5 Strategies for Learning How to Say the Right Thing When it Matters Most

When the feeling hits you, there’s no mistaking it.

The moment you realized you just said the wrong thing, or what was intended to be the “right thing,” until it got twisted inside your brain’s neural cobwebs before it left your mouth.

For some, it can be the same “heart in your throat” sensation of accidentally hitting “reply all” to an email that was supposed to be to just one person.

For others, it is a feeling of being disappointed with yourself after not knowing how to convey your appreciation for something someone did for you, or even expressing sympathy for a hardship someone is going through.

Lately, it’s even been suggested by some that we should no longer ask one another, “how can I help?” as some argue that it places an unfair burden on the one we intend to help in the first place.

So what do we do? How can we become more thoughtful and strategic in our interactions if it seems that no matter what route we take, another misstep or social faux pas awaits?

There is an undeniable power in words, but even more so in knowing how and when we wield them. Learning how to more effectively describe, articulate, and convey what you mean provides you with an incredible advantage in every area of life- and these five strategies can help anyone improve.


5 Strategies for Learning How to Say the Right Thing


Look in the Mirror

No, I don’t mean rehearse speaking in the mirror; though, that can be helpful for some. I mean, actually, analyze what you say and how you say it more closely.

Use the voice memo app on your phone or buy a cheap voice recorder and start using it throughout the day whenever you are speaking. I take mine on walks with me as those moments tend to be when most of my creative ideas come to me. 

Capturing the audio allows me to go back and more closely analyze my own tempo, tonality, and forms of clarity- even when I’m talking to myself.

It can be equal parts embarrassing and frustrating to hear yourself at times, but it’s also incredibly enlightening.

This is also where the proliferation of virtual meetings due to the pandemic has become a blessing. Ask others on the call if they are comfortable with you recording, or ask your boss for a copy of the video once the meeting has wrapped up.

These recordings are great opportunities to not only hear yourself but also watch yourself at the same time. This allows you to get a baseline for the tendencies of any verbal or non-verbal tics you already lean on, as well as words and phrases you are most likely to subconsciously repeat.


Treat Silence Like a Skill

We’ve all heard the “silence is golden” cliche, but it’s much more than that.

In truth, most people don’t know how to speak because they haven’t truly learned how to listen.

Silence is a skill, and you can’t say the right thing if you don’t fully even know what “the thing” you should be commenting on is, to begin with. 

Before you chime in with your two-cents or a verbal contribution of any kind, just…breath. 

Whenever I lead workshops or virtual meetings, I’m hyper-conscious on doing all I can to ensure anyone attending gets maximal value. The issue is that sometimes I’ve let that guilt me into feeling like I always need to be teaching or talking, so no minutes are wasted.

Do you see the irony in that sentence? 

I almost felt like they would attribute any silence on my part as time “wasted.” Yet, an attentive pause following an initial response can be used as a silent probe, indicating a desire for further responses on behalf of the other party.  

This presents an invaluable opportunity for them to be heard and for us to better understand their frame of reference.

Allowing for some silence to seep into the conversation will ultimately give you more insight as to exactly what issues they are facing and how you can most appropriately respond. One of the worst mistakes you can make is expecting someone else to actually tell you exactly how they feel, what they value, or what they may be struggling with.

You have to do the digging, and listening skills serve as the shovel needed to unearth the real issues.


Timing Is Everything

It goes without saying that for us to know the “right” thing to say, we must be better about identifying the “right” moments in which we say it. 

By improving our timing and conversational tactics, we can prime the other party to receive our message with a more open mind. This enhances our message’s likelihood of being accepted with more grace, even if it wasn’t conveyed as perfectly as we had hoped.

This is an especially critical consideration for high-stakes professional conversations such as asking a boss for a raise, and deeply personal situations such as conveying one’s condolences or expressing compassion.

Think of this as practicing the skill of emotional timing. The process of asking yourself, “Is the person I am speaking to in the right frame of mind to receive the message in the first place?”

Telling someone who was recently furloughed about the raise you received is an example of poor emotional timing, as is telling an employee who just gave birth to a child that they have many emails waiting for them when they come back to the office.

Focus on having patience in allowing the other party to come to you. If you must go to them, work on creating associations that may allow the conversation or disclosure to occur less overtly.

Which brings me to our next tip…


Embrace the Non-Linear

Much of life exists in the gray area, and when trying to figure out how to navigate a complex conversational topic, this truth is amplified.

We are often told the quickest way between two points is a straight line, and in some contexts, this is true. But when it comes to people and the relationships between them, it is not that simple.

If it were indeed this simple, we would see everyone in the world moved into action through statistics and research; outputs that state things “as they are.”

This doesn’t happen.

Ultimately, people are not moved by statistics; they are moved by stories.

And many of the best stories, just like many of the most robust relationships built over time between people, share a non-linear relationship.

For the most part, the physical world’s timing and structure may move uniformly, but our lives unfold unpredictably. So too does our narrative of how we experience the events in our lives; the stories we live.

Many of us can recall fireside chats that started casually, with no planned agenda, yet ended in spirited discussion and improved self-disclosure.

That’s the power of the non-linear—the power of being open to experience and alternative narratives.

It’s why human beings have connected for thousands of years based upon common causes told in story form. Research shows that when it comes to jurors making decisions on a trial, “brute facts are secondary to story structure because jurors are primarily moved by good stories.”

Interpersonal conflict occurs at many levels; therefore, so must our conversations with others.

So what am I telling you? If you are trying to think of the right thing to say, do your best to think of a story, movie, or situation you’ve experienced in the past and reverse engineer it.

Properly orient yourself in the situation by considering the moment in a 3-act structure:

  • The Inciting Incident: What is the actual conflict the individual is facing? Where are they right now emotionally? Do you even know?
  • Confrontation: How will the stakes continue to be raised for them if the issue is not addressed? What level of pressure will they continue to face down the road?
  • Resolution: What’s the final result? Regardless of good or bad. How will they ultimately be impacted by what happened?

No matter how “make believy” this exercise seems, it allows you to get some distance from the situation, in the same way, taking a skilled pause does. It opens you up to looking at the problem with a different frame of reference, which, in turn, provides you with an expanded quiver of metaphors, analogies, and ways of phrasing the very point(s) you hope to get across. 

Besides, as Robert McKee states, “story is about thoroughness, not shortcuts.” This is precisely how you should approach any conversation you genuinely care about.

This brings us to the final point.


Be Real

The best communicators are those who engage with their audience on a personal level.

This is true with one caveat; think less Dr. Phil and more down-to-earth.

It’s true that all of us wear masks at times. We all have some level of a facade that we put up, but regardless of the face you wear in the moment just keep your focus on the other person as much as you can.

When you find yourself stuck, simply level with the other person. 

Taking a moment to state that you want to add value to their life and then backing that up with action is doing more than the vast majority of “well wishers” will ever do.

The bottom line? There’s no lasting “hack” for helping people in the long-run. There’s no drop-down list or pop-psych book that can help you simply start to care more if you truly are not already driven to do so.

Knowing the “right thing to say” boils down to you knowing yourself, seeking to better understand the other person, the context of their emotions and the environment they are operating within, and finally the communication tactics available to us at any given time.


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