On a Chief People Officer’s Approach to OKRs


Brad Wilkins headshot
Brad Wilkins

Chief People Officer at 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.

What you will learn

  • 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.

Show notes

  • [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 toward 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 headshot
Brad Wilkins

Chief People Officer

Brad Wilkins is the Chief People Officer at a startup currently in "Stealth" Mode. He is a practitioner and leader that built and led people functions at hyper-growth and transformative companies across a wide array of industries. Brad has managed teams globally including EMEA, APAC, LATAM and emerging markets.

Additional resources