As a leader, it's your job to help motivate, engage, and coach your people. And to do this, you need to have ongoing conversations with each member of your team to learn more about what makes them tick--and what ticks them off. This can be easy and rewarding when you're working with a direct report who is open, easy to talk to, and readily shares their thoughts and feelings. But when you have a member of your team who tends to respond to your inquiries with "I'm good," "I don't know," or just a shrug, it can make connecting with them tricky.

So, what do you do when you want to learn more about someone who doesn't seem to be meeting you half way? One common approach is to get more assertive and push for responses that don't seem to be forthcoming. But saying things like, "What do you mean, 'I don't know'?" or "Just good? Come on!" can contribute to your employee shutting down even more. 

Another approach is to just stop trying. And while it might make sense to stop putting more effort into a relationship that doesn't seem to be progressing, it's still your responsibility to develop this person. And you can't develop someone whom you've given up on.  

Here are four approaches to try when you haven't been successful in drawing someone out:

1. Ask yourself: "How am I contributing to this dynamic?"

While it's tempting to think the other person is the problem, assume that you have a contribution to what's not working here--even if it's small. Perhaps you schedule one-on-one meetings at the end of the work day, when your employee is already thinking about heading home to their family. Why open up a conversation when it might delay getting home?

Or perhaps tend to discuss your personal life openly with your team members--and this team member doesn't want to be asked about theirs (or even hear about yours). There are dozens of ways you might be playing a role in what's going on, so before you try to change the other person, see if you can identify what you might need to change in yourself.

2. Get comfortable with silence.

As Will Rogers said, "Never miss a good chance to shut up." Many of us would rather have a root canal than sit in silence. But if you're looking to draw someone out who may be less verbally expressive than you, you can't ask a question and then fill up the space with your own answers. Recognize that some people need time to think through their responses, especially if they're concerned about getting it "right."  Be willing to sit quietly while someone else processes at their own speed. And, if you really can't help yourself, you might say, "I notice that you're quiet. I just wanted to check to see if you're thinking, or if something else is going on."

3. Model vulnerability. 

Your colleague may not want to talk about your baby's explosive diaper, or your hernia surgery, or bad blind date. But they may be interested in learning about the recent piece of feedback you just received that was hard for you to hear. Or the pitch you worked on that bombed. Or the work-life balance you're wrestling with. Share some of your own challenges without oversharing (or undermining your credibility) can go a long way towards modeling what you'd like your direct report to be willing to share with you.

4. Start with common interests--and common gripes.

What do most of us have in common? Vacations, families, hobbies, food, movies, TV, weekend plans, the weather, work-life balance, commuting, projects around the house, etc. Start with one of these topics, and see which ones generate a spark of visible interest for your employee. And then follow their path down the conversation. A good start might be sharing something like: "I'm tired of going to the same couple of restaurants on the weekends. Where do you like to go out?" And if their response is: "I don't eat out much," you might try, "So what do you like to cook?" and see where that takes you. It doesn't really matter what the answer is; what matters is that you've opened the door.

Getting someone to open up to you can feel like hard work, but without it, the work will feel even harder.