Dirty Secrets of Small Business

Dirty Secrets of Small Business


How Important Is Timing When Having Tough Discussions?

August 03, 2023

In This Episode

Can’t I just say it!  Why can’t I just tell them how I feel?  These and many other thoughts have likely gone through your head at some point.  Perhaps you are frustrated or feeling some pressure and you’re just about to burst!  Take a deep breath, in through the nose and out through the mouth.  Take another one and take a step back from the situation.  Should you say what you’re thinking or should you bite your tongue and look for a better time and situation to make your point?Perhaps after you’ve had the chance to calm down a bit.


Like many things in business or life, we often look back on situations and we are glad that we didn’t say something in the moment and let our emotions get the best of us.  It can often feel great in the short term to get something off your chest, but if the message isn’t delivered right it can just add more fuel to the fire vs. correcting or calming the situation down.  Keep in mind that rarely will your job as a business owner be to add more fuel to the fire.  You’ve got to maintain your cool and be the adult.  We have to tap our inner James Dalton (that’s the character Patrick Swayze plays in the movie Road House).  Sometimes this is easier said than done to “be nice” and “stay cool”.


Here are some things to consider from a timing perspective when you are looking for the right time to have some difficult discussions:


  • Alone: do it in private vs. public if at all possible.  The last thing you want when trying to have a difficult discussion is an audience.  You may have heard strategies that talk about having these discussions in public to help temper someone’s response (e.g. Jerry Maguire being let go at a crowded restaurant).  That’s certainly an option, but we just haven’t found that to be the best environment to have a real conversation.  So if you have the ability, try to do it when the two of you can be alone.
  • Role Play: practice makes perfect, or so the saying goes.  It’s best to do some practicing (i.e. role playing) when getting ready for a tough discussion.  Perhaps you have someone else in the company who can practice with you.  Maybe it’s your spouse or a friend who can help.  There are a couple of key to role playing: i) the more you hear yourself talk the better you’ll get at delivering your message, and ii) the person you’re role playing with should be asking questions and trying to cover all the potential responses of the person you will be speaking with.  This last point is key as you’d like to make sure you are ready with a response to whatever the person says to you.
  • Brief: whatever you have to say, now’s the time to say it.  Keep it short and sweet.  Say what you have to say and then wait.  This can often be the hardest part…letting something just sit in the air and not talking over it.  Give the person you’re talking with the time to digest what you just said.  Chances are 10 seconds of silence is going to feel like 10 minutes, but stay patient and let that person respond.  Keep in mind that you’ve had plenty of time to prepare for this discussion, whereas the person you’re speaking with is hearing it for the first time.  Some might react by keeping quiet themselves while others will start thinking out loud.

Not too many people relish having difficult discussions, but the timing of when, where, and how you have these discussions can help make them go better and hopefully make them less painful and more productive.  We’ve dealt with these difficult discussions in everything from families transitioning their business from one generation to the next to business partners and spouses working together.  No matter your situation, we’ve likely been there and done that before so reach out if we can help.


People, Companies and Resources We Mentioned in the Show