It’s Sunday evening. Tomorrow morning your leadership team is sitting down for quarterly OKR planning. You open a blank document and stare at the cursor. What should your team’s objectives be for next quarter?
You think about what went wrong last quarter. You remember a few customer complaints. You recall something the CEO mentioned in an all-hands three weeks ago. You write down two objectives that sound reasonable, wordsmith them for twenty minutes, and call it done.
Those objectives are almost certainly mediocre. Not because you’re bad at strategy, but because you just tried to compress three months of organizational learning into twenty minutes of rushed thinking.
The worst objective is the one you write the evening before OKR planning.
The Problem with Quarterly Brainstorming
Most organizations treat OKR planning as a discrete event: block half a day, gather the team, brainstorm objectives, debate priorities, leave with a plan. It feels productive. It’s also fundamentally flawed.
Here’s why: the best objectives come from pattern recognition, not brainstorming. They emerge from noticing recurring customer pain points over weeks, from observing what’s blocking your team repeatedly, from spotting a market shift that hasn’t fully materialized yet.
Pattern recognition requires time and accumulated observations. A brainstorming session asks you to synthesize months of information in real time, under the pressure of a room full of people and a meeting that ends at noon. The result is objectives based on whatever’s top of mind — which is usually the most recent or the most dramatic thing that happened, not the most important.
Research by cognitive psychologist Daniel Kahneman shows that humans are subject to “availability bias” — we overweight information that’s easy to recall. In a brainstorming session, that means last week’s fire drill gets disproportionate attention while the slow, systemic issue that’s been quietly eroding customer satisfaction for six months gets overlooked.
The Objective Backlog
The solution is surprisingly simple: maintain an ongoing backlog of potential objectives at both company and team level.
An objective backlog is exactly what it sounds like — a living collection of candidate objectives that are captured throughout the quarter, long before planning day arrives. It’s the strategic equivalent of a task backlog: a place to capture ideas when they surface, evaluate them over time, and select from them when the moment comes to commit.
How It Works
Throughout the quarter, anyone can add candidate objectives. A customer success manager notices three enterprise clients requesting the same integration — they add a candidate objective: “Our platform integrates seamlessly with the tools enterprise teams already use.” An engineer realizes the deployment pipeline is causing two days of overhead every release — they add: “Our deployment process is fast and reliable enough that shipping is a non-event.”
Each candidate captures context, not just a title. Why does this matter? What triggered the idea? What evidence supports it? How urgent is it? This context is crucial because by the time planning day arrives, the person who added the objective might not remember why it felt important — or might not be in the room.
The backlog is regularly groomed. Once a month or every few weeks, the team reviews the backlog briefly. Are these still relevant? Has anything changed? Can any be combined? Should any be promoted to “high priority” based on accumulating evidence? This grooming takes 20-30 minutes and keeps the backlog healthy.
At planning time, you select — not create. When the quarterly OKR planning session arrives, you don’t start from a blank page. You start from a curated list of objectives that have been collected, discussed, and prioritized over the past 12 weeks. The planning session becomes about choosing and committing, not brainstorming and debating.
Company-Level Backlog
The company objective backlog is owned by the leadership team but fed by the entire organization.
Sources of company-level candidate objectives:
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Customer feedback patterns. Not individual complaints, but recurring themes across multiple customers over time. When the same friction point appears in five different customer conversations across three months, that’s a signal.
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Market observations. A competitor launched a feature that’s gaining traction. A new regulation is approaching. A technology shift is opening new possibilities. These observations rarely warrant immediate action but deserve to be captured for quarterly consideration.
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Internal friction. Cross-team coordination is consistently slow. A particular process creates bottlenecks every sprint. Engineering and product disagree about quality standards. These organizational challenges often deserve strategic attention but get lost in tactical firefighting.
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Data trends. Churn is creeping up by 0.5% per month. Activation rates for a new feature are below expectations. Revenue per customer is declining in a specific segment. Trend data is easy to ignore in real time but powerful when reviewed in aggregate.
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Strategic opportunities. A partnership possibility. A new market segment showing interest. A technology that could transform a core workflow. These deserve exploration and might become objectives.
The leadership team doesn’t need to evaluate every candidate when it’s added. The value is in capture — getting the observation out of someone’s head and into a shared space where it can accumulate alongside other signals.
When quarterly planning arrives, the leadership team reviews the backlog and asks: “Given everything we’ve observed this quarter, what are the 2-3 most important things we need to achieve next quarter?” The answer is informed by weeks of accumulated evidence, not a single brainstorming session.
Team-Level Backlog
Team-level objective backlogs follow the same principle but are closer to the work.
