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“It’s OK, I’m Fine” – What Do You Say When You Know Something Isn’t Right

Whether it’s in your work life, your personal life or a mixture of both, you may often find yourself in situations where it’s hard to know what to do for the best. This is where an open and honest conversation can help.

Sometimes team leaders will feel like there’s a line they can’t cross when it comes to conversations with their team members. As if they can’t delve into team members’ personal lives.

While this is understandable in a workplace setting, what happens when you can tell something isn’t right with your team member? You may be tempted to just leave it there, but sometimes a team member may need you but not be vocal or direct about it.

It can be even more difficult if your team works remotely, as it’s harder to pick up on the signals you might be able to see if you were both working face-to-face. So, when you know something isn’t right, what can you do without intruding into a team member’s personal life?

What can you do?

What you can do will vary depending on each team member, as everyone is comfortable with a different level of involvement when it comes to communication. But it’s still possible to form a great relationship with all your team members. Here are some things you can do to help.

Keep track of things

It can sometimes be tricky to stay on top of how people are feeling. This is especially true if you have a big team. A simple grid can really help you to determine whether you have your finger on the pulse when it comes to how your team members are doing.

The above grid allows you to carry out regular sense checks to assess how people are feeling according to your own scale. For each team member, decide whether they tend to be open or private about whether they’re OK. If they tend to be open, it’s usually easy to say if they are OK currently (3) or not OK (4). Sometimes the 1s & 2s can be a little trickier, so you might need to let them know that you are there if they want to talk to you and probe a bit deeper if they tell you they’re fine when you suspect they’re not OK.

Create a ‘neutral’ space

While individual personality traits can vary, creating some ‘neutral’ space can help everyone. A neutral space is like a safe area where open conversations can happen. For example, if you spend all your time with your team members talking about tasks, before you rush to your next meeting it can be helpful to have a space in which to catch up. Without this crucial step and important space, you might be missing out on a conversation that needs to happen.

So, what questions is it acceptable to ask people, and how direct should you be? The best question to start with will be something open, such as, “how’s it going?” or, “how are you doing this week?”. If the response you get is “fine” or “I’m OK”, but this doesn’t feel true, then you can follow up with, “how’s it really going?” or “how are you really doing?”.

Following up like this might be enough for someone to open up, as people usually give an automatic response to the first question that doesn’t vary from week to week or reflect how they really feel. If you’re still getting stonewalled, you could say, “you don’t seem your usual self this week, what’s going on for you/how can I help you?”. If you still get nowhere and you’re worried about someone, you could say, “why do I have this feeling then that things aren’t good with you?”.

If you still get nothing, then you might need to let them know that you’re there if they do want to talk to you and then leave them to reflect and decide whether they want to come back to you. This is where having neutral space will provide a place for this in the future. It gives people the option to have a confidential chat in a safe space if they want to.


While you may be a little nervous about treading on your team members’ toes if you ask them about their personal lives, it’s important to remember that more and more people are seeking a good work/life balance. As long as you have good intentions, it’s fine to probe a bit. After all, there’s no harm in letting people know you care about them. You could always ask again a few days later so they know you haven’t forgotten.

After all, what’s the worst thing that can happen from taking this approach? People will know you are concerned about their wellbeing, and even if you feel it’s a bit clumsy at first, if you ask these questions quite frequently, then people will usually start to open up more. Just make sure you listen attentively to their response.

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