Wood Group's half-year results on Tuesday will be his last as chairman, ahead of the retirement in November that he promised his family he would make before turning 70 (he is out by a few months, but who's counting?).
On Wednesday, Aberdeen City Council will decide whether the City Garden project will go ahead. Wood's proposal to give the city centre a little Continental swagger, involving £50 million of his own money, has been the subject of a great row for the past couple of years. Barring a last-minute volte-face from coalition leaders Labour, it looks doomed.
If so, it will be a rare failure for a businessman whose company has become one of the country's great successes. It employs 41,000 people in 50 countries, its share price has never been higher and Tuesday's results are likely to be music to investors' ears.
But if this sounds like boring corporate efficiency, Granite City style, think again. In the past 18 months the Wood Group chieftains have laid a couple of massive bets on the its future. They have either pulled off the master stroke to ensure a spectacular future or sown the seeds of an eventual break-up.
Watchers will be scrutinising every word on Tuesday for signs that point one way or the other.
The Wood Group dates back exactly 100 years to when Wood's grandfather, William, co-founded ship repair and marine engineering firm, Wood & Davidson. By the time the then plain Ian arrived as a first-class psychology graduate in 1964 for what was famously supposed to be a stop-gap, it had been renamed after his father, John, and owned half-a-dozen trawlers. The younger Wood helped diversify into fish processing and then into North Sea oil, taking advantage of the nascent oil majors' business model of outsourcing much of the business.
By the early 1980s, having become an increasingly important player in the industry, he took over as chairman and chief executive of the newly formed John Wood Group, which had been split from the remains of his father's business. Knighted in 1994 and with the company finally floating on the stock market in 2002 after years of agonising, Wood passed the chief executive's stripes to his unassuming finance director, Allister Langlands, four years later. He even appears to have stepped away from the business with some grace.
Iain Armstrong of stockbroker Brewin Dolphin says: "He really gave it over to Allister and Alan [Fellows, the next finance director]. He was basically saying, 'I trust you guys'. Same with the operational heads."
So when the decision was taken to make major changes during 2010, it was Langlands and Fellows steering the ship. They were coping with wild oil price fluctuations, rocketing to nearly $150 (£95) per barrel in mid-2008 before crashing below $40 a few months later. This had knocked about 20% (almost $100 million) off top-line profits between 2008 and 2009 and then dragged them down by a few million dollars more in 2010 as belts tightened for the economic winter.
A key weakness in the Wood Group business was staring the execs in the face, making the company more susceptible to a takeover. Little wonder they ran the rule over each of their four businesses, roughly comparable in size, considering the best way forward for future growth and stability.
Their first business was production facilities support, which runs and maintains rigs and other platforms for oil operators. It came under the same division as engineering, which designs and procures everything from rig topsides to pipelines as well as equipment for refineries and other sectors of industry.
There was the well support division, which manufactures pumps and other equipment, and gas turbine services (GTS), which engineers and maintains equipment in gas-fired power stations and other types of turbines. The four businesses had little to do with each other and had various advantages and disadvantages.
Production facilities made low profit margins, but weren't affected too much by the oil price because once a platform is extracting, it is economic to keep going in most circumstances. Wood Group had a strong international reputation in the area but was a bit too reliant on the lower-margin North Sea and long relationships with Shell and BP. It was also facing cut-throat competition, not least from fellow Aberdeen outfit Production Services Network (PSN), which had poached a couple of Wood Group contracts.
The engineering business, which would have become the dominant segment had Wood Group's 2007 talks about merging with fellow UK group Amec flourished, did about double the margins of production facilities.
Here Wood Group had a truly world-beating reputation, with some of the best know-how for assisting the rush into deep-water drilling, but this business was much more affected by the oil price.
So was well support, which was also high margin. Its electrical submersible pumps were doing great business with the operators of shale oil and unconventional gas fields in onshore US, another big if controversial sector for the future. On the other hand, it devoured working capital and Wood Group would have to invest heavily to keep up with big beasts such as Baker Hughes and Schlumberger.
