How To Productively Disagree With Anyone— Even Family!

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1:33There's no safe like SimpliSafe. Just before the July 4th weekend, I got a text from a friend. She's an entrepreneur. And she said, I'm driving up for the weekend to spend time with my family. And this was the perfect podcast episode to listen to before I arrived. And that it was a screenshot of a podcast episode that I produced called How to Productively Disagree with Anyone, Including Family. And so I think that we can all assume what she was in for when she arrived to spend the holiday weekend with family. Now, here's the thing. Maybe you're wondering, well, wait a second. How do you productively disagree with anyone, including family?

2:22I didn't hear that on your podcast. And that's true because that wasn't an episode from this podcast, Problem Solvers. That was an episode from another podcast that I host called Help Wanted. Help Wanted is a little different than Problem Solvers. Problem Solvers is an interview show where I am talking to experts and entrepreneurs who solve problems. Help Wanted, I'm talking to other people. I have a co-host, Nicole Lappin, best-selling money expert, and we are usually digging into the most uncomfortable and biggest mistakes that we have made in business or that people have reached out to us asking about, and then we talk through solutions.

2:58But then we also sometimes bring on listeners who have problems and talk them through it. And this episode that my friend had just listened to, How to Productively Disagree with Anyone, including family, was an episode. I actually just taped it myself. Nicole wasn't available that day. And I talked with a guy who works with family. And they've been having a longstanding disagreement about a fundamental decision in their business. And it has caused a lot of tension. And he disagrees with his family and he doesn't know how to get through it. And I spent time understanding this with him and gave him a script that he could use and a different way of thinking about the disagreement entirely.

3:43It was a really wonderful conversation and I hope headed off some real family drama. And I wanted to air it here on Problem Solvers as well because it is very much in the spirit of Problem Solvers. And as we go into the summer months, maybe you have some tensions with family you're spending time with, with colleagues, with co-workers. And I hope that the conversation that I had on Help Wanted can be useful to you. So if you want more like this, you can go find Help Wanted wherever you get podcasts, wherever you get problem solvers, you can find Help Wanted. I hope you will. In the meantime, here's Help Wanted.

4:27Charles Cicalo, welcome to Help Wanted. Hi, thanks for having me. Thanks for being here. So you reached out to me with a question about how to separate work from family, which is something that you were dealing with at work. Why don't you tell me more about that? I primarily work in an e-commerce business. It's the function of an online branch of my dad's retail stores. Around 35 years ago, my dad came to this country as a refugee and established a bunch of retail stores across New York and New England, Connecticut and Massachusetts be particular. and about seven years ago, I was in college and my two other brothers were about to enter college.

5:06We said, you know what? We have to get started with something within our lives. I was originally planning on going to law school. So with two years left to college, I said, let's give this thing a shot. We poured our life savings into this online business and thankfully it grew. Instead of turning on the heat, we just wore extra layers. Okay. We really bootstrapped this thing. My dad said, listen, you can use the name, but I'm not giving you a penny. He was sort of that entrepreneurial cheerleader. A tough entrepreneurial cheerleader. Totally. And from a very young age. It goes back to my first job was at 10 years old, working for my grandfather in a greenhouse.

5:44I got paid like$10 a day. By the way, these are the stories that you often hear from the most successful entrepreneurs. Mark Cuban tells a version of this where he wanted something. I can't remember what it was. And his dad said, well, then you can earn enough money to get it. And so Mark started going door to door selling whatever it was that he sold. And he learned how to do it and built upon those skills for the rest of his life. And now he's Mark Cuban. Yes. So I mean, it goes back to that. And thankfully, we built it to a place where, you know, we have our own White House now and actually multiple locations.

6:16So the e-com operation really built its way up. We had a decent amount of success. And 2022 actually had a decline. We didn't make what we thought we would be making. In our annual assessment of the prior year, we were brainstorming different causes of how it ended up being that way. And my brothers, who are my formal partners, thought idea A. And my dad, who's not a formal partner, but definitely an advisory partner and somebody who has a lot more retail experience than anyone we can ever have access to. His word is taken at a very, very high degree of respect. So dad and two brothers are for idea A.

7:03I'm thinking idea B. Formally, I guess I'm outvoted, even though we don't really function like that sort of corporate structure where there's a board of directors and stuff. There's not an official vote or anything, but just to be clear on your team, you are the sole opposing force. I'm alone. Yeah. And after all, they're my brothers. They're my dad. I love them. They love me, but I vehemently disagreed with them. So it was in separating what happens at work stays at work and then, you know, having dinner together a few hours after a huge disagreement. So it's been a while since you were outvoted and what's happened since then?

