7 Surprisingly Easy Steps to Handle Difficult Conversations with Ease

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As a business owner, you will face conversations that you perceive as "difficult" or "confronting" from time to time.  Some of you may have more experience than others by holding a managerial position at a corporation.  But even then, having rather unpleasant conversations as a business owner is a whole other category, as you are the face of the company.

There are no other bosses to blame.  There is no brand name to hide behind and say, “They made me do it!  I’m just a messenger!”

As your business grows, your responsibility of looking after your business as a whole and assessing the overall well-being of it also grows significantly. 

It could be about firing one of your employees, especially when you break my golden rule- "No family or friends for hire."

It could be about unhappy customers demanding to speak to you.

In some cases, it's about your customers wanting a refund.

It may be that you need to tell vendors you want to stop working with them.

Or, you want to fire your client. 

They all sound unsavory, don’t they?

How would you say you feel when realizing you may have to handle these business matters?


Is your immediate reaction:

Wanting to avoid it at all cost?

What if I told you, by the end of this post, you may look forward to having these conversations because you have just acquired a new perspective? 

That’s right.  I am about to share my go-to 7 easy steps on how to have difficult conversations while at complete ease.  I know you are skeptical.  But I hope you give this post a chance, as mastering these steps alone can help your business grow much faster by eliminating this unnecessary source of stress on yourself. 

Probably to your surprise, I LOVE those conversations, but it did not start out that way.  I used to dread having these conversations just like you do.

So, what changed?

I simply made some changes in terms of how I look at these conversations.  I focus more on the fact that they satisfy my innate desire to understand human emotions and behaviors better.  I'm always super fascinated by the way other people react to situations that call for making hard decisions.

If I can look at difficult conversations as learning opportunities, why can't you?


Step #1: Free Yourself from Any Negative Emotions.

If you feel anxious about having these conversations, it's because you decided that these are hard conversations to have.

The minute you attach a certain negative emotion to a task or a project, it starts to dictate your course, and you lose control of the situation because you are giving power to your emotion.  

For example, if you are skeptical about what you are about to embark on, rather than going "all in" with it, the entire process will be shaky, as you’ve already decided it's not going to go well.  By being skeptical, your brain will look for all the evidence to support your belief that it won’t go well or it won’t go smoothly.

The reverse can also be true. If you decide that whatever you are about to embark on will go well, regardless of what others tell you or what the data shows, your brain will search for all the evidence to support that what you are attempting is going well.

This is called confirmation bias or cognitive bias

“I’m not good at confrontations.”

I hear this a lot from my clients.  My usual response to this statement is, “Who said it needs to be confrontational?  What makes you believe that this calls for a confrontation?”

Most of the time, I don’t see it to be a confrontational conversation, unless you label it as confrontational because you feel the need to fight for an outcome.  

Have you ever heard a story like this?

A young manager is tasked with firing one of his subordinates.  He is dreading it all day long, trying to figure out the best way to break the bad news.  Since he can no longer put it off, he finally works up the courage to call the subordinate into his office, only to find out that the subordinate has been seriously considering leaving the job and that she is actually relieved to hear the news.

The manager feels a huge weight being lifted off his shoulders, after she reveals her true feelings about the job.  He then chuckles about how stressed out he had been as a result of not knowing what she was thinking.

This is not to say that this will be the outcome for all occasions.  However, what if the manager had approached this conversation with a different perspective? Would he still have been so stressed out all day? 

Some people are waiting to be fired, as they also decide they have no control over the predicament they are in.  By the way, they have choices too, but they decide they don’t. 

In this case, wouldn't you be doing them a favor by being transparent?  Have you thought of looking at it this way?  Doesn’t this ease the tension significantly if you feel confident in your core that this is a beneficial conversation?

Next time when you feel that you need to have a difficult conversation with someone, free yourself from attaching negative emotions to it.  Understand that you have the power to dictate how it’s going to turn out. 


Coffee and Laptop_Maiko Sakai


Step #2: Keep in Mind at All Times - You Are Not on Trial

Let’s take a step back to examine where these negative emotions associated with so-called difficult conversations are coming from. 

Notice that I have been using the term, “so-called” in this post to make my point clear that these conversations are often “perceived” as difficult.  You can choose to look at them as difficult or easy.  The choice is yours.

So, where are your feelings and emotions coming from?

Perhaps, you feel that your competence is questioned.

You might fear that you are about to be judged or criticized.

Your concern might be that you will be disliked by proposing something that may not be well received. 

