"I know I'm failing him as a leader"

I think you are doing really great according to your actions and go further than a lot of managers I've experienced in my last 20 years in the IT-industry.

"..and what did you do to get things back on track?"

We once had this issue with a long-term intern in our company working on minor tasks of our flagship-product.

It seems that this junior is still uncomfortable in tackling tasks and acquiring tech-related knowledge by himself and maybe needs some assistant/co-worker on his side.

If your departments budget and internals allows for such, maybe you could pair him up with someone that builds up his skills, helps him when needed and oversees his progress.

But sometimes situations don't allow to take care of somebody like this all of the time, especially when you walked those extra miles for him already and that someone is refusing to colaborate on certain backlogged projects/features - then it's time for you to step up and explain to him that he was hired for being productive and not for bailing out whenever things become difficult.

There's one thing that seems to be missing in the steps you said you did:

Evaluate his skills, and based on that, what tasks he can do. If needed, if his skills include some that you're not proficient at, find other employees, senior ones whom you can trust, to evaluate his skill level.

Based on that, estimate whether there is a place for him at all, or not. Also, based on his skill level, identify the series of steps for improvement. After all, one cannot learn multiplication and division until he has first learned addition and subtraction. Find out what is the immediate next lesson he needs - that is, just one step above what he is capable of now.

It may happen that, after evaluating his current skills, you find him to be at a level too low to be useful - in which case you will have to make a decision, keep him and invest in training him... or let him go.

If you do decide to train him, make a reasonable plan step by step. It cannot be based just on whatever task is available; it has to start from his current skill level and then go one step at a time. Same as in a school, first the 1st grade, then the 2nd and so on - and only move him to the next grade of training after he has successfully passed the previous one, not in his opinion, but in opinion of an independent evaluator.

If even in that situation he does not advance, then for all intents and purposes, in the context of a business that needs to make profit, he is a black hole that will suck up any and all efforts and resources, and produce nothing.

A decision to not train him but let him go is also a valid one, in the context of a business.
You're not his parent, and you're not primarily his teacher either. If he wants help, he needs to do his part. If he is not willing to do his part, you cannot help him, and your primary duty is to the company, not to him.

I think you need to involve HR (am I really saying that? :-) ) in a formal review process.

A manipulator is at work here.

A few serious red flags here (and not your fault at all).

he'd tried to deliver the work package we'd agreed upon, but that he'd hit a dead end and was giving up.

That's not his choice. You agreed a goal and he can't just opt out (as an employee) when he feels like it. That's not something any organization can or will deal with.

This is where a formal process of review is needed. A formal goal must be set and reached. There's no "bail out" clause in these things.

And they do (eventually) lead to termination.

A few minutes later he appeared at my desk asking me to "give him something to do".

Tail wags dog.

I had a co-worker like this once and my conclusion was that she was a master at manipulating people. She faked a "can't do, too difficult" front, but a few times I noticed that when it suited her she was as quick witted and eager as anyone I'd ever met. The "can't do" front was convincing, but the end result was the same: she got an easy ride and no real responsibility.

This person you have may (that's may) be doing something similar. Whether it's conscious or sub-conscious - who knows?

I said I hadn't had time to process his email, but asked about whether he could start one of the other packages we'd spoken about. He said: "No, something else, please".

Again, he has you well trained, doesn't he?

No offense here, but I again see the traits of manipulation at work. You have all been conditioned to do this, I suspect quite deliberately.

We spent a few minutes looking through our backlog and identified something he was comfortable taking on. We agreed some goals, identified an approach, and he took it away.

Agreed goals mean no unilateral jumping overboard. But ...

This morning I get another email saying he's hit a dead end.

Seems a very common issue - maybe he needs glasses? :-) This is not how agreed goals with your boss work. Advice on technical issues you can ask for (within reason), jumping ship is not an option.

Note this is another trick of the manipulator: ask lots of questions and needs lots of help. Way, way, way more than anyone wants to deal with. People then start working around them to avoid the questions. It's a con.

I suggest someone who can help and he says he doesn't know how to contact that person. (They are in the company directory!)

