Let’s say you’re responsible to lead someone who doesn’t take initiative. They’re always coming to you with questions they could answer themselves, especially if they can use their question as a way to avoid making a decision themselves.

To talk with this person about their attitude, first you need to find out what’s stuck. You might say, well, their initiative is stuck. But that’s too simplistic. Telling them, “You need to show more initiative” probably won’t get results.

Are they stuck in thinking it’s more important to avoid mistakes than it is to achieve excellence? Are they stuck in a lack of personal confidence? Are they stuck in really not liking their job? Are they stuck in caring for aging relatives or worrying about a delinquent teen, and they just don’t have the energy to take on any more responsibility?

In order to help them get unstuck from any of these, you have to know which it is. What’s actually stuck?

You can’t change something you don’t understand.

The second question is: Why is it stuck? Are they focused on avoiding mistakes because, in spite of the organization’s values statement on the wall of the reception area that says, “We value initiative and risk-taking,” the person knows all too well from past experience that the subtle punishments for failure are severe?

Or if they’re stuck in some other way, why is that?

The Conversation Roadmap

So here’s a conversation roadmap that can help you uncover what is stuck. You’re part is all questions, so you can follow the three rules for effective questions:

• Open-ended questions are your friends.
• Accusations and directives are your enemies.
• And leading questions, accusations and directives disguised as questions, are snakes in the grass.

One point is really important because it sets the tone for the whole thing: expect the best from them. They’ll be able to tell if you’re expecting the worst, and that’s what you’ll get. So expect the best.

Also, what’s the minimum outcome that will make this meeting worthwhile? If they deny there’s any kind of problem, but they’re surprised to hear you think there is, that surprise may be all you need as a first step, because it invites them to look more closely. Then you can ask them to think about it, see if it’s true, and talk with you again in a while. There may be several stages in this process. Don’t force too much into the first stage.

You might start your conversation with, “How‘s the job going for you these days?” This can invite the person to talk about the parts of the job they really like, letting them remind themselves of what’s good about their situation. If they don’t talk about the parts they like, you can ask.

Then, if they haven’t brought the problem issue up themselves as part of their first answer, you might say, “I notice you come to me a lot for direction. Is that how it feels to you?”

If they say no, what are you talking about, you take a different approach that we’ll talk about in another post.

But if they acknowledge that they do come to you for direction, then ask, “Why do you think that is? What’s it about?”

Keep Asking Questions

When they answer, go deeper. Try to get below the surface. “But why is it like that? Where does that come from? What’s your insight into what’s really going on?”

If they make a point, invite more by saying, “Tell me more about that. Can you flesh that out a bit more for me?”

At some point, gently begin to bring some weight to the issue. Ask them, “What do you see are the consequences of this issue? Do you find that it’s getting in your way?” Or the team’s way, or the customer’s or client’s way? This is very different than asking, “How is it affecting your performance?” That’s a snake in the grass, implying their performance is a problem. Asking if it’s getting in the way implies that if you could remove this obstacle together, their performance would be unhindered.

Only at this point, when you’ve really looked at the issue from their point of view, can you begin, gently, to direct the conversation toward them. “Do you have a role in that yourself? Is there anything about what you’ve been doing or thinking that you feel contributes to that problem?”

The New Attitude

At this point, if they acknowledge that their attitude may have a role in the problem, you can ask, “Are you getting what you want to get out of this situation? Are you getting the best results you can imagine? Or is there a different approach that would be better for you?”

If they have any suggestion to make here, any at all, you’re off to the races. End by asking what they will do to implement a different approach, and when they want to talk with you next about their progress. Wish them good luck, and give them a warm goodbye.