InsideOut Development

How NOT to Communicate

by Joshua Joseph
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Are you ready to have terrible conversations with your boss, employees, or peers? You already know what creates effective communication. You even have the key ingredient to communication. But if you want your team to see conversations for the waste of time you know they are, these tips are for you. Check out this blueprint for a poor conversation that will keep your team from bothering you ever again.

Just Wing It

You’re a world-class boss—you don’t need to prepare, especially for something as trivial as a conversation. Conversations are supposed to be casual. Walking into a conversation with an agenda could set off some serious red flags to the person on the receiving end.

You’ve been having conversations your whole life. 99% of all meetings are a waste of money so why would you schedule prep time when you already know what has to be said?

Don’t Plan Ahead.

Planning is important for marketing plans, budget audits, and strategy meetings; not for everyday conversations. You’re a competent manager. Details are second nature to you. Just jump into execution.

Jump Right In.

Practice makes boring. You wouldn’t be where you are today if you needed practice. The best practice is a real conversation. There is no better feedback than what you receive from the reactions that someone has to what you say in the exact moment.

Up the Ante.

People work best under a hard deadline. There isn’t a better motivator than tying results and job security with the same knot. Creating a safe environment at work is the equivalent of handing out participation awards for last place. Besides, you’re not asking for a lot, just perfection.

Make It Meaningless

Conversations are best spent asking questions about the weekend and how disappointed we are about the Game of Thrones finale. Meetings, memos, and emails should have all the important details. A meaningless conversation has neither structure nor agenda. Maybe you’re making a point and maybe you’re not.  

Wait a Minute...Rewind!

Hopefully you’ve realized that was all really bad advice. You wouldn’t really do any of that—right?

Successful leaders understand that meaningful conversations improve productivity, increase employee satisfaction, and drive profits. The best leaders follow a better blueprint:

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Successful conversations address an issue with an expected outcome. Casual conversations require almost no planning, but it’s a whole different ballgame in an Alignment Conversation. You’ll need to prepare for emotions between both parties. The hardest conversation that you’ll need to have is with yourself. Here’s how you prepare:

  1. Articulate the Issue—Be direct. Conversations should be held to help achieve a goal. Put the problem into one concise sentence. “We’re meeting today about XYZ.”
  2. Determine Expected Outcomes—Walking into a conversation without the end in mind is a recipe for trouble. You might not know the exact outcome at the start of the conversation, but you should be able to articulate what a good solution would look like.
  3. Examine Your Emotions—This is the hardest part. When we wear our ‘boss hat’ we like to pretend like these types of conversations have no effect on us, but they do take an emotional toll. Take a personal inventory of your feelings before the conversation, and make sure that you are fully prepared.


You can’t steer the conversation if you don’t know where you’re going. Don’t worry about making sure the conversation follows a direct path, be flexible within your scope. There are only two things you absolutely need to map your entire conversation: the issue to be resolved and the expected outcome. Plan some questions and things that you have to say and anticipate responses. Also consider when and where is the best time to engage in this conversation.


Practice doesn’t make conversations perfect; it makes them permanent. Practice in your head, on the drive to work, or even in the mirror. Practice is a form of visualization that allows us to navigate between our perceptions and reality. Practicing with another person is the best source of feedback. Other people can tell us about things that we would never notice or thought of like our tone, emotions, or even the way the conversation is making us feel.

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Create an Engaged Environment

You need to create a safe environment for employees to give and receive feedback to create an engaging environment. So where do you start? Begin by establishing trust, regularly initiating a two-way conversation, and listening more than you talk.

Gallup reports that environments with low employee engagement experience 18% lower productivity, 16% lower profitability, and 65% lower share of price.

A safe, engaging environment can be destroyed no matter how much time you’ve spent building that culture. No matter the conversation, make other people around you feel safe. If you prepare, plan, and practice that’s a great start. Be aware of the other person’s emotions and do your best to be accommodating to all circumstances. Check out these 7 essential behaviors for better coaching conversations that can facilitate a safe, effective method.

7 Essential Coaching Behaviors

Make It Meaningful

You’ve spent a lot of time with everyone you work with. You spend more time with them than you do with your own family. Conversations can be a little scary. Hearing, “we need to talk,” “when you get a second, step into my office” and similar phrases can overwhelm us with possibilities.

The greatest conversations have left you in awe, inspired, and excited for change even if they didn’t start out as a positive dialogue. Don’t waste time, get to the meat of the problem and collaborate to find the ideal solution. Collaboration requires a shift away from monologue to dialogue.

How to Help New Managers Communicate Like a Boss: The Ultimate e-Book for Onboarding New Managers

Managers who communicate well will have a better understanding and flexibility to turn tough conversations into opportunities for a great conversation. They welcome conflict and the progress it brings while still maintaining a positive outlook and composure.

Category: Conversations Alignment Conversations Listening

Picture of Joshua Joseph

Joshua Joseph is an intern with InsideOut Development. He is currently getting a degree in Digital Marketing at Utah Valley University. When he's not writing, you'll find Joshua practicing photography, flying a drone, rock climbing, or on a casual 4-hour nap.

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