Planning Toolbox

A Tech Leader's Guide to Strategic Planning for 2025

No tech leader wants to scramble last-minute to finalize their budget. Yet here we are, often caught in this painful cycle. Traditional finance frameworks don't do us any favors - lumping tech costs into broad buckets like "Vendor," "Infosec," "Payroll," and "Cloud." These categories rarely capture the nuanced reality of our needs.

This guide offers an opinionated toolbox for tech and product leaders to get ahead of the planning process. While I use a fixed model, the focus is on gathering the right data upfront. Yes, it seems like a lot of work initially, but once you adapt it, it becomes a progressive effort rather than starting from scratch each time.

The Machinery Behind Planning

Understanding how the Wishlist funnel works is crucial.

We're trying to transform strategy (what we believe drives success) into outcomes (products, features, new verticals, sales increase, investment, IPO) while juggling constraints (time, money, headcount, market).

Here's the thing about strategy - it's not always about building the shiny new app. It's a delicate dance between bottom-up and top-down approaches, trying to find the sweet spot where customer needs, market trends, stakeholder goals, and your vision intersect.

Understanding Your Constraints

Ongoing Work & Running the Business

This is where wishes collide with reality. Consider:

• There's a finite impact of hiring on team growth
• Running the business is everyone's responsibility
• Start your planning from this baseline

Hiring Realities

The recent industry layoffs taught us a harsh lesson - doubling team size to tackle everything isn't sustainable. Key considerations:

• Decisive prioritization directly impacts team size
• Decisions must align with leadership context
• Focus on what not to do is as crucial as what to do

Team Capabilities

Your team's current skills shape what's possible:

• Consider expertise gaps in M&As, coding stacks, cloud infrastructure
• Evaluate readiness for new business verticals
• Assess legacy platform maintenance capabilities.
• Factor in transitions like B2B to B2C moves

Cost Management

Watch your baseline costs carefully:

• Cloud economics aren't free
• Internal applications carry hidden costs
• Watch for SaaS duplication
• Monitor third-party dependencies that could impact your profit margins

The Planning Canvas

The planning canvas translates constraints into actionable columns, creating a space for group discussion. This isn't an agile board - it's a clarity tool that bypasses complex methodologies like OKRs.

Pro tip: If an initiative impacts multiple columns (like both operational efficiency and revenue), duplicate it. This signals high prioritization potential.

1. Revenue: Current revenue sources Protection initiatives and what are new Growth opportunities?
2. Operational Efficiency: Cost optimization Process improvements Legacy system decisions.
3. Commercial Efficiency: Sales process optimization Time-to-market improvements. How we sell, how fast we bridge it
4. Future Business/Revenue: Major bets for new revenue Valuation improvement initiative. What is the single bet that will generate new revenue or improve our valuation ?

OKRs, KPIs, Canvas users: You’ll see plenty of familiar items here. If something feels like a task, it doesn’t belong. If it’s just a single word, add more detail to make it clear. And if it’s an OKR, don’t worry about it. Your OKRs are already the column titles!

Common Key Results and items in the Canvas

Essential Information Gathering

Track the % percentage of time each team spends within the "Run the Business/Grow the Business" framework:

Running the Business: Focused on maintaining operations and retaining customers. Keeping the lights on!

• Handling incidents
• Implementing small fixes and improvements
• Performing manual tasks to keep things running (e.g., scripts, API calls, back-office work)

Growing the Business: Focused on generating new revenue and expanding market share. what you do to get new revenue and expand market share

• Developing new products
• Adding features to attract new customer segments to existing products
• Launching new business lines

Describe and measure key acquisition and retention flows:

• Onboarding Friction: Identify obstacles new customers face during onboarding and their impact on conversion rates.
• Customization and Professional Services: Assess how tailored solutions and support contribute to sales success.
• Client-Perceived Complexity: Measure how internal disorganization translates into challenges for clients.
• Red Paths: Analyze the most-used flows that directly influence current revenue, focusing on areas for optimization.

Team Structure Clarity- Know your numbers and Headcount.

• Team Names: Use descriptive names that clearly reflect what each team does. Avoid relying on internal jargon or cultural references. For example:
• Shared Headcount: Identify team members who work across journeys and initiatives, such as L2 support, QA, Product Designers, and Data Analysts.
• External Support Headcount: Include headcount that supports other teams or departments outside of Product and Tech.
• Management Layers: Regularly assess management layers based on:
• Team Journey Templates. Ensure the template captures all the above areas with clear and actionable inputs.

Budget and Market Context

Gather:

• Cloud and vendor expense projections
• 3-month forecasts
• Product-specific revenue data
• ARR projections
• Burn rate analysis
• Expenses and Headcount- Selling, General and Admin expenses.

Dream Work Exercise

Have each team envision their ideal scenario:

Sales:

• Revenue-generating bets
• Market expansion opportunities

Product:

• Next-horizon innovations, where do we go from here?
• Competitive positioning

Marketing:

• Growth initiatives. Acquisition strategies

Rules of Engagement

Keep these principles in mind:

• Be concise and direct
• Acknowledge capacity limits
• Prioritize maintaining existing value. There is work being done to keep what we have. Is it more important than what we want?
• Leave politics and ego aside
• Be open to organizational change

Hope you liked reading this. Wish you the best of 2025.

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