BusinessLawGuy's Blog

Look, I’ve seen it a so many times. A client sits across from me, eager to close a deal or settle a dispute, convinced that this deal is the only way or is that breakthrough they’ve been chasing. The terms are terrible. The other side is asking for everything and giving nothing. But they’re ready to sign anyway because walking away feels like failure. But walking away from a bad deal isn’t failure, it’s good business sense. No deal is almost always better than a bad deal, and if you don’t internalize this principle, at some point in your career you’re going to learn an expensive lesson.

The problem with bad deals is that they don’t just cost you money upfront. They consume your resources, your time, and your attention for months or years afterward. Bad deals create ongoing liabilities, disputes, and headaches that compound over time. They tie up capital and management bandwidth that could be deployed elsewhere. Meanwhile, the opportunity cost is staggering because while you’re trapped in a bad arrangement, better opportunities are passing you by.

The pressure to close deals can make people lose perspective. Maybe you’ve been negotiating for months, you’ve spent money on due diligence, and the sunk cost fallacy kicks in hard. Maybe you’re worried about looking weak or indecisive if you walk away. These psychological factors are powerful, but they’re also dangerous.

Having the discipline to walk away when the terms don’t work, even when it’s uncomfortable, is a superpower. It means you understand that your willingness to walk away is actually your greatest source of leverage because once the other side knows you’ll sign anything just to get a deal done, you’ve already lost.

So what does a good deal look like? It’s not about getting everything you want or crushing the other side. A good deal creates mutual value, allocates risk fairly, and gives both parties room to succeed. Most importantly, a good deal makes you excited about the future relationship. If you’re having doubts, trust your gut. If the terms don’t work, don’t sign. Always remember that your ability to say no is one of the most valuable assets you have in business.

Beginning in 2014, many of you probably read my blog regarding having a checkup for you and, if you have one, your business. This does not involve the doctor, but it does involve all of the other professionals in your personal and business life. Based on the positive feedback, I have made this an annual tradition. I originally made this post the week between Christmas and New Year’s but that’s too late, which is why I now share this a few weeks prior to the end of the year to give you time to take action and look into possible changes before year end.

It’s good to check in with various professionals you or your company work with, be they attorneys, accountants, insurance professionals, financial planners, investment professionals, etc. The list depends on you and your business.

Some of you said “What a great idea. I am definitely going to do that.” Others said “Sounds like a good idea, maybe I will look into that.” Another response was “I wish I had thought about this before the end of the year or when certain contracts automatically renewed.”

I’ll bet in most years the majority of you were busy with or recovering from the holidays and probably did nothing in response to my push for you to do this type of “annual checkup.” To be honest, this response is okay and ignoring my advice may not have had negative effects to you or your business.

The point of the advice is that you only know what you know. For example, I always check in with my accountant prior to the end of the year to ensure that all is right with taxes and withholding because I don’t want a big surprise that I owe more money or am being assessed penalties for under withholding.

A few years back I had a reminder related to a different item you should check on annually, auto insurance. We had teenagers on our policy at the time and a number of vehicles, and the premiums always seemed so high to me. But my insurance person knows me and shops the policy every year looking for the best rates rates for similar coverage from quality insurers. He did that for me and we ended up with a new insurer, with pretty significant savings.

Does your  insurance person do this? If not, why not? You should ask. Or you should switch to a new insurance person who cares as much about you as they do about the commissions and income you represent to them.

With life being so busy, sometimes it’s hard for me to move beyond the higher-level checkup, but when I do I usually end up with some benefit. Unfortunately, in our time-crunched world, the question of who to check in with at year end is expansive, from your estate planning attorney, to your investment person, to your insurance person, to vendors you may use such as a yard or pool maintenance company, or your cell phone carrier or your Internet provider. You may be surprised what a company will do in lowering monthly costs to satisfy or keep a current or longtime customer. Try it and see what happens. Start with your cell phone provider – there always is a promotion happening that will lower your monthly costs.

I know, I know, who has the time? None of us do, which is why the choices are yours. Are your contracts up to date? Did you pay enough estimated taxes or withholding? Are you paying too much for the cleaning service at your office or your lawn service for your home ? The choice of what professionals to consult, what costs to check or compare, and what services to put out to bid is yours. Choose wisely.

In a few days it will be Thanksgiving 2025, in what seems like a world gone crazy. In thinking about writing about being thankful or gratitude, I looked back to my posts from the week of Thanksgiving in prior years. I can’t say it better, so here is my annual blog for the week of Thanksgiving.

This is a good time of year to think of gratitude generally and what you’re thankful for specifically. At the same time, it’s a great time of year to spread good feelings, which you can do by letting others know when you appreciate something they have done for you. It may mean a phone call, email, or text, but it’s import to take the time to reach out, thereby investing in your relationships.

Those of you who have younger children (or older ones…) know you end up reminding them to say “thank you” all of the time. That is because thanking someone or showing gratitude is a learned behavior. If it came naturally or from observing others we wouldn’t have to teach children to do so.

Hopefully you remember to thank people as appropriate in your daily life. This may be thanking someone holding the door for you when you get to your office, for holding the elevator for you, or for making a pot of coffee so you can get that needed caffeine injection upon arriving at your office. For me, it includes thanking people on my team for their hard work to complete tasks needed to serve clients’ interests. Many of these situations are universal to all of us, but I am sure we all remember holding a door for someone when they walked through without saying anything.

