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3 Tips to Turn Difficult Conversations Into Productive Ones

Giving negative feedback or letting an employee go is an unfortunate part of being an entrepreneur. Follow these tips to make the process a productive one.


Letting an employee go or giving them a negative review is never easy. In fact, negative conversations are difficult for virtually everyone, but they are especially difficult if you are a new business owner or haven’t had this type of conversation before. In fact, even if you are more experienced and think you are wonderful at these types of conversations, you may not be. One study indicated that about one-third of managers think that they handle workplace conflict well, but only 22% of their employees agreed with them.

These conversations don’t have to be a bad thing, and if handled correctly, they should lead to increased performance. According to one study, 81% of employees saw positive outcomes that originated with workplace conflict. Employees will often be unable to tell that their behavior or performance is unacceptable until you actually sit down and talk them through it. These conversations are a necessary chore, but following a few key suggestions can make them much easier.


1. Approach the conversation with a positive outlook.

Do not think of the conversation as being a “difficult” one. Framing the conversation differently in your mind can significantly help the situation.When you think you must have a difficult conversation, you may become nervous or tense. You may even put it off or avoid it all together. (In case you’re one of those guys who liked to break up with your ex-girlfriends over text message, here’s an important tip: do not give performance reviews via e-mail–face-to-face discussions are much more productive.)

If you must give a negative review, for example, think of it as a constructive conversation about how the employee can improve. Do not put it off any more than you have to. Addressing the problem immediately not only dampens the possibility of future problems, it also shows other employees that certain behaviors or poor performance is unacceptable.

When dealing with difficult conversations, one of the most important aspects is to keep your emotions in check. If you become emotional, your employee may become emotional. Once emotions are in play, the possibility of a productive conversation could go completely out the window. Be sure that you wait to have a conversation until you have had time to think about the implications; reacting based on emotions alone will usually be negative in the long run.


2. Be prepared–mentally and with empirical proof.

Planning is important in difficult conversations. Make a list of all of the things that you want to discuss and be sure to hit all of them. Know the objective of this conversation beforehand. Simply reprimanding the employee may not be an effective use of your time. Instead, include a discussion about what needs to happen so that the behavior does not recur or so performance can improve. Do not leave the conversation without putting some action items for improvement in place.

Keep in mind that some employees may become defensive when their behavior or performance is mentioned. They may deny behavior or performance problems exist at all. This type of reaction is not productive, so have empirical evidence to show to the employee in case it becomes necessary. Show them their sales numbers or customer complaints, for example, or state specifically when an undesired behavior occurred.

If the employee starts comparing themselves to other employees, steer the conversation back to them. (“We are not talking about Jane today. We are talking about you.”) Of course, consistency is important, so you may need to be sure that your employee’s accusations are just a defense mechanism and not based on something more factual that you may have overlooked.

If the situation is exceptionally difficult for you, you may also want to rehearse the conversation ahead of time or make notes to keep you on track. There’s nothing worse than leaving something out of a negative performance review and then having to go back and have a second conversation with the same employee about something you forgot. This is demoralizing for the employee and embarrassing for you.


3. Put yourself in their shoes.

If you go into the conversation attempting to find your employee’s perspective, that will not only make your employee feel heard, but you may also determine the underlying cause of a problem. Ask questions and really listen to your employee’s response. Why are they behaving a certain way? Is there anything that you can do to make it easier to achieve their performance goals? What do they think is preventing them from meeting their performance goals? At the same time, you should keep in mind that your employee cares more about how this conversation affects them than how difficult it is for you, so do not be the victim in the conversation. (For example, “I really hate to do this…” or “This is really hard for me to say because…”).

Difficult conversations are just that–difficult, but they are a necessary part of running your own business. Have these conversations the right way, and you can turn them into positive growth instead of negative experiences.


This article was originally published on in April 2015.
Ariana Ayu is the author of the Business Mojo column on (a website and magazine geared toward entrepreneurs) which was published between 2014-2016. Ariana is the CEO and founder of several companies, including Ayutopia International, LLC, which develops profitable collaborative corporate cultures, personal celebrity brands, and custom branded websites. Her press and media appearances include USA Today, International Business Times, ABC, CBS, CBS Money Watch, the CW, Eyewitness News, FOX, NBC, Newsday,Virtual-Strategy Magazine, World’s Luxury Guide,, Miami Herald, BlogTalkRadio, and Hollywood Industry, among others.

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