How to win high-stakes conversations without being manipulative

High-stake conversations don’t often end up as expected. They go sideways regardless of how good effort you put in place.

As a result, you don’t generate the outcome you wanted in the first place.

Here’s the thing. You don’t have so many other chances to make it right. Most of the time, you have only one shot. And it must be 100% right.

It may be a conversation with investors or with an A-type client, or maybe with the CEO as you don’t have easy and direct access.

You can make a huge win as well as fail dramatically.

People believe that these conversations get derailed primarily for personality clashes, lack of empathy around the table, differences of opinions, or because there is too much pressure as the stakes are high.

Although this is true, in my experience it’s less about dealing with the emotions during a high-stakes conversation and more about how we prepare for these conversations.

When I work with professionals to help them build their influence, I often see that they jump onto key meetings with no clarity of what they want to achieve, how they can help the other person, how to deal with rejection and more.

In other words, it’s the lack of system and structure that prevent many from either having these conversations or not getting what they truly want.

In my experience, there are five steps to take before starting any important conversation:

1.Set a clear goal (and one only)

Whether you are planning to talk with your boss, a direct report, or a client, be very specific in what you want to achieve at the end of the conversation.

My recommendation is to focus on a goal that is time-bound and achievable in a meeting. If your goal is to get a yes for a decision that requires time and the involvement of other stakeholders, break the goal down into smaller wins, and then focus on each win at the time.

2.What’s in it for the other person

Too many high-stakes conversations are a one-way direction. This happens when people don’t care much about the other person. They want to win regardless of what the other person wants.

With this approach, influence doesn’t happen.

How much do you know about the other person? What is it motivating him/her? How can you both win?

People take action primarily when there is personal gain for them.

3.Choose the communication style

Following point 2, the more you know the other person, the better you know how to approach the conversation.

Most professionals know and use only one communication style regardless of who is in front of them. They don’t touch the right chords with the right message. They believe that what resonates with them will also resonate with the other person.

For example, it’s pointless to bring facts or data to convince someone who makes decisions with stories and visions. This is a risky mistake.

4.Rehearse. Rehearse. Rehearse.

95% of professionals don’t rehearse.

They do have a sort of structured thoughts in mind, but then their castle collapses very quickly when the other person derails the conversation. They realize only too late they could have said things differently and better. Other times, they feel they missed something important out of the conversation.

Build your structure. Follow a written script. Rehearse with someone you trust who can give you honest feedback.

5.Prepare for the worst.

Finally, if you followed all the previous points, it will be much easier to anticipate resistance, conflict, roadblocks, and issues.

In other words, I want you to build a plan B in case things go south. What can go wrong? How would you react if they say no or the conversation fires up? What other things can you offer to the person to convince him/her further?

I hope you realize now that winning high-stakes conversations is possible and it doesn’t include any hard sell, persuasive tricks, or, worse, manipulative tactics.

It’s all about preparation and hard work. It’s not about talent or sales magic.

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