How to Set Yourself Up for Big Conversations

In one of my consulting sessions a while back, my client was preparing for an important meeting with a business partner. They asked me for advice on how to approach a difficult conversation about their current business situation and what the future might look like. Instead of their usual casual discussion over beers, my client wanted to go into the meeting with more structure to ensure the conversation stayed on course.

My client bounced around a little as we discussed what they wanted to cover in the meeting. They said they were worried that the conversation would get waylaid or confused because there were several pieces to the conversation, and they didn’t want it to devolve or get heated.

As we talked, I thought of the quote,

“If you can't explain it simply, you don't understand it well enough”.
- usually attributed to Albert Einstein

In this case, my client wanted to cover some specific areas, but they needed to clarify them (as well as the outcome they were driving to) before presenting them to their partner.

I recommended they write up an outline of the issue.

Explain it to yourself, then explain it to others

An outline of issue is a write-up that lays out all the relevant information for a discussion. It’s one of the most powerful exercises I’ve learned over the years because:

1. It sets expectations for what will be discussed.
2. It allows everyone to think about and prepare feedback and questions.
3. It reduces time in the meeting by allowing you to jump straight into the discussion instead of going over all the background and context.

Those are all great reasons. 

An even more compelling reason to prepare an outline of issue is the preparation of the document itself.

Even if it’s not something you send beforehand, writing it out forces you to clearly articulate the challenge or issue, how you came to a decision point, and potential options.

If you can explain it to yourself, you can explain it to others. 

It forces you to explain something simply.

Beyond the benefits it provides in the meeting itself, you get more clarity on the issue and often discover new angles, things you might not have considered initially, and additional details that will enrich the conversation.

How to write an outline of issue

1. Summarize the issue

This is the elevator pitch. Can you clearly describe the issue in a single sentence? While this is the first item in an outline of issue, I recommend making it the last thing you write because your understanding of the issue will change as you work through the exercise.

2. Provide the relevant background context

Why did this issue come up? What’s important about it? What happened to make this come about? What’s at stake? Give specific examples or even a timeline of events.

3. Explore your options

The power of an outline of issue is you go through the work to identify your potential choices for responding to the issue. 

List every option you can think of, even if the options you don’t want to pursue. Articulate why you don’t want to. 

List the ones you tried but didn’t work and analyze why you think they didn’t work.

This is the most valuable section to work through because it gets you to map out everything you’ve been thinking about. Writing down the options often results in the discovery of additional ones you hadn’t considered and either strengthens (or sometimes even weakens) your resolve for which option you think you want to go.

4. What do you think you should do, and why?

This is the end of the path you have led yourself and the people you are sharing it with.

Sometimes, you might be unsure which option to pursue. In this case, the purpose of the meeting is to get others' feedback.

In other instances, you know exactly what direction to take. If you’ve done a good job outlining the problem, background context, and options, so should everyone else.

5. Questions

After presenting the outline of issue,  your initial instinct may be to ask an open-ended question like “What do you think?”. Avoid this! You need to get more specific. 

You will get more out of the conversation if you have targeted questions prepared. Some general examples include:

• Do you have any experiences you could share that are similar to this?
• Are there any other options or directions I didn’t cover here?
• Is there anything I didn’t consider in enough detail or not at all?
• Are there any risks I haven’t considered?
• Are there any reasons not to go forward with the option I am leaning toward?

You will also likely have questions specific to your issue that you can ask.

Another thought exercise I like to do in this section is to ask, “What do I think they will ask me?”. It’s interesting to anticipate the kinds of questions the specific people in the room might ask, given what you know about them, to fill in any gaps or assumptions you might have made throughout the document.

When should you write an outline of issue?

1. You want buy-in on your preferred option

This is the situation my client was in. They knew the outcome they wanted to drive toward in their conversation with their partner. Working through the outline of issue helped prepare them with everything they needed to keep the discussion on track and make a clear case.

2. You want feedback on the options

The other situation where you would want to write an outline of issue is when you don’t know which option or direction you want to go. You might have an idea of what you will do, but you are unsure and would like feedback or advice on how you came to where you are and to see if you missed anything.

The outline of issue lays everything out in a way that shows you’ve thought it through… because you have!

Here’s a handy template!

To help you get started on writing your own outline of issue, I’ve created a template:

Ashley Janssen Consulting - Outline of Issue Template

To make it your own: Go to File → Make a copy.

Give it a try next time you are struggling with a big question or a big conversation and need something to help you work through it.

Do you have a big conversation you want to work through? Feel free to book a free consultation!