There’s a growing debate in the OKR community: Should Milestone Key Results be allowed at all?
Some argue that milestones are dangerous. Others believe they are necessary for execution. As with so many things in life, the truth is somewhere between these two extremes: some milestones are helpful, some are not.
And the fact is in my experience with 300+ organizations deploying OKRs: too many milestones (or even just a handful of “bad milestones”) can kill your OKR program. The real issue isn’t whether milestones are “allowed.” The issue is how to include milestones while preserving the shift from output-to-outcome that OKRs promise to deliver. It’s critical to recognize the difference between bad OKRs and good OKRs.
Let’s analyze this by taking a step back:
What Is a Milestone Key Result?
A milestone Key Result typically does not have a number or metric, but is intended to measure progress or movement toward the achievement of an objective.
Examples of “Bad Milestone KRs”:
Launch new website by June 30
Release Version 2.0
Hire Head of Marketing
Milestones like these tend to measure completion of tasks and activity, rather than results and business impact. Including such output-oriented milestones translates to poor OKR quality which is one of the major reasons people come to us for coaching support.
Key Results Should Measure Outcomes
OKRs are about focusing teams on outcomes that matter. Outcome-based Key Results look like:
Increase conversion rate from trial to paid user within 30 days from 2% to 4%
Reduce churn from 12% to 8%
Increase qualified pipeline by 30%
These metrics reflect behavior change, customer impact, or business performance, not just checking the box. But not all milestones are “bad.”
“What about Good Milestone Key Results?”
Milestones can be good! And this is especially true in early-stage or transformational initiatives.
Milestones are helpful when:
A capability does not yet exist
Foundational infrastructure must be built
A new process is being introduced and more time is needed to move a metric per se
The organization lacks baseline data
For example:
If a company has no CRM system,
Milestone KR: “Implement CRM by Q2 as measured by sales reps are tracking their accounts in the system and have their first set of opportunity reports”
may be a legitimate transitional Key Result.
Why?
Because without that capability, you cannot yet measure sales pipeline growth accurately. And, the KR includes the magic words “as measured by” which allows the KR to be clearly defined and not subject to opinion.
In these situations, milestones act as bridges to outcome-based measurement as they are moving a bit closer to value rather than measuring work effort.
The real problem
So, the real problem is not using milestones. The real problem is overusing them, and never evolving beyond them.
When every Key Result looks like:
Launch feature X
Hire role X
Complete project X
Publish report X
You no longer have outcome-driven OKRs. You have a structured project plan. But, as you probably already know by now, structured project plans do not create strategic focus. They create a bunch of work to do that may or may not lead to results.
From “Output Milestones” to Outcomes
In high-performing OKR programs, I often see a predictable evolution:
Stage 1: Milestone Heavy
Teams are new to OKRs. They feel more comfortable mostly using OKRs as yet another system for tracking deliverables like “feature launch by x date”.
Stage 2: Mixed
Some Key Results are milestone-based, others are outcome-based. Here we see more metric KRs like increase metrix A from x to y.
Stage 3: Outcome Driven (This is where you want to be)
Milestones move to project plans. Key Results measure real impact. The shift from Stage 1 to Stage 3 is a maturity journey. Strong OKR coaching accelerates this shift. And it’s hard! Even John Doerr included a KR in his book Measure What Matters that simply reads “produce a demo.” And it should be no surprise based on reading the analysis thus far, that some experts advise avoiding milestone key results entirely. On page seven of his OKRs book, John Doerr credits Marissa Mayer with her observation, “it’s not a key result unless it has a number.” However, in this same book, Doerr provides examples of milestone key results such as “develop a demo.” Marissa might not be happy with this key result!
As coaches, we help you transform draft key results that often look like a to-do list into refined key results that reflect measurable outcomes.
Here is a hypothetical OKRs coaching conversation to make this concrete:
Client: My key result is to develop a demo.
- Coach: What is the intended outcome of developing this demo? How will we know the demo is a success?
- Client: Well, the demo is a success if we can get positive customer feedback, but all I can commit to is developing the demo this quarter. It will be quite a stretch to get feedback.
- Coach: OK, what will be demo’d and how will we know it is developed?
- Client: We’re developing a demo for product X and our sales team decides if it’s developed and ready to be used. Ultimately, it is our customers that will decide if it’s a valuable product.
- Coach: Are you committing to presenting the demo to the sales team or to customers?
- Client: I can’t commit to showing it to customers. That is the decision of the sales team. I can commit to presenting the demo to our sales team.
By the way, in reviewing John Doerr’s book, Felipe Castro, an OKRs expert and friend of mine, notes: “Out of the 60 Key Results listed, 32 (53%) lack numbers. They include things such as “Create a retirement plan for all legacy technology,” and “Focus on hiring player managers/leaders.”
Why This Debate Matters
Organizations deploy OKRs to:
Increase focus
Improve alignment
Drive measurable progress
Move from output to outcome thinking
When Key Results drift into milestone territory, OKRs may lose their strategic power. Teams feel productive, but executives struggle to see measurable impact.
This is when leaders say:
“OKRs aren’t working.”
In reality, outcome measurement wasn’t working.
The Right Way to Use Milestones in OKRs
Milestones are best used:
As short-term transitional Key Results
In capability-building phases
In early implementation cycles
When baseline metrics do not yet exist
They should not:
Dominate every objective
Replace impact measurement
Become permanent fixtures
Serve as disguised task lists
High-performing teams separate:
Objectives (qualitative direction)
Key Results (measurable outcomes)
Projects and milestones (execution steps)
When these layers blur, confusion follows.
Final Thought: Are Milestones Helping or Killing Your OKRs?
Milestones are not the enemy. But if all your Key Results are milestones that look like outputs rather than outcomes, you don’t really even have functional OKRs yet. You have a delivery tracker. The goal is not to eliminate milestones entirely. The goal is to ensure milestone KRs mostly reflect outcomes and that most your KRs are actually metric KRs like “increase metrix A from x to y.”
Want Help Strengthening Your Key Results?
If you’re unsure whether your Key Results are milestone-heavy or outcome-driven, I’m happy to review them.
You can: Share a Key Result and I’ll provide feedback in the comments here. Or, better yet, send a note to Ben@OKRs.com and request a 1:1 consult to explore how I can help make your OKRs program add value on a fast track.
The shift from milestones that look like “output” to measurable KRs that reflect “outcomes” is one of the most important inflection points in an OKR program.
Let’s get it right!
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