A playbook

Fix a pipeline that stalled

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

4 steps, 16 questions underneath, read for doing the work

  1. 1
    Who you sell to

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

    How do I qualify a deal properly instead of just hoping the enthusiastic person can buy?

    The gist Enthusiasm is not authority. Before you invest another hour, you want four things: a named pain the buyer can quantify, the person who controls the budget, the steps the company takes to approve a purchase like this, and someone inside who will argue for you when you are not in the room. If you cannot name all four after two calls, you have a conversation, not a deal. Learning one framework properly, MEDDIC or MEDDPICC, is worth doing not because the acronym is magic but because it forces you to ask the awkward questions early rather than in week nine.

    MEDDIC / MEDDPICC Sales Methodology and Process The reference explanation of all eight elements from the people who own the trademark, so you are learning it first hand rather than through a tool... 4 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.

    My cold calls die in the first ten seconds. What do I actually say when they pick up?

    The gist Stop asking whether you caught them at a bad time, because it hands them an exit and Gong's data across hundreds of millions of calls shows it cuts your odds badly. Open with a pattern interrupt and then a proactive reason for the call, something like "How have you been?" followed by a plain sentence about why you are calling them today. Your goal on a cold call is not discovery, it is selling the next fifteen minutes, so do not try to qualify the whole account in ninety seconds. Successful cold calls run roughly twice as long as failed ones, which means your job is to earn the next sentence, not to deliver a pitch.

    Proven cold call opening lines that work Almost everything written about cold call openers is opinion. This is 90,380 recorded calls scored by whether a meeting got booked, including the f... 4 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.

    How do I know if a deal is real or if I am being strung along?

    The gist Write down what you know against a qualification frame and the gaps become obvious. MEDDPICC is the common one: metrics they care about, the economic buyer, decision criteria, decision process, paper process, the pain you are implicating, your champion and the competition. If you cannot name the economic buyer or describe the paper process, you do not have a deal, you have an interested person. The single best test of a champion is whether they will do something for you, like get you a meeting with their boss or send you the security questionnaire. Be willing to disqualify early and loudly, because a clean no in week two is worth more than a maybe that dies in your forecast in month four.

    MEDDIC / MEDDPICC Sales Methodology and Process The reference explanation of all eight letters from the people who own the methodology, free to read. Use it as a deal checklist: the letters you c... 4 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.

    How do I calculate conversion rates by stage, and what do I actually do once I have them?

    The gist Calculate them on a cohort, not on a snapshot. Take every opportunity created in a month, follow that same set forward, and measure what share reached each later stage. Snapshot ratios (stage two divided by stage one today) mix cohorts moving at different speeds and will mislead you. Once you have the curve, do three things: find the single worst step, since one stage usually leaks far more than the rest and that is where your attention belongs; measure time in stage alongside conversion, because a stage where deals sit for eleven weeks is a qualification problem wearing a conversion costume; and use the rates to work backwards into how much pipeline each rep needs, which turns a vague target into an activity plan.

    The Bowtie Standard The clearest single document on what a revenue data model should look like end to end, from lead through renewal and expansion. It is the vocabular... 4 questions on forecasting and gtm metrics →

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