It's hard when you're working with a tough audience. Especially someone who contradicts and challenges every point you make.
I've come to the conclusion one has to first understand where these naysayers are coming from and what their ultimate goal is to be able to debate them successfully. I've come up with four positions your opponent might be taking:
1. They Disagree With You
This is probably the easiest one to tackle because it's based upon an honest position where your opponent is factually disagreeing with you. They still have an open mind, but for the immediate future, they are factually on the opposite side of the track.
Solution: These are rational people, so use facts, figures, and reasoned logic to bring them over to the dark side. Acknowledge their position, but show them your way will ultimately be a better direction.
2. It's Their Personality
We've all met them — the naysayers of our lives. Those people who take pleasure in contradicting an established belief, position, or idea because it's hard-wired into their personality.
It's a mix of cynicism and pessimism which ultimately drives the contrarian engine in this person. I've always felt people do this to be recognized and appreciated for their intellect — but ultimately, they just want to be acknowledged and heard.
Solution: Listen to them. Ask lots of questions and delve deeply into their position. Acknowledge some of the merits of their belief structure.
Then begin to get them to understand some of the tenets of your position by aligning the more minor tenets of their areas. "I see where you're going — we want to save money. If we take this idea, it looks like we are going to save a huge chunk of cash." Also don't use the words "My idea" — use "This idea" or "Our option".
3. They're Afraid Of Change
Oh my — they're all over the place lately — people afraid of change who will do almost anything to keep the status quo, even at the detriment of their institutions.
The main driver in these people is FEAR. Even if you present a clear example of a successful position, they will endeavor to undermine it and counter with the status quo — "things are fine if we just leave it alone".
When you lift the covers, you'll see they're temporarily irrational and will be impossible to move unless you show them a 'safer' position.
Solution: They need to feel safe, so show them their current 'safe' position is actually an unsafe decision long-term. Use facts to bring them along slowly and get them to understand the ramifications of their current 'fear-based' behavior.
If you get them to incrementally understand their unfounded fears by seeing your clear direction for change, they will ultimately (and usually quickly) side with you. If you are working against a group, pick off some of the weaker adherents and use them to convince some of the more immovable opponents.
4. They Want Power
These are the toughest people to turn. Why? They really don't care about the facts at hand or where it will ultimately go — they only care about their current power structure and how to maintain and grow it.
It's the typical situation in politics. Don't try to convince someone with facts, figures, and reasoned ideas — follow the power and money. Once you understand what's under the kimono, you'll easily see where they are coming from and how you can speak their language.
Solution: Be very, very careful here. Since this is the toughest nut to crack, these people will lash out quickly and go for the jugular if you are in any way affecting the status of their power structure with your ideas.
You need to move slowly and build a power base behind you. Appeal to their nobler motives first (give them that chance) and then slowly chip away at their resolve. If you can, show them your idea will ultimately give them even more power. But wear your seatbelt, you will be on a very bumpy ride.