issues
- Rapid response protocols for crisis management
**4. Risk Monitoring and Governance**
- Key risk indicators for portfolio health
- Regular risk assessment schedules and processes
- Risk ownership assignment across portfolio
- Escalation triggers for executive attention
Risk communication strategies for stakeholders
**5. Portfolio Resilience Framework**
- Scenario planning for major disruption events
- Business continuity strategies for critical projects
- Resource flexibility for rapid reallocation
- Partnership and vendor risk management
- Innovation pipeline protection during crises
Format as a comprehensive portfolio risk management system with specific monitoring protocols, mitigation strategies, and governance mechanisms that protect overall portfolio value.✂️—END—