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Lefcentreright I'm glad to see that politicians from countries usually neglected on Wikipedia are getting some attention. I'm a little concerned about some sourcing and due weight issues here that would normally be grounds for failure, but given that this is your second nomination, I would be willing to go through them in detail, if you're willing to do some substantive revamping.
To begin with; self-published sources are a problem anywhere, but they are especially a problem on a politician's bio, because a politician (any politician) needs to promote themselves all the time. Self-published sources are okay for the most basic biographical information, but nothing that could be contentious or promotional; so, for instance, using twitter as a source for saying Winde was acting premier isn't okay; using his bio from his party's website to talk about entrepreneurship isn't okay. These need to be replaced.
With respect to due weight; it is vere easy, and tempting, to write a politician's bio from accounts of their day-to-day activities that appear in the news media. This also almost always creates a neutrality issue, because they will be heavy on announcements and intentions, and light on analysis and impacts. Ideally, the whole thing would be based on scholarly sources; but that is hard, for less-known regional figures. So what you should look for are more in-depth profiles from larger newspapers, and base the article on that; in the absence of those, at least sources looking back at policies he enacted, rather than those covering announcements. At the moment, the page reads like a CV. This also relates to my next concern;
Structure. It's really difficult to get something to GA status if it's written as a list of activities. Inevitably, "early career" sections tend to be this way, but you should try to see what substance you can find besides statements he made and lists of positions he held.
I'm going to place this on hold for a week to let you work on these issues. If you need more time I'm happy to extend that deadline. I do think it needs more work, though, and there's not much point in my looking through very specific prose issues before the concerns above have been addressed. Best, Vanamonde (Talk)18:34, 30 April 2020 (UTC)[reply]
@Vanamonde93: Hi, there. I have done some revamping to the article. Can you maybe just go take a look and give your opinion on the current state and if there is more work to be done. Regards, LefcentrerightTalk(plz ping)14:40, 1 May 2020 (UTC)[reply]
@Lefcentreright: It's vastly improved, but before I get to specific prose points; you're now using an interview instead of the party source, which isn't much better; and the "tenure" section is still heavy on announcements and positions, without much substantive detail. I don't think you need to remove anything else major, but it wouldn't hurt to look a little harder for any media pieces that are more substantive. Surely, when he was elected premier, some longer profiles must have appeared in the national media? Vanamonde (Talk)00:48, 2 May 2020 (UTC)[reply]
@Vanamonde93: I have substituted the interview source. Also, information of Winde during his early political career is scarce, especially pre-2009. Now for the "tenure" section, I have incorporated all the major events that have occurred during his premiership, such as the announcement of his provincial cabinet, the deployment of the national defence force and the R3 billion safety plan, etc. It is still early in his premiership (barely one year in office), so not many things have happened. What else must be done to the article? Regards, LefcentrerightTalk(plz ping)23:02, 2 May 2020 (UTC)[reply]
I think you've addressed (to a first approximation) my general concerns, so I'll go over the article in detail now. Comments to follow. Vanamonde (Talk)18:00, 4 May 2020 (UTC)[reply]
There's a substantial amount of redundancy in the lead; most of his positions are mentioned twice.
The bit about him managing companies isn't in the body any longer
In general, check to ensure there's nothing in the lead that's not covered and sourced in the body
I don't think you need the father's date of death; we don't usually mention that in biographies except when the date is directly relevant to something else covered in the article
Are there no details available in reliable secondary sources of what businesses Winde started?
The "Municipal councillor" section is very short; I'd suggest subsuming into the next section, which you can simply title "early political career" or equivalent. Alternatively (and this is what I'd prefer) collect all the political material into a single section, with subsections for "early career", "provincial ministerships", "2019 electoral campaign", and "premiership"
I would link "Premier" when it's first mentioned in the body. "Premier" means a national leader more frequently than it does a regional leader; it's potentially confusing without the link.
You should try to link as many of the offices as possible the first time they are mentioned in the body; WP:OVERLINK generally allows for a link in the lead, infobox, and body.
@Vanamonde93: I have made some changes. Please take a look. In relation to his business career, I could not find any other sources specifically describing the businesses he managed in Knysna. Only the interview, which is now located in the "External links", names the businesses. Let me know. LefcentrerightTalk(plz ping)23:03, 5 May 2020 (UTC)[reply]
That's better, but the point about businesses in the lead hasn't yet been addressed.
The NWI source is described as a blog, and is therefore not reliable; it seems not to be necessary, so you could just drop it.
After she has been introduced in the body, Zille needs to be referred to as just "Zille", not "Premier Helen Zille"
"Immigration regulations introduced by the national government" Do we know what these regulations were?
"Winde has served as acting Premier of the Western Cape on various brief occasions" any details on when and why? Zille seems to have held her post continually...
"quite early on in the nomination process" the nomination process for what? a little more detail would be helpful; nomination processes for any electoral office vary tremendously.
"Winde defeated prominent candidates" similar problem; in what sort of vote?
"The party celebrated their election win in the province on 16 May 2019." unnecessary detail; I'd drop this, and tack the previous sentence onto the previous paragraph
"The cabinet granted the request and it ended in March 2020" the "it" is ambiguous; I assume you mean the deployment.
Link Harry Malila and Brent Gerber
Is "Director-General of the Western Cape Provincial Government" an important post? If so, it should be linked and/or explained; if not, that sentence could likely be dropped.
Similarly with the last sentence of this section; if the address was held elsewhere for an important reason, that ought to be mentioned; otherwise, it seems like trivia.
I performed some spot-checks for verifiability; ref 34 does not quite support what it's used for; it says he is expected to do those things, not that he did.
In general, I think I'm going to pass this once the ref issue has been addressed, but I do so somewhat reluctantly. The article just barely clears the "broad coverage" criterion, and as a result, barely clears the neutrality criterion, too. I will pass this because it's above the standard GAs are usually held to, and because as far as I can tell you've done a reasonable job with the available material; but I'd urge you to keep an eye out for any more substantive analysis of his policy that becomes available, and/or more biographical detail. Considering that he just became a provincial leader, I would expect this material to grow fairly quickly. Vanamonde (Talk)22:26, 8 May 2020 (UTC)[reply]