Alas, poor strategic planning! I knew it well, dear reader – a process of infinite complexity, of most excellent frameworks. Business leaders find themselves at a crossroads: to OSKR or not to OSKR? That is the question that haunts many a sleepless CEO, wrestling with the ghost of traditional strategic planning past while gazing into the promise of a more agile future. (Note: I used to avoid Shakespeare and Strategic Planning like the plague. And now, I somehow learned to love ’em.)
Shakespeare? Strategic planning? Both often get a bad rap. Some founders need to avoid it altogether, convinced it’s a corporate relic too cumbersome for their fast-moving startup. Others overcomplicate it, turning what should be a guiding framework into an unwieldy binder of PowerPoint slides and vague aspirations. Somewhere between avoidance and paralysis lies the genius of a simple, practical framework: OSKR.
Yes, OSKR—Objectives, Strategies, and Key Results—”To OSKR or not to OSKR, that is the question” may not have graced the stage at the Globe –or any stage for that matter, but the timeless genius of this method proves its worth in the modern-day stage of startups.
Let’s break it down.
The Anatomy of OSKR
Objectives: What Matters Most
At its core, an objective is a north star—an ambitious yet achievable statement of what you aim to accomplish.
Good objectives are:
- Inspiring: They should make your team’s hearts beat a little faster.
- Concrete: Not “be the best” but “double our active user base in six months.”
- Aligned: Objectives connect directly to your startup’s mission and the outcomes you’re building toward.
For example: “Establish product-market fit in the enterprise market.”
Strategies: How You’ll Get There
Strategies answer the “how” behind your objectives. They’re the actions, approaches, or initiatives you’ll undertake to achieve your goals. Think of strategies as the main plot points of your story—the deliberate choices that propel you forward.
Great strategies are:
- Actionable: Clear steps your team can execute.
- Focused: Prioritized efforts, not a laundry list.
- Creative: Bold moves, not status quo.
For example: “Train the salesforce on ‘social selling’ to the enterprise market,” or “Hold a thought leadership roundtable event for prospects.”
Key Results: Measuring the Impact
Key results are the punctuation marks on your progress—the measurable outcomes that indicate whether your strategies are working. They provide clarity and accountability, answering the question: “How will we know we’re succeeding?”
The best key results are:
- Quantifiable: “Increase leads by X%” rather than “Do better marketing.”
- Time-Bound: Deadlines matter.
- Challenging but Realistic: A stretch goal with a foot in reality.
For example: “Secure 3 pilot customers from Fortune 1000 companies.” or “Reduce time-to-value (TTV) for enterprise customers by 20%.”
Why OSKR Works
OSKR works because it combines focus, clarity, and accountability. It forces founders and teams to ask the hard questions:
- What truly matters right now?
- What’s the best way to get there?
- How will we know we’re succeeding?
By boiling down strategy into its essential components, OSKR eliminates the noise and creates a shared understanding of what’s important. Done well, it’s a playbook for execution and a rallying cry for your team.
Avoiding OSKR Pitfalls
Even a simple framework like OSKR isn’t foolproof. Here’s what to watch out for:
- Confusing Strategies with Objectives: Objectives are “what,” and strategies are “how.” If they’re interchangeable, they’re not clear enough.
- Vague Key Results: Avoid metrics like “improve engagement.” Be specific—define what improvement looks like and how you’ll measure it.
- Too Many Priorities: The beauty of OSKR is its focus. Don’t dilute it with a dozen objectives. Choose the few that matter most.
Putting OSKR to Work
If you’ve been avoiding strategic planning or overcomplicating it, start small. Pick one objective for the next quarter. Define the strategies that will move you toward it and the key results that will tell you if you’re on track. Test it, tweak it, and build from there.
Your strategic plan doesn’t need to be perfect; it needs to be actionable. The brilliance of OSKR lies in its simplicity—a framework that’s easy to adopt, adapt, and amplify as your company grows.
Final Thoughts
To OSKR or not to OSKR? Much like Shakespeare’s works have been needlessly buried in a world of intimidation, we’ve managed to wrap strategic planning in layers of unnecessary complexity. Strip away the fancy consultancy speak in business and the academic jargon surrounding “the classics,” and you’ll find that both Shakespeare and strategic planning share a simplicity at their core: they’re both about human nature, clear choices, and decisive action.
If you’ve read this far and have participated in planning exercises prior, you may be asking –”isn’t it OKR? And why is there an “S” in there?!” The OKR framework is popular, but OSKR takes it further by adding the ‘how’—Strategies—to ensure your big objectives translate into actionable outcomes. If you’ve ever found yourself stuck between vision and execution, it’s time to try OSKR! Embrace the simplicity. Lean into the structure. And write your own great story. After all, as Shakespeare himself might say, “The readiness is all.”