A Chief People Officer’s Approach to OKRs


Brad Wilkins
Brad Wilkins

Chief People Officer currently at a Startup in “Stealth” Mode

Episode notes

Human relations leaders are uniquely positioned to leverage OKRs cross-functionally — an impact-driven approach that yields transformational benefits across the enterprise. This episode of Dreams With Deadlines features Bradford Wilkins, a visionary Chief People Officer who has successfully rolled out data-driven programs that have measured and optimized OKR initiatives executed by C-level leaders through teams from sales, marketing, logistics, product development, and beyond.

Key things discussed

  • How OKRs can shift company cultures towards more outcomes-based approaches – especially relevant for Covid-inspired distributed workers.
  • The difference between OKRs, KPIs, and their sometimes complementary goals.
  • How to infuse company-wide meetings and employee evaluations with OKR-oriented measures and priorities.
  • Deployment of CLEAR – Career Path, Learning Objectives, Expectations, Accountabilities & Rewards – in a sales context.
  • How leaders who are vulnerable to personal challenges set a tone that trickles down and encourages OKR adoption throughout the ranks.
  • Why creating an environment where it’s safe for employees to ask questions – and fail – is a key element to successful OKR implementation.
  • Tips and tactics for anyone getting ready to adopt an OKR approach.

What you will learn in this episode

  • [00:20] Growing up in a big, rambunctious family, Bradford realized early on that he was energized by two things: Making people happy and understanding how business works.
  • [02:25] Bradford defines the HR function and its multi-dimensional role in showcasing and aligning departments across the enterprise.
  • [03:30] About Bradford’s take on the freight industry and Loadsmart, a provider of digital solutions to manage industry logistics. As CPO, he was part of creating a powerful, scalable, synchronous clearinghouse for automating communications and industry flow.
  • [07:10] What it will mean for Loadsmart to provide an AI-driven platform that coordinates and connect not only shippers, who are the primary customers, but also carriers, ports, customs, warehouses — the many dispersed elements that have never before had access to shared data.
  • [10:00] Throughout his career and multiple engagements, Bradford has been building on OKRs that weren’t much more than KPIs when he started on the journey — a journey, he says, that never ends.
  • [12:00] Defining the core difference between an OKR and a KPI, based on the lens used and varying indicators.
  • [15:10] Bradford highlights the transformational impacts on company-wide meetings that focus cross-functionally and creatively to expand ideation and stretch goals.
  • [16:58] KPIs do have a place within organizations, particularly in areas where baseline goals are important for level-setting.
  • [17:42] About linking OKRs and evaluations, for Loadsmart a quarterly process based on four check-in questions focused on exceptionality.
  • [19:50] “Loadee” evals include results-focused OKR questions that flip the paradigm to emphasize effort and output rather than a check-the-box mentality.
  • [23:49] About CLEAR (Career Path, Learning Objectives, Expectations, Accountabilities & Rewards), an automated progression program that offers employees flexibility from quarter to quarter in how they pursue objective goals. Bradford shares examples from sales, where he recently rolled out a highly successful program.
  • [29:27] Accelerated by Covid, workplace culture is rebranding performance management to shift from a performative (long hours, butts in seats) mentality to an impact- and measures-based orientation.
  • [31:09] Ideation and expectations at the senior level in terms of how to bring OKR strategy to life, starting with the pyramid of progress:
    • At the individual level, it’s about initiatives and tasks and making progress towards long-term team objectives. Then measuring for key results.
    • Expectations can be set top-down, but individuals are empowered bottom-up to try things, fail fast, and drive initiatives autonomously.
    • Ideation comes into play as observation and opportunity-oriented rather than imposed problem-oriented solutions as a starting point.
  • [34:45] Testing ideation is a critical next step in successful OKR deployment:
    • Build tools (they can be fairly basic) to create evidence-based data analytics rather than blindly pursuing initiatives based on hearsay or intuition.
    • Test adoption and outcomes via KPIs by tracking things like revenue.
  • [37:25] Bradford explains how he once used the creation of a cricket league for employees in India as a strategic initiative (including data metrics) to drive corporate OKRs like employee engagement and productivity. It was a fun and popular way to get there!
  • [40:48] Why employees have to be empowered to fail in order to be successful.
  • [42:45] Bradford’s advice for how people managers should respond when employees fail? (Which they inevitably must …)
    • Whether an individual or a team: Do they have clarity as to what went wrong?
    • Be prepared to do a retrospective to uncover the reasons for derailments.
    • OKRs can be as critical for indicating what not to do as what to do.
    • Meet regularly to go over OKRs and identify what’s red, yellow, green – and why.
    • Is it psychologically safe for people to proactively raise a hand and get help?
    • Leadership should not shy away from being vulnerable. Humility and authenticity trickle down through the ranks in liberating ways.
  • [46:10] When it comes to OKRs, sales is a somewhat different animal. There are, however, great opportunities to partner and leverage in a marketing context.
  • (46:52] Quick-Fire Questions:
    • What’s your dream and, if you’ve got a deadline, what’s that? It’s changeable based on his evolving family life and the new dimensions it brings.
    • What do you appreciate most about your team? Their openness to trying new things, which is critical when rolling out unfamiliar, innovative initiatives.
    • What’s top of mind these days? Budget planning and performance.
    • No. 1 tip for launching new OKR initiatives?
      • Less is more! It’s much easier to measure quality through patient sequencing. It’s all about progress.
      • Are you developing metrics and milestones rather than “to do” lists?
      • When success is clearly defined and measurable, OKRs are lots of fun!

About Our Guest:

Brad Wilkins
Brad Wilkins

Chief People Officer currently at a Startup in “Stealth” Mode

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Brad has built and led people functions at hyper-growth and transformative companies across a wide array of industries.

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