How to lead strategic discussions

Have you ever walked into a room, confidently delivered your pitch and noticed a series of blank stares? Maybe you were saying something as straight forward as “We should target X audience with Y product to solve Z problem” and were met with puzzled looks. What seems incredibly obvious and intuitive to you is lost to the rest of the room. You’ve spent months thinking about this strategy and boiled it down to the the utmost clarity, yet people are still confused.

Another common scenario is that you craft a beautiful and well thought through strategy doc and send it out to colleagues (or leadership) for feedback and hear crickets. There is no disagreement, there is no agreement, only silence. Are they aligned? Do they agree and are just waiting for you to make it happen? Unlikely.

My favorite example from my career: “We see 46% growth month over month of Weekly Active Users on mobile. Therefore, we should invest in a mobile website.” I was met with a series of questions like “How do we know they will actually purchase?” and ultimately failed to convince everyone in the room.

Why does this happen? You’ve presented a series of conclusions but failed to bring everyone along with your assumptions. The series of leaps that seem intuitive to you are actually not obvious to everyone else because you’ve been deep in this problem space for quite some time and they haven’t. You can’t just expect them to catch up. Your job is to bring them along.

Luckily, you can fix this with one change:

You need to unpack and explain your assumptions.

What do you mean by assumptions? By assumptions I mean any strategic decision, whether explicit or implicit, that you’ve made in the document or pitch. You can identify these by taking your document and looking for declarative statements like “We should target teens in the United States.” There are three assumptions here: a) We should target a specific audience b) We should focus on teens c) We should focus on the United States. Each of these statements are assumptions that you’ve made and need to be validated.

Step One: Take each of your declarative statements and start listing them out (call this your ‘FAQ'). Write down each one independently. We’ll call these statements ’conclusions.’

What do you mean by unpack? By unpack I mean to break down the decision making framework or logic that you had in your head when you made that decision, even if you made it implicitly. You can identify these by walking through a series of steps that you walked through mentally to reach that assumption. Here’s an example from a hypothetical product:

1. People are struggling to affect change in their community.
2. Our research has shown that people under the age of 40 have the hardest time manifesting change in their community.
3. We’ve spoken to a bunch of customers and found that people in the 16-20 age bracket feel this pain most accutely and don’t have a good solution in place.
4. Therefore, we should target teens.

Each of these statements is a logical conclusion based on some sort of analysis (or intuition).

Step Two: Write an ordered list for each of the conclusions listed above. The list should contain a series of logical leaps (ideally including data or research) that you made to reach this conclusion. We’ll call these statements ‘rationale.’

What do you mean by bring my audience along? Your audience (whether it be your peers, leadership, etc) does not have all of the knowledge in your head. Ultimately you’re trying to convince them of your pitch, but to do so you need to help them see the underlying assumptions so that they can make the same logical leaps (or challenge the ones they don’t agree with). This is a little bit like showing your work in math class. It’s hard for people to react to a final statement/solution (or to critique it in a constructive manner) but it’s much easier to see a series of logical conclusions and pinpoint the place you disagree (or have questions). You should constantly be working to understand which assumptions are held by the room as true and which need to be discussed.

Imagine a set of early conversations that start with: “I’m in the early stages but want to get your thoughts to help me make my pitch clear.” Give your rough pitch on a whiteboard or send an early copy of your pitch document. Make sure you walk through each of your assumptioms and rationale explicitly. Be on the lookout for two types of responses: “This is unclear / I don’t understand” or “I disagree.” You can then fold the specific statements called out back into your pitch to make sure it’s easy to understand and the disagremeents can be discussed. We’ll call this process “Pre-flighting.”

Step Three: Identify 2-3 people you trust and share your (rough) pitch with them along with assumptons and rationale. Mark any item that is unclear and any item that someone disagrees with. Move the ‘unclear’ items into your pitch and flag any ‘disagremeent’ items for discussion.

If you do this right, the actual pitch will be a discussion focused not on ‘what does this mean’ but on ‘is this the right plan?’ You’ve clearly communicated the ideas in your head, and now your audience is equipped with the knowledge to debate them.

Have you tried this approach before? Do you have tips for what worked for you? I’d love to hear from you. Share your thoughts via twitter: @bdickason

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Post last updated: Nov 19, 2020

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