Jacob Kaplan-Moss has written a post about one of the most stressful things
that can happen to you as a manager: when someone on your team is getting
along well with the team, apparently trying their best, but unable to do the
work. Incompetent,
but nice.

I have some relevant experience with this issue. On more than one occasion in
my career:

1. I have been this person, more than once. I have both resigned, and been
   fired, as a result.
2. I’ve been this person’s manager, and had to fire them after being unable to
   come up with a training plan that would allow them to improve.
3. I’ve been an individual contributor on a team with this person, trying to
   help them improve.

So I can speak to this issue from all angles, and I can confirm: it is
gut-wrenchingly awful no matter where you are in relation to it. It is social
stress in its purest form. Everyone I’ve been on some side of this dynamic
with is someone that I’d love to work with again. Including the managers who
fired me!

Perhaps most of all, since I am not on either side of an employer/employee
relationship right now¹, I have some emotional distance from this kind of
stress which allows me to write about it in a more detached way than others
with more recent and proximate experience.

As such, I’d like to share some advice, in the unfortunate event that you find
yourself in one of these positions and are trying to figure out what to do.

I’m going to speak from the perspective of the manager here, because that’s
where most of the responsibility for decision-making lies. If you’re a
teammate you probably need to wait for a manager to ask you to do something, if
you’re the underperformer here you’re probably already trying as hard as you
can to improve. But hopefully this reasoning process can help you understand
what the manager is trying to do here, and find the bits of the process you can
take some initiative to help with.

Step 0: Preliminaries

First let’s lay some ground rules.

1. Breathe. Maintaining an explicit focus on explicitly regulating your own
   mood is important, regardless of whether you’re the manager, teammate, or
   the underperformer.
2. Accept that this may be intractable. You’re going to do your best in this
   situation but you are probably choosing between bad options. Nevertheless
   you will need to make decisions as confidently and quickly as possible.
   Letting this situation drag on can be a recipe for misery.
3. You will need to do a retrospective.² Get ready to collect information as
   you go through the process to try to identify what happened in detail so you
   can analyze it later. If you are the hiring manager, that means that after
   you’ve got your self-compassion together and your equanimous professional
   mood locked in, you will also need to reflect on the fact that you probably
   fucked up here, and get ready to try to improve your own skills and
   processes so that you don’t end up this situation again.

I’m going to try to pick up where Jacob left off, and skip over the “easy”
parts of this process. As he puts it:

The proximate answer is fairly easy: you try to help them level up: pay for
classes, conferences, and/or books; connect them with mentors or coaches;
figure out if something’s in the way and remove the blocker. Sometimes folks
in this category just need to learn, and because they’re nice it’s easy to
give them a lot of support and runway to level up. Sometimes these are folks
with things going on in their lives outside work and they need some time (or
some leave) to focus on stuff that’s more important than work. Sometimes the
job has requirements that can be shifted or eased or dropped – you can match
the work to what the person’s good at. These situations aren’t always easy
but they are simple: figure out the problem and make a change.

Step 1: Figuring Out What’s Going On

There are different reasons why someone might underperform.

Possibility: The person is over-leveled.

This is rare. For the most part, pervasive under-leveling is more of a
problem in the industry. But, it does happen, and when it happens, what it
looks like is someone who is capable of doing some of the work that they’re
assigned, but getting stuck and panicking with more challenging or ambiguous
assignments.

Moreover, this particular organizational antipattern, the “nice but
incompetent” person, is more likely to be over-leveled, because if they’re
friendly and getting along with the team, then it’s likely they made a good
first impression and made the hiring committee want to go to bat for them as
well, and may have done them the “favor” of giving them a higher level. This
is something to consider in the retrospective.

Now, Jacob’s construction of this situation explicitly allows for “leveling
up”, but the sort of over-leveling that can be resolved wi