How to Have a Heart-to-Heart Conversation

Do you have an employee or a peer who is in pain and needs some very honest advice? 

In your battle-scarred life as a leader, knowing when and how to have a heart-to heart-talk is critical to your success and to help your employees stay focused and engaged. 

However, having an effective heart-to-heart conversation is not something most companies provide on the job training for. And, who wants to prepare to have a heart-to-heart? No one.

Instead, we usually learn how to have them through trial and error, often making mistakes along the way. 

In my work coaching leaders, I see that knowing how to have these intimate and oftentimes intense conversations is a necessary skill. 

So, I’m going to show you a straightforward, foolproof way to cut to the chase so both you and your employees come out ahead in such conversations. 

First, let’s talk about what we mean by a “heart-to-heart” conversation. 

I define a heart-to-heart conversation as a discussion that requires a deep level of honesty and a fair amount of vulnerability. Oftentimes, these are conversations leaders know, in their hearts, they should be having or already have had–but they are nervous about it and put it off. 

The word “vulnerability” often makes people wince, but it can be a shortcut to both parties feeling they are having an honest conversation in which mutual trust can be established. 

When you initiate a vulnerable conversation, you open up yourself. The person who receives your honest opinions begins to see that they, too, can open up to you and trust. 

Heart-to-hearts are delicate, difficult conversations that are most likely about decisions. Decisions you—as a leader—will feel compelled to help someone focus on fast. These decisions and the emotions around them can feel like quicksand, so before you sink, listen to my tips.

#1: Think Carefully About Where and When to Have a Heart-to-Heart

Some leaders prefer to hold heart-to-hearts away from the office, in a more casual setting. Doing so creates some anonymity: you’re placing an individual where he or she will not feel surrounded by stares and eavesdroppers. This strategy is helpful if you feel someone may be feeling emotional. However, who wants to cry over lunch in a restaurant? 

My alternative recommendation: use an empty office and start the dialogue towards at the end of the day. This tactic is professional, private, and relies on perfect timing. You cannot expect to pose a career-changing question to someone at 9 in the morning and then ask them to work productively for the rest of the day. In each situation in which you find yourself needing to have a heart-to-heart, work on a case-by-case basis depending on the person and what you know already about how they handle difficult or vulnerable conversations emotionally. 

#2: Separate the Personal from the Professional

When you feel compelled to have a heart-to-heart, you likely also feel invested in that employee’s career and life. Having a vulnerable conversation can cross over from the professional to the personal before you know it, which can also cause people to get emotional. 

Ask yourself: are you crossing the imaginary work line? 

If so, acknowledge it with the employee so they understand where you are coming from. You can do this by prefacing your comments to separate this conversation from the other professional conversations you have with this employee each day. Remind him or her you are speaking from the heart—not just the employee handbook. 

For example, if you notice an employee struggling with an emotional problem, you might say something like, “Anita, I want to talk to about something a friend of yours might bring up. Yes, I’m your manager, too. But right now I want to give you some unsolicited and personal advice. I made a decision—on my own—to talk to you. I’m doing this because I’ve enjoyed working closely with you for over three years and your work is stellar. Right now, though, I can see that you are in pain.” 

Offering this preface ensures that you won’t catch the employee off guard and will allow them to process that you are speaking to them outside of just your professional relationship. 

#3. Explore Ideas—But Don’t Offer Suggestions

Once you kick off a heart-to-heart conversation, you need to do more listening than talking. 

Ask guiding questions of your employee that allow him or her to reveal what they are comfortable with, but do this cautiously. Be clear that you are helping him or her to brainstorm possible solutions or to discover options; but that you are not making recommendations. 

For example, you might say, “We’ve talked before about how you feel passed over for a promotion. I know you are still upset about it because you’ve told me. What is going on now is that many of your peers are describing you as disgruntled. Is that how you want to be perceived? If not, what do you think you can do about it? What can you change?” 

Offer the employee support by asking them what you can do to help. By doing this, you will guide them to understand that they are responsible for the solution to the underlying issue, but that they are not alone. Some people just need a sounding board to work out their frustrations, and when you offer mutual exploration rather than advice, you allow them to arrive at their own conclusion and therefore feel more empowered. 

Notice how in the above example I did not suggest that it’s time for the employee to start exploring other options. I didn’t say, “You seem to be feeling really bitter here, why stay? Perhaps you should work somewhere else and be happy!” I want the individual to come up with ideas herself. 

You may want to be so direct as to offer solutions, but you spin the wheel of fortune when you start a heart-to-heart conversation with your ideas in mind. 

When you allow for the employee to arrive at their own conclusion, you ensure that all parties feel heard, trusted, and respected. The goal of a heart-to-heart conversation is to create space and time for that to happen. 

A final thought to remember: nothing is really ever off the record during a heart-to-heart, and your manager hat should be glued to your head at all times. 

You don’t want you to be accused of having suggested that someone quit, or of having offered advice that backfired. You’re smarter and savvier than that, manager. 

Next time you have a heart-to-heart conversation with an employee, follow these tips for the best possible outcome. The more practice you get, the easier they will become.