_{Inside the Deal Room is where I share what’s happening behind the curtain as we source, negotiate, acquire, build and scale businesses through Vyterro and our deal ecosystem.}

There is a fine line between being thorough and being difficult to work with. Everyone knows someone who crosses that line. What should be simple drags on and becomes an argument. Every email turns into a debate. Decisions take twice as long as they should.

On the other side of the coin, everyone has worked with someone easy. They're responsive, reasonable, solution-oriented, and just good to work with. When a new project comes up, everyone wants that person on their team.

This applies everywhere in life. Whether it's a co-worker, a group project in school, or a customer of your business – people naturally want to work with someone reasonable. Buying a business is no different.

This last lever of this series is less tangible than the previous ones, but I've found it's just as powerful. Sellers, brokers and lenders want to work with buyers who make the process smoother. Showing you are reasonable is a skill you can master and benefit from.

This doesn’t mean you become a pushover. There are definitely times to run through brick walls to get a deal done. But, there are also times to simply ask the guy building the wall if he'll move it. Knowing when to push and when to pull is one of the most underrated skills in acquisitions.

Once the broker and bank fade away post-closing, the seller will likely still be around for a while. This makes your relationship with them essential to long-term success.

Remember, this is often the biggest financial and emotional decision of their life. They're deciding who to hand what they've spent decades building. If every interaction feels adversarial, overly legalistic, or unnecessarily difficult, they're going to wonder what it will be like to work with you for the next few months during diligence and beyond, post-closing.

The easiest way to stand out is surprisingly simple:

That starts with the little things. Be flexible with scheduling. If they need an extra day to gather information, give them the extra day. Don't argue over insignificant details just because you can. Every time you let the seller win on something that doesn't materially impact the deal, you build goodwill for the moments that actually matter.

The same applies during the transition discussion. Instead of walking in with rigid demands, ask questions.

"What would make this transition easiest for you?"

"What works best with your retirement plans?"

"How involved would you like to be after closing?"

You're negotiating together, not against each other. More often than not, if the seller feels like you're genuinely trying to build a solution that works for both sides, they'll reciprocate that level of reasonableness.

Again, this doesn't mean being indecisive or accepting a bad deal.

Every acquisition has a limited amount of negotiation capital. If you spend it fighting over every small issue, you won't have much left when a truly important one comes along.

The buyers who consistently win aren't always the toughest negotiators. They're often the ones who make the process feel collaborative instead of combative.

If there's one person who appreciates a reasonable buyer more than anyone else, it's probably the broker.

Most brokers are juggling multiple deals at once while fielding calls from sellers, lenders, attorneys, accountants, and buyers. They've also dealt with enough difficult buyers to know exactly what one looks like.

One of the easiest ways to build goodwill is understanding how to balance requests, when to push, and when to be patient. Don't send twenty diligence questions in your first email after getting the CIM. Ask a few key questions after reviewing and save others for a broker call. Save another handful for the seller call. Save the rest for diligence. The process is designed to unfold in stages. If you try to pull all those stages into the first email, you will immediately signal that you’re going to be difficult to work with.

If a broker needs another day to gather financials, don't immediately assume they're disorganized. They're usually waiting on the seller, who's busy running the business. If they take a few hours to return your call, don't assume they're ignoring you. They're probably dealing with five other buyers at the same time.

I know it can be frustrating, but giving brokers the benefit of the doubt goes a long way.

The nuances of your communication with the broker also matter. I intentionally use phrases like "No rush," "Take your time," or "Whenever you get a chance.” The goal is to show them you aren’t putting pressure on them constantly. There’s a time and place for that.

If you hold yourself to a high standard while giving the other side grace, you will naturally build goodwill. Getting the broker to respect your work ethic and appreciate your patience at the same time is the sweet spot you want to be in.

Another habit I've developed is looking for opportunities to give instead of always trying to take. Be flexible with meeting times, don't make an issue out of small delays, etc. If something isn't material to the economics or structure of the deal, let the broker have an easy win. Every one of those moments builds goodwill that you can draw on later when something actually matters.

That's really what this positioning lever is about. You're not being reasonable because you're tentative. You're being reasonable because long-term goodwill is often more valuable than short-term urgency. Every email, conversation and reaction creates an opportunity to build trust or create friction. Acting intentionally to do the former gives buyers an advantage.

And, remember, brokers are your lead source, not your opponent. The better your reputation becomes, the more likely they are to bring you future opportunities.

The bank is the one party where the leverage is more often in the buyer’s court.

With the seller and broker, you're competing for a unique opportunity. There's only one business for sale, so you're trying to convince them that you're the right buyer. With the bank, the dynamic flips.

There are dozens of SBA and conventional lenders happy to finance a good deal. Assuming the transaction makes sense, they're trying to earn your business just as much as you're trying to earn their approval. Understanding that changes how I communicate.

I'm still professional, responsive, and easy to work with. I submit documents immediately, answer underwriting questions quickly, and do everything I can to make the process smooth. That said, I'm also much more willing to push when timelines slip or communication breaks down. If I need an update, I'll ask for one. If I think something is moving too slowly, I'll say so. I take a more aggressive approach than I'd take with a seller who's deciding whether to sell me their life's work.

Most lenders are normal people working a 9-to-5 job. Your acquisition might be the biggest financial decision of your life, but it's one of several files on their desk that week. Treat them with respect and give them the same benefit of the doubt you give the brokers. Assume they're trying to help – just don't be afraid to hold them accountable when it's appropriate.

Reasonableness still matters with the bank because your reputation follows you. Loan officers move between banks and credit teams remember good borrowers. If you’re a serial buyer, you’ll likely run into the same people more than once. The smoother you make their job, the easier they’ll be to work with.

At the same time, don't be afraid to remember who's hiring whom. The bank is providing a service. It's perfectly reasonable to expect responsiveness, professionalism, and clear communication in return.

In most deals, no one cares about getting the deal done more than the buyer. That means it’s your job to manage the timeline, the process and the other parties involved as best you can.

Be reasonable, reduce friction, and make the process as easy as possible for everyone involved. If you consistently carry yourself in a calm, understanding, and stoic manner, you'll often find the people around you doing the same. Having the highest emotional intelligence in the room can be the difference between a deal blowing up and getting across the finish line.