Summary - employee under-performing, but I know he can sort it out and do well.
Not a good day at work yesterday. The guy working for me - my best mate - is having a really tough time of it in the office. He's very much a confidence guy; when things are going well he's a great employee, when they're not he really struggles. Once he gets the hang of things and knows what he's talking about then he's very comfortable in a role, however if he doesn't fully understand what he's doing/talking about then he totally loses composure. His last position before joining was pretty simple - he had a framework of about 10 questions to run through with his clients and about 20 actions to undertake when completing paperwork, etc. With his current role here it's going to take a good 2 years of hard work to become completely competent and autonomous in the position.
He comes from a relatively wealthy family, and while he's absolutely not bothered or interested in his family wealth (always had to have weekend jobs as a kid and never expects or asks for anything from his parents), he also doesn't have a fantastic grip on money and how it works. A while ago I asked him where he thought the money to employ him came from? He genuinely didn't have a proper clue and hadn't even considered it actually came from my own back pocket. I did this to make him properly realise quite how much I wanted this whole thing to work out and that he was aware of the investment in him. He's a character who'll endeavour not to let anyone down and will always work hard. I made it clear that the company is in a very healthy place in terms of cash, assets and liquidity, and that he shouldn't have any concerns about this.
In hindsight it was probably a terribly thing to bring up, but at the time I wanted him to realise that I properly backed him, that I'd essentially written off the cost of his employment and had faith in it working out. He instead started feeling the pressure and burden of the cost - it's totally understandable that he'd look at it this way, and unfortunately he and I regard such issues in completely different lights. He sees it as a pressure, whereas I see it as a challenge to hit.
He voluntarily offered to take a salary cut and give up his commission share until his financial contribution to the firm improved. I protested and indicated that it wasn't necessary at all, but he made a valid point that by shouldering less cost he'll feel under less pressure and will then be able to focus and perform better. I agreed - I'm side-pocketing the difference in salary and will pass this back on to him when things pick up, so he won't actually miss out on anything cash. The actually salary level isn't really a concern for him - he just sold his flat and will probably never have to worry about his immediate finances for the rest of his life.
Unfortunately since this happened a couple of weeks ago it's all be downhill. His performance is tanking and he's on a bizarre downward spiral. As mentioned previously, being a confidence type of person, he very quickly picked up the basics of this role and progressed to a decent level at rapid speed. However he then developed this "I know what I'm doing" attitude whereby he would listen to advice and training from me but then completely ignore it, and instead apply his understanding of the basics to more complicated situations... and his work has massively suffered. He knows what's going on and we speak about it daily, but having achieved confidence in a low level of the role he's now lacking the confidence to develop further. This fist part of his training is to pick up standard and relatively straight forward themes. The second part of the training is to start thinking for yourself - it's not easy, but it's a system whereby you learn from your mistakes. Unfortunately he's making the same mistakes over and over without learning anything at all - the odd thing is that he knows he's making the mistake but lacks the confidence to try a new approach. I've literally tried everything I can think of to advise, guide and show him how to develop to confidence, but nothing seems to be working.
Also, his personal admin is a complete mess. I've talked and guided him through how to structure his affairs in a really basic but effective manner... and he completely ignores this, with pieces of scribbled-on paper littering his desk, etc. When I question him about what he's got going in this day, or what's the situation with that client, etc. he struggles to answer fully as he has nothing proper to refer to. Unfortunately his mental organisation is a mess too, being negatively impact by the pressure he feels under, and isn't being supported by his own personal admin. His concentration is non-existent and he works hard in a robotic way without applying thought and analysis to what he's doing.
Yesterday we were meant to be going to meet with one of the largest private equity firms in the world. He'd spent four months trying to get this meeting and, if it went well, we were potentially looking at half of his annual targets being generating through this one client. When I arrived yesterday morning he had done zero work on the meeting prep whatsoever - didn't know the backgrounds of the people working there, had an incorrect understanding of the fund's focus and strategy, didn't know who the necessary people in their London office were, didn't have a pitch sorted out, when I questioned him he couldn't answer basic questions about his own experience, etc. He then spent the next couple of hours putting together all the necessary notes under my guidance - btw this is stuff he learned in his second week in the role. Upon arrival it turned out that he's not actually looked at their website for their correct address, and had instead found their old address off an outdated database. Suffice to say, they weren't very impressed when we turned up on the other side of town at their old office. We'll not be given the chance to meet with them again.
The issue is, having known him for almost 25 years, I fully know he can push on and do really well. He's got a fantastic work ethic and is totally honest, but trying to get him to think for himself and get organised is going to be his biggest hurdle.
