Leadership Philosophy & Operating System

Evan Goodwin

Leading With Clarity + Systems:

With 20+ years of experience and an entrepreneur's mindset, I translate vision into disciplined execution — through frameworks, governance models, and strategic planning practices.

This document serves as both a personal reference and as a resource for potential employers, partners, and investors to understand how I think and lead.

Leadership illustration

Core Principles

Strategic Decision-Making Framework

The fundamental truth about business decisions: Most strategic choices are made with incomplete information. The skill isn't waiting for perfect data—it's knowing how to make qualified decisions with whatever information exists, and structuring those decisions to limit downside while preserving upside.

I've developed a systematic approach to evaluating major strategic opportunities and risks:

Phase 1: Frame the Decision

Define what you're actually deciding - Most strategic mistakes start with fuzzy problem definition. Are you deciding whether to enter a market, or whether to invest resources now versus in 6 months? Clarity on the actual decision point prevents scope creep.

Identify the decision criteria - What does success look like? What are the dealbreakers? This sounds obvious, but most people skip this step and end up moving the goalposts mid-process.

Determine the timeline - When does this decision need to be made? What's forcing the timeline? Can we buy more time to gather information?

Phase 2: Information Gathering & Risk Assessment

Map what you know vs. what you need to know - Create an explicit gap analysis. Separate facts from assumptions. If a critical assumption is wrong, what's the impact?

Identify asymmetric risks - What risks have catastrophic downside? What opportunities have outsized upside? This shapes whether you need bulletproof data or can move on directional information.

Test critical assumptions with minimum investment - Before committing major resources, can you validate assumptions cheaply? This might mean mockups and ad campaigns, customer conversations, limited pilots, or financial modeling scenarios.

Phase 3: Portfolio-Level Resource Allocation

This is where most companies fail - They evaluate opportunities in isolation rather than as portfolio decisions. When you're running 10-20 major initiatives, saying yes to one thing means saying no to others.

The discipline:

  • What are we already committed to?
  • What resources (people, capital, leadership attention) does this require?
  • What gets delayed or killed if we proceed?
  • Is this the highest-value use of these resources right now?

Ruthless prioritization beats distributed mediocrity - I'd rather fully resource 3 initiatives and kill 2 others than spread resources across 5 half-funded projects.

Phase 4: Execute with Clear Off-Ramps

Structure decisions to preserve optionality:

  • Stage commitments rather than all-in bets
  • Build clear decision gates: what evidence triggers go vs. no-go at each stage?
  • Define success metrics upfront, then hold yourself accountable

Know when to cut losses - I've learned to amputate fast when something isn't working. The sunk cost is already gone—the question is whether incremental investment generates sufficient return.

Operating Cadence & Organizational Alignment

Organizational performance depends on cascading information and decisions across time horizons. I've built operating structures that create alignment from strategic planning down to daily execution.

The Cadence Framework

Daily Standups (15 minutes)

  • What shipped yesterday, what's shipping today, what's blocked
  • Surface issues before they cascade
  • Action-oriented: every blocker gets an owner and timeline

Weekly Operations Review (60-90 minutes)

  • Weekly metrics against targets
  • Production/delivery schedule review
  • Cross-functional coordination and resource conflicts
  • Issues escalation to leadership

Monthly Business Review (2-3 hours)

  • Deep dive on KPIs vs. targets
  • Root cause analysis on variances
  • Resource allocation decisions
  • Project portfolio status (RAG reporting)

Quarterly Business Review (half day)

  • Strategic progress against annual goals
  • Financial performance and forecasting
  • Market conditions and competitive positioning
  • Major investment and strategic decisions
  • Set priorities for next quarter

Key Principles of Operating Rhythms

Cascading information: Strategic decisions flow down, issues escalate up. Each level has clear inputs and outputs.

Consistent format: Same structure every time eliminates ambiguity and builds muscle memory.

Action orientation: Every meeting ends with clear owners and due dates. No meeting without decisions.

This creates organizational discipline: When you have the right people organized with clear operating rhythms and defined goals, alignment stays clear. People know what's expected and have autonomy to deliver.

Multi-Time Scale Planning

Operating rhythms handle execution cadence; planning processes handle strategic alignment. I've adapted a planning methodology to create coherence from annual strategy down to daily priorities.

