$23 Million Is Not a Plan
How to transform vague revenue targets into objectives your technology team can actually deliver
I’m standing at a whiteboard in a CTO Compass session. Six executives are seated around a conference table. The CTO who invited me is anxious. He’s been trying for three months to get his technology roadmap approved, and every conversation ends the same way: more questions, no decisions, mounting frustration.
“Walk me through what happened in your last planning meeting,” I say.
The CTO exhales. “The CEO presented the annual target. $23 million in revenue. Everyone nodded. Then she asked for the plan to get there, and the room just... fragmented.”
He describes the scene. The COO wanted more aggressive outbound. Sales wanted better product differentiation. Marketing wanted to double down on content. Finance wanted operational efficiency. Every suggestion reasonable. None of them connected.
“And where did that leave you?” I ask.
“Nowhere. I still don’t know what to build. Every feature request feels equally important because we never decided what actually matters.”
I turn to the whiteboard and write a single question: How much of that $23 million do you already have locked in?
The CFO in the room pulls up a spreadsheet on her laptop. Contracted renewals. High-probability deals. After ten minutes of calculation, we have an answer: $17 million is essentially guaranteed. Another $3 million is probable from the existing pipeline.
“So you’re not solving for $23 million,” I say. “You’re solving for a $3 million gap.”
I watch the tension in the room shift. A $23 million target feels abstract, almost oppressive. A $3 million gap feels like a problem with a solution.
Over the next two hours, I facilitate a conversation that transforms their revenue target into three specific business objectives. By the end, the CTO finally has what he needs: clarity on what the company is betting on, what they’re deliberately not pursuing, and how his technology organization will drive the outcomes.
This is the work that separates CTOs who are seen as cost centers from CTOs who are seen as strategic partners. And it’s the work that has to happen before you can build a technology roadmap that means anything.
The Translation Problem
Revenue targets are not business objectives. A target like “grow revenue by 20%” tells you where to go, but not how to get there. Business objectives are the strategic bets your company makes to reach that destination.
Most C-Suites skip this translation step entirely. They hand technology teams a financial target and expect magic. The consequences cascade through the organization: initiatives multiply without prioritization, resources spread thin across competing interpretations of “what matters,” and year-end retrospectives devolve into debates about what “success” even meant.
A 2023 study by Bridges Business Consultancy found that 67% of well-formulated strategies fail due to poor execution. But the problem often starts earlier. You can’t execute a strategy that was never translated into actionable objectives in the first place.
The CTO sits at a unique intersection. Deep visibility into technical capabilities. Understanding of business constraints. Access to data that reveals customer behavior, system performance, and operational bottlenecks. This position makes the CTO the natural facilitator for the conversation that transforms targets into objectives.
Five Levers, Not Fifty Ideas
Every revenue target is achieved through one or more of five fundamental levers. Understanding these levers is the first act of strategic discipline.
Acquire — Bring in new customers who weren’t buying before. Land new logos. Enter new segments.
Retain — Keep existing customers from leaving. Reduce churn. Increase renewal rates.
Expand — Grow revenue from existing customers through upsells, cross-sells, and increased usage.
Price — Increase pricing on existing offerings. Capture more value from what you already deliver.
Enter — Access new markets, whether geographic, vertical, or product-based.
Most companies cannot effectively pursue more than two or three of these levers simultaneously. If your executive team claims all five are priorities, you don’t have a strategy. You have a wish list.
In that CTO Compass session, we identified the primary lever as Expand (grow existing accounts) and the secondary lever as Acquire (new enterprise logos). The constraint of an EBITDA target meant they couldn’t just throw resources at growth. They needed efficiency improvements alongside revenue expansion.
This clarity eliminated dozens of potential initiatives before we even started discussing them. The CTO visibly relaxed. For the first time in months, he could see a path forward.
The Five-Phase Facilitation Process
Here’s the process I use to guide C-Suite conversations from revenue targets to actionable objectives. Each phase builds on the previous one, and skipping phases leads to objectives that fall apart under scrutiny.
