How To Be a Good Bad Guy

There’s no doubt about it…being a supervisor can really stink.

Sure, it has its moments of grandeur and power.

But if you do it right…

  • …if you hold staff accountable
  • …if you have difficult, awkward conversations
  • …if you play the role of boss before you play the role of friend

It can stink.

When I started out as a supervisor, I can’t deny that I was a terrible one.

Was I supportive? Sure. Did my staff like me? You bet.

But they never got better at their jobs. And they were allowed to mess around. And they got away with breaking company policy.

And I didn’t do a thing.

Because I didn’t know how to be a good bad guy. And, frankly, I didn’t want to be.

But I knew, deep down, it was my job.  So I got better at it.

The first time I was a good bad guy, when I had a real hard talk, was one of the toughest.

I had a fundraiser who couldn’t raise funds, and my organization was suffering.

And even then, despite the fact that I’d written out what I needed to say, that I was absolutely certain I needed to say it, I still almost backed out.

Instead I swallowed my fear, held my head high, and did it.

And it was awful. My voice shook and I avoided his gaze. I was sick to my stomach. I felt like a horrible human being.


I got my message across and I’d done the right thing for my organization.

For seven years after that I managed an organization filled with 40 professional, passionate people.

Some of them didn’t always like me. A few never did.

And even though I knew I was doing my job, it hurt.  Because, let’s face it…in the end, we all want to be liked.

I touched on this in my blog why your staff doesn’t like you very much, which has turned out to be my most popular, well-read, most searched out blog of all time.

In that blog I basically said you need to suck it up – that dealing with being disliked comes down to knowing that you are doing what’s best for your organization.

But we all know that’s so much easier said than done.

And so I now offer a few ways to get good at being the bad guy – and how to ease that feeling of ick in the process.

#1: Know when it’s time

We often know in our gut when the time has come for the hard talk.

The staff member hasn’t improved and your efforts to inspire them haven’t worked.

The outcomes haven’t gotten better, the attitudes haven’t gotten better, the behaviors haven’t gotten better.

I remember it well…that sinking feeling I got once I had this realization…when I knew it wasn’t going to get better until I had the hard talk with them. And that it wasn’t going to be pleasant.

I had a rule. Once I got the feeling, I had to do it. I would not allow myself to consider turning back. Not for a second.  

It’s a good rule. Think about adopting it.

#2: Prepare

And so I got down to figuring out what I would say during the hard talk. I got very clear on the issues at hand…if they were performance based or attitude based.  I thought of examples to help illustrate the problem.

I figured out my 3-5 talking points, and planned how I would use “I” statements in the discussion (”I’ve noticed this”…“I cannot allow this to continue”… “I have concerns about this”).

I also got clear on the improvements I needed to see and what would happen if I didn’t see them.

#3: Do it soon

I then scheduled the hard talk as soon as possible – within a day of that gut feeling. There was no point in waiting…I just needed enough time to prepare my thoughts so I could be clear, succinct and fair when we spoke.

I also did it first thing in the day, which meant two things.

First, it really got done. The later in the day I put off the hard talk off, the more I then found reasons to push it even later…sometimes pushing it to the next day. Which was torture.

Second, it got it off my mind. Since it took up so much space in my head, making it later only served to distract me until I got it done. Which made me less effective at everything else.

#4: Do it separately
Don’t do the hard talk as part of a regularly scheduled supervision meeting, where you’re going to be talking about everything from their timesheet to their latest contact log. The situation is serious, so reflect this by giving it its own time and space.

#5: Start with the following…

“I need to have a hard discussion with you today.”

Let them know right from the start that this is serious. Don’t give them the chance to throw you off guard by charming you, telling a joke that gets you laughing, or distracting you.

Switching up a mood in a casual conversation to address a serious issue is much harder than just starting with that issue from the very beginning.

#6: Do it quickly

This is one discussion that doesn’t need to take tons of time. It’s not point-counterpoint. It’s not consensus building.

It’s you, saying what you need to say, being crystal clear, stating what improvements need to be made, and then ending the conversation.

Those examples you came up with? They are for illustration purposes only. If you find yourself debating each one, you’re getting off point. Stick to the core issue.

If the talk goes on for a while, if it turns around to your supervision abilities, if you are engaging all kinds of their excuses, know that you’ve gotten sucked in. Put an end to it.

#7: Know who has your back

You need someone on the outside to help you deal with the ick.

Figure out your best champion, someone who is truly supportive, someone with whom you can be vulnerable.

Then, talk it through…before the hard discussion and after it’s over so you can remember there are people out there who really do like you.

Just as importantly, avoid those who will make you feel worse…those who are competitive, those who are critical, those who might be having a bad day and be looking for some company.

And finally…

…let it go.

Know that you did what you needed to do. One that many supervisors won’t.

And even though it’s really, really tough…know that being the bad guy does a world of good for your organization.

Kudos to you. Really.

Now, go to good…and do it well.

PS – for more tips on handling conflict, you can also check out my previous blog: the thing that makes us squirm

4 thoughts on “How To Be a Good Bad Guy

  1. I LOVE this post. It is so accurate for so many tough decisions I have had, not only in a supervisory capacity, but with all kinds of conflicts. Great examples and illustrations. I will definitely be using these recommendations… and soon!

  2. Patty Costa says:

    Deirdre thank you for such wonderful down-to-earth info. Most of us don’t grow up learning how to deal with conflict and confrontation. I love the keep it on the “I’s” and keep it as short as possible. Words to keep the ulsers away!

  3. Patti Testerman says:

    Almost painful to read because it is so accurate. Lots of helpful advice here, especially “Do it soon” and “Do it quickly.”

  4. Deidre…as usual you hit it on the nose. I enjoyed reading this to process my uneasiness with these type of confrontational and conflict genesis conversations. For some of us, they are brutal but real facts as to why we don’t enjoy these conversations or receiving them. Thanks for sharing your thoughts and your candid approach to some “icky” situations.

Leave a Reply

Your email address will not be published. Required fields are marked *