Sources of team-level candidate objectives:
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Sprint retrospectives. Every retro surfaces things the team wants to improve. Most are tactical and belong on the task backlog. But some are strategic: “We keep shipping features without proper documentation” or “Our test coverage is too low to move fast confidently.” These are candidate objectives.
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Weekly planning observations. When the team consistently can’t fit important work into the week because of overhead or technical debt, that pattern suggests a potential objective.
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Cross-team feedback. When another team repeatedly struggles with your team’s API, documentation, or response time, that’s a signal worth capturing.
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Individual observations. A team member attends a conference and sees an approach that could transform the team’s workflow. A new hire with fresh eyes notices an inefficiency everyone else has normalized.
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Unfinished objectives. Not every objective is achieved in a single quarter. Objectives that were partially achieved or missed entirely don’t just disappear — they go back into the backlog for re-evaluation. Maybe the objective was right but the timing was wrong. Maybe it needs to be reframed. Maybe it’s no longer relevant.
The Prioritize View for Objectives
Just like tasks, candidate objectives benefit from prioritization before planning day. Not all candidates are equal, and the Eisenhower Matrix applies here too:
Urgent and Important: Market shifts or competitive threats that demand a strategic response next quarter. Regulatory requirements with approaching deadlines. Customer pain points that are causing measurable churn.
Important but Not Urgent: Platform reliability improvements. Team capability building. Process optimization. Strategic positioning for a market shift that’s 6-12 months away. These are the objectives that matter most but are easiest to defer quarter after quarter.
Urgent but Not Important: Requests from stakeholders that feel pressing but don’t align with company strategy. Competitive reactions that would distract from your own roadmap.
Not Urgent, Not Important: Nice-to-have improvements. Vanity metrics. Projects that sound exciting but don’t connect to meaningful outcomes.
When planning day arrives and the team is choosing from a prioritized backlog, the conversation shifts from “what should we do?” to “are we choosing from the right quadrant?” It’s much easier to make good decisions when the options are already laid out and evaluated.
Why This Changes Everything About Planning Day
Organizations that maintain objective backlogs report dramatically different planning sessions:
Planning is faster. Instead of spending the first two hours brainstorming and debating what to work on, the team reviews a curated list of 8-15 candidates that have already been discussed and prioritized. The session focuses on trade-offs and commitments.
Objectives are higher quality. A candidate that’s been in the backlog for two months, with context notes from three different team members and evidence from multiple data sources, is inherently stronger than one brainstormed in a meeting.
Fewer surprises. When the leadership team arrives at planning with an objective the rest of the organization has never heard of, it creates resistance and confusion. A backlog that’s visible to the team means objectives have been socialized long before anyone has to commit to them.
Better alignment. Teams can review the company-level backlog before planning. They arrive at their own planning session already thinking about how their work connects to likely company objectives — not retrofitting connections after the fact.
Reduced politics. When objectives emerge from documented observations and evidence over time, decisions feel more data-driven and less like whoever argues loudest in the room wins.
Building the Habit
Starting an objective backlog doesn’t require a new process or tool. It requires a habit: when you notice something that might be a strategic priority, write it down.
Week 1-4: Start a simple backlog. After each significant meeting, customer call, or retrospective, spend two minutes asking: “Did anything come up that might be a strategic priority for next quarter?” If yes, add it to the backlog with a sentence of context.
Week 5-8: Review the backlog as a team. In a 20-minute session, look at what’s accumulated. Group similar items. Note which themes keep recurring — that’s the signal.
Week 9-12: Prioritize candidates. As planning day approaches, apply the Eisenhower Matrix to your backlog. Which candidates are important? Which are urgent? Which are both? This prioritization makes planning day dramatically more productive.
Planning day: Select from your prioritized backlog. Define key results for the objectives you commit to. Return non-selected candidates to the backlog for next quarter’s consideration.
The Compounding Effect
The first quarter with a backlog will feel slightly better than brainstorming — you’ll have more candidates and better context. The real payoff comes in quarter two and beyond.
Objectives that weren’t selected don’t disappear. They accumulate evidence. The candidate that seemed marginal in Q1 might have five more supporting data points by Q2 planning. The pattern that one person noticed becomes a theme that the whole team recognizes.
Over time, the backlog becomes your organization’s strategic memory — a running record of observations, opportunities, and challenges that might otherwise be forgotten between planning sessions.
And when planning day arrives, instead of staring at a blank page on a Sunday evening, you open a well-maintained backlog full of thoughtfully captured, thoroughly discussed, carefully prioritized candidate objectives.
That’s when OKR planning stops being a stressful brainstorming exercise and becomes what it should be: a confident, informed commitment to what matters most.
