Your mentee sits down and starts telling you about a problem with a colleague. After about thirty seconds, you already know what they should do. So you say it. "Have you tried talking to her?" They say yes. That's a good idea, they say. They'll try it. And that's the end of the conversation.

Three weeks later, nothing has changed. You never found out what was really stopping them, so your advice fixed the wrong problem.

"Have you tried" isn't really a question. It's an instruction. It just sounds like a question. And nobody argues with an instruction.

These conversations fail in the same five ways every time. Michael Bungay Stanier trained managers for years before he wrote a book called The Coaching Habit. The book gives one question for each of the five. Seven questions, because two of the five mistakes need two questions each.

Mistake one starts with your very first question. Ask "how are you?" and you get "fine." And if you name the topic first, that becomes the topic, even when your mentee arrived with something more urgent. So the first question should be, "What's on your mind?" It just means: what are you thinking about right now. Wide enough that your mentee picks the topic. Narrow enough that they do not just make small talk.

Mistake two: your mentee names a problem, and you start solving it. The first thing people say is usually the version they worked out on the way to see you. There's almost always more they haven't said. So ask this, and it's only three words. "And what else?" Ask it two or three times, until they have nothing left.

It is the simplest of the seven, and it is the one closest to something that has been tested. Not tested in coaching. In a clinic. Researchers gave twenty family doctors one of two questions to ask their patients. The only difference was one word. Anything, or something. One group asked, "Is there anything else you want to raise today?" The other group asked, "Is there something else you want to raise today?" The "anything" version changed nothing. With the "something" version, 78 percent fewer of those worries went unsaid. Those are the worries a patient takes home and never mentions. And it didn't make the visit any longer. "Anything" makes it easy to say no. "Something" says there is more.

Ask what else a few times and you'll have several problems, not one. Mistake three is picking the one that interests you. Or your mentee keeps describing somebody else's problem. The patient who refuses to cooperate. The department that never answers emails. The colleague who is difficult. All true. And none of it is something they can change tomorrow. So the third question is, "What's the real challenge here for you?" Two words change the whole question. For you. They move the conversation away from the person who isn't here, back to the one sitting in front of you.

Mistake four is harder to notice. You know the real problem now, so you start helping, and you help with something your mentee never asked for. Two questions stop that. Ask, "What do you want?" Ask it kindly. It is not a challenge. Most people have never said it out loud, even to themselves. The answer often surprises both of you. And then ask, simply, "How can I help?" It is meant to be direct. It stops you from guessing. And it makes them ask for one specific thing, so you don't spend twenty minutes on help they never wanted.

Mistake five is the one this episode opened with. Your mentee agrees, they leave, and three weeks later nothing has changed. So before they go, ask this: "If you're saying yes to this, what are you saying no to?" In other words, what will you stop doing? In a hospital, saying yes to something new means saying no to something already on your list. If your mentee cannot say what they will stop doing, the plan will probably not happen. Better to find that out now than in three weeks. And as they leave, ask, "What was most useful for you?" It makes them say the useful part out loud. Saying it out loud is how people remember. And it tells you what to repeat next time.

Five mistakes. Seven questions. You won't use all seven, and you don't need to. If you only remember two, remember these. First, ask "and what else," more than once. Second, ask "what's the real challenge here for you?" If you ask three or four together, explain why you're asking. Say, "I'm not testing you. I don't know the answer either." Otherwise it can feel like a test. And when you do have an opinion, say it clearly. Just don't hide it inside a question.

Go back to the start. You saved thirty seconds. It cost them three weeks. So this week, one conversation with one rule. Nothing that starts with "have you tried." Every time you notice yourself about to say it, ask "and what else" instead.