Don’t Over-Prepare

How much should you prepare for a crucial conversation?

When we know we need to have a conversation and we expect it to be hard, it is tempting to prepare exactly what we are going to say. There is wisdom in this impulse and also danger. When emotions get heated, people struggle to generate clear thoughts. In the moment, prepared talking points provide a reference and a safety net. The pre-conversation thinking acts as a substitute for creative thinking in the moment.

Over-preparation, however, leads to two problems.

First, you risk sounding like a bad actor. Memorizing lines and making them sound fresh and new each time you say it is a difficult skill to master. Professional actors spend years of training learning how. And even if we do mean what we are saying, when people we are talking to hear lines that sound memorized, they don’t trust us.

Second, no plan survives contact with the adversary. No matter what you prepare, the person or people you are talking with are going to behave in unpredictable ways. You need to be ready to engage with what they are actually putting on the table and not with your expectations of how the conversation will go.

So what is an appropriate level of preparation?

There are three elements to effective preparation for challenging conversations:

  1. Know what you want to accomplish.
  2. Know how you want to be.
  3. Practice brevity.

Know what you want to accomplish.

In my negotiation class at Harvard Law School, I learned that the three things you need to know before entering a negotiation are what you really want, the minimum that is acceptable, and your opening offer. And this is a good foundation for any conversation that you are preparing for.

Know what you really want.

It is important to know what you really want. You may ask for a specific action, but there is generally a reason you want that action to be taken. And often, the true goal can be achieved in many different ways.

For example, if you want to feel close to your mother, you could share something vulnerable with her, ask her questions to get to know her a little better, give her a gift, or engage in an activity with her. At work, you might want to have more opportunity to use your creativity, and the particular project you propose may not be the only project that would require you to be creative.

One of the challenges of being human is that we don’t always know exactly what we want. It is often easier to identify a tangible action or result than the underlying motivation. Here are a few questions you can use to help you understand what you really want.

  • How will I feel when I get what I want?
  • What would the impact of accomplishing this be?
  • What will be missing in my life or work if this doesn’t happen?

What is the minimum that is acceptable?

What is the point at which no agreement is better than agreement?

In business, any deal has a break-even point where the cost-benefit analysis shifts from a positive outcome to a negative outcome. It isn’t always strictly financial. There may be good business reasons to take on a single deal that loses money in order to achieve a desired outcome in the bigger picture.

In personal relationships, the deal-breakers are often in the realm of values. Do you need to feel respected? Will you feel resentment down the line if you accept this arrangement? Is there trust in this relationship?

Know what you won’t accept. Claim the power to walk away. Not needing this deal gives you the freedom to explore what is possible without sabotaging yourself out of fear. And it gives you the backbone to stand up for what really matters without second guessing yourself in the moment.

Knowing the minimum that is acceptable and being willing to walk away instead of accepting less gives you power.

What is your opening offer or request?

If you initiate a conversation, you need to be prepared with an initial offer or request. You may not be the first person to present a specific proposal, but you should to be ready to answer the question: What do you want from me? If what you want is abstract, like respect or more responsibility, have an idea of what that would look like.

Know how you want to be.

People respond to who we are as much or more than to what we say. How you are in any conversation will impact the outcome. You can have the perfect words and still fail to have effective conversations if you aren’t also paying attention to who you are as a person.

Is it important to you to be straight-talking, honest, and direct? Do you want to be defensive or self-protective? Are you willing to be deceitful or manipulative? Do you need to be courageous to stay calm in the face of things you imagine might be said to you? Do you want to be a warrior protecting an idea or person without regard to your own safety? Are you more committed to a big goal than to your fear?

Do you need to be compassionate towards the other participants? Do you need to be receptive to witnessing their emotions without taking them on yourself?

Who do you want to be? Different qualities in you will have different impacts on people you are talking to. Which will serve your goals and the relationship?

Once you have a sense of the kind of person you want to be in a particular situation, you can strengthen your ability to be that way. Here are two exercises that have helped my clients.

  1. Find a metaphor for that kind of person. And think of that before the conversation and anytime you feel yourself losing focus during the conversation.
  2. Think of an archetype or famous character who embodies that quality. Pretend you are that character. Become a statue of them. Walk around as them. Get a feel for how you stand and move when you are that character. Practice being the statue of the character right before you initiate the conversation to remind you of who you want to be during the conversation.

Don’t memorize particular words. Practice brevity.

Memorizing an opening sentence is appealing because it minimizes the risk of stumbling over word choices and not effectively stating an important point. The danger of memorizing words is that you will appear inauthentic.

There is a way of preparing that increases you ability to be both authentic and clear. Practice brevity.

Often, people who are emotional beat around the bush, hedge one’s bets, hem and haw, and otherwise obfuscate. Which reduces their effectiveness as communicators. Practicing brevity creates a pattern of making a point clearly that guides the brain unconsciously when needed.

The elements of practicing brevity are:

  1. Know what you want to say.
  2. Imagine a variety of people you could say it to and say it out loud as if to them using only one sentence. Then, do it again with 3 sentences.  Repeat with 5-7 different people you are pretending to talk to.

This practice creates a default of using no more than 3 sentences when talking about the topic. When the moment to actually have the conversation arises, you can focus on how you want to be with the other person and trust that the words will come out well enough.

Knowing what you want and how you want to relate to the other person plus practicing brevity creates a foundation you can stand on and be strong and real during hard conversations.

Which element of appropriate preparation for hard conversations would you get most benefit from?

Let me know in the comments or on my Facebook page.


This post is part of the 2017 Blogging from A to Z Challenge.

Inertia is Just a Speed-Bump



How often have you found that getting started is the hardest part of a project?

What was your latest project that seemed daunting until you got started and then was much easier and faster than you expected?

Stepping into something new often requires overcoming inertia. And along with inertia, there is often a voice of fear coming along for the ride.

That voice of fear will always be there. Every time you start a new project, the part of you that is hard wired to worry about anything new will speak up. And the trick to getting things done is to start anyway.

3 tips for getting starting despite fear.

  1. Take a tiny step forward. What is the smallest step you can take towards your goal? Is that step small enough not to trigger paralyzing fear? Taking the first step without worrying about what comes next can tame the fear.
  2. Identify your motivation. What are you moving towards? Why is it important to you? Who other than yourself will benefit? What will happen if you don’t do anything?
  3. Get an accountability buddy. Find someone to report in to when you have finished. It might help to choose someone who will celebrate your small milestones with you. If fear of negative consequences motivates you, you might devise a consequence that they will arrange if you don’t take steps within a certain time frame.

Once you get started, you will be on your way.

Many times, the first taste of momentum is what it takes to get inertia working for you instead of against you.

An object in motion tends to stay in motion.

What is the smallest motion you can start now?

This post is part of the 2017 Blogging from A to Z Challenge.