Of course, if you go through your day looking for when people should be thanking you, you will be disappointed. Instead, you should think about how you want to come across to others, as well as how you don’t want to come across to others. We all have bad days, but most days we should recognize when thanking someone is proper and appropriate.

This time of year is a reminder to says things you may usually only think to yourself. Positive feedback is energizing, and hopefully the person you provide it to pays it forward. Plus, it has the added bonus of making you or the other person feel good, making it a great way to go through life.

Think about how to make gratitude part of your daily life all year long and have a great Thanksgiving.

Almost nobody hears too many sincere compliments. We’re all walking around with positive thoughts about colleagues, clients, and people in our professional circles, but we keep most of them to ourselves. It’s as if there’s some invisible force field that stops us from just saying what we’re thinking when we appreciate someone.

The solution is simple. Compliment people to their face, and then compliment them behind their back. When you think something nice about someone’s work, their judgment, or just their presence, say it right then. “It’s always fun to see you” or “You handled that situation really well” or “I trust your instincts on this”—these aren’t grand gestures, just honest observations spoken aloud. The key is treating these statements as casually as commenting on the weather.

What happens when you do this consistently is interesting. People remember the direct compliments, of course, but the ones you give behind their backs come back around in ways that build real trust. Someone hears that you praised their work when they weren’t in the room, and suddenly they know your appreciation is genuine rather than performative. This creates a completely different dynamic than the typical professional environment where people can be careful, measured, and withholding.

We underestimate how much people need to hear that they’re valued, that their work matters, that someone notices what they contribute. The legal and business world can be a grinding place where feedback is mostly about what needs fixing. Being the person who also points out what’s working, who acknowledges effort and skill and character, doesn’t cost you anything. It just makes everything better for everyone involved, including you.

We’ve all heard countless times that listening is a lost art, an undervalued skill that could transform our businesses and relationships if only we’d slow down and truly hear what others are saying. Management books devote chapters to the practice of being present and attentive. And they’re right to do so—listening matters enormously. But while we’ve been busy diagnosing one side of the communication equation, we’ve completely overlooked its equally essential counterpart, which is candor.

We worry about hurting feelings, damaging relationships, or creating legal exposure. We’ve built entire industries around softening our words, from HR compliance training that teaches us to sandwich criticism between compliments to communication consultants who help executives say difficult things without actually saying them. The result is a business world where everyone talks endlessly but few people say what they actually mean.

What makes this particularly troubling is that candor and listening aren’t separate skills—they’re two sides of the same coin. Someone can be refreshingly direct, but if no one’s truly listening, that candor accomplishes nothing. We’ve created a peculiar dysfunction where we’ve trained people to listen better while simultaneously training them to speak less directly and honestly.

The irony is that most business issues involve a failure of candor rather than a failure of listening. What happens is that someone spotted the warning signs but didn’t want to be the bearer of bad news or disagreed with the strategy but went along to get along. These aren’t listening problems—these are candor problems.

If we’re serious about improving business communication, we need to recognize candor as a fundamental skill that can and must be developed. This means creating environments and cultures where direct but respectful speech is rewarded and where respectful disagreement is valued. This requires leaders to model candor themselves, even when it’s uncomfortable. By focusing on candor in addition to listening we create the opportunity to transform our businesses and relationships.

Confidence is the most valuable currency in business, but most people trade in counterfeit bills. It’s easy to mistake volume for conviction and swagger for certainty, and later watch that same person crater when the pressure actually arrives. Real confidence isn’t about never showing weakness. It’s about knowing your value so thoroughly that you don’t need to perform it every minute of every meeting or day.

People with confidence show themselves in how someone handles status. I’m talking about people who can laugh when they’re the punchline, who can take a younger co-worker’s criticism of their strategy without getting defensive, and who don’t need to dominate every conversation to prove they belong in the room. These are people who understand that confidence isn’t a rigid posture you hold. Instead, it’s fluid and adaptive. It’s something you can afford to relax because you know it’s still there when you need it. Watch someone’s face when they’re gently ribbed at a dinner meeting. The secure ones smile and volley back. The insecure ones catalog it as a debt to be repaid.

But here’s where it gets tricky, because confidence isn’t the same as that false modesty routine that everyone’s running these days. You know the type. They accomplish something significant and then spend ten minutes explaining how it was really everyone else, how they barely contributed, or how they were just lucky to be in the room. That’s not humility, but another kind of performance. When you’ve actually done the work and delivered results, you don’t need to diminish yourself to make others comfortable. Real confidence means accepting credit without apology, standing in the spotlight when it finds you, and saying “thank you” instead of deflecting with some rehearsed speech about how you’re just a regular person who got lucky.

What I’m describing is actually a balance, something I think of as the space between dignity and humility. It’s about occupying your proper place without either shrinking from it or expanding beyond it. The truly confident people I work with know when to defer and when to direct, when to listen and when to speak with authority, when to acknowledge mistakes and when to defend their decisions. They’re comfortable moving up and down the status ladder because they’re not desperately clinging to any particular rung. Their sense of self isn’t dependent on always being the smartest person in the room or the most liked or the most humble. They just are who they are, and that consistency creates trust.

This matters in business because confidence is contagious and so is its absence. People are reading your signals constantly. They’re asking themselves whether you believe in what you’re doing, whether you can handle adversity, or whether you’re going to fall apart when things don’t go according to plan. The leader who can take a joke, accept being wrong, and still project calm certainty when decisions need to be made—that’s who people want to follow and builds something that lasts. Everything else is just noise from people trying to convince themselves as much as they’re trying to convince you.