Student Question
Master, I’m currently working as an English teacher at a key city high school. The school has a small contract opportunity — essentially logistics work: maintaining the multimedia classrooms, repairing desks and chairs, heating systems, that sort of thing. My family has solid experience in this area, and I’d like to bring them in for the job. I’m planning to take the relevant school leader out to dinner to discuss it, but I’ve never done this before. I’d appreciate your guidance.
Master Chi’s Response
When you need a favor, the most critical moment in the entire dinner is what happens after the meal — the private moment alone with the leader. All that groundwork you laid during dinner? That’s when it finally pays off. That’s when you make your ask.
Many people make this mistake: once dinner winds down and everyone’s had a few drinks, they think, “The leader must be tired — I’ll let him rest and go to his office tomorrow to talk.”
That thinking will cost you.
Strike while the iron is hot. By tomorrow, the leader is sober, sitting upright behind his desk, back in full professional mode. No alcohol, no warmth — everything reset to default. When you bring up your request, he’ll give you one of two non-answers: “We’ll look into it” or “We’ll think about it.” He almost certainly won’t give you a straight yes or no.
So you must seize the moment.
Aim to wrap up dinner around 9:30 PM. This leaves enough room to talk real business afterward. If you let dinner drag or pile on after-dinner activities, you’re looking at 11 or midnight before you know it — and there’s simply no time left for anything substantive.
As you walk out of the restaurant with the leader, lean in quietly and say: “There’s a small tea house nearby — would you like to sit for a bit? I also have something I wanted to briefly mention to you.”
If he says, “No thanks, just say what you need to say” — don’t give up. Respond: “Fair enough. How about we just take a short walk — help with digestion.”
The purpose here is simple: buy yourself more time to talk. Yes, you can make your pitch on the walk to his car, but that gives you maybe ten to fifteen minutes at most. If he brushes you off or gives you a vague answer, you have no room to follow up.
There’s another issue: you’ve both been drinking, so he’ll almost certainly have a driver or a car service. Any leader with half a brain won’t say anything that could be used against him in front of a third party. The harder and more sensitive your ask, the more it requires him to bend the rules — and the less willing he’ll be to commit to anything with someone else in earshot.
So the goal is: maximize your time and eliminate any audience.
As for exactly what to say — that depends on the specifics of your situation, so I can’t script it for you. But here is what you must understand: don’t expect one dinner to get you a yes. Even if he showed up, watch his mood carefully. Don’t beg, don’t complain, don’t perform loyalty all at once. That combination makes you look desperate and cheapens your position.
If the leader flatly refuses you — that’s fine. Be gracious, show that you understand. You don’t have a choice anyway; the decision is in his hands. You can leave the door open with something like: “If a suitable opportunity comes up, I hope you’ll keep us in mind.” Then shift to lighter conversation and let him head home.
Is it over then? Not quite.
He turned you down, yes — but now you know where his limits are. You can still approach him with smaller favors in the future. If he won’t handle the big things, small things should be no problem. The relationship has been planted; that’s already worth something.
Now, there’s another scenario: you make your ask, and he doesn’t refuse outright — but he doesn’t agree either. He says something vague, or mentions that it might be complicated. This is actually a good sign. It likely means your request has a real chance. He may just be being cautious, or he may want to observe you a little longer first.
In this case, patience is everything. Don’t push him for an immediate answer. There are plenty of people who want a piece of the pie — did you really think it would come that easily?
There’s one more scenario worth noting: you barely know this leader, yet after you state your request he agrees on the spot. Rather than feeling pleased, you should feel alert.
Ask yourself: is there a hidden problem here? Some entangled dispute? Some unresolved issue with the stakeholders involved? If none of those apply — why did he agree so readily? A quick yes from someone with no prior relationship with you often means this is a hot potato that insiders know better than to touch, and you’ve just walked in without knowing the full picture.
Finally — regardless of how the evening goes — I’d suggest you prepare a thoughtful small gift as a gesture of goodwill. How much to spend? Read the situation and use your judgment.