Same as my former colleague. Tell her how to do a thing and somehow she could not manage (until it was something she wanted to do). I again think you are (all) being manipulated.

Note that this "worker" can be quite assertive when they want to jump ship or something else done their way, but contact someone that might leave them working on the project they now want to leave? Suddenly they're not assertive enough to do that but assertive enough to say they won't.

It's a con, IMO. You are all being manipulated.

Some more points.

The member who is struggling had a really great idea over the summer that enormously simplified one of our annual processes. I publicly recognized his contribution in one of our departmental meetings

So no problem with doing what he wanted to do. Time to do the work you want him to do and - no.

In comments you said:

Looking back, I feel like both he and I overestimated his skills and/or capabilities at interview.

That was probably not an over-estimate by you, but simply a manipulation by him.

People like this come across the way they want. You were convinced because they performed the way they wanted to at interview(s). Now they have what they wanted from that, they're performing a different way to get something else, i.e. an easy life with no responsibility and paid to do it.

I would say in closing that you are a dream boss in IT. I'd (almost) pay to work in a company with bosses like you. But you are the victim (IMO) of what amounts to a con artist.

Part of what con artists do is manipulate you into feeling that you're at fault. You're not. You're practically perfect by boss standards.

Start a formal review process via HR (or at any rate a formal review process with no loop holes for the "work escapee"). I'll make a small wager (with myself :-) ) that they breeze through the review process with no problems (if it suits them to) and just walk away if they don't fancy it.

Also watch out for lawsuits. By the book - do it all by the book and with witnesses.

My son has anxiety, among other things, and exhibits many of the same behaviors as your employee. I have some insights I think will help.

His self esteem is largely because he isn't finishing things. When you let him not finish something, it reinforces that you also think he isn't capable. He is probably capable, he just needs a strategy for getting past his anxiety about getting stuck.

He doesn't react like other people do. Gentle encouragement and indulging mostly just results in him wallowing, and prolonging his suffering. It feels unnatural, but you have to be not so much harsh, but blunt. Snap him out of it, so he can move on. Don't let him get away with lies like he doesn't know how to contact someone. Say something firmly like, "Yes you do. She's in the directory. You can do this. Go do it."

He needs an intentional strategy for getting unstuck. Most people have never really thought about how they get past roadblocks. In their minds, they just sort of "press on." In reality, you have specific strategies, like taking a short break to clear your head, whiteboarding the problem, rubber ducking, writing a list of questions that need answering, writing a list of possible approaches, learning background information, brainstorming techniques, etc. Those strategies don't come naturally to your employee, so suggest them. In other words, he probably needs a lot more coaching in soft skills than technical skills.

Potentially reconsider his assignments. I know it's difficult with knowledge work, but if there are tasks that are fairly repetitive with well-defined procedures, those may be a better fit. If he asks for more challenging work, you should grant it on a trial basis. If he wants to continue receiving more challenging work, he needs to actually finish it.

Helping other people become successful is the true hallmark of a leader. Your goal to help this person when he is down in the dumps (per your description) is laudable indeed. You will need a number of ingredients to give yourself a good chance of success:

1. Patience: For a person who has regular panic attacks, it is a long road ahead to get back on track. You will estimate his tasks taking that into account, and it will likely still take longer. You need to be patient and be prepared to deal with it.




2. Belief: Everyone hits a trough once in a while, but things eventually start getting better. If you do not have the belief that they will (specifically, in this person's case, not in the general philosophical sense), then trying to improve things is pretty much a waste of time.



3. 
   

   Plan: Since you are clearly willing to walk the extra mile kilometre with this person, you need to have a clear plan of where you want to reach and how you want to get there.

   
   
   

   I have dealt with quite a few underperformers in my career. I have typically achieved good results by breaking down their tasks into small chunks, getting involved with their work into greater detail, and in general, doing a little more hand-holding than usual.

   
   
   

   You need to be careful not to appear condescending while doing so. You also need to be careful not to let this phase drag on for too long, lest they take this hand-holding for granted. How you achieve that balance varies based each person and also on your own personality. It is one of the important managerial skills, and I think you will be able to handle that.

