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There’s context, and there’s CONTEXT.

Granular HYPER-CONTEXT.

Context creates expectation AND anticipation in any conversation. It invites complex inquiry. It inhibits a conversational shut-down. It hopefully normalizes a measure of discomfort. It quite simply demands a better conversation.

I’m reminded of the power of conversational context as I reflect on John Lilly’s advice on context-setting in my favorite leadership column, Adam Bryant’s “Corner Office” in the Sunday Business Section of The New York Times. Lilly is a partner in Greylock, a Silicon Valley Venture Capital firm. Lilly meets about 400 CEOs a year and invests in maybe two of them. At first, Lilly explains, I would just ask my questions and poke, poke, poke. Here’s how a wizened Lilly now sets context in his conversations:

Look, I’m going to ask some things, and this might be kind of awkward, but I’m just going to say it. And it doesn’t mean I don’t believe in you and your company. I just want to understand where you are and what you think. I’m going to ask some things and they might be wrong, but let’s figure some things out together. (11/27/2016)

Human, complex, helpful. HYPER-CONTEXTUALIZED. Helpful and clear. And Lilly’s clearer context undoubtedly creates a more compelling conversation.

Do you long to fashion more compelling conversations, as well? I urge you to consider the following 4 ways of creating context:

1. Outcome Context: It’s the classic in most Western business conversations. We’re here to come up with a Strategic Plan for bringing our new Microblender PLUS to market by March 15.

Deservedly a classic. It sets a clear results-focus. It does little, however, to focus the quality of either the conversation or the outcomes.

2. Historical Context: In our recent two strategy conversations we have consistently suggested go-to-market tactics that haven’t worked too well for us in the past. Let’s challenge ourselves to come up with tactics that we have not tried before.

Clear, right? Not the same old crap, please. Let’s change the substantive quality of our conversation. Let’s leave past choices in the past.

3. Contrasting Context: We’re here to get clear on the optimal go-to-market tactics for our Marh 15 launch. We’re NOT here to figure out how to sell Microblender PLUS 3 years from now.

By defining what we’re NOT doing we give ourselves permission to fully sink our teeth into the conversation we DO want to have. Clear boundaries contain the urge to drift and digress.

4. Qualitative Context: To make sure that we come up with the most effective plan, I may at times ask some tough questions to challenge our thinking and assumptions. And I urge every one of you to do the same. That’s how we ensure that we come up with richly examined action steps that will deliver.

Clear as well, right? Let’s be a little tough in our conversation. We want things to get a bit rough as we fully examine our ideas. Rough is desirable. Let’s not avoid it!

John Lilly knows. In case of doubt, HYPER-CONTEXTUALIZE. Context defines the substance of a conversation and the quality of your outcomes.

Contextualize explicitly. Contextualize beyond the Outcome Context. Contextualize well. HYPER-CONTEXTUALIZE. HYPER-CONTEXT demands a better conversation.

Demand it. You will set everyone up to be more successful. And we all want that, don’t we?