Fix a pipeline that stalled

Deals are sitting, the number is slipping, and nobody can say exactly why. Diagnose it in order.

4 steps, 64 questions underneath

1. 1
   Who you sell to

   Picking a customer worth chasing, and knowing early when a deal is not one.

   What is an ICP and how is it different from a persona? People use both words for the same thing.

   The gist An ICP describes the company you want as a customer: size, industry, what they already use, what has to be true for your product to matter. A persona describes the human inside that company: their title, what they get judged on, what makes them look good or bad. You need both and they do different jobs. The ICP tells you which doors to knock on, the persona tells you what to say when someone opens. A useful ICP is uncomfortably narrow and written as filters you could actually apply to a list, not as adjectives like 'modern' or 'fast growing'.

   📰 Defining our ICP is the most important thing we ever did A real company showing its ICP before and after, including the messy middle where they were guessing. The point that narrow ICPs beat broad ones, a... 16 questions on who you sell to →
2. 2
   Outbound that works

   Cold email, cold calls, LinkedIn, sequences and lists. How to start conversations with people who have never heard of you.

   I have never sent a cold email in my life. Where do I even start?

   The gist Start with twenty companies, not two thousand. Pick people you can describe precisely (job title, company size, the specific problem you think they have) and write each of the first twenty emails by hand so you learn what makes someone reply. Keep it to four or five sentences: why you are writing to them specifically, the problem in their words, one line of proof, and a small ask like fifteen minutes. Your reply rate on the first batch will be embarrassing and that is the point, you are collecting evidence about your message, not building a machine yet. Only once a message reliably gets replies should you think about tools, sequences or volume.

   📰 How to find and win your first 10 B2B customers It orders the seven ways early customers actually arrive (network, cold outbound, investors, community, content, press, launch) by how much trust e... 16 questions on outbound that works →
3. 3
   Running a sales process and closing

   Discovery, demos, qualification, champions, procurement and the last mile to a signature.

   I have a call booked with a real prospect tomorrow. What do I do on it?

   The gist Ask questions and shut up. Gong's analysis of more than half a million calls found the sweet spot is somewhere around eleven to fourteen questions, spread through the call rather than fired off at the start, and the best calls surface three or four real business problems. Aim for a talk to listen ratio near forty six to fifty four, which will feel like you are barely talking. Open by stating the purpose of the call, the benefit to them and a check that it works for them, then dig into what happens today and what it costs. Do not demo until you know what to demo, and end with a specific next step and a date, not "I will send something over".

   📄 Effective strategies for successful sales discovery calls Gives you numbers to aim at on your next call instead of vague advice: roughly 11 to 14 questions, spread through the call rather than front-loaded... 16 questions on running a sales process and closing →
4. 4
   Forecasting and GTM metrics

   Pipeline coverage, stage conversion, CAC payback, magic number, and calling a number you can defend to a board.

   What is pipeline coverage and how much pipeline do I actually need to hit my number?

   The gist Pipeline coverage is qualified open pipeline divided by the target for the period, and the honest answer to how much you need is one over your win rate. The famous 3x rule comes from a time when good B2B teams closed about a third of qualified pipeline. If you close twenty percent, you need five times coverage, not three, and using the rule of thumb instead of your own number is how teams cheerfully walk into a miss. Two cautions: only count opportunities with a real buyer, a real need, and a date, because inflating the numerator is the easiest way to feel safe and be wrong. And measure coverage at the start of the period, not at the end, since coverage is only useful as a leading indicator you can still act on.

   📄 Pipeline Coverage Ratio: What Your Number Actually Means Explains why the 3x rule of thumb is wrong for most teams and shows how to derive your own coverage number from your actual win rate. Weighted vers... 16 questions on forecasting and gtm metrics →