Phase 1: Establish the Gap
Before discussing strategy, everyone must understand the mathematical reality. This grounds the conversation in facts rather than aspirations.
Ask these questions:
What is our current run rate, and what does the target require?
What revenue do we have locked in through contracts or high-probability renewals?
What’s our current pipeline, and how much is realistic to close?
What gap remains after accounting for the probable?
In our session, the target was $23 million. Contracted revenue was $17 million. Probable pipeline was $3 million. The actual problem we needed to solve was a $3 million gap. This reframing made the impossible feel achievable.
Phase 2: Identify the Levers
With the gap defined, determine which revenue levers offer the best opportunity to close it.
Ask these questions:
Of the five levers, which one or two represent our best opportunities this year?
Where are we currently strongest? Where are we leaving money on the table?
What did we try last year, and what worked?
What constraints eliminate certain levers from consideration?
Watch for warning signs. If no one can articulate why one lever is better than another, you need more data. If the chosen levers change every meeting, you have an alignment problem, not a strategy problem.
Phase 3: Surface the Obstacles
If pulling a lever were easy, you’d already be doing it. Understanding what’s blocking progress reveals where objectives must focus.
Ask these questions:
If this lever is so promising, why aren’t we already pulling it harder?
What would have to be true for us to succeed with this lever?
What are we missing—capabilities, resources, information, alignment?
Where do deals get stuck? Where do customers leave? Where does value leak?
For the Expand lever in our session, the obstacles were clear: existing customers didn’t know about add-on products, account management was reactive rather than proactive, and there was no visibility into usage patterns that indicated expansion readiness.
For the Acquire lever: long sales cycles, extensive custom implementation requirements, and a small sales team.
These obstacles pointed directly to where the objectives needed to focus.
Phase 4: Formulate the Objectives
Now synthesize the lever choice and obstacle analysis into three clear business objectives. Each objective should be specific enough to guide action but broad enough to allow creative solutions.
Use this formula: [Action verb] + [Specific outcome] + [For whom/what] + [Measurable target]
Compare these:
Weak: “Grow revenue”
Better: “Acquire new customers”
Best: “Land 10 new enterprise healthcare accounts representing $500K in annual recurring revenue”
Why three objectives? Research on cognitive load and organizational behavior consistently shows that more than three strategic priorities creates dilution rather than ambition. Three objectives allow for depth of execution while maintaining strategic coherence. Richard Rumelt’s work on strategy in “Good Strategy Bad Strategy” emphasizes that focus is the essence of strategy—spreading attention across too many objectives guarantees mediocrity in all of them.
The three objectives from our session became:
Increase platform seat count within existing accounts by 30%, generating $3M in expansion revenue
Land 5 new enterprise accounts representing an additional $3M in first-year revenue
Reduce services delivery cost by 20% through productization and automation
Phase 5: Validate and Commit
Before finalizing objectives, stress-test them against reality.
Ask these questions:
If we accomplish these three objectives, will we hit our revenue target?
Do we have—or can we acquire—the resources to pursue all three?
Are these objectives within our control, or dependent on external factors?
Can we measure progress monthly or quarterly?
Is everyone in this room willing to make trade-offs to achieve these?
The commitment step is operational, not ceremonial. Document the objectives, the owners, and the timeline. Make explicit what will NOT be pursued as a consequence of these choices.
Earning the Right to Facilitate
I can already hear the objection: “This assumes I have permission to lead this conversation.”
Fair. Many CTOs weren’t hired to run strategy sessions. They were hired to ship software. Walking into a planning meeting and asking “How much of that $23 million do we have locked in?” could land as presumptuous. Out of lane. The CEO views strategy as their domain. The CTO’s job is to execute.
If that’s your situation, you don’t start by facilitating the whole C-Suite. You start smaller.
