The LEAD Series | Episode 2 of 4: Engage
One article for each pillar of the LEAD framework: Link, Engage, Align and Deliver.
TL;DR: An OKR planning session decides who owns the quarter. When leadership arrives with the team’s objectives already written, the team spends the session polishing someone else’s draft and treats the result as leadership’s goals by week three. Run the session so the team writes its own objectives and key results inside the company’s priorities, and give leadership the job of pressure-testing them hard. The session takes about 90 minutes of team time plus one or two review rounds, and it is the cheapest ownership you will ever buy.
What is an OKR planning session? An OKR planning session is the meeting where a team turns the company’s strategic priorities into its own objectives and key results for the coming cycle. A good one ends with the team holding a draft it wrote and can defend. Leadership supplies the context beforehand and the hard questions afterwards, and stays out of the drafting.
The slide deck that shows up already finished
Planning season has a familiar shape in the rollouts I get asked to look at. Over a long weekend or a holiday break, a senior leader writes every team’s objectives. The writing is good. Nobody knows the strategy better than that leader, and the drafts show it.
In January the team sees those objectives for the first time on a slide. People nod and ask two clarifying questions about scope. Somebody offers to “tweak the wording.” By week three, the OKR doc is open in nobody’s browser, and when a customer escalation lands in week eight, the OKR work is the first thing to slide.
Everyone in that room was doing their job. They were handed a finished answer and asked for feedback, and feedback on a finished answer is editing. The thinking that produces commitment already happened, in the leader’s kitchen, without them.
The fix sits in how you run the OKR planning session itself.
Why the team has to hold the pen in an OKR planning session
There are two reasons to hand the team the pen, and the second one gets less airtime.
The first is ground truth. People who run a function every day know things a leadership team writing on a whiteboard does not: which process breaks on Thursdays, which customer segment started churning in August, which dependency on another team has been stuck since spring. That knowledge belongs inside the objective. A draft written without it reads, to the team, as out of touch, and they are frequently right.
The second is ownership. People value what they helped build. Researchers at Harvard Business School documented a version of this in lab studies they called the IKEA effect: participants who assembled a product themselves valued it well above an identical one assembled for them, and the effect disappeared when they didn’t finish the build. The studies used flat-pack boxes and origami, so I read them as a clue about goals and leave the proof to your own planning room. It fits what I see. A team that finished writing its objective defends it in week eight, and a team that edited a pre-draft calls it “the one leadership gave us.”
There’s a context problem running underneath both. In a study of 124 organizations published in MIT Sloan Management Review, only 28% of the executives and middle managers responsible for executing strategy could name three of their company’s strategic priorities. The steepest drop came between the top team and their direct reports. An OKR planning session is the moment to close that gap, and the team can’t write good objectives against priorities it can’t name.
What leadership brings and what the team brings
Bottom-up OKRs still need leadership in the room. The work splits.
| Leadership brings | The team brings |
|---|---|
| The company’s strategic priorities and company-level objectives | What changed in the team’s own situation since last cycle |
| Cross-team dependencies leadership can see from above | A read on capacity and what’s feasible in their domain |
| Hard questions: why now, and what changes if this slips a quarter | Proposed objectives and key results |
| Final approval, a send-back with specifics, or a decision to drop | A defense of the proposal under pressure |
Both columns are active work. Leadership’s column is also easier to do badly, which is where the next section comes in.
How to run an OKR planning session in five steps
This agenda assumes a team of five to ten people. For a larger group, run it with team leads first and have each lead repeat the structure with their own team.
- Send the context a week ahead. Share the company’s strategic priorities and the company-level objectives with the whole team, and ask each person to arrive with two or three objectives they think the team should own next cycle. Nobody shows up cold, so the OKR planning session is spent on synthesis. If the pile of ideas runs long, the free OKR prioritization matrix helps people score their own before they arrive.
- Open with what changed (20 minutes). Have the team list what shifted since last cycle: a strength they can build on, a weakness that surfaced in the numbers, an opportunity or threat outside the team. Force-rank the top few and stop at 20 minutes.
- Pick the anchors (20 minutes). Walk through the six anchors from the LEAD framework and ask which ones need an objective this cycle. Settle on one or two. Every objective that leaves the room has to link to at least one anchor, or it’s an Orphan.
- Draft the objectives together (40 minutes). One person holds the pen on a shared doc and everyone else proposes language. Disagreements get argued out in the room while the draft is still soft. Leadership stays out of this part, even when they’re in the building.
- Run the why-now test (10 minutes). For each draft objective, ask “why this cycle?” and “to what end?” Any objective with a fuzzy answer to either stays open for another round.
Key results come after the objectives are approved, drafted by the same team and held to the same rule. If the team is new to writing them, our guide on how to write OKRs your team will care about covers the outcome-versus-activity test in detail.
If you want the full Engage pillar in one place, with the self-assessment we use to find where a program is weakest, the LEAD Toolkit has it.
What should a leader do when the team’s draft is weaker than theirs?