7:42The company has been executing the strategy that you disagreed with? And frankly, it worked. Oh. It worked. Thankfully, our company is on a great trajectory for 2023. And yeah, thank God. I mean, it worked and I'm happy it did. So not only was I outvoted, I was actually tasked with taking action on their ideas. And I did that. I said, you know what? I'm outvoted. We're a democracy. We're a loving family. I'm going to continue. and I'm going to oblige just as we've discussed. And I did. I did it to the best of my ability. I did it with a little bit of a flair just because I didn't agree with what I was doing.

8:20But I said, I'm going to go with emotions for now. You didn't try to tank it. You didn't say, because I disagree with this, I'm going to do a crappy job at this. I mean, there was a part of me that said, yeah, tank it. But that was all emotional. I try to isolate those impulsive reactions that entirely have to do with emotion. I sort of try to distance myself or isolate that and then make a logical decision. So why did you reach out to me? Because it sounds like you knew exactly what to do here. You understood that you can't call every shot, that you have to put the relationship and the shared goals over any individual disputes about how to get there.

9:05You understood very well, which I think is something that people lose sight of, that even though you all disagreed on what to do, you shared the ultimate objective of doing well by the company and doing well by the family. There was never any confusion about that. So is there something that's still lingering inside of you throughout this experience? Sure. There's a few things. I mean, we keep on obviously running into this issue because we're all three individual men and don't always have the same opinion. And it's a roadblock that keeps on coming up. There are constant disagreements. And thankfully, all cases, we worked it out very respectfully and amicably.

9:49And then there's also the lingering thought of, hey, what about idea B? I still want to implement idea B instead of idea A, or not instead of in addition to. Just to be clear, they're not mutually exclusive. You could do both. That is correct. It's just, it's a matter of my focus. Is it spread across idea A and B or do I just stay focused on idea A? Because to be honest, idea A worked. I think idea A and B is better though. Ah, so this is interesting because I was going to ask you, how do you feel about being wrong? because what you're thinking here is their idea was right, but your idea could still be right.

10:29That's correct. That is absolutely right. Why don't they want to explore your idea too? They think mastering their initiatives is the first step to taking on mine. So they're saying, I want to run, but they're saying master crawling first. Then we can walk. Then you can run. And what do you think about that? That doesn't sound unreasonable. Yeah, but I'm saying this is part of learning how to walk. I'm thinking maybe in this year's annual review, do I bring up, okay, now we're ready for idea B? Or really any other disagreement for that matter. I feel like there's sort of a limited supply of patience where you disagree with family members and it starts to rupture the family relationship.

11:17it's in what idea do I reinforce in myself that there is a light at the end and everybody's ideas will be sufficiently implemented or given the attention they deserve. Do you guys have what you would feel like is a defined structure of who's in charge when and where and a roadmap of when things happen? Because the way that you're talking makes it feel like what you've got here is a kind of constant decision by consensus or decision by working it out amongst you all. And when you introduced your dad into all this, you said, well, he's not technically a partner, but his word is very valued. It all sounds a little amorphous to me.

12:07And I wonder if, as you're trying to feel through these challenges, part of what you're running into is that there's no clear, very specific decision-making process that could govern the way that you all act with each other? There's nothing written in writing. I think I probably alluded to it earlier, how we don't really function with a board of directors and that whole bureaucracy. I mean, the way that the roles are divided up is really by skillset. I'm more administrative. I had an inclination towards the legal field. So all that stuff is really my department. I'm also more technically abled than my brother's.

12:45So anything technical comes to my desk. My other brother's skill set is warehousing and logistics. And my other brother is merchandising. So it's really whatever skill set happens. Now, if any partner feels like they're about to take something on that rises to the level of we need unanimity or we need to at least inform the others, then they bring it up. It's totally up to their discretion. There's no sort of thing in writing or any plan of action that we fall back on. It's just a matter of just use your common sense. If you feel that others need to be involved, involve them. I like this, but I have to say that there's part of me that doesn't like it.

13:25And the reason for this is because you're running into these lingering questions that no system or pre-agreed upon path are really addressing, right? Like that you all are functionally the leaders within your domains makes all the sense in the world. I remember the closest that I've ever come to working with family in the way that you are doing, and this was a much smaller version of this, was that I wrote a novel with my wife many years ago. It was a romantic comedy. It's called Mr. Nice Guy, in case anyone wants to check it out. And we have been asked a bazillion times, how did we do that without killing each other or at least getting divorced?

14:10And the answer that we came up with was distinct roles and responsibilities. We knew basically who was the CEO of a particular kind of decision. So if it was a question of character development, for example, it was generally Jen, my wife, who had the final say over this because she has an MFA in fiction. She's written novels before. She knows how to do that in a way that I don't. But if it was a decision about, let's say, It was set in the media world. And so if there was a kind of logic to how something would happen in this universe, then we would really defer to my judgment because I've spent my career in the media world.

