To level up, figure out what a far more capable version of you could have done
Let’s say you’re doing a retrospective on a hiring round which led to you hiring a candidate who didn’t work out. The most obvious question to ask is: what should you have done to prevent this at the point that you were making the offer? How could you have known that you should have hired your second-best candidate?
I claim that the most obvious question is not the most useful question.
Sure, if you’ve made a clear mistake, then you can correctly make an update and avoid the mistake in future. That’s great. But between you and your manager, you’re probably not making all that many clear (ex ante) mistakes.
So your options are:
Making a minor update to your approach. For example, you might slightly upweight a given characteristic in your next hiring round.
Making an incorrect update to your approach. This update would have been better in the particular case you’re thinking about, but for future cases it will on average worsen your decision-making.
Not updating at all (and just concluding that you got unlucky).
As a result, in a case like this, you don’t actually learn much by thinking about how you could have improved your selection between Option A and Option B. Almost all of the valuable learning lies beyond that.
Instead, I think a better prompt for retrospectives is to imagine yourself as a total badass.
Ask yourself this question instead:
‘What would a dramatically more capable version of me have done?’
Importantly, the person you imagine should be a more competent version of you — not someone you admire with a completely different skillset and personality and without any flaws. This isn’t someone who’s stratospherically out of your league, but the person you’re striving to become over the next few years.
When I take this approach, I tend to notice that there are actually an enormous number of decision points where I could have done something differently, each of which could have caused the situation to go better.
Here’s an incomplete list of ways that a dramatically more capable you might have done better:
Mechanism 1: They saw more options at the final decision point
Instead of framing the hiring decision as ‘make an offer to Candidate A’ or ‘make an offer to Candidate B’, a more capable you might have: offered Candidate A a slightly different role that was better suited to her strengths; done a one-month trial; hired both people; asked the new employee to work on a particular project which they’re a strong fit for; or something else.
Mechanism 2: They set you up to have better options at the final decision point
The stronger version of you would more deeply understand what your team really needed from the new role. They would also have a clearer sense of what types of people were available in the hiring pool and how to appeal to them. As a result, their job ad and strategy for reaching out to people would have been stronger.
Mechanism 3: Their badassery gave them better options by default
Who you are — your skills, judgement, speed, reputation, relationships — shapes which options are actually available.
A more capable version of you would have had stronger candidates than these two trying to work with you.
Mechanism 4: They developed a clear ‘diagnosis and approach’ faster
A novice chess player in a complex situation needs to think ‘manually’.
‘If I move my bishop there, he could take it with the knight... but then I’d take back with my queen, and then he might move his rook to the open file, which would threaten my king… Is my king safe enough?... ’
Similarly, as a junior doctor, when considering a patient’s symptoms, I would have to manually think through all the options before arriving at a diagnosis. Experienced physicians and grandmasters, on the other hand, have such sophisticated mental representations that they’re able to mentally move much faster: they just have a sense that that bishop move is wrong, or this diagnostic pathway is more promising. They don’t need to think through the options as explicitly. Using this skill, experienced doctors can ask the right questions to navigate to the diagnosis, and grandmasters can quickly make strong moves.
In the hiring situation, a more competent you would have understood the job requirements, created a strategy, and considered candidates faster and more instinctively, allowing them to complete the whole process faster.
Unfortunately, for this effect to happen, you need to ‘get the reps in’ - do something, reflect on it, and repeat. Fortunately, for this to happen, you just need to ‘get the reps in’.
(H/t Peak for this mental model.)
Mechanism 5: They built infrastructure that allowed them to move faster
Maybe a consulting arrangement for your prospective hire was a good idea in principle, but in practice it would have taken three weeks for you to set up — figuring out the contract, the rate, the scope, the review timeline. A more experienced you might have drafted template contracts, scoped consulting work, and had rates approved before, so it would have taken them only two days.
Maybe you would have ideally gone to a conference where you could have met a standout candidate. A more capable you might have created a pipeline-focused recruiting team for your organisation, so that person would be in your pipeline already.
Competent people build the infrastructure that makes options cheap enough to deploy that they become real options.
Mechanism 6: They had more and better information at the decision point
For example, their work test better distinguished the top two candidates, or they knew to drill down into something a candidate mentioned in an interview.
How to relate to this emotionally
When I do a retrospective which only focuses on a particular choice point, it feels very unsatisfying. It feels like it’s really hard to make things go better in future — I struggle to draw out lessons which will really improve my performance. This ‘more capable me’ frame, on the other hand, generates interest and curiosity for me.
The orientation is something like: I understand I’m ~never doing anything perfectly, but that’s ok. I’m navigating super complex choice points, doing a pretty good job, and learning along the way about how to do better. Also, there’s just so much to learn, and so many processes that could be better. How exciting!
Among people I’ve worked with closely, the most remarkable example of this is Niel, the CEO of 80,000 Hours.
He understands in his bones that he’s making mistakes all the time, but his instinctive reaction to feedback is rarely defensive.
Each time he learns about a specific way he fell short, he’s curious to understand what happened and how he can improve — and after over a decade of having that attitude, it seems like the guy has become good at approximately everything.