Your emotional response towards what you are about to do originates from your ego being threatened by thinking this is a case of “you vs. them.”  You feel the need to defend or protect yourself, as well as your position, and you aren’t sure whether you have what it takes to get this done.

This is an enormous pressure you are putting on yourself, and naturally it impacts the outcome of these conversations negatively.  Remember, you are not on trial.  Also remember that this is NOT about you or you vs. them. This is not about who is right and who is wrong.  This is not about protecting your popularity.

So, what is this about then?

This is about you taking responsibility as a business owner to make a sound decision and execute it accordingly for the well-being of your business.

Once you shift your thinking from protecting your ego to protecting the well-being of your business, your mind can focus on taking care of the issues and challenges at hand.  Understand that even if a conversation does not go smoothly, it does not mean that you will be denied as a human being. Unsurprisingly, if you approach these conversations with genuinely good intentions, people will respect you more, even while they receive bad news.

I have witnessed this time and time again.  People can tell the difference between you being preoccupied with protecting yourself in a situation or you trying to resolve issues with care.



Step #3: Remind Yourself What's at Stake 

Your reactive and negative thoughts surrounding a conversation you are about to have can muddle your vision as to why you needed to have this conversation in the first place.  This is why it’s important to take a step back and consider what’s at stake. 

The reason may be that you must deal with inefficiency in your business that is causing unnecessary expenses.  Or, it may be that this person is holding up others, and as a result, slowing down the growth of your business.  Or, your company’s reputation is on the line, and your swift action is required. 

These are legitimate concerns for any business owners, and they need to be dealt with immediately.

Be crystal clear on what kind of outcome you are expecting to generate by having this conversation.  Sometimes, it is easier to start by considering what could happen if you don’t take action to have this conversation instead. 

I've seen many business owners run and hide from various challenging situations.  And although I have continuously worked on myself not to do so, I am still occasionally guilty of this.  So, I know all too well what happens when you run from them.  As the saying goes, "What you resist will persist."

It never goes away.  Worse yet, the burden gets heavier and heavier.

When you feel like putting off the unideal situation you are trying to resolve, ask yourself, “Which one would I prefer- Continue letting this hang over my head longer, or just ripping the Band-Aid off and moving on?” 

Immediately, you will notice that it is not such a good idea to set it aside for too long. 

By having a clear vision of the desired outcome, you are less likely to be baffled by the other party’s reactions, comments and behaviors.  You will also regain confidence in what you are about to do.  It provides a sense of calm, which will allow you to maintain power in leading such conversation. 


Discussion_Maiko Sakai


Step #4: Strategize - Prep with Facts & Reasoning

Prepping for such conversations may require some time and research.  Don’t let this be the reason to skip this step, as this can make or break a conversation you are about to have. 

If you are the initiator of a conversation, chances are the person you will have this conversation with may not be aware this is on the horizon.  In this case, it’s easier for you to allocate some time to organize your thoughts, get some facts and give some thought to how you would like to lead this conversation ahead of time.

On the other hand, if the other party is the initiator, say, an angry customer demanding to get someone on the phone immediately, then there is a couple of extra steps you want to consider taking. 

First, respond to a person immediately via email letting him or her know that you are aware of the issue, and someone from your team will reach out to schedule a call.  Then, either you or someone from your team should arrange a scheduled call at a later time within 24 hours.

This method covers 2 crucial factors:


1.     It allows an angry customer to have some time to cool off.  If you respond quickly to say that the help is on the way to resolve the issue, the customer feels less agitated.  Key here is to respond in a timely manner, but do not engage in a full-on conversation.  Give some time for this customer to cool off to avoid having an emotionally charged, unproductive conversation.

2.     It allows you to buy some time to strategize.  Scheduling a call in the near future affords you to do some planning and organize your thoughts before the call. 


If a conversation involves some aspects of negotiation, have on hand a few options that you can live with.  What you want to do is to limit the amount of surprises during a conversation, so that you can stay calm and collected throughout.  Feeling unprepared can derail a conversation, which will result in losing your ability to lead a conversation.

Also, doing a walk-through or running a simulation in your head can also prepare you for a conversation.  When you work on this, try focusing more on what the other party might say and how you want to respond to them instead of what you will say.  Remember, Step #2 it is not about you. It is about resolving an issue. 



Step #5: Compassion, Always – “Let Me Understand Why”

Instead of being defensive, position yourself to be the “observer” and “facilitator” of the conversation, even if this is in a one-on-one setting.  This comes in handy, especially when you have to face dissatisfied, unhappy and, possibly, angry customers. 