14:52And so we knew always we would have disagreements, and then we knew whose domain it was and therefore who to ultimately defer to. And without that, I think it would have felt like chaos because somebody has to make a decision. And you generally have that within operations, when it gets down to the operational level. But what you don't seem to have is any kind of system for what happens for decisions that go above the operational level, right? Because what you're just counting on is that you'll all come to some kind of agreement. And the crazy thing is, Charles, that it happened. It worked. You had a disagreement.

15:36You were the odd person out. you understood that you had to set your ego aside and execute for the good of the company and the family. You essentially said, instead of agreeing to disagree, I'm going to disagree and commit, which is a great management system. And yet the problem lingers. And the problem lingers because you're a human being. And human beings aren't actually just cogs and systems. And so now you're sitting around and you're thinking, okay, well, I'm really happy with what happened. The company is more successful as a result of a thing that I disagreed with, but I could still be right.

16:19And the things that I want to do are still good. And that's fine. That's great. That means you're a human being. But the problem is that you guys don't really have a system for what to do with that. That's just about right. Right. And we also have somewhat of a phobia or what is it? A restraint against binding ourselves to anything that we don't have to, especially if it's not time pressing. I just want to say that I've heard that in the way that you keep describing the company, right? Like you said, like twice, you're like, oh, we don't have a board of directors. Oh, we don't have this bureaucracy, which is great in some ways.

16:51But what you've also done is eliminated systems that are designed for exactly these kinds of purposes, right? Yeah. You know, just from our personalities and the way the company functions, I can't see ourselves, let's say, abiding by an agreement. I mean, I can see my family laughing that off. And you don't need that. Maybe you don't need that. Systems don't have to look the same for everybody. And you guys are family. So you're not just sitting down at designated times in designated places. You're probably talking about work all the time. And that's a different issue. The wives hate it. Right.

17:32I can totally understand that. So you're not going to formalize those kinds of things. That doesn't make sense. But it makes me wonder what else could be formalized that would make some sense. I'll give you an example. You pursued option A, and it worked out. And you're now holding on to option B. And your brothers and your dad are not saying option B is a terrible idea, we should never do it, right? Instead, actually, they're giving you this frustrating, like, oh, we'll get there, we'll get there, we need to do other things first. But when? Do you have benchmarks for when option B would get executed?

18:11Because if not, that sounds like a good system to build into, right? Maybe not, hey, is it time to think about this? Rather, maybe it's, okay, I think we all agree option A was a great idea. We all seem to agree option B can work too. What we don't seem to have is any idea of when option B gets executed, which means that you guys keep saying, oh, later, later. And I keep saying now, now. So what if we have some benchmarks? When we reach X in revenue, when we reach X in growth, that will be the time to execute option B. Can we agree to that? Let's figure out what that looks like so that when we get there, we know.

18:45And that means that they feel in control of the roadmap, and you feel like you're being heard and that there is some moment in time, a defined moment in time, when you're actually going to get to do the damn thing that you want to do. That I can get to. And while I'm playing it out in my head, I'm thinking, we're in this meeting, all four of us, and I say, but when? And then I can imagine the response being, we'll figure it out instead of 2025. No, but I guess I'd have to insist. And that's been the answer. And that's the reason you're so frustrated. I think what you just said there actually is a perfect encapsulation of where your frustration is.

19:25Because when they say, we'll figure it out, whose terms now are these decisions being made on? I guess the answer would be the board. We'll figure it out as theirs. Because your answer would be now. And their answer is like, some other time. So even though your answer of now is not pleasing to them, it is specific in a way that theirs is not. You're trying to take control. You say now. Now is a controlling idea. I'm going to do this now. When? Now. But they're saying, we'll figure it out. Some other point. There'll be some other conversation. Something else has to happen. That is not an answer.

20:05That's the absence of an answer. And because there is an absence of an answer, only they now can create the answer, which is incredibly frustrating. And that's why you're frustrated. So we need to replace, right? And this goes back to, so now let's just hit pause on that and like now reapply that to what I was saying a minute ago about systems. You don't need to operate like your PepsiCo or something, right? With layers of bureaucracy and middle management or whatever, you're not that company. But systems aren't one specific thing. Systems are basically, what do we need in place so that everyone knows what's going on?

20:42And that's going to be different for everybody. And I feel like what I'm hearing here is just a weakness in your organization, because there is a lack of specifics about when things are going to happen so that everybody knows and can commit to the plan. And right now, there's no plan. Yeah. And the way specifics are generally treated is why would I bind myself or limit myself ever? It's leave it open-ended. I'll figure it out if I have to. Yeah. Stick around. Help Wanted will be right back. Well, here's where there was an ad that ran on Help Wanted, but that advertiser did not buy to run on Problem Solvers.

