You can run a textbook OKR planning process and still fail. I see that often when companies seek my help.
They have kickoff workshops, clean templates, alignment meetings, and neat grading rubrics. Everyone does their part, the calendar fills up, and yet nothing important changes. Priorities don’t shift. Tradeoffs aren’t made. The quarter ends, and the business looks the same.
What’s missing isn’t effort.
It’s substance and coherence.
Teams sweat the KR format and measurability while the objective itself stays thin. Departments write OKRs in parallel, and the end-to-end story breaks. Bullet points replace a narrative of cause and effect, and more.
If your OKRs don’t change what you shipped, how you sequenced work, or what you said no to this quarter or year, they are a ritual, not a strategic planning method. Here are five things that would turn your OKRs from an exercise into a real lever.

Content over structure
People love OKRs because they create structure. They feel like a simple fill-in-the-blanks template: write an objective, drop in a few KRs, done.
But the goal isn’t to fill the blanks. The goal is to fill them with the right things.
And that takes thinking, debate, and real research – all of which are not listed in the template, but you still need to do them.
Your words matter as much as your numbers, if not more. Make sure you have the right objectives and are going to measure the right things (hint: even if they are not measurable) before you dive into debating the specific number that you need to hit.
It’s tempting to focus on the format, especially with such a structured framework. But remember that the format isn’t going to get you anywhere, the essence is.
Connection over independence
Many companies set a few company-level OKRs and then unleash departments to write their own. That’s where things start to fail, and here’s why:
Suppose the company says “win enterprise.” Marketing optimizes for 1k-seat fintechs, product builds for 10k-seat telcos, and sales courts the public sector. Even a single sale becomes challenging because the leads arrive for a value that the product does not deliver, while pricing or enablement tells a different story altogether.
While OKRs are an operating system that scales infinitely, don’t rush there. Instead, create a solid hierarchy of OKRs: start with a few at the company level, then break them down – still at the company level – to what each would take to win. Only after 2-3 such levels you typically get to OKRs that are well-defined enough for each department to go and pursue them, and keep alignment intact.
Decisions over workarounds
Companies often show me lists of 20 OKRs. Even small startups show a dozen. That isn’t excellence, it’s indecision. The OKR template won’t force choices for you, but you still need to do that.
As a rule of thumb, have 2-5 OKRs at each level.
These levels are the way to convert these long lists into something that people can work with.
When you read those long lists carefully, they almost always collapse into a hierarchy: a few outcomes at the top, with drivers and enablers beneath them. That hierarchy matters. Embedding OKRs inside one another clarifies what is primary vs. supporting, which work comes first, and what gets dropped if capacity is tight. Promote the few objectives that truly move the business, demote the rest to child KRs or lower-level sub-OKRs, and send the leftovers to a backlog outside the plan.
If everything stays top-level, nothing is a decision. Fewer, sharper OKRs create real focus.
Story over bullet points
OKRs are not a checklist, they need to tell a story.
The story is about why you chose these few bets, and why now.
It should be able to explain why you think it would work (strategically, not technically), and how you are going to navigate all the way to success.
Your story should also include clear and explicit assumptions. So many times I have seen teams “agree” on something while in fact they were saying yes to what they had in their heads, not what the other person was thinking – because it was never said explicitly.
I often like to accompany major assumptions with a counter explanation: by saying that, we mean that we will not do X (if X is what other people expect).
A simple practice: narrate through the OKRs with explanations for each next sentence. It could look something like this: “To win [segment], we believe [assumption]. We considered the following alternatives, but chose to go with [objective A] because [explanation or assumption]. To make A possible, we must win these two fronts: [objective B] and [objective C]. If [risk], we will do [mitigation].”
If a new teammate cannot retell the logic in 60 seconds, you have bullets, not a story.
OKRs are not about filling the blanks, they are meant to help you craft your strategy. To do it well, you must go beyond the temptation to get the details right and focus on the bigger picture and the hard decisions first.