   
   



4. Plan B: Things don't always go as planned. You need to have a backup plan in place. In your case, you might have to keep an eye on other projects or teams where this person might meaningfully contribute if things don't work out with your team.




5. Thick skin: As you would readily realize, there are people besides you two around you, who will have differing views on this arrangement. In particular, your managers might question why this person isn't pulling their weight, or even worse, raise questions on your role in managing them. If you believe what you are doing is right, you need to have a "thick skin" (if you will) to defend your decisions. You cannot put your own job or reputation on the line while helping this person.



6. 
   

   Communication: Last and most important, you need to communicate clearly with all the parties, particularly this person and any stakeholders in their work. My personal interpretation from your description is that your approach, while well-intentioned without doubt, could do with some improvement. Asking them to pick one task from the backlog, and presumably, picking some other task at random after that is done, without a clear line joining the dots would leave them even more confused as to their role, especially when they are already down on morale.

   
   
   

   Instead spend a little time going through the backlog, pick 3 or 4 tasks that form a logical "sequence" towards some goal (such a feature, albeit a "nice-to-have"/"not-so-urgent" one), then break it down into smaller chunks as mentioned above. Involve this person in these steps to the extent you feel appropriate, then agree on a plan with them. Thus, when this "sequence" of tasks is done, it can be presented as an "achievement", which can help boost morale, and help them tackle the next goal with some more confidence.

   
   

I have noted above a few points that I have found helpful. I think you will be able to put them together, along with your own, and apply them to your specific situation as appropriate. Good luck. :-)

I've never answered an SE question before, but I felt I needed to do this.

I recognise what this person is going through, and with high confidence. I have gone through similar stresses myself, and can strongly relate to the described person's issues.

As one answer mentions, although buried hence warranting a second look, the issue is:

Fixed Mindset

Here's a pretty graphic to describe the ugliness going inside this person's head (it's ugly for them; I use the word empathetically, not judgementally):

Source: https://www.mindsetworks.com/science/Impact (Courtesy of Nigel Holmes)

This individual is getting anxiety attacks since they perceive everything as a form of judgement upon them. Every task, every encounter with a colleague, every look they get from someone, may be considered an instance of judgement.

They get thoughts like "Why are they looking at me? Is the way I dress bad?" or, more likely given the context, "Oh I failed at this task", "Uh oh, I'm taking too long on this second task, what's going on with me?", "I've taken too long on this! I'm a failure!", "Oh, they're looking at me again; they know I'm a failure", etc. This is a vicious cycle that one enters and it keeps spiralling down until you get to the situation you see yourself with.

Solution

1. The individual in question needs to realise that they needn't be judged. But you can't tell them that, especially as you're probably one of those sources of judgement (I can't say for sure though from the info I have in your question). A possible way to do this is to give them a copy of Mindset by Carol Dweck.


2. 
   They need to speak to a counsellor. For months-long time, perhaps year-long. They need to open up to the counsellor, feel that they have a safe space to work on their perceived deficiencies, and the space to fail. But ultimately, they need to WANT to work on this issue themselves. This is something that goes beyond your ability to determine; from your info they appear to be unwilling to push themselves or try, but if I'm wrong, you can try to pressure them to have sessions. The only reason I suggest pressure is because the only alternative for you is to literally pressure them out of the office (i.e. fire them).

Let me be clear here: You're going far above and beyond your duties, but humanity will (already is, silently) thank you for this. This individual is going through a crisis and your patience and support will help. If you fire them, there's a significant chance their situation will only deteriorate to the point of homelessness or worse, and end up a statistic.

Most of the current answers focus on this team member's skills and performance as an employee. You've already tried a variety of approaches and I think it is because you are trying to treat a symptom, not the underlying cause.

This person suffers from anxiety disorder and has a lack of self esteem. This is affecting his performance at work. Sure, as JRodge01 points out it is not your responsibility to solve this. However, I suggest that you do consider that as his leader you can try to provide him the tools and opportunities to work on this. That may or may not be enough, but it is worth trying before giving up. As paul says, the way this person comes back for more tasks indicates that this person is willing to work, but just faces internal difficulty tackling certain tasks.