21:25So it's just me here. And I will just use this space to remind you that if you are into what you're hearing, you can go find more like it at Help Wanted. You can find Help Wanted wherever you get podcasts, including Problem Solvers. Just search for Help Wanted. Okay. Welcome back to Help Wanted. Let's get to it. Something I've been thinking a lot about recently, which is how we sometimes give ourselves too much choice. We like options. Everyone likes options. But the problem is that there's a thing called choice overload, which is if you have too much choice, you make no choice. And sometimes the thing that you need to do is just narrow your options, at least artificially, so that you can actually focus on a decision.

22:13So fine, they don't want to build in some kind of trigger where if we reach X dollars in revenue, then option B becomes executed. That maybe sounds too frightening to them. But if that doesn't work, can we create a trigger that feels a little more comfortable for everybody? Which is like, when we reach X in revenue, we will very seriously consider how to implement option B. Doesn't get triggered immediately, but now we're going to really talk about it. Right now, you guys don't even want to talk about it. You want to say, oh, later. But now we're going to really talk about it. Can we do that? Right.

22:56Like, I mean, that puts a huge degree of separation between a commitment and action. So if I say, all right, it's at this revenue threshold, we discuss this, not we implement it, that discuss becomes very comforting. They may yield and give in that commitment towards a conversation, not an action, which is all feared or all limiting or whatever like that. Right. Right. So on that degree of freedom, I think is a perfect medium to meet at. And I think that that's great because now you're building a system that's built for you all, right? Which is to say, it's taking into account how they think and what they're going to be comfortable with.

23:42And frankly, we know, I don't know your brothers and I don't know your dad, but based on the conversation we've had so far, if you talked them into some kind of binding thing and then that binding thing got triggered, what would they do? I'm going to guess they would be be like, oh, well, I don't know about this. Maybe. I guess their answer would be like, we'll see when it gets triggered. Yeah. Right. But then if you say this is going to happen when this gets triggered and then they don't go along with it, then the trigger meant nothing. And then the focus is now on whether or not it should get triggered rather than on doing what you guys all seem to be comfortable doing, which is talking things out.

24:22And right now, it's like, I do not introduce this to be political, but it's worth noting that this kind of thing keeps playing out in national politics all the time. There's many examples of this, but we'll just bring up one, which is that there will be a horrible shooting, a school at somewhere. And then Democrats will say, this is a reason to talk about gun control. And then Republicans will say, this is exactly not the time to talk about, this is the wrong time to talk about gun control. And then Democrats will say, but when is the right time to talk about gun control? And there's no answer to that.

24:56And so we just go back and forth. It's a loop that never gets resolved. And that's because you have two totally opposing forces that don't agree on the policy, obviously, but also can't even agree on how to have a conversation about the policy. And that's death. If you can't even agree on how to have a conversation over something, then nothing is going to get done. Now, you guys, as a family, don't have that problem. You agree to talk all the time. You do talk all the time. But funny enough, when there is a disagreement, what seems to be happening is that there's not actually an agreement on when to have a conversation about something, right?

25:39It gets kicked out. So why not formalize that? When is a good time to have this conversation? Which I think, frankly, is something that as I think about it, people who are in relationships should have this kind of thing built into their relationship. When is a good time to talk about our future? You don't want to just bring it up at random. But you know what? Maybe every six months we talk about this. We're going to see where it goes. It's a reason to face it. And the answer that we will get in six months from now could be different from the one now. So let's just make sure we're having that conversation.

26:14I guess if you were to equate this to a relationship, you'd be able to call for a meeting at any time. Obviously, we have a group chat. Say, hey, we need to meet about this. Let's figure out a time. And we do. Just like you'd be able to meet up with your significant other. Now, if you want to discuss your future together, they'd be more of the partner of let's take it slow instead of the I want to get married in February. So any one of us can call a meeting. And yes, everybody will treat that as a pretty important thing that, all right, we all have to meet together. There's a serious matter at hand.

26:46And they'll give me the meeting. But it's in the implementation. That's where I guess a commitment factor has to be worked out. Yeah. They'll give you the meeting, but they won't take the subject seriously because they feel like this conversation is exactly like that conversation. Because what has not been built into it is any new reason to have the meeting. So you have to add something to it. And the thing that you're going to add to it is their own agreement that now would be a good time to talk about this. and I had achieved that through, hey, we met this threshold. Yeah, that's right. Didn't we all agree that when we meet this threshold, we will have X, Y, and Z and it will be a much better time to have this conversation.