Start with the problem, not the process. Go to your CEO with the symptom: “I’m getting conflicting priorities from different stakeholders, and I need help understanding which initiatives actually matter for hitting our number.” You’re not claiming strategic authority. You’re asking for clarity so you can do your job.
Bring data as your entry point. The CTO has access to information no one else sees. Customer usage patterns. Feature adoption rates. Support ticket trends. Churn indicators. When you surface an insight like “Customers who complete onboarding within 48 hours retain at 3x the rate,” you’ve earned a seat in the strategy conversation because you brought something valuable.
Propose a working session, not a takeover. Instead of announcing that you’ll facilitate quarterly planning, suggest: “Would it help if I pulled together some data and we spent an hour pressure-testing our assumptions about next year?” Frame yourself as a resource, not a rival.
Document what you hear. After any planning conversation, send a follow-up: “Here’s what I understood our three priorities to be. Am I tracking this correctly?” If no one corrects you, you’ve just created the clarity that didn’t exist before. If they do correct you, you’ve surfaced a disagreement that needed surfacing.
The goal isn’t to seize control of strategy. The goal is to be so useful in clarifying strategy that people start expecting you in the room.
When the Room Won’t Align
The five-phase process reads as linear and rational. Real C-Suites are not.
Executive teams are full of competing agendas, protected budgets, and information people aren’t sharing. What happens when the CFO and Head of Sales fundamentally disagree on which lever to pull? What happens when the CEO has already made up their mind and this “facilitation” is theater? What happens when someone in the room is actively working against alignment because clarity threatens their position?
Name the disagreement explicitly. When two executives are advocating for different levers, don’t let the conversation drift. Say: “It sounds like we have two different hypotheses here. Sarah thinks retention is our best opportunity. James thinks acquisition is. Can we look at the data that would tell us which is right?” Force the debate into the open where it can be resolved, rather than letting it fester as passive resistance.
Identify who owns the decision. Not every strategic choice is democratic. Sometimes the CEO decides, full stop. If that’s the case, your job shifts from facilitating consensus to ensuring the CEO has the information needed to decide well. “I want to make sure you have visibility into the technical implications of each path before you choose.”
Watch for the pocket veto. Some executives agree in the room and undermine in the hallway. The best defense is specificity. Vague objectives are easy to reinterpret. “Grow the customer base” can mean anything. “Land 5 new enterprise accounts representing $3M in first-year revenue” is harder to quietly redirect. The more specific the objective, the harder it is to claim you’re pursuing it while actually doing something else.
Accept that perfect alignment is rare. Your goal isn’t unanimous enthusiasm. Your goal is enough clarity that you can build a roadmap and defend your prioritization decisions. If the Head of Sales is still grumbling about not getting their pet feature, that’s fine—as long as the CEO has committed to the objectives and you have that commitment in writing.
When Q2 Blows Up Your Plan
Even if you get three perfect objectives defined and committed, business conditions shift. A key customer churns. A competitor launches something unexpected. The board changes their mind. Six weeks later, the CEO walks in and says “we’re pivoting.”
This is not a failure of the process. This is reality. The question is whether you have a foundation to work from when things change.
Objectives are more stable than tactics. When conditions shift, the first question is: “Do our objectives still hold, or do the objectives themselves need to change?” Often, the objectives remain valid even when the actions underneath them need adjustment. “Land 5 new enterprise accounts” might still be the right objective even if your original approach isn’t working. The pivot is in how you pursue the objective, not whether you pursue it.
Re-run the gap analysis. If a major customer churns or a big deal falls through, the math has changed. Go back to Phase 1. What’s the new gap? Does the size of the gap change which levers make sense? A 15-minute recalculation can prevent months of misdirected effort.
Protect the process, not the plan. The value of this framework isn’t that it produces a perfect plan. The value is that it gives you a shared language for adapting when things change. When the CEO says “we need to pivot,” you can respond: “Okay, let’s revisit our gap calculation and see which lever gives us the best shot at closing it now.” You’re not starting from scratch. You’re updating the model.
