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Home Columns Personal Development

Who Benefits from a Tough Conversation?

Wes Dove by Wes Dove
December 31, 2024
in Personal Development

Photograph of Wes DoveThink back to both scenarios I shared last time, detailing the tough conversations I had with my son and with the co-worker that I cared about… In all too many cases, rules and policies are developed in a business or boundaries are set in a family after something has happened with hopes of preventing it from occurring again in the future. If we were looking at this strictly from a business perspective, it can often be simple to tie one of those work rules back to safety, quality, or productivity. As a parent, safety is still a priority, but we also need to set some expectations to maintain at least a little bit of order.
In either case, I’m sure we can picture at least one example of someone, be that a former (or current) boss or a parent (our own or a friend’s), who was known for ruling with an iron fist and justified their approach with reasoning that was almost as interpreted as “because I said so!” Don’t get me wrong here, I’m a proponent of law & order. While I’m certainly not someone who struggles with OCD (you should see my desk…), I absolutely have systems and processes in place for nearly everything I do; not because I develop a twitch if something isn’t done just right but because it saves a ton of time and helps me get way better results than I could ever hope to otherwise.
Whether you’re picturing a heavy-handed boss or a dictator-dad, I want you to consider how that “because I said so” approach yielded results… In either case, I’m guessing there were times where that produced the desired results. But I’d also guess there were times where that did just as much to drive a wedge between the person barking the orders and the individual on the receiving end. Oh, and how about the times where complying with said guidance just didn’t make sense? A stern directive might guide behavior while they’re looking over our shoulder but while I can’t speak for everyone, I’ll certainly admit that I’m less likely to follow a rule that I don’t see a clear purpose for when it’s unlikely I’ll get caught!
Before you tune me out completely here, have you heard the phrase “when the cats away, the mice will play”? I’m convinced that it’s not referring to just cats and mice…
There may be times where we need to take that firm, immediate stance when we’re communicating with someone we care about but in the cases where we have some wiggle-room, and we want to be sure to balance our candor with care, we’d do well to make sure the topic we’re addressing as well as the approach we take serves the other person’s interest just as much as it serves our own. Not only will that be much easier for them to digest, because the more DETERMINED folks like me often stay awake at night just thinking about ways to prove someone wrong, making sure they understand exactly how that thing we’re asking them to do will benefit them too can make a significant difference in getting them to follow through even when we’re not around – not to mention how much less strain it puts on the relationship!
Once we’ve made the decision that the relationship is more important than the issue AND we’re sure the issue being addressed serves their interests just as much as it does our own, we have a strong foundation for being candid while still showing our friend or family member that we really do care. Then we need to be prepared to do more than talk about it so we’ll pick up there next time!

Wes Dove

Wes Dove

Wes Dove is the founder of Dove Development & Consulting, focused on helping organizations improve profitability by building better leaders. Prior to that, Wes did extensive work in behavior-based safety, as well as safety and human resource compliance. As of August 2025, Wes has published two Amazon #1 Best Sellers: What’s KILLING Your Profitability? (It ALL Boils Down to Leadership!) and Leading With A Clear Purpose. His third book, The Values Advantage, is scheduled for an early ’26 release and he’s currently working on the manuscript for a fourth. Wes and his wife, Cindy, speak to and provide training for organizations across the United States on the topics of leadership and workplace communication.

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