Build up a Sim's cooking skill beforehand. Whether or not your Sim's children get into private school depends on three factors: the state of the house, the ability to schmooze, and the meal. Because the meal is an important factor in the Headmaster's decision, you'll want at least one Sim with a very high Cooking skill - preferably eight or more points. (You can get by with fewer, but you'll need to put more focus on the house or schmoozing to pass.)
Have your Sim invite over the Headmaster. Click on a phone and select Invite Headmaster to start the process of getting your Sim's children into private school. Confirm that you want him to come over, and he'll agree to come to dinner at 5 PM.
Greet the Headmaster as soon as he arrives. You have one hour to greet the Headmaster, or he will leave. Have a child or older Sim available to greet him as soon as he arrives at 5 PM. Once he has been greeted, you have six hours to gain 90 or more points.
Give the Headmaster a tour of the house. Select the Sim that you want to give the tour, click on the Headmaster, click Entertain..., and choose Give Tour. Once he agrees to the tour, have your Sim enter each room in the house, then click on the Headmaster and choose Show Room. (Once you've finished showing him the house, click on him and choose End Tour.) Things that will boost your score include expensive wallpaper and flooring, well-lit rooms, artwork or other decorative objects that raise the Environment score, and a tidy garden (or other outdoor plants). Things that will hurt your score include unpaid bills, broken objects, weeds, or rooms that are missing paint, flooring, or roofing. You might not get to show the Headmaster every room if the house is large. Prioritize the nicest rooms to boost your score - once the house tour is over, you can't restart it.
Have dinner after the house tour. Having dinner after the tour is a good idea, because it ensures the Headmaster doesn't get too hungry, but also leaves plenty of time for schmoozing afterwards. Click on the Headmaster, click Entertain..., and choose Call for Dinner to make sure the Food score is counted. The Headmaster's preferred meals are pork chops, salmon, and lobster thermidor. Don't prepare chef salad - the Headmaster doesn't like it. If you have Seasons and your Sims grow their own crops, the Headmaster will be impressed and the Food score will significantly increase. Have at least one Sim eat dinner with the Headmaster. This will raise both the Food and the Schmooze score. (That being said, be aware that Sims take a long time to eat when talking to each other, so be careful!)
Schmooze with the Headmaster. The Schmooze score is largely dependent on your Sim's daily relationship with the Headmaster, so most positive social interactions with the Headmaster will have an effect. You can pick an option directly from the Schmooze... menu, or just have your Sims chat and joke with the Headmaster to raise their relationship. At first, you can only Schmooze About School with the Headmaster. More topics become available if his relationship with your Sim increases.
Aim for some bonus points. If you're not quite at the 90 points needed to pass, there are a few activities to do with the Headmaster that can gain you an extra ten points. Activities that will raise your overall score include: Drinking coffee Drinking from the bar Getting in the hot tub (though be careful with this one, because he tends to stay there for some time!)
Wait for the results. If you don't reach 90 points or more by the end of the six hours, your Sim's children will be rejected from private school, though you can try again as soon as the next day. If you reached at least 90 points, the Headmaster will accept the children, and they'll attend private school starting from the next school day onwards. Only the household's current children and teens will be accepted into private school. If you have any babies or toddlers in the household, you'll need to invite the Headmaster over again when they're children.
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