Here are some things to consider:

• Read "Mindset" by Carol Dweck. This person suffers from a fixed mindset, and needs to work on changing this to a growth mindset. I would highly recommend you read the book yourself as well, in addition to requesting your team member to read it.


• There are some exercises in the book. Consider doing this together with the team member.


• For a few months, focus with this team member on how to change his self-esteem. When a problem is encountered, work and talk through it. Don't focus on what code was wrong or how a script can be improved. Instead, focus on what was blocking him from finding a solution. Try and unpack why he is inclined to give up.


• During this period make it clear that you don't care (for a while) about his productivity. He can take however long he wants to solve something. Make it clear that you believe that he can do it. And that you are there to support him to work on taking away the psychological issues that are blocking him. Help him find out how to solve it - don't solve things for him.


• Of course you are not a psychiatrist so try and help him using literature like the book mentioned before. However, if you have the option to send him to a specialist to work on these issues, please do so.

If you spend some of your time and accept lower productivity from this team member it will come at a time/monetary cost. However, firing someone and having to recruit a new person will come at a price for the company as well. So I think both at a personal at professional level it is worth trying one last time.

You seem to already be going out of your way to help this team member. Kudos for your hard work.

It sounds like it is time for you to start The Process.

You need to talk clearly about the issue with the employee in a frank and open manner. The usual stuff: "I" messages, objective observations and such; no emotions. Google "radical candour". Whatever you do, at the end of the meeting, the employee should really be aware that there is an issue here, and that you are aware, and working on it. You need to make a plan together. Find S.M.A.R.T. goals to work on, and a clear timeline. Involve him, let him make suggestions. Your stance that you are there to help him is good and still correct, but he needs to put some effort in as well - and if that only means that you get to the result that he is simply wrong where he is in your organization, that's an acceptable result at this point, as well.

If you are in an at-will country, you can be plain about the fact that if no solution is found, his time with your company will be limited. If not, then you need to follow whatever practices your company has. Obviously, you will want to involve HR before you talk with him; and HR will also let you know whether they should be present. If you are in a country like Germany, you might wish to bring the Betriebsrat along.

I have been in your situation, and while I much prefer empathic and consensual management, at some point in time this is not helpful anymore (and maybe even makes it worse).

You are mixing 2 things:

• being supportive of an employee


• letting him dictate what he wants
  to work on

Despite what recruiters say work is no Disneyland.

The sooner the employee learns that better for him and you.
And if he does not want to do that better for you to find that ASAP.

This is your first failure as a leader.

Second failure is the belief that everybody can become good developer if you just manage them properly. This is cozy belief, but it is just wrong.
I know plenty of smart people that suck at being a developer for similar reasons as you mention.

So although everybody hates PIPs because they are paperwork BS that prevents company from getting sued...

You should do start one in an informal but precise and strict way.
Sit down with an employee, explain him that we all have work that we do not like, that you try to pick fun work items for him but you are limited by reality.
Next explain he will need to improve, both in technical and other ways(looking for solutions alone) or you will be forced to part ways with him.
Ask him if he wishes to look for other job that may be more aligned with his interests and if so offer to give him help.
If employee expresses desire to stay specify clear criteria he needs to meet in next 3 months, and that is it. After 3 months do the evaluation objectively, and if the employee did not perform as required terminate his contract. Again try to do it in a polite and professional way, but do not let your regrets/sunk cost fallacy cloud your judgment.

Some remarks/ideas:

Ask him about if he has some hobby he is really good at, such as playing the guitar. Then ask him how he got there. Did he play it perfect from the beginning or was it lots of practice? Anytime he is about to give up remind him it's like playing the guitar, he needs to try more and practice.

Ask him to write down a checklist. Every time he is stuck and somebody helps him, let him write down what exactly helped (google, stackoverflow, some programming trick, ..). Whenever he is stuck, he should check the list first if he forgot something. Experienced people have this list built-in after a while, but even then we often forget and need a colleague or the internet to remind us.

Talk with him and try to find out what exactly is triggering the problem, maybe it is some misconception that can be fixed. I once saw a kid that did not want to eat soup alone and wanted to be fed because it was too hard. After watching a few attempts they realized the kid did everything right, but at the end it lifted the spoon vertically and some drops of the soup drooled down the spoon onto its hand. Keeping the spoon horizontal, with some reminders, solved the problem and the kid was happily eating alone and very proud.

