Win Over the Person Blocking Your Deal

After two and half decades of doing deals in Silicon Valley I could write a dissertation on what I’ve discovered. Instead, I’ll posit one big, bedrock idea that eludes even the most seasoned of dealmakers: Success in deal making is not primarily about numbers or relationships or even timing. What matters most at the highest levels in business is the ability to leverage the dynamics of position.

When I was younger I spent a year as a professional poker player. After doing some statistical analysis of my playing, I realized that I made almost all of my money when playing hands “in position.” In other words, understanding where I sat at the deal table in relation to everyone else was the single most important factor in winning the game. Contrary to popular lore, being a winning poker player has little to do with bluffing or reading people or being a statistical wizard, and everything to do with maximizing the value of position.

In deal making the same thing holds true. Where someone sits within an organization determines both their underlying motivations and their risk profile — the two factors that determine whether they will say yes or no.

In a previous article, I wrote about the triangle of stakeholders: champions, decision makers, and blockers. Each of these individuals is uniquely positioned to influence a major deal and ultimately get it done or shut it down. In this piece, I’ll focus on the player in the triangle with the sharpest sword: the deal blocker.

There are numerous books, seminars, and courses on the subject of getting from “no” to “yes.” Whether the topic pertains to sales, diplomacy, or politics, the advice canon is vast. Yet there’s precious little available on the dissenter’s rationale.  In order to turn deal blockers into advocates (or silent agnostics, worst case), we need to understand their motivations — and we do that by considering their position at the table. Blockers nix the deal because, from where they sit, it is in their best interest to do so. The job of the dealmaker is to turn that around.

What shapes the deal blocker’s motivation? In my experience, it comes down to three basic drivers: respect, advantage, and self-preservation.

RespectFor some blockers — I’ll call them experts — saying “no” is a simple matter of personal pride. They know far more about a specific domain (finance, technology, law) than you do and they want everyone to see that. Why? Because these blockers are less powerful than they are respected — and they want to maintain that high level of respect. This is why lawyers seldom recommend a deal. It’s not their job. Their job is to point out everything that could go wrong. Experts will dissect your pitch with a magnifying glass, looking for flaws. And because of where they sit in an organization, experts are risk-averse. If a deal they support goes south they are an easy scapegoat because they don’t have a lot of political clout.

Winning over experts is a two-step process.  First, you have to speak to them in language they understand (legal, technological, or what have you). Remember, these are not business owners, so presenting the corporate upside of what you are offering won’t help. What they care about is preserving the respect and trust of their colleagues, and that requires that they maintain a critical stance. Therefore, you need to help the experts look smart. By simply showing them the respect they deserve, you are giving them part of what they need to get out of your way. Next, surround yourself with powerful internal and external supporters. Creating an environment where experts can safely jump on board, and insulating them from the side effects of failure, allows them to maintain their prestige and support the deal.

Advantage. Other blockers say “no” to the deal because it’s actually to their advantage to knock it down.

One such blocker—the competitor—is the champion of a competing idea or solution. From where they sit, competitors can enhance their own prospects by using your deal to make theirs look like a better alternative. Competitors are open to risk because they are willing to raise the stakes to ensure their own success. The best way to encourage competitors to support you is by forming an alliance that will help them close their deal. Perhaps your deal will create a market for theirs or serve as a test case?  Your deal will look good to competitors if they can tether their success to yours. If that doesn’t work, your only option is to isolate that person so his/her opinion doesn’t have the necessary gravitas to block you.

A similar breed of blocker, the doubter, doesn’t ever really say “no” to the deal—but he won’t support it either. Since he has nothing specific to gain by saying yes (he isn’t the champion), he plays devil’s advocate. Why? Because if the deal goes bad, it’s safer on the sidelines. In reality, many doubters are looking for a reason to get in the game and say yes. They want to be champions. The key to converting doubters, then, is to offer them enough upside to coax them out of the shadows. This can be in the form of a promise to include them on the team, have them speak at an event, introduce them to an industry luminary, or whatever that person might value.

Self-preservation. The last type of blocker, the traditionalist, is someone who’s always done something a particular way. Traditionalists rely heavily on precedent. It’s how they’ve made their mark in the organization—with one specific process, technology, or incumbent account. By saying yes to something new, the traditionalist is putting his old-line position in jeopardy. Traditionalists are risk-averse because their livelihoods depend on it.

The wholesale adoption of “cloud” computing is one example. There are huge numbers of people who have built their careers installing and maintaining software and systems. With cloud computing, 90% of that disappears. What happens to the traditionalists who spent 20 years overseeing the last generation of technology? They either get on board or they disappear. The best way to get this type of blocker on your side, then, is to make change seem inevitable. As much as traditionalists fear change, they are more afraid of missing out or being left behind. Bringing the traditionalist on board gives him hope that he can transition his domain into the inevitable new normal.

The reality is that all blockers say no (or yes) because it is in their best interest to do so. And their motivations, like your own, are dictated by their positions around the deal table. By leveraging that, you can neutralize their concerns in a way that allows them to either benefit from the deal or get out of the way with their credibility intact. This understanding, in deal making as well as poker, is what separates the professionals from the amateurs.

Originally published in the Harvard Business Review: