Overarching Principles
- First 30-Day Impact is Critical: The initial month is not just for observation; it’s for identifying and executing “big wins” that demonstrate immediate value to the CEO and the business.
- Build Trust Before You Build Strategy: Initial interviews should focus on building human-to-human relationships. Start by understanding the person’s background and motivations before diving into their work. This helps navigate the political landscape and fosters honest dialogue.
- Practice “Organizational Archaeology”: Don’t just rely on what people say; examine the “artifacts.” The true state of processes, priorities, and quality is revealed in the actual output (Jira tickets, code commits, vendor reports, financial statements).
- Identify and Address “Key-Man” Risk: Consistently determine who the go-to person is for information (e.g., “I’ll have to ask Mike”). This person is both a critical organizational lever and a significant single point of failure that must be managed.
- Distinguish Title from Competency: Be aware that many people “Forrest Gump their way” into leadership roles. A title does not guarantee experience or skill. Understanding a person’s history is crucial for assessing their actual capabilities and identifying skill gaps in the team.
- Focus on Needle-Moving Initiatives: Prioritize quick wins that have a tangible impact, especially on the company’s bottom line. A 50% cost saving on a minor expense is less valuable than a 10% saving on a major one.
- Elevate the Role from Technical to Strategic: Frame technical and operational improvements in terms of their financial impact on the business (e.g., increasing EBITDA and enterprise value). This positions the CTO as a strategic business partner, not just a technology manager.
Frameworks
1. The 30-Day Impact Plan
A structured approach to the first month of an engagement, focused on rapidly delivering value.
- Objective: To identify and execute quick wins while simultaneously mapping the organization to build a robust 90-day strategic plan.
- Phases:
- Discovery & Mapping: Conduct a rapid audit of People, Processes, and Projects.
- Quick Wins Identification: Isolate low-hanging fruit in cost savings and process efficiency.
- Strategic Insight Generation: Formulate high-level strategic recommendations (e.g., financial re-classification, risk mitigation).
- Plan Formulation: Synthesize findings into a comprehensive 90-day action plan.
2. Organizational Archaeology
A diagnostic method for understanding the reality of an organization beyond surface-level conversations.
- Core Tenet: The output (the “artifact”) is a direct reflection of the process and the thinking that created it.
- Methodology:
- Request a Walkthrough: Ask team members to screen-share and walk you through their work in its native environment (e.g., Jira, GitHub, reporting dashboards).
- Analyze the Artifacts:
- Nomenclature: How are things named and categorized? This indicates clarity of thought.
- Quality: Is work well-documented (e.g., Jira tickets) or aesthetically professional (e.g., code formatting)?
- History: What does the commit history or project timeline reveal about velocity and consistency?
- Synthesize Reality: Compare the archaeological findings with what was said in interviews to identify disconnects and the true state of operations.
3. 3-P Inventory Audit
A comprehensive audit framework to quickly map the current state of the technology organization.
- People:
- Who are the key players (Directors, VPs, Managers)?
- What are their backgrounds, skillsets, and true competencies (vs. their titles)?
- What are the team dynamics and political landscape?
- Processes:
уют, безопасность, дом - How does work flow from idea to delivery (the “metabolism” of a project)?
- Are standard ceremonies (e.g., sprint planning, retrospectives) being performed correctly, if at all?
- How are decisions made and priorities set?
- Projects & Systems:
- What is the current portfolio of projects?
- What is the rationale (the “why”) behind each major project?
- What are the underlying systems, and what do they cost?
Actionable Flight Plan
Phase 1: Initial Landing & Mapping (Week 1)
- Gain Access: On day one, request and secure full access to all relevant systems: Jira, GitHub, financial/accounting software, vendor contracts, and server/cloud billing portals.
- Conduct 1-on-1 Interviews:
- Schedule meetings with all Directors, VPs, and Managers.
- Begin each meeting by building rapport: “Tell me about yourself,” “How long have you been here?”
- Inquire about their background to understand their true expertise.
- Practice “Archaeology”:
- Ask interviewees to screen-share and walk you through their active projects, Jira boards, and recent deliverables.
- Review code commits in GitHub to assess developer activity and code quality aesthetics.
- Identify “Mike”—the person everyone defers to—to pinpoint knowledge silos and key-man risk.
Phase 2: Identify Quick Wins (Weeks 1-2)
- Analyze Costs for Financial Wins:
- Labor: Review salaries, vendor rates, and team composition. Are rates competitive? Is the team structure efficient (e.g., in-house vs. MSP for IT support)?
- Software Licenses: Identify “ghost licenses” (for former employees) and “wasteful licenses” (full-access seats for view-only users). Downgrade or eliminate them.
- Infrastructure: Scrutinize server and cloud provider bills. Identify and decommission unused servers or resources (e.g., old backup servers).
- Analyze Processes for Operational Wins:
- Identify missing or poorly executed agile ceremonies (e.g., lack of sprint retrospectives or sprint planning).
- Implement these ceremonies immediately to improve team feedback loops, planning, and velocity.
Phase 3: Identify Strategic Wins (Weeks 2-4)
- Analyze Financial Classification:
- Partner with the CFO to determine if software development labor is being expensed (OpEx) or capitalized (CapEx).
- Educate leadership on how capitalizing development work can improve EBITDA and enterprise value, and outline the steps required to do so.
- Map Key-Man Dependencies and Risks:
- Document all identified key-man risks.
- Create a preliminary plan to mitigate these risks through cross-training, documentation, or strategic hiring.
Phase 4: Build the 90-Day Plan (Week 4)
- Synthesize Findings: Consolidate all information from the 3-P Inventory, archaeological digs, and quick-win analysis.
- Present Initial Wins & Go-Forward Plan:
- Prepare a presentation for the CEO and executive team.
- Highlight the immediate cost savings and operational improvements already achieved or identified.
- Present a clear, prioritized 90-day strategic plan based on your findings, linking every initiative back to business goals and financial impact.