8 min read

đŸ« DORA, Ambiguity, Time Thieves, Human Skills, Conflict, Motivation, Bad Thrashing, Team Sizes: TMW #450

Do you use OKRs as metrics for individual performance management?
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Hello hello hello, it's Monday!

OKRs as Performance Metrics?

This week, the CTO Craft community dove into one of the most persistent head-scratchers in tech leadership: How do you connect OKRs to performance reviews without totally messing things up? The core of our chat really came down to balancing organisational alignment (what OKRs are for) with individual evaluation (what performance reviews are for).

A clear theme emerged: most of us agreed that a direct tie between hitting an OKR target and an individual's performance rating is a dangerous game. Why? Well, you've likely seen these possible behaviours:

  • Sandbagging: Engineers start setting less ambitious goals just to ensure a "win" on their review.
  • Misaligned Incentives: People start prioritising the easy-to-measure, short-term OKR tasks over crucial things like code quality, long-term stability, or helping another team who really needs it. Suddenly, technical debt looks shiny because it's not on the quarterly report...

Instead, the preferred strategy is to focus on team-level OKRs and then evaluate individuals on their competencies, behaviours, and commitment to helping the team succeed. If a team consistently falls short, that's your cue to dive in, but the resulting performance discussion centres on growth, skill gaps, and collaboration, not just hitting the number.

What do you think - are you using OKRs, and do you have a direct link to how you do performance evaluations? What's working, and what isn't?

That's it, on with the links! See you next Monday

Andy @ CTO Craft

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Reads of the Week

Announcing the 2025 DORA Report | Google Cloud Blog
The 2025 DORA Report, State of AI-Assisted Software Development, is now available to download.
Stop scoring everything: how to prioritize with strategy ‱ Jenny Wanger
Stop scoring everything. Prioritize with strategy by filtering ideas against goals to save time, improve accuracy, and focus your roadmap.

Leadership, Strategy & Business

Leading Through Ambiguity
Create Alignment, Not Illusion
The Ten Commandments of a Good CTO
The key principles a good tech executive should abide by to be successful in his role.
What Is Human-Centered Leadership? 6 Human Skills for the Future of Work
Unlock the 6 human skills that make leaders truly impactful like empathy, curiosity, and adaptability. These are your edge in an AI-driven world.
Five quick questions for better strategy
Or is it just all BS?

Culture, People & Teams

Two Things Can Be True
Sometimes it is necessary to criticize both sides in an argument and challenge each to consider the other.
The Value of Inclusion in Successful Leadership | The Leading Blog: A Leadership Blog
Leadership Now is a leading source for leadership development and analysis. We believe that anyone can make a difference by leading from where they are.
The Bowling Alley
One of my strongest beliefs as a leader is that I want to create an environment where everyone has the chance to excel. Over the years, the best way I’ve found to explain this is through the bowling alley analogy.
Our Favorite Management Tips on Motivating Your Team
Our Management Tip of the Day newsletter continues to be one of HBR’s most popular newsletters. Here are seven of our favorite tips on motivating people, covering topics like resetting a team that’s lost its spark, weaving kindness into the fabric of your team, helping employees feel seen, and more.
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Technology, Operations & Delivery

The real efficiency bottleneck isn’t planning, it’s thrash
Why planning aversion isn’t productive and how to find the sweet spot
It’s Not How Much AI, It’s How Well: A Practical Spectrum for Advanced AI Use | zach wills
I’ve been in a number of conversations over the past couple of years where I’ve shared an idea or a piece of work, and someone has chimed in with a question that’s meant to be a gotcha: “Cool. But how much of this was AI?” The question is often delivered with a subtle implication that [
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Team size and the Scrum master’s breaking point | Agile Alliance
Discover three lessons on why large Scrum teams lose focus, fracture dynamics, and weaken collaboration.
Agile Is Both Iterative and Incremental
Scrum, like other agile processes, is both iterative and incremental. Discover why neither is great alone, but together, they’re fantastic.

Stress, Wellbeing & Growth

The Yes Habit and the Five Thieves of Time
Discover how the “Yes Habit” invites five thieves of time into your team’s workflow. Learn to transform overcommitment into strategic boundaries that protect capacity and enable flow.
Burnout is Not Ambition, It’s Self-Neglect
Burnout wears a fancy mask these days — people call it “ambition.” But let’s be honest: working yourself into the ground isn’t ambition

How can I influence others without manipulating them? | Andi Roberts - Executive Coach | Leadership Trainer | Facilitator
How can I influence others without manipulating them? I explore five doors of influence: rationalising, asserting, negotiating, inspiring and bridging, to persuade with respect.
Ness Letters: When Freedom Feels Heavy
The Ness Letters are a weekly newsletter by Ness Labs, exploring how we can think better, work smarter, and live happier.

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Have an amazing week!

Andy