How to Make Discovery Questions Easy

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👋 Today, I’m answering a question I got from a newsletter chap, a jolly good question at that. So I’m just answering it here.

Killing two birds with one writing stone aside, let’s dive in! 🚀

How to Pitch & Propose

Here I was minding my own business (literally), and a good friend of mine had the audacity to ask a brilliant question. Outrageous.

His question had two parts, which ultimately could be boiled down to:

A) How do I do discovery questions effectively?

I think I know their pain points, but as a pitch is via cold outreach they expect me to do most of the talking.

B) How do I send a proposal that is clear and concise, but also comprehensive and customisable?

Let’s get it…

🔬 How do I do discovery questions effectively

There are a few different problems challenges in this question, with various solutions.

🏛️ Structure the conversation

It can be useful to summarise the conversation right at the start, after the chit-chat. Benefits of doing this include:

• Come across as professional/organised

• It can ground yourself and keep you on track

• Traditional or formal industries/individuals may appreciate it

• AND it can justify starting with asking that discover questions

This could look like:

“Let’s get down to it. To structure the conversation, I’d love to first learn about your current marketing goals, I’ll walk you through who we are and how we can help, and then if there’s alignment we can go from there. To make sure I focus on the most relevant parts of our offering I’d love to ask some questions, if that’s ok…”

Or something along those lines, adjusted to suit you/your business.

⁉️ What type of questions to ask

There’s no perfect one question to ask. But there are guiding principles:

• Start with very open-ended questions. For example:

  ❌ NO: Have you sponsored any newsletters before?

  ✅ YES: Tell me about your marketing strategy.

• Reciprocity. Some people are more willing to talk about their problems and goals. Some are much more closed off. If you counterpart is playing hard to get, use the principle of reciprocity. Give a little before before you ask. This could be giving a brief introduction to your brand, a case study, or an audience stat, before asking a related question. You’ll be surprised how effective this can be.

• Get more specific with each question.

🫏 Don’t make an ass out of anyone (don't assume)

Regarding knowing their pain points. Even if you have spoken to 17 similar companies and 14 of them had the same problems. You shouldn’t go into a call assuming that this prospect is the same. For various reasons:

• They might have vastly different problems and goals, company-wide or individually.

• Even if they do have the same problems people want to feel understood. They want to feel heard. They want to feel like you care. Like you’re a professional and can help them.

• Even if they do have the same problems, why leave it to chance? Plus, they might approach the problem with a completely different perspective, terminology and perceived solution. For example, you can safely assume that all AI startups want new users. But some may think the solution is affiliate marketing, some may think branding, lead generation, influencer marketing, and so on.

Never assume… it makes an ass out of U and ME.

🤸 Keep it flexible

Having structure in a pitch is vital. Alas, there is nuance.

To effectively run discovery questions with tight-lipped prospects, retain the flexibility to allow the conversation to deviate from the ‘script’. For example, if the prospect jumps in at the beginning and starts asking a bunch of questions, you don’t have to shut them down, panic and get straight back to discovery questions. You should make them feel heard, answer their question comprehensively.

To make sure you don’t skip discovery completely, you can get back on track by segwaying into discovering questions, naturally or explicitly:

Naturally - If the prospect asks if you’ve worked with any similar companies. You could say:

"Yes, we’ve worked with X, Y and Z, which is why I reached out. I assume they have similar target audiences to you? Tell me more about your target audience.”

Explicitly - If the prospect asks if you’ve worked with any similar companies. You could say

“Yes, we’ve worked with X, Y and Z, which is why I reached out. We helped them with slightly different goals each time, so to make sure I’m not making incorrect assumptions about your goals, I’d love to ask a few questions if that’s ok?”

🎯 How to propose effectively

Actually, the answer(s) to this question will be in next week’s Revenews.

See you there.

Cheerio.