Crush your next high-stakes conversation

While any conversation is an opportunity to learn and to build relationships, some have more at stake: your next career step, a sale, financing your start-up, or that new hire all come to mind. If you think about it, most good things manifest through conversations.

A high-stakes conversation is one where disagreement about priorities and desired outcomes is expected.

For some leaders, merely asking for help is always a high-stakes conversation because the person is not comfortable appearing to need assistance. One woman, we'll call Vicky, successfully navigated her executive career path in a Fortune 100 company for 15 years. Then, as often happens, hit the proverbial wall.

Because she didn't handle the new challenges as well, she ended up being reassigned to a smaller and less strategic division. Yet during this exceptionally turbulent and stressful period of her career, she never asked a mentor or coach for help or direction.

Some consider asking for help to be a sign of weakness instead of an opportunity for collaboration. Or they fear being turned down.

The reality is most people actually LIKE to help.

Mastering the skills of steering high-stakes conversations makes you recession-proof, objection-proof, and competition-proof.

1. Relationships first. Business second.

No matter what the outcome of the conversation, you want to build relationships with your conversation partners. This point of view relieves pressure as you shift your perspective from succeed/fail to relationship builder regardless of the immediate result.

Understanding the importance of the relationship means you understand the importance of researching your conversation partner. Search LinkedIn to see this person's most recent achievement so you can make a meaningful comment about it.

That is ‘shows me that you know me’ in action and it smooths the road to getting what you want.

Doing your homework means you're prepared. And preparation = confidence = competitive advantage = being essential, priceless, and irreplaceable.

2. Know your desired outcome.

What specifically do you really want to happen as a result of this conversation? Or in broader terms: how do you want the relationship to develop?

A lot of times you don't get what you want immediately, but through this conversation "fail," you build the relationship so that you win in other ways, possibly getting that thing you want later on.

Your desired outcome is easily framed as what you want your audience to feel about you, know about your topic, and do as a result. Happily, there is a specific tool for this, the Feel Know Do. (Read my Forbes article on how this works.)

3. Prepare for multiple conversation pathways.

What will you do if the person says "Hell to the yes!" after the first request? It does happen. You want to have next steps in mind no matter which direction the conversation moves.

It's your job to steer this conversation, even if it's not moving in your ideal direction. That is where skill in conversation determines the ultimate outcome.

What will you do if you get a "no"? Sometimes "no" means "not now" or "I need more information". You want to have a next step in mind for this scenario as well.

Three examples of follow-up to a no.

  1. Thank you for carefully considering my proposal. I appreciate your taking the time to meet with me. I'll check back in 6 months to see if anything has changed.

  2. Thank you for setting up this interview. What recommendations do you have to make me a stronger candidate in the future?

  3. Thank you for looking at this proposal. Is there anyone you think would be interested in this?

What will you do if you get a ‘let me think about it’? Your next step might be to set a date for follow-up or make sure there are no lingering questions you want to answer right now.

Just like with everything else, practicing with high-stakes conversations raises your skill level. Seek out opportunities to develop your proficiency by creating stakes in conversations by asking for small things. I used to practice by asking for water with no ice, even if the waiter had just brought me a nice glass of water with ice.

If you practice asking for things before it's mission-critical, you'll be ahead when that next true high-stakes conversation pops up on your calendar. You'll be essential, priceless, and irreplaceable.

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Fixing Difficult People