You did a great job fitting a ton of narrative into a flash fiction story of only 300 words. Having a complicated relationship between a father and son-in-law, wrapped up in the running of a major corporation and a bit of succession drama all in just a few hundred words is really impressive.

Some of the specifics of the story didn't quite work for me. Hiring a particular contractor (without context for how large the contract is) seems like a day-to-day kind of decision that wouldn't give Hugh a ton of insight into the business management skills that Hugh seems to be looking for. I think it would be more effective if it were a larger-scale thing the son-in-law did, or something that had implications for the entire business empire so the reader understands the gravity of the change Wilbur was trying to make.

Transferring the business to his granddaughter already creates some confusing implications for the story, including why Hugh is still in charge, and what his granddaughter's ownership means in terms of big picture. While I like the sentiment, I think it would be more effective to either allude to her being groomed for the position (or as a would-be inheritor one day), rather than implying the entire company is already under his granddaughter's control.

Overall, this was an enjoyable flash fiction story with a lot of potential. Nice work!