Ask a question. Rewriting it hands the work back to you.
This is the hardest behaviour change in bottom-up planning, and I’d rather name it than pretend it’s easy. A VP who has spent a career being rewarded for deciding and directing now watches a team produce a draft that’s softer than the version in their head. Taking the pen back would cost about 30 minutes. It would also cost a quarter of ownership. Part of what makes this hard is that doing the work well and developing other people to do it well are two different skills. Leaders who were promoted for being excellent doers feel the pull to step back in most strongly, and the review round is where that habit shows up.
A question keeps the pen with the team and sharpens the draft at the same time. Phrases that work in the review round:
- “What’s the outcome you’re trying to cause here?”
- “What would have to be true for this objective to be hit?”
- “Why this anchor over the other one you listed?”
Send-backs are healthy. When a team’s first proposal clears review with no changes, I’d suspect the review before I’d praise the proposal. Two or three rounds is a normal pace for a team doing this for the first time. The payoff builds across cycles. Each question you ask in the review round is a small piece of coaching, and a team that has heard “what’s the outcome you’re trying to cause?” for three quarters starts asking it of itself. Its first drafts get sharper, and that habit of thinking critically and strategically carries into the rest of its work.
Disagreement belongs in the OKR planning session as well. A room where everyone agreed with everything was a presentation. To draw out the objections people are holding back, try “What’s the strongest argument against this objective?” or “Who isn’t bought in on this one? Say it now, while we can still change it.” A team that can’t push back on an OKR in the room will drift away from it by week three, and the pushback you hear in planning is the engagement you were hoping for.
A team that can’t push back on an OKR in the room will drift away from it by week three, and the pushback you hear in planning is the engagement you were hoping for.
Signs your OKR planning session produced real ownership
You won’t know for certain until mid-cycle, when the work gets hard. A few signals show up early:
- Team members proposed their own language during drafting, well beyond small edits to a shared starting point.
- Someone argued a key result target was too low, and someone else argued it was too high.
- The team changed an objective substantially during the session.
- In the first two check-ins, people refer to the objectives in their own words without opening the doc.
The warning signs look like a room that agreed with everything and let vague objectives through without sharpening them. When you see those, the recovery move is a short re-planning conversation in week two, while there’s still time to let the team rewrite what it didn’t write.
Running an OKR planning session across a whole organization
A VP of Strategy runs twelve of these, or forty, in the same three weeks, and the temptation to standardize by pre-drafting comes back at scale.
Standardize the structure and leave the content to each team. Every team works from one pre-read and one agenda, with the anchor list and the review questions identical across the org. What each team writes stays theirs. The consistency you want across the org comes from every objective linking to a named company priority, which you can check in the review round without writing a word of it yourself.
Two practical moves help here. Stagger the sessions so leadership isn’t reviewing forty drafts in one afternoon, and name one person per review round whose only job is spotting where two teams’ objectives depend on each other. Those dependencies are far cheaper to catch in planning than in week seven, when one team is waiting on work the other team never put in its plan.
I’ll add one honest caveat. A well-run OKR planning session is one habit inside a larger practice. It buys you ownership at the start of the cycle. Keeping that ownership alive depends on what happens every Wednesday afterwards, and on leadership protecting the time the work needs. If the rollout is already meeting resistance, our post on rolling out OKRs to a team that resists change picks up from there.
Frequently asked questions
How long should an OKR planning session take?
Plan on about 90 minutes of team time for the session, with a week of preparation beforehand and one or two review rounds with leadership afterwards. The review rounds can happen asynchronously on a shared doc. A team doing bottom-up planning for the first time will need the extra round, and a team in its third or fourth cycle moves faster.
Should leadership attend the OKR planning session?
Leadership should attend the review round and stay out of the drafting. When a senior leader sits in on the drafting, the team starts writing for that person’s approval and the draft shifts toward what they think the leader wants. If the leader has to be in the room, give them one job: answering questions about the strategy when the team asks.
What if the team’s objectives don’t match the company strategy?
That’s what the anchor step and the review round are for. Every objective has to link to at least one of the six anchors, and advancing a strategic priority is the first of them. When a team proposes something that doesn’t connect, send it back with the specific priority it should serve and ask the team to redraft. Writing it for them undoes the ownership you ran the session to build.
Are bottom-up OKRs slower than top-down OKRs?
Bottom-up planning adds about a week of calendar time up front for the review rounds. It saves time later, because a team that wrote its objectives doesn’t need to be re-sold on them at week six. Top-down planning finishes faster and then spends the quarter paying for it in check-ins where nobody owns the number.
The LEAD Toolkit: Free Download
The LEAD Toolkit covers all four pillars of the LEAD framework, including the Engage pillar this post draws on, and includes the twenty-question self-assessment we use to find where an OKR program is weakest. It’s built for leaders running OKRs without a coach in the room.
If your next planning cycle is already on the calendar and you’d like a second set of eyes on the agenda, we’re glad to talk it through.
