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Hmmm.. the advice given here seems to open the door to a lot of biases. Why might you not "enthusiastically" rehire someone? It might not be for their fit to the role, their job performance, or any other important factor. It may just be...your enthusiasm. Which very often wanes with your personal prejudices.
> It may just be...your enthusiasm. Which very often wanes with your personal prejudices.

Isn't that the rub overall? The whole reason that it's easier to get a raise by jumping ship than it is to stick it out?

I don't think that tracks with my experience, not as a manager.

Consider this: I hate hiring. Most managers I know do. Interviews are contrived; you are making decisions that will impact both your company and their lives; if you get it wrong, you're going to have your team impacted and letting someone go for performance or behavioral reasons are even worse.

For every person I've worked with at any given place, I can tell you within 15 seconds that, if they re-applied a few years after they left, if I would hire them back. I can tell you yes or no and the interview would only be for purposes of leveling. (How have they grown, for example?)

I can tell you based on how I felt when I found out they were leaving. If they were the wrong fit for a team or role, then you get them into a role that fits them!

Now, I have people that I would conditionally hire. There is one former coworker that comes to mind: he's brilliant in some cultures but will quickly grow frustrated in others. However, given the right culture, I would enthusiastically hire him. (And he is self-aware enough to know that he needs the right culture - if he's being called for a reference check, he's probably aligned with that culture.)

I think you're saying that you would enthusiastically rehire everyone you ever hired? Not sure I'm getting the intended meaning
He's saying he can tell you yes or no within 15 seconds if a rehire was on the table.
Incredible how this obvious advice, of firing people who are not doing a good job, needs to be couched as deep insight and a mental trick (reframing it as rehiring) in order to get past the absurd levels of agreeableness among the wealthy, cosmopolitan people running companies these days.
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It's the highest signal question to ask in reference checks as well. It gives the reference an out to be honest and not feel like they're being disloyal. It's a very direct question that is hard to fudge without lying.

"I would rehire them in a heartbeat" = yes, "I have been trying to recruit them for months, you lucky bastard" = yes, "If the right role came up, I would certainly consider them" = no, "Uh.. yeah, I think" = no

What's interesting is that people with Charisma fit this bill better than people who are competent.
Exactly, every knows a company is run on good feelings from managers.
It's run by the people who are spending political capitol to get difficult things done instead of worrying if they'll be enthusiastically rehired.
What this misses is that you might be the problem.

I've worked at a startup where the exec team has turned over 100% multiple times. This advice would not surface that issue, it would perpetuate it.

If you are a leader, and you are having a problem with a report, you need to ask yourself first: is it them, or is it me? Emotionally hard to do.

Great advise. I'd go so far as to suggest asking yourself "am I the problem" in pretty much any conflict or struggle. The answer may usually be no, but asking the question can help avoid a lot of cognitive traps we all tend to fall into.
Is there some checklist for those who find this a daunting question?
As someone who has difficulty asking this question to themselves:

- Is anything I'm seeing similar to a previous effort that I under-performed in?

- Do my own expectations of success make sense if I weren't me? (would a random stranger agree with my goal criteria)

- How different (currently) is the other person's expectations of success? In my current role does it make sense (for the project/customer) to try to change those?

These are good. I've going to be difficult to make an exhaustive checklist as each of us will only have identified certain problems

To a large extent it's about trying to see the issue from the other person's eyes, which has two parts: try to remove your context, and try to understand their context.

Your context: it's easy to assume that someone else has the same information and motivations that you do, and understand the underlying strategy. But actually as a leader it's your responsibility to make sure all these are in place, one the one hand recruiting someone with the necessary background and motivations, and on the other making sure that they understand the strategy behind what the team needs to deliver and that the team shares and builds it knowledge. So look at all the things you are assuming - in the context of the problem - that they know or understand or are motivated by, and check whether they might be missing and what information, strategy, and incentives you might have failed to convey.

You also need to look at your own behavior from the perspective of someone who doesn't have your context. If you saw someone acting as you are, without knowing why, what would you think?

Then there is their context. They may come from a different cultural/class background. They might have different personal priorities. They may be at a different life stage. They may have less/more savings. They may need to take less/more risk. They may need different things as part of their career (for example, one boss I had assumed that 'working with famous person X' was a huge thing for me. Nope - well, it's cool and all but its not going on my CV, as an engineer. Whereas for a designer it's totally going on their CV).

All these things play into what information a person will have, what they find motivating, what they find reasonable, what understanding they will have about you and what you are saying/how you are acting.

Yes I just left a startup (resigned) where most of the tech leadership had been fired and rotated at least once, always with lots of complaints from the CTO about how "terrible" they were. I took his word for it the first two, but afterwards it became clear "it's you dude...", and left soon after.
Maybe I've always worked for little napoleons but in my experience a manager never thinks they are the problem.
What this also seems to miss that most startups have a limited budget and thus a limited talent pool. While your existing team members might not be an "enthusiastic yes", to the superstar prospects the startup isn't either.
I’ve found there’s a way to ask this question without assigning blame:

Hmm… how am I creating this situation?

It’s a more multi-dimensional exploration.

Often, we repeat experiences because there’s something we aren’t willing to face - about ourselves or how we relate to life.

It’s quite freeing to seek that out.

> if the position was open today and this person was available – with full knowledge of their strengths and weaknesses – would you enthusiastically offer them the job?

> I think enthusiastically is an important word in the question because it drives clarity. You can’t say maybe to that question. If there is any doubt, you have your answer.

> I would suspect that very few people would want to be at a place where their boss would not be excited about rehiring them. I sure wouldn’t.

Huh? This excludes 100% of all jobs to several significant digits. Most jobs aren't important enough that you need someone in them whose very presence brings joy to your otherwise dreary life. And almost no one is aspiring to fill their role that way.

This sounds great if you trust yourself to rehire someone better, reliably enough to cover for the friction of re-hiring and the collateral effect of firing on the morale of the rest of the team.

If you're likely to see a new candidate's strengths, but the incumbent's weaknesses, then they're cooked. If the other employees have a different perception of the situation than you do, then the morale hit is assured. I have a rule of thumb, that upon firing a well-liked, or even not-disliked employee, it takes about a year for morale within their team to recover.

The question could also be: "will you enthusiastically want to rehire them 6 months after they are let go?". It seems fairly common for C-level execs to have a limited understanding of what people actually do.