Small tasks that change all the time might be too much, try to find a small project that runs for a while and where the whole context does not change, or multiple small tasks in the same domain. Switching focus is already hard when you do stuff you know, but when you have to permanently learn new things to do it, it is very bad and can destroy self-confidence.

The trick is to have achievable goals outside of the well known comfort zone, in this case it seems like a little outside is already enough. Also learn/focus on one thing and then apply it a few times to similar problems.

There are of course people who don't want to learn or work, but they usually don't come running for more tasks. If he says he wants to learn, teach him how to learn on his own. There's also lots of free or paid courses where you learn stuff by doing it, udemy seems a good platform for that. Let him learn a topic there before giving him a corresponding task.

From a programmers perspective:

This answer isn't really an "on its own" answer, but too big for a comment:

You say he runs into a dead end, quits and wants a new task. If I'd do that, I would get fired pretty fast. Part of the job is fixing those issues, we get paid to fix exactly those kinds of problems.

My view on what I think the relation between a manager and programmer should be is very simple:

• The programmer should program/fix stuff


• The manager has to enable that (preparing work, making decisions, etc).

If the programmer runs into an halting issue, s/he should first try to overcome the hurdle her/himself. If that doesn't work (that happens), the programmer goes to the manager, presenting the issue. The programmer should ask how to go forward, not ask for something else, leaving the issue for what it is.

I think that has to be explained to your employee. If you don't climb the obstacles, you will never improve.

I've had some panic/depression issues myself while trying to do my job. The principle above didn't change, I still had to fix issues. My boss enabled me to work by allowing me to go home when I had a bad day. He enabled that by understanding it's going to take a bit. He understood that sometimes I'd switch tasks because that day I wasn't fit enough for that task but could make myself useful with a lighter task, but then come back to the main task later.

But not doing the job at all wasn't an option. In my experience does the "not giving up"-attitude also work a lot better with the panic attacks :)

You'd first have to comprehend what anxiety disorder means for someone who has it - which should already explain why he refused two of the proposed jobs right away, no matter the excuse he may have presented... while there are ten different kinds of (which the OP does not specify). Also "not knowing how to call a colleague listed in the directory" likely was an excuse, in order to avoid a trigger situation. On the intensity level, where it affects his work performance, he should probably seek professional help. The point is, that fear disables logical thinking; leave alone uncontrollable panic.

Whatever reasons provided for "why not" may be excuses for something he cannot control - and he has to learn in little steps, that there is no danger involved - while a crash course might only amplify it and cause more retreat. He should be asked about the trigger situations, which he constantly tries to avoid - else one cannot create a suitable trigger-free environment for him. I'd suspect social anxiety - when not wanting to perform (in person) support work & phone calls. But when he lacks the know-how for development tasks, this would require some training, so that he can work retreated or from home. There are sites alike udemy.com and many other, which offer online training.

The German term Angststörung (fear malfunction) is even more telling and this is an instinctive disorder, because humans only have two basic emotions: love & fear. All the other emotions are derived from these. It really depends how hard-wired it is, whether one can rewire it - or not. The cause for this is most often a traumatic experience, which cannot be processed unless revisited.

Your best chance, in order to better oversee possible technical difficulties, which might only lead to more anxiety, you have to create setup with a rather emphatic colleague, who he can work with and who can coach him a little, in order to provide him with some confidence in what he is doing (kind of a safe-space within the office). On his own he might simply get lost quick and give up - therefore constant guidance and support is the only way to properly support him to grow into the role he had been hired for. If he desires development work, pair programming might be the best option - while it is important to set reachable goals - because as you've described it, as soon as the goal appears to be out of reach, he will instantly give up and demand a whole other task. But when micro-managing him (in a self-managed team of two), giving up on one of the smaller goals is not that bad as giving up altogether - because his colleague can continue with it (demonstrating to him, that giving up is not an available option). However, if this doesn't help him to build up some confidence over time - one would have to consider if the situation is sustainable.