Quarterly Planning

  • Review annual objectives and strategic initiatives
  • Set 3-5 critical goals for the quarter
  • Allocate resources and capacity to key projects
  • Ensure alignment between long-term vision and near-term execution
  • Identify what to curtail or automate

Weekly Planning

  • Review quarterly plan and upcoming calendar
  • Choose 3-5 priorities for the week
  • Time-block deep work sessions
  • Identify potential conflicts and risks
  • Coordinate across teams and external partners

Daily Planning

  • Identify top 3 priorities from weekly plan
  • Block time for focused work on critical tasks
  • Adjust for emergencies while protecting strategic work

Why this matters

Clear organizational alignment accelerates execution and improves decision-making at every level. It prevents strategic drift and enables proactive leadership instead of crisis reaction.

Project & Portfolio Management

PMO Governance Structure

Companies often have 10-20 major projects running simultaneously. Without governance discipline, they collide, compete for resources, and stall. I've built lightweight PMO structures that provide discipline without bureaucracy:

  • Project intake process - How do projects get approved? Who decides priority? What's the business case threshold?
  • Standard project framework - Charter template (scope, owners, timeline, budget), stage gates (concept, design, build, test, launch), consistent status reporting
  • Portfolio-level resource management - Track who's working on what, identify conflicts when someone is on three projects simultaneously, capacity planning for key resources
  • Governance meetings - Weekly project leads sync, monthly portfolio review with leadership, steering committees for major initiatives

Light PMO vs. Heavy PMO: I favor light structures—standard templates, simple tracking, focus on communication. Heavy PMO creates dedicated PMs for everything and elaborate stage gates that become bureaucracy.

Cross-Functional Coordination: RACI Framework

One of my primary tools for preventing ownership ambiguity on cross-functional initiatives is RACI—Responsible, Accountable, Consulted, Informed. It sounds simple, but it's incredibly powerful when applied with discipline:

The golden rule: Exactly one person is Accountable per decision.

RACI breakdown:

  • R = Responsible - Does the work (can be multiple people)
  • A = Accountable - Owns the outcome and has final decision authority (must be exactly one)
  • C = Consulted - Provides input before the decision (minimize these to avoid committees)
  • I = Informed - Kept in the loop after the decision (be liberal with these)

Why this matters: Shared accountability doesn't work. Someone needs to own the outcome. When you have two people who think they're Accountable, you have conflict and slow decisions. RACI forces the conversation about ownership upfront.

I use RACI matrices for major initiatives—it clarifies scope boundaries, prevents ownership gaps, and speeds up decisions by limiting consulted parties. At Vector, implementing RACI discipline dramatically reduced finger-pointing and delays on cross-functional projects.

Demand & Supply Alignment: S&OP Process

In manufacturing and product businesses, I've implemented Sales & Operations Planning (S&OP) as the monthly rhythm that bridges commercial forecasts with operational capacity:

Week 1 - Data Gathering: Sales updates pipeline, Operations reports actual vs. plan, Finance updates constraints

Week 2 - Demand Review: Commercial presents updated forecast, identifies changes and new commitments

Week 3 - Supply Review: Operations presents capacity plan, identifies gaps, Materials/Procurement confirms supply

Week 4 - Executive S&OP: Leadership reviews demand vs. supply, decides on capacity/timing trade-offs, commits to plan

Key outputs: Rolling 12-18 month forecast, production plan for next 3 months, capacity gaps requiring action, financial impact analysis.

At Vector, I built this process from scratch—creating weekly production plans based on order pipeline while managing custom requirements and long lead-time components.

Systematic Problem-Solving

After 20+ years, I see projects as systematic steps with identifiable critical paths and risk points:

  • Decompose complexity - Break large projects into manageable phases with clear dependencies and stage gates
  • People as puzzle pieces - Fit the right people to the right problems at the right time, with clear RACI assignments
  • Proactive risk mitigation - Identify critical problem points before they emerge
  • Resource allocation - Focus energy on the next most important step, with transparent portfolio-level visibility

Managing External Partnerships

Many projects require coordination across organizational boundaries:

  • Clarity on scope boundaries - Who owns what, where handoffs happen, clear RACI for joint decisions
  • Communication cadence - Regular touchpoints prevent misalignment
  • Mutual success criteria - Everyone understands what winning looks like

Team Building & Talent Development

What I Look For: Problem-Solving Ability

The most important capability in any team member is creative problem-solving. This reveals itself in how people approach questions and challenges.

In interviews, strong problem-solvers connect their experiences—even from outside work—to demonstrate relevant capabilities. When someone shrugs and says "I don't know" without attempting to bridge their experience, that reveals narrow thinking.

