How to write your Career OKRs
Free from the problems of 'other people' here's some OKRs that might actually be useful. And a human prompt to make them happen.
I love the idea of OKRs, but when I've experienced them in practice within an organisation all too often they crumble. And 99% of the time it's for one reason: other people.
It's 'other people' who kick against the whole idea of OKR's because 'we don't do that here' or 'we tried it and it didn't work'. 'Other people' argue about whether this one is actually an 'objective' or a 'key result' and who say 'isn't that too ambitous?' or 'it's not ambitious enough'. And what about all these KPIs that we're reporting on every month?
And all this before the joy of actually tracking their status, let alone acting on it .
But here's the good news. When you're writing OKRs for your career, there are no 'other people'.
You are the primary stakeholder, CEO, CFO, CPO and CMO of your career, so you can basically write what you want, how you want it.
The only criteria is that you do it in a way that is meaningful and useful for you.
Ah - but how to do that?
In the background, I've been working on a GPT that will do it for you (more on that some other time). To do that, I've had to create a system prompt.
Reading it back, I realised that with a few tweaks, that would actually make a pretty good human prompt. Given that 'The Hot new programming language is now English' - and we are pretty good English interpretation machines..that's hardly surprising.
So right here, right now (to quote HRH Lord Fatboy of Slim) here is a human read-able, and hopefully actionable prompt for you to create some career OKRs.
The Career OKR Prompt
CONTEXT: You are a product professional who loves their job but feels frustrated by their career progression. You want to set career OKRs to ensure you're giving as much systematic attention to your career development as you do to your day-to-day work.
PREREQUISITES: Before setting OKRs, you must have taken stock of where you stand and identified your highest-priority career challenges. If you haven't done this analysis, stop here and do it first. (I can recommend the Vital 9 framework for this, but any systematic assessment will work.)
IMPORTANT: Don't just identify surface problems. Do a 5 whys analysis to get to root causes. For example:
- "I'm not getting promoted"
- Why? "I don't have the right experience"
- Why? "I'm not working on initiatives that demonstrate next-level capability"
- Why? "I haven't put myself forward for stretch projects"
- Why? "I don't know what projects are available"
- Why? "I don't have relationships with people who would offer these opportunities"
Root cause: Lack of internal network and visibility, not lack of capability.
CALIBRATING YOUR AMBITION: You are the only stakeholder that matters for these OKRs. Consider your motivational style:
- High-bar setters: You find ambitious, almost-unattainable goals motivating. You'll feel successful hitting 70% of a stretch target. Set bold objectives.
- Achievement seekers: You prefer the satisfaction of fully completing goals. You're motivated by ticking things off. Set challenging but achievable targets.
There's no right or wrong approach—only what works for your psychology.
EXPERIMENTATION OVER ASSUMPTION: If you're uncertain about the best path forward, build experiments into your OKRs rather than making big commitments. Test your assumptions with small actions first.
Instead of: "Build my professional network" Try: "Contact one new person in my target domain each week for three weeks, then assess what approach generates the most meaningful connections" (read 'Tiny Experiments' by Anne-Laure Le Cunff if you'd like to know more about this approach)
BALANCING OPTIMISING VS POSITIONING: Your career OKRs should include both "optimising" activities (improving your current situation) and "positioning" activities (lining you up for your next move and beyond).
- Optimising: Getting promoted in your current role, improving relationships with your team, mastering skills relevant to your current job, increasing your impact where you are now
- Positioning: Building external network, developing skills for target roles, creating visibility in new domains, establishing relationships at companies you might want to join
If you're setting 3 OKRs (and you can set between 1 - 3), the balance depends on your satisfaction with your current career direction:
- Happy with current trajectory: 2 optimising, 1 positioning
- Want to change direction: 1 optimising, 2 positioning
Even if you love your current role, you need some positioning activity. Even if you're desperate to leave, completely neglecting your current situation can damage your track record.
OKR STRUCTURE: Create 1-3 Objectives . (Don't feel a need to create three if one will do just fine for you). Each should have 1-3 Key Results. Make them specific, time-bound, and measurable where possible.
Remember: these are for you, not your boss.
SAMPLE CAREER OKRS:
These are examples..and not all for the same person! (P = Positioning / O = Optimising)
Objective 1 (P): Build the market visibility I need for senior product roles
- KR1: Try doing 3 reactions; 2 comments; and 1 professional post on LinkedIn twice a week for 1 month from tomorrrow.
- KR2: Attend at least 2 industry events per month for the next three months - speak with at least three new people at each one.
- KR3: Arrange coffee with one product leader at a company I'd love to work at within the next 30 days.
Objective 2 (O): Develop the strategic influence needed for promotion to Head of Product
- KR1: Lead one cross-functional initiative involving at least 3 departments by Q3
- KR2: Present quarterly product/ business review to CPO, including strategic recommendations
- KR3: Complete 360 feedback process with manager, peers, and reports to identify leadership gaps
Objective 3 (P): Test whether transitioning to B2B SaaS is the right move for my career
- KR1: Have 3 informational chats with B2B product leaders by end of March
- KR2: Attend 3 B2B focussed product events in the next three months
- KR3: Apply for 2 B2B roles to test market reception (even if not actively looking to move)
Objective 4 (P): Establish financial foundation for future career flexibility
- KR1: Increase emergency fund to 6 months expenses by September
- KR2: Meet with financial adviser and create 5-year wealth-building plan
- KR3: Research and set up tax-advantaged investment accounts for equity compensation
OUTPUT: Write your career OKRs using the above framework. Be specific about timelines and success metrics. Focus on actions you can control rather than outcomes that depend entirely on others.
EXECUTION GUIDELINES
- Make them visible and unavoidable: eg: put them up on your wall/ have them as a pinned note in your Notes app.
- Review progress monthly (calendar block this now)
- Have an 'accountability partner' - friend (even better if they don't work in product), colleague, coach.
- Adjust Key Results if you learn something that changes your approach.
- If an experiment reveals a better path, pivot rather than stubbornly sticking to the original plan
And now, the little plug bit at the end..
I’m pretty much done on the beta testing and signing up early birds for the Vital 9. Thank you for everyone who took part, it’s given me clarity on what to focus on (something very different to what I started on). I’ll share more at the end of the summer!.
I do have a limited amount of capacity for 1:1 coaching for the next few months. If you’re interested just reply to this email with the phrase: ‘Right here, right now’.