By shifting your role to be an observer and a facilitator, you will be able to digest his or her response objectively rather than taking it personally.  To do this, first you give the person a chance to talk.  It can start off accusatory, emotionally flared up, and, perhaps, downright insulting, but just listen calmly and avoid rushing to offer explanations.

In my experience, it is common to see business owners and entrepreneurs feeling like they “owe explanations” to the other party.  Because of this, they tend to be the one to talk more and talk faster, letting a conversation go all over the place with no solutions. 

Also, if you attempt to get this over with rather quickly by jamming words into a conversation, it becomes apparent to the other person.  The person on the other side of the table can sense it from miles away, and it makes an unpleasant conversation even more unpleasant. 

Sure, you do need to be able to explain why you and the other party are having this conversation when the time is right.  However, there is no need to rush into it.  If you give the other person enough time to outline why he or she is dissatisfied or treated unfairly or whatever the case may be, it shows you are willing to invest time to work with them to get through the process.  

Keep in mind that you can’t fake compassion and empathy.  Once you master Step #1 & 2, you will be able to commit to resolving the issue at hand.  You don’t attempt to wrap up as fast as you can, and you don’t bombard the other party with mounting explanations. 



Step #6: Stay Firm & Calm Throughout – You Set the Pace

While I emphasized the importance of being compassionate in the previous step, it is also vital to maintain a good balance between caring and standing your ground.

Remember that you are going to be in control of a conversation, even if you are starting it from the point of listening.  People who are overly concerned with protecting their own ego have no chance of staying firm and calm throughout their conversations to maintain the right balance, because they are too busy trying to think of a way to defend their position. 

After giving the person enough time to say what he or she needs to say, you can reset the course of the conversation by asking different questions or by opening with a statement like, “I’m comparing notes, and here is something else I want to shed some light on.” 

How you ask these questions matters.  Avoid asking questions that are leading or that insinuate his or her faults.  Rephrase those questions to be more neutral, like the one I shared. 

The more you pay attention to subtle wording and expressions, the better you become at asking questions that are not accusatory.  Instead, you will learn to ask questions that make them rethink their behaviors, but without making them feel like they are being told how wrong they are. 

Don’t just listen and label their feelings, thinking that your job is done.  Your job is actually to analyze while you listen and to stay in control of the conversation so that you can measure how close you are to achieving the outcome you desire from this conversation.

Your ability to balance compassion and firmness on where you stand provides a structure and stability in a conversation.  In the end, it promotes the idea of being fair and having a productive conversation rather than getting into a fight.


Discussion2_Maiko Sakai

Step #7: Simply Don’t Have that Conversation If You Truly Feel Conflicted

At times, I decline to have these types of conversations when I determine I cannot own them fully.

What do I mean by this?

These situations occur when one or more of the below is true:

1.     A decision seems to be based on reactive and emotional response rather than a sound decision.

2.     There are other readily available options to be explored before resulting in this particular decision.

3.     Some facts are fabricated or untrue to favor one party over another.

4.     There is proof that no necessary steps have been taken to legitimize the decision.

If a situation presents any of the above, I will not have a conversation, as this would be against my goal of having a meaningful conversation to benefit all parties involved.  There is a difference between strategically declining to have a conversation and just avoiding a conversation.

When you know it must be done, and you believe in a solution you want to present, you are more likely to lean in to get it done.  On the other hand, there are times where you just can’t put your finger on it, but something isn’t right for you to fully commit to a conversation, it calls for further inspection. 

Here is an easy way to test whether having this conversation is the only way to resolve existing challenges or issues, and it goes like this:

Ask yourself if you can confidently explain the reasons by telling the person, “You may not feel this way right now, but this is best for both of us.  And here are the reasons why.”

If you don’t believe in the reasons followed by this opening statement, then you are not meant to have this conversion. 

When this happens to you, it means that you need to go over Steps #1 through #4 again to identify where the gap is and why you don’t feel aligned with the action you are about to take.  If you don’t sort this out, you are sure to have a disastrous conversation.  If you can’t fully own a conversation, then you will stumble every step of the way. 

That’s why I want to make sure to include this last step.  Sometimes, not having the conversation is a strategy of its own. 

In a nutshell, getting behind the idea of so-called “difficult conversations” does not have to be difficult at all.  Instead of associating negative emotions with resolving issues, focus on what you can gain and the positive impact it will have on your business.  If you firmly believe in a solution, care for all the parties involved, and are willing to stay objective, you will be able to handle difficult conversations with ease.