I like to think of myself as a good guy. I think most guys do. But don’t nice guys finish last? That’s not true, is it?

A couple of weeks ago my partner Tom came into the office and lamented the fact that he was “too nice” and sometimes felt as if people were taking advantage of him because of it.

I told him that I often felt the same way. But I also said that I didn’t think he could or should ever change. And I am pretty sure that he won’t. It just isn’t in his DNA. Nor is it in mine.

But that doesn’t mean that we just simply let people walk all over us, because that is not the case either. Tom and I have a lot of traits in common, and of course we are different in many ways as well.

One of our common traits is empathy. We are both quite good at looking at things from other people’s perspectives, and then being able to understand how they feel about a situation. This is exactly what Tom was getting at when he talked about being too nice.

Getting back to the conversation we had that morning, I asked him if these feelings occurred more often in his personal life or his work life. I already knew that he would answer “personal” when I posed the question.

I have worked with Tom in many situations and seen him when he is acting for someone other than himself. When he is representing a company, a client, or another person, he is still polite and generally friendly. But when things get hairy, he can quickly lose the “good guy” persona.

I’m not sure why it is, but it is far easier for me to take on the “bad guy” role when I am representing someone else as well. Maybe we just don’t like it when we have to resort to tough tactics for our own good. Do we really want to be thought of as an A–hole? Not really.

The other day I was explaining this blog idea to my daughter, who is 11. I told her that when it comes to representing someone else, I find it easier to be the bad guy and ask the tough questions. Or to raise my voice when that is what is required.

She loves drama class and has taken improv and acting classes, so I told her that when I am in a position where I am representing someone else, I look at it kind of as a role, or, as I put it, a “schtick”.

She has heard me raise my voice more than once, and also remembers her grandfather and how it was better to remain on his good side. “Do you think I can play the role of the bad guy when I have to?” I asked. She nodded and gave me that “oh yeah” look.

We have all seen cop shows where they use the “good cop bad cop” routine to try to get a suspect to confess. What I have been talking about is different, but not completely.

Both my partner and I prefer to be the good cop, and the good cop can usually handle 90% of the situations anyone confronts. But in those situations that require it, sometimes you need to switch into the bad guy schtick.  From our experience, it is always easier to be the bad cop when you are doing it for someone else. Otherwise, you risk being the A—hole.


Steve Legler “gets” business families.
He understands the issues that families face, as well as how each family member sees things from their own viewpoint.
He specializes in helping business families navigate the difficult areas where the family and the business overlap, by listening to each person’s concerns and ideas.  He then helps the family work together to bridge gaps by building common goals, based on their shared values and vision.
His background in family business, his experience running his own family office, along with his education and training in coaching, facilitation, and mediation, make him uniquely suited to the role of advising business families and families of wealth.
He is the author of Shift your Family Business (2014), he received his MBA from the Richard  Ivey School of Business (UWO, 1991), is a CFA Charterholder (CFA Institute, 2002), a Family Enterprise Advisor (IFEA 2014), and has received the ACFBA and CFWA accreditations (Family Firm Institute 2014-2015).
He prides himself on his ability to help families create the harmony they need to support the legacy they want. To learn how, start by signing up for his monthly newsletter and weekly blogs here.