Mastering OKRs: An Expert Q&A with Ben Lamont

TL;DR:

Ben Lamont’s core guidance: nail it before you scale it, document clear deployment parameters, train internal coaches and KR champions, embed alignment everywhere, run focused check‑ins (team weekly/bi‑weekly; one mid‑cycle multi‑team), and treat OKRs as a learning system (Reflect &
Reset), not a performance weeder. Executive sponsorship is best won by coaching them directly with OKR questions—not by pitching.

Q1. What’s the fastest path to scale an OKR program for ~1,500 people?

Ben: The word fastest worries me. Nail it before you scale it. If you roll out to 1,500 people at once, you’re experimenting on the whole company and risk failing at scale.

Start with deployment parameters (your FAQ): how many OKRs per team, whether you allow milestone KRs, why you’re doing OKRs, your template, scoring model, and whether KRs are stretch or commit. Get these nailed first.
Then training. Three layers:

• Basics workshop- how OKRs work; start drafting.
• Internal coach training- about 1 coach per 50 people and teach them how to keep quality high.
• KR Champion training-for the person whose name sits on the KR; teach them the role.

Realistically, scaling takes 6–12 months—two cycles minimum; a year is more realistic.

Q2. How do I quantify the ROI of OKRs in hard business terms?

Ben: You can’t. You can’t credibly attribute revenue growth or cost savings directly to OKRs. At Sears we saw a lift, but it looked like the general effect of setting goals, not something specific to OKRs. So don’t chase a phony ROI model. Look for qualitative value, clarity, prioritization, and better visibility.

Q3. What’s the ideal percentage of stretch OKRs, and how do we prevent sandbagging?

Ben: Use a stretch–target–commit framing. Write every KR at target (50/50 shot) and note what stretch and commit look like. Cultures vary, some write everything as stretch, others as commit, so document the standard in your FAQ to keep quality consistent across teams.

Q4. How do we validate that a stretch is truly a stretch across departments?

Ben: Make stretches team‑proposed, not top‑down. Define “stretch” explicitly, say 10–20% likelihood, or treat it as a “moonshot.” At quarter end, audit outcomes: if you hit almost none, your stretch was too high; if you hit almost all, you’re likely sandbagging.

Most importantly, run Reflect & Reset. Any time a stretch is achieved, tell the story of how it happened, what changed, and what surprised you, and apply those learnings to the next cycle.

Q5. How much time should we spend planning in Q1 vs later quarters?

Ben: The first cycle usually takes 4 weeks; with experience, aim for 2 weeks. Don’t over‑optimize the timeline,there’s a minimum viable planning time.

Also reconsider cadence: many teams move from 4 cycles/year to 3 because the extra planning overhead isn’t worth it. Be careful starting Q1 on Jan 1—holidays make it inefficient. Sometimes it’s smarter to start Feb 1. As you adopt Reflect & Reset, subsequent planning speeds up.

Q6. How do I address cross‑functional dependencies during OKR planning?

Ben: My “sixth mantra” is embed alignment into every aspect of your OKR program.
Tactics that work:

• Run cross‑functional training/workshops with dependent teams in the same room.
• Draft OKRs together; rotate members between teams.
• Use dual KR ownership (e.g., one business + one tech owner) to force healthy conversation
• Consider merged OKR teams (e.g., Sales+Marketing; CS+Support) when work is tightly coupled.
• Reflect alignment in your FAQ and examples—don’t write them from one function’s lens.

Done right, OKRs reduce silos instead of reinforcing them.

Q7. What are best practices for OKR review meetings (cadence + agenda)?

Ben: Two types:

1. Team check‑ins (weekly or bi‑weekly). Keep it crisp: for each KR, share current value, predicted score/confidence, blockers/risks, and next steps. Alternate full reviews with lighter weeks to avoid fatigue
2. Multi‑team check‑in (once mid‑cycle). Each team reports two items: the Big Win (celebrate progress) and the Big Learn (what’s not working and why). This keeps leadership updates engaging and useful.

Q8. How do we judge OKR program maturity beyond adoption rates?

Ben: Adoption ≠ maturity. Look for:

1. Objectives tied to strategy (OKRs aren’t the strategy—they express it).
2. Each objective has a clear Why and Why Now (educates, motivates, creates urgency).
3. A robust OKR FAQ that explains parameters and reflects your culture (e.g., “radical focus” → 1 objective, max 4 KRs).
4. Outcome‑based KRs instead of task lists
5. Pulse checks from leadership and from the rest of the company confirming OKRs add value (not overhead). In big orgs, expect pockets that love it and pockets that struggle, find and fix the latter.

Q9. When people aren’t performing well on OKRs, what’s the best intervention?

Ben: Don’t weaponize OKRs as a performance system. That creates fear and gaming. Instead, evaluate how KR champions manage: Did they build the right team? Keep cadence? Escalate risks early? Communicate clearly? Treat KR ownership as exposure and recognition, not a trap.

Q10. What’s the most effective way to train new joiners or teams new to OKRs?

Ben: The only way to learn OKRs is to do OKRs. But give new hires a quarter to observe. Include a short 1:1 onboarding about how OKRs work here and how they’ll contribute next cycle. If you’re onboarding in large batches, formal training helps; otherwise use targeted coaching.

Q11. What’s your advice for running effective OKR retrospectives?

Ben: Combine Reflect & Reset. Go KR‑by‑KR:

• Achieved? Yes / No (matter‑of‑fact; no judgment)
• What did we learn?
• Keep / Modify / Remove for next cycle

Leave the meeting with draft OKRs. For cross‑functional work, do joint sessions; having the “other team” in the room raises the bar and improves shared learning.

Q12. How do I get skeptical executives to actively sponsor (not just passively approve)?

Ben: Don’t pitch; coach them. Ask: What’s our most important objective? Why? How will we measure success? What’s the right time horizon? Once they experience that clarity, they usually flip and become champions. Experiencing OKRs beats reading about them.

Closing: Ben’s Quick Start idea + a challenge

We’re piloting a Quick Start OKR Program with Profit.co and OKRs.com: a small, pilot group, best practices from day one, and time‑to‑value in about a month. If you’re curious, reach out to explore.