On How to Get your Team OKR-Ready


Natalie Webb headshot
Natalie Webb

CEO at Cloud Peak Enterprise Group, LLC

Episode notes

When it comes to anything in the realm of OKRs, there are few practitioners anywhere with the depth of expertise and insight Host Jenny Herald’s guest brings to this episode of Dreams with Deadlines.

Natalie Webb, owner at Cloud Peak Enterprise Group LLC, has worked with the full spectrum of process and change management methodologies. But nothing, she says, delivers results on par with the OKR programs she has helped roll out over the years at companies across sectors from Health Care to Aviation, Manufacturing to FinTech.

What you will learn

  • How to get executives onboard with the level of transparency associated with tracking and measuring performance and other indicators
  • What naysayers bring to the equation and how to open their minds, ease their fears and allay their concerns
  • Why it’s important to keep teams honest about reporting their outcomes from quarter to quarter – not just wasting everyone’s time with “serial cloning”
  • The cultural and financial effects to the bottom line when work and efficiencies are improved
  • Tips for establishing new Standard Operating Procedures and ingraining teams with the benefits of OKRs

Show notes

  • [00:02:25] Jumping Right In: Natalie starts off with a look at transparency on the OKR journey and how that sits with executives across the gamut of business sectors.
  • [00:04:34] Where workplace culture fits into the conversation about OKR adoption, especially in times of upheaval and when there’s a lack of alignment across leadership.
  • [00:06:31] Turning Naysayers Around: Natalie shares the case study of an executive whose resistance she was able to surmount by listening effectively, building trust and breaking the process into digestible, credible pieces.
  • [00:09:20] What’s top of mind strategically for companies riding the tide of economic uncertainty:
    • A “radical shift” from being understaffed and struggling to find quality hires to now enjoying an abundance of talented resources
    • A strong focus on high-quality, selective hiring with an emphasis on DEI
  • [00:13:10] About shifting efficiencies and maintaining revenue with fewer resources – both in terms of personnel and workplace tools.
  • [00:14:36] Inputs to Get to Outcomes: What it looks like to run KPIs and OKRs in tandem, leveraging their complementary nature and measurable results based on already ongoing performance metrics.
  • [00:17:05] Putting Serial Cloners on Notice: How Natalie audits and holds accountable leadership that phones in OKR results from quarter to quarter, undermining the hard work, collaboration and team efforts.
  • [00:20:22] Measuring the body of work for results and making course corrections in real time is critical to OKR success and requires foundational support, including: 
    • Linking directly to project plans
    • Tracking milestones
    • Creating transparency and visibility into processes 
    • Building humility into planning
  • [00:23:35] How OKRs can be deployed to create the cross-leadership alignment and team habituation that ensures sustained change across the enterprise:
    • Increased communication around goals and outcomes
    • Increased understanding of interdependencies and dependencies
    • Setting the stage for improved collaboration
    • Accountability as a tool to increase efficiencies
  • [00:27:11] Natalie’s best practices for enlisting executive leadership’s commitment to helping teams find the time to set, report and confer about OKRs and OKR progress: 
    • Create a streamlined, agile, one-stop-shop environment for all OKR processes
    • Integrate regular and easily accessible project reporting functions
    • Pause to assess – and celebrate – quarterly benchmarks, improved efficiencies/time savings and progress toward goals
  • [00:29:36] Making It Stick: Natalie shares two examples of environments (health care, lithium-battery manufacturing) where sustained adoption occurred not because of enforcement or coercion but because leadership championed – and teams witnessed – direct benefits, including:
    • Agility based on transparency
    • Timely risk identification and mitigation
    • Access to nimble course correction
    • Rapid, effective inter-departmental communication and collaboration
    • Time- and effort-saving efficiencies
    • Clarity and recognition around the value of and purpose behind the work
  • [00:35:19] Quick-Fire Questions for Natalie:
    • What’s your Dream with a Deadline? A legacy of having helped clients whose work is about making important contributions, effecting positive change, and touching lives. For instance, a hospice organization she works with in New York
    • What are some strategies you’ve seen organizations deploy that boost the success of OKRs? Be truthful and forthright in calling out inflated objective or key results – sooner, not later. Staying honest and authentic upfront saves time!
    • What advice would you give to an OKR champion trying to turn around naysayers? 
      • Listen to and validate the skeptic’s concerns or fears on an ongoing basis
      • Explain the purpose of the methodology and how it showcases bodies of work
      • Emphasize that nothing is carved in stone and agility is built-in
      • Figure out the key results and metrics that resonate and matter culturally
      • Accept that there will always be naysayers – some of them harder to win over than others

About our guest:

Natalie Webb headshot
Natalie Webb


Natalie Webb is an executive with 6+ years of OKR Expert experience and 15+ years’ experience in Global Consulting Engagements & Technical Leadership. She has led OKR implementations at 18+ global companies to include the framework, tools, facilitation of strategy sessions and 1000s of executive level coaching sessions.

Additional resources