Successful dealmaking is part art, part strategy. These industry leaders share the tactics that give them an edge.
Some people can talk their way into a room. The best dealmakers know how to walk out with a “yes.” But getting there takes more than a persuasive pitch or a well-timed handshake. It requires a sharp read on people, a clear understanding of what they’re after and the confidence to make a compelling case without overselling it. Those skills matter whether you’re raising millions from investors, landing a major client or building relationships that could pay dividends for years.
The key is in nailing the approach. The members of Maxim Sphere—an exclusive group of accomplished founders, executives, investors and industry leaders—share their insights on how the best in the business get to “yes” faster, and what it takes to turn a promising opportunity into a done deal.
1. Know Your Stuff
“The best dealmakers know their product or service inside and out and genuinely believe in its value. This level of knowledge and authenticity fosters an immediate sense of trust, one rooted in respect for the salesperson’s expertise, passion and conviction. Once you’ve established trust, communicating value to a potential investor can become a simple conversation, instead of requiring a highly polished and persuasive speech.” – Chelsey Hinsenkamp, Mecum Auctions
2. Speak Their Language
“They speak in terms that are relatable to their audience. When raising capital for InList, we had to pitch investors who understood the demographic (high-net-worth individuals) better than they understood the actual product itself (reservations for clubs and high-end restaurants).” – Gideon Kimbrell, InList
3. Lead With Trust
“Emotional trust goes a long way in business. When an entrepreneur or salesperson approaches a business conversation with boilerplate ‘ladder’ strategies and template tactics often taught religiously in sales lectures, their audience can usually sense what feels like a coordinated plan of attack rather than the authentic curiosity, compassion and ambition required to satisfy their needs. When dealmakers prioritize earning trust in business discussions, they create space for the listener to feel comfortable. This allows their audience to move past delicate details and arrive at a ‘yes’ more quickly, because they are less concerned with the minutiae. Rather, they’re more concerned with how much their gut trusts the individual feeding them with the facts. Sometimes, the most faithful strategy a great dealmaker brings to the table for a faster ‘yes’ isn’t their product, track record or polished proposal, but their word.” – Brian Thalhammer, Mecum Auctions
4. Listen More Than You Talk
“No frills, no secret method unable to be leveraged by certain demographics—just active listening. Understanding your client above all fosters relationships that motivate, collaborate and help discover the true ‘why.’” – Kate Morello, evoJets LLC
5. Remove Any Friction
“In the world of retail, I relate this to our ‘time to convert’ metrics. Targeting the right audience naturally drives higher conversion rates. Once you know you are marketing to the right people, you can zero in on the friction points delaying your conversion funnel. To get a shopper to make a $1,500-plus purchase immediately after discovering your brand, you have to earn that trust instantly. We build this trust by investing heavily in brand building, customer service and overall experience. We strategically integrate review requests into our customer workflows and produce consistent content across our blog and social channels to stay relevant and ensure algorithms place us right in front of our followers. We also look at our most popular landing pages, where users drop off and which product features or policies they review before purchasing. We’re continuously running A/B tests to find the fastest, most effective ways to surface the right information during the purchase journey.” – Sam Bodine, Scout & Nimble
6. Be Clear About What You Can Offer
“Be authentic, real and straightforward about what you can offer to your customers and clients. That kind of ‘straight talk’ is seldom seen and the highly prized currency of business relationships and connections.” – Matt Avery, Mecum Auctions
7. Think Beyond The First ‘Yes’
“The best dealmakers get to ‘yes’ for one reason: They understand it’s a process. Saying yes keeps you in the game and allows the deal to continue. Most times, the original yes to the deal isn’t the actual deal. But a delay or a no puts you on the outside with no ability to move the process along in your favor. Say yes, and stay in the game and shape the deal as it moves through the process.” – Brendan Keegan, bFEARLESS Ventures
