Dreams with Deadlines

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.

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 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 for 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!

Relevant Links:
Follow Our Guest: Website | LinkedIn

Key Things Discussed

- What led to the decision to implement an OKR system at ChargeBee
- Reducing the number of priorities teams were focusing on and mapping all these out
- Getting company buy-in on implementing OKRs by having the leadership team paint the vision of what it is and why it’s important
- Learnings, experimentation, and refinements made since the program has been implemented

[00:02:54] About Lavanya’s origin story and how she came to stewarding objectives and key results (OKRs) at the billing and revenue management platform Chargebee.

[00:04:49] How and why OKRs play a pivotal operational role at Chargebee. 

[00:06:12] About prioritizing goals in a way that quickly aligns leadership and teams.

[00:06:59] The Chargebee journey has not been without stumbling blocks.

[00:08:24] Defining key results: What to communicate about and when.

[00:09:29] About the Why: Strategies for motivating teams to adopt OKR processes.

[00:12:19] How Chargebee articulated cultural values and objectives designed to resonate across the enterprise.

[00:13:39] About Chargebee’s key objectives: growth, value-add, an empathetic ethic, fast learning cycles.

[00:14:49] How outside OKR coaches helped define and respond to challenges.

[00:16:49] Learning Curve Lessons: The process takes time and people need prodding. 

[00:18:00] About experimentation and failing fast, which are part of the OKR journey.

[00:20:43] How Chargebee layers OKR and operations into quarter-end close-outs. 

[00:23:27] Rules of the Road: How to set your OKR process up for success.

[00:23:35] The role of internal OKR champions deployed across all business functions.

[00:25:54] How OKR champions are identified and recruited.

[00:27:57] About the cadence of Chargebee’s quarterly and annual OKR milestones.

[00:29:49] What occurs during monthly OKR reviews and how the tracking works.

[00:32:39] Rolling out recognition at the functional level.

[00:33:29] Special ways of honoring (and reinforcing) individual contributors.

[00:34:50] About blending OKR methodology with other performance metrics.  

[00:37:14] How OKRs differ by function and in a cross-functional context.

[00:38:19] What’s comes next in Chargebee’s evolving OKR journey.

[00:40:26] Quick-fire questions.

[00:43:07] Operational issues that are top of mind for Lavanya.

Relevant links:

Webinar featuring Lavanya: How Chargebee Uses OKRs to Inspire Collaboration and Manage Hypergrowth.

Follow Our Guest: LinkedIn

Alexis is a firm believer that change starts with the self. He is the author of two books: Changing Your Team From The Inside and I am a Software Engineer and I am in Charge.

We discuss how they’re making hybrid work work at Red Hat. He shares a wonderful technique called impact mapping which he uses to facilitate OKR setting sessions. And Alexis shares an example of how incentive structures can reinforce collaborative behaviour.

“I bumped into so many issues trying to help people work with each other where the root cause were their individual incentives.” – Alexis (30:17)

• (01:27) A day in the life of Alexis Monville
• (02:53) How Red Hat is supporting hybrid work
• (08:09) Culture on a plate
• (12:17) What is the most important thing right now?
• (16:00) Impact mapping OKRs
• (19:55) A not-so-great method to facilitate OKR creation
• (27:05) Customers get the answer to their question in their first call, 80% of the time
• (30:17) Individual incentives as the root cause of collaboration issues
• (31:18) An example of incentivising sales teams to collaborate
• (35:50) Quickfire questions

“...if OKRs are focused on our growth as a company, there's a second area that's equally critical and that's our business strength.”- Christine (20:47)

What You Will Learn in this Episode:

• (01:09) Christine on getting Groupon back to agile.
• (06:13) Why she is an advocate for other women in technology.
• (12:17) How COVID was a forcing function for Groupon to innovate.
• (15:45) Pre-requisites for working with OKRs.
• (17:41) How Groupon's OKR process works.
• (21:28) The three things OKRs cannot solve—organizational indecision, a lack of discipline, and a lack of muscle around estimating.
• (33:05) OKRs and portfolio management.
• (36:51) OKRs and day-to-day delivery.
• (39:20) The three places we need to measure performance: business growth, business strength, and personal development.
• (41:33) Christine answers quick fire questions.

Relevant Links:

• Website 
• LinkedIn
• Instagram
• Twitter
• Want Progress? Measure 
• OKRs do not measure human performance
• Abandoning your work: The key to unconventional and effective strategic planning 

“If you don’t bring OKRs into the regular management agenda, you will set it and forget it.”- Dan (20:47)

What You Will Learn in this Episode:

• (02:20) Dan on his interest in people’s organization plus the different career paths he’s undertaken.
• (03:35) Why he wrote his book Start less, Finish More, which is about strategic agility.
• (04:56) How to do more strategic thinking – begin with the end in mind rather than focusing on a to-do list. 
• (07:04) How to create a minimum viable strategy – creating holistic value for all your business’s stakeholders.  
• (10:37) The difference between the traditional mechanical business planning and today’s trying and scaling strategy.
• (13:48) The 5-steps of building strategic agility as outlined in his book; access, focus, commit, act, and learn. 
• (29:34) Overburdened matrix – not being agile and operating in silos plus how to use shared OKRs to cut across those silos.
• (33:09) Dan answers more quick-fire questions.

Relevant Links:

• Website: https://agile-strategies.com/
• LinkedIn: https://www.linkedin.com/in/montgomerydan/

“At that time, I never would have said that or thought that, but in hindsight, being in a band is like being in startups.” – Jeff [02:04]

What You Will Learn in this Episode:

• [01:31] Who Jeff is and what he’s all about
• [04:50] What Jeff means by “planning season”
• [08:19] A better way of planning
• [14:59] Adjusting the definition and borders of planning
• [16:00] The freedom of assumptions and hypotheses 
• [18:42] How Jeff defines value
• [20:55] Introducing friction instead of fuel
• [24:18] Why organizations should be thinking agilely
• [28:45] Organizational roadmaps and how they work with OKRs
• [34:50] What organizations do after OKRs and what that looks like 
• [38:17] Whether Jeff is considering putting out books 
• [39:12] Quickfire questions