Finally, GTS was a ragbag business, making profits somewhere between production facilities and the others and somewhat cyclical too. The engineering part was capable of winning big contracts, such as the $200m prize in 2010 to build the Dorad power station in Israel. The maintenance part was more patchy, vying with other players to steal long-term contracts from big power station suppliers such as GE and Fujitsu.
The board's game plan suddenly started taking shape towards the end of 2010 when it announced it was buying PSN for $955m. Wood Group had never bought a business of this size before. Investment banker Goldman Sachs was apparently enraged, since it had been in the frame to make big fees from taking PSN on to the stock market.
When Allister Langlands was quoted at the time, he made clear the board's thinking. This segment of oil services was "stable and consistent" and "doesn't have the cyclical nature that capital expenditure businesses have [meaning engineering and well support]".
He said it meant the company could enjoy "good performance through the cycle" while still enjoying the "high-growth capital expenditure market when it's booming".
The two companies fitted each other so well they appeared to have been designed to come together one day. PSN, whose boss Bob Keiller would take charge of the combined production facilities business, brought a strong relationship with Exxon and presence in areas like Eastern Australia, the Caspian Sea, Cameroon, Tunisia and Egypt. The Wood Group part of the business was well regarded, but most observers say that PSN was considered better.
It was more profitable, more aggressive and less shackled to the North Sea, and recent contractual problems with jobs in Oman and Colombia that have taken the shine off the combined division's profits came from the Wood Group side and not the PSN.
Wood Group's balance sheet could have coped with the deal, but there was something else brewing. Early in 2011, the company pulled out of manufacturing by selling well support to GE for $2.8 billion, a price no business could turn down.
"GE paid far too much for it. It was probably 40% to 50% more than should have been paid," says Brewin Dolphin's Armstrong. "Wood Group did a fantastic job."
Then Wood Group announced it would return £1.7bn to shareholders. This is sometimes seen as a sign of a board running out of ideas, but the market didn't take it that way. One analyst who prefers to be anonymous says that this is more of an issue when the return is because the company does not know what to do with cash flow.
Wood's retirement plan, announced last month, was the coda to this trilogy of huge announcements.
From November, Langlands becomes chairman and Keiller chief executive. Allowing the outsider to take over is a big risk, albeit Keiller has a formidable track record and is part of the fabric of the Aberdeen oil world.
Many suspect he will let the GTS business go, arguing that it does not have much in common with anything else in the stable.
Keith Morris of Evolution Securities says: "Sir Ian always liked gas turbine business. While he has been chairman, I suspect there has been some resistance to knocking it out. He might have a slightly different approach."
This would leave engineering and production facilities, which Morris says are not exactly heavily dependent on one another either, albeit that they at least centre on the oil and gas industry. He sees arguments for splitting them off from one another, which would increase the chances of takeovers. Equally, Morris acknowledges that engineering benefits from being with a less cyclical business and helps win production facilities contracts.
Armstrong, who thinks Wood Group may have backed the wrong division in the 2010-11 transformation, points out that production facilities' margins are now coming under pressure from North Sea operators renegotiating contracts more often to screw down prices. This could spell trouble. The balance of power in the oil world is also moving away from majors such as BP towards state-owned operators like Petrobras of Brazil.
In this area, Wood Group production facilities have much ground to make up next to the likes of London-based Petrofac, which is also streets ahead of its rivals in the all-important Middle East.
Against these negatives, there is one basic but very important counterpoint. The days of easy oil are over. It costs more money to get oil out of deep water, tar sands, shale and the like. As Keith Morris says: "There is more money going to be spent to get the oil out of the ground. The oil price is going to stay fairly high and the oil companies are going to spend more money."
As Sir Ian Wood contemplates nearly 50 years at Wood Group and waits to see if City Garden wins a reprieve from the council, that should bring plenty of comfort for the future.