Role-Based Hiring Philosophy

Technical/Skills-Driven Roles

CAD designers, engineers, specialists

  • 2/3 weight on demonstrable skill
  • 1/3 weight on leadership ability: independence, self-starting capability, ability to drive projects forward

Leadership/Vision-Driven Roles

Sales, marketing, management

  • Focus on vision, creativity, and execution capability
  • Specific skills are teachable if the person is open-minded and has problem-solving ability

Providing Resources for Success

It is the manager's job to give people the resources they need to be successful. It is the employee's job to execute.

Resources include:

  • Training and development - Understanding what skills or knowledge gaps exist and providing paths to fill them
  • Tools and budget - The right equipment, software, and financial resources
  • Access to expertise - Knowing when to bring in external help
  • Clarity on scope and timeline - Employee buy-in on what success looks like and when it's due
  • Time and space - Protecting time for deep work on complex problems

I train people to recognize when they need to stop and learn versus reach out for external help. This judgment is critical for maintaining momentum.

Managing Performance

I don't micromanage. I work with people to understand time and skills required, identify gaps, and ensure they have what they need to succeed.

Accountability through structure: When you have the right people organized across multiple time scales with defined goals and clear operating rhythms, alignment stays clear. People know what's expected through daily standups, weekly reviews, and regular one-on-ones. They have autonomy to deliver within that structure.

The right team is paramount. Slow to hire, fast to fire. It's uncomfortable, but having performers who fill and exceed their roles is critical to organizational success.

Leveraging AI & Technology as Force Multipliers

The Pragmatic Approach

I view AI tools the same way I viewed CAD in the 1990s and ERP systems in the 2000s—as infrastructure that fundamentally changes what's possible with limited resources. The question isn't "should we use AI?" but rather "what work should humans stop doing?"

Small teams with the right technology can now execute strategies that previously required departments.

How I Use AI in Practice

Knowledge capture and documentation: I've built comprehensive knowledge bases that capture technical expertise, decision frameworks, and institutional knowledge. This prevents knowledge loss and accelerates onboarding.

Research and analysis: Competitive intelligence, market research, and technical literature reviews that used to take days now take hours. I use AI to synthesize information and identify patterns, then apply human judgment to make decisions.

Documentation and communication: First drafts of process maps, proposals, technical documentation, and training materials. The AI handles the grunt work; I provide the strategic direction and refinement.

Data analysis and modeling: Pattern recognition in operational data, scenario planning, and financial modeling. AI surfaces insights; I determine which ones matter.

The Philosophy

AI amplifies judgment, it doesn't replace it - The human makes the decision; AI eliminates the tedious work that precedes decisions.

Start with high-volume, low-risk applications - Test on work where errors are easily caught and stakes are low.

Build systems, not one-offs - Create reusable frameworks and knowledge bases rather than treating each task as standalone.

Train the team - This isn't just a personal productivity tool. Everyone should understand how to leverage these capabilities.

The Competitive Advantage

Organizations that integrate AI effectively operate with fundamentally different economics. The leverage ratio—output per employee—can be 3-5x higher than competitors still doing everything manually.

This isn't about replacing people. It's about enabling small, high-performing teams to accomplish what previously required much larger organizations. The strategic advantage goes to whoever figures this out first in their market.

Sales & Client Philosophy

Consultative Selling

In technical settings, sales means providing expertise first. In less technical settings, it means providing value through support—site visits, sharing ideas and vision.

The goal is not to push products. The goal is to solve problems and build relationships.

Multi-Time Scale Approach to Sales

Pipeline management (present) - Stay on top of active opportunities, move deals systematically through stages

New opportunity identification (near-term) - Search out new markets and segments, test new approaches with minimal risk

Strategic positioning (long-term) - Build market presence that compounds, develop partnerships, create defensible advantages

Knowing When to Say No

It's critical to understand:

  • What should be within your organizational scope
  • What you should walk away from
  • Where you can team up with other companies to provide complete solutions

Building teams internally AND externally is important. Not every opportunity is a good fit. Saying no to the wrong opportunities protects your ability to say yes to the right ones.

Client-First Decision Making

The North Star: Put the client first and add value.

This takes many forms:

  • Recommending simpler solutions even if it means less revenue
  • Walking away from projects where we're not the right fit
  • Over-delivering on technical support
  • Building long-term partnerships over short-term transactions

Let's Connect

Interested in discussing leadership, strategic partnerships, or business opportunities?

Ideal for: Technical B2B businesses with long sales cycles, complex projects requiring cross-functional coordination, manufacturing or operational businesses that need both strategic vision and execution discipline, or scale-up companies building operating infrastructure from scratch.