Document the change. When objectives shift mid-year, write it down. “As of June 1, we’re deprioritizing Objective 2 and reallocating resources to Objective 1 because of X.” This protects you at year-end when someone asks why you didn’t deliver on the original plan. It also forces the decision-makers to own the pivot rather than pretending it never happened.
The companies that struggle most aren’t the ones that have to adapt. They’re the ones that never had clarity in the first place, so every shift feels like chaos rather than a recalibration.
Why the CTO Leads This Conversation
The CTO brings four capabilities to this facilitation that no one else in the room possesses.
Data visibility. The CTO sees patterns others miss: user behavior analytics, system performance metrics, support ticket trends, feature adoption rates. In our session, the CTO knew that customers who completed onboarding within 48 hours had 3x the retention rate. That data point shaped which obstacles we prioritized.
Possibility awareness. The CTO knows what technology can enable. While others debate strategy in the abstract, the CTO can inject feasibility and timeline reality. “We could launch a free tier within 8 weeks, but European localization would take two quarters. That changes which objectives are achievable this year.”
Constraint transparency. The CTO understands technical debt, infrastructure limitations, and team capacity in ways that affect what’s realistic. Their payment infrastructure didn’t support the pricing model someone proposed. Knowing that constraint saved them from committing to an objective they couldn’t deliver.
Translation capability. The CTO bridges business intent and technical execution. Well-formed objectives emerge from the ability to translate business language into actionable terms and back again.
From Objectives to Actions
Once the three objectives were defined, the CTO could finally do what he’d been trying to do for three months: build a technology roadmap that connected to business outcomes.
Each objective spawned specific actions. Objective 1 (expansion revenue) required implementing customer health scoring, building an expansion recommendation engine, ensuring usage data privacy compliance, and creating an account manager enablement dashboard.
Objective 2 (new enterprise accounts) required accelerating implementation timelines, developing self-service onboarding, completing SOC 2 certification, and building an interactive demo environment.
Objective 3 (services efficiency) required automating data integration workflows, developing reusable configuration templates, documenting proprietary methods, and creating a services-to-platform migration path.
Without clear objectives, a technology roadmap is just a list of features someone asked for. With clear objectives, every item on that roadmap has a reason to exist and a way to measure its impact.
Your Next Planning Conversation
Before the meeting, prepare the math. Calculate the gap between current state and target. Pull relevant analytics on customer behavior, feature adoption, and churn patterns. Have informal conversations with key executives to understand their perspectives. Come with potential objectives to react to, not a blank slate.
During the meeting, start with agreement on the numbers. Use the whiteboard to make thinking visible. Draw the gap, the levers, the obstacles, the objectives. Name the trade-offs explicitly: “If we pursue X, we’re choosing not to pursue Y. Are we aligned on that?”
Inject technical reality gently. “That’s achievable if...” works better than “We can’t do that.” Summarize relentlessly: “So what I’m hearing is... Is that right?”
After the meeting, document the objectives in writing within 24 hours. Circulate for confirmation. Begin translating objectives into specific technology actions. Schedule the first progress check-in.
The first time you facilitate this conversation successfully, you’ll feel the shift in how your C-Suite perceives you. You’re no longer the person who explains why things take so long. You’re the person who helped the company figure out what actually matters.
Revenue targets are destinations. Business objectives are the strategic bets that get you there. The CTO who masters this translation becomes indispensable.
Learn This Framework in Depth
If you want to experience this process firsthand and learn how to facilitate these conversations with your own C-Suite, join us at the next CTO Compass workshop. We work through real scenarios, practice the facilitation techniques, and build the artifacts you’ll take back to your organization.
Register at ctocompass.com/7ctos
What business objectives is your company betting on this year? If you can’t name three, you have work to do before your next planning session.
👏👏👏 excellent breakdown. couldn’t agree more with nearly every statement.