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The 3 Common Mistakes Supervisors Make During Difficult Conversations

Difficult conversations are uncomfortable, and it’s tempting to brush them aside. But avoiding these discussions can lead to frustration and a buildup of tension. If you’re feeling overwhelmed, you’re not alone—many people feel nervous approaching their supervisors with difficult questions.
Kenzie Koch
Kenzie Koch
Contributors:
Mark Penrod | Project Manager

Mark Penrod, Project Manager at GUARDIAN RFID, has over 12 years of experience with the Fort Bend County Sheriff’s Office, finishing his journey as the Operations Lieutenant. During the seven years prior to his last day, Mark led the Detention Bureau Investigations Unit, otherwise known as the Internal Affairs for his jail. 

Throughout his career, Mark observed a recurring issue: communication breakdowns between officers and supervisors. In an era of advanced data analytics and video surveillance, many staff members feel as if “Big Brother” is always watching, ready to pounce on even the smallest mistakes. As a seasoned Internal Affairs investigator, Mark knows that mistakes are inevitable. 

Every employee in any field will mess up at some point; it’s simply part of being human. You may be familiar with the phrase “It doesn’t matter how many times you fall as long as you get back up.” Mistakes can foster creativity and innovation, and people can learn from these mistakes. Mistakes are not failures but rather stepping stones.

Mistakes Happen

Punishing an employee for a mistake is counterproductive—like beating a dead horse. They know something bad happened, so there’s no need to rub it in. However, ignoring a mistake is equally harmful. Acting as if a serious problem never happened is just as, if not more, dangerous as punishing an employee for a mishap because the problem will happen over, and over, and over again.

Instead, view mistakes as opportunities for learning and growth. While it may be uncomfortable to address these issues, difficult conversations can serve as building blocks for better operations. Supervisors should be leaders that people want to follow. You don’t want to be the supervisor that employees are afraid to come to when something goes wrong. You want to keep an open-door relationship with your subordinates and have fluid transparency, honesty, and respect. 

Mark's experience has shown him that much of the tension arises from supervisors struggling to engage in effective, difficult conversations. Avoiding these discussions is detrimental not only to your own credibility but also to your department. Consider the analogy of someone who hears an odd noise in their car but simply turns up the radio. This delay can lead to a breakdown—the same goes for your staff, if you ignore the critical conversations then eventually every shred of respect your staff has for you will vanish.

The three most common errors a supervisor will make during a difficult conversation are what Mark likes to call: Rapid Fire, Stay Puff, and the Gotcha Sandwich.    

1. Rapid Fire

In this situation, all you do is unhinge and completely unload your laundry list of complaints onto your subordinate. Meanwhile, this officer likely stopped listening a quarter of the way through your rant and is contemplating, “Do I punch this sucker in the face?” or “I’ll just quit and be done with this place.” 

Typically, this error happens due to a couple of reasons: the issue at hand has you so upset you can’t restrain yourself, or you’ve avoided the problem for so long that you’ve built a giant pile of dry ammo that just finally met its match.

2. Stay Puff

The opposite of Rapid Fire is a Stay Puff situation. This happens when a supervisor is so uncomfortable about having a difficult conversation with a staff member that they go above and beyond to minimize any negative impact. This supervisor blames other parties such as the Sheriff's Administration or the Warden for the mishaps. These supervisors “puff” themselves up to be the “friend” and deflect from their duty of supervising and counseling this employee.  

You may recall conversations that start with, “I don’t have a problem with what you did, but those idiots upfront want a paper on you” then in the same breath turn into something like, “Oh, by the way, your attendance has been good, keep it up.” With conversations like these, your staff won’t know if they’ve been given a disciplinary or a promotion.

3. Gotcha Sandwich

Have you ever been the victim of a compliment that ended with wishing you had worn some lead pants to work?  The Gotcha Sandwich is served when a supervisor says something to an officer like, “Hey Officer Johnson, great job catching that contraband in 2A tank… by the way, you were late on a round that day. If you’re late again, trust me you won’t like what happens.”  This supervisor reels the subordinate in with a compliment and then drops the hammer on them out of nowhere.

Think about the mistakes you made as an officer; you weren’t perfect. It’s crucial to remember, everyone makes mistakes. It’s only human. While we have advanced technology to help manage correctional facilities, it can never replace the people who drive operations. Regardless of how precise or sloppy someone may be, the human touch is irreplaceable.

Supervisors owe it to themselves and their teams to transform negative experiences into authentic coaching and mentoring opportunities. Approach difficult conversations with an open mind. Who knows? Once you look through their lens, maybe you’ll have a different perspective. Some of us might end up looking into a mirror.