The Experimental Marketer · Chapter Companion

02Engage

Build the stakeholder buy-in and cross-team support your initiative needs to ship.

Prefer pen and paper? Print this. Every section works offline.

Hitting Print swaps this page to a clean paper workbook — same sections, no interactive scoring. Every section works offline.

Section 1

Self-Audit

Rate 1–5·1 not at all·3 sometimes·5 always

Rate each statement from 1 to 5. 1 = not at all · 3 = sometimes · 5 = always.

  1. 1

    Before I pitch a marketing technology project, I can state what IT, legal, finance, and my executives each care about most, in their own words.

    ◄ tap to rate
    1   2   3   4   5    (circle one)
  2. 2

    I can describe the same initiative four different ways, so the version finance hears sounds different from the version IT hears, without any of them being untrue.

    1   2   3   4   5    (circle one)
  3. 3

    When a stakeholder pushes back, I can tell whether they are reacting to the practical facts, an unspoken worry, or a question about who they are in this change.

    1   2   3   4   5    (circle one)
  4. 4

    I can name, for my current initiative, one small first project that proves value before I ask anyone to commit to the full thing.

    1   2   3   4   5    (circle one)
  5. 5

    I know which specific people in my organization already back this initiative, which are undecided, and which quietly resist it.

    1   2   3   4   5    (circle one)
  6. 6

    I have given at least one stakeholder a real way to shape this initiative, not just a chance to approve or reject what I already built.

    1   2   3   4   5    (circle one)
  7. 7

    When someone raises a concern I cannot answer, I say so and follow up, rather than talking around it.

    1   2   3   4   5    (circle one)
  8. 8

    I make small commitments to stakeholders and keep them, so my word carries weight before the big ask.

    1   2   3   4   5    (circle one)
  9. 9

    I have had an honest one-on-one with a skeptic about what is really driving their resistance, instead of trying to win them over in the meeting.

    1   2   3   4   5    (circle one)

Score yourself

Add your three answers in each zone and write the totals.

Translation: Q1 + Q2 + Q3 = ___  ·  Coalition: Q4 + Q5 + Q6 = ___  ·  Credibility: Q7 + Q8 + Q9 = ___

Your lowest total is where you start.

Section 2

Next Steps

This section unlocks once you have rated all nine statements above. When you do, your three zone scores will appear here as a small chart, and the lowest one will turn pink with a short diagnosis and three concrete moves. Nothing is hidden — the paper workbook prints all four possibilities so you can self-score offline.

If Translation is your lowest:

Your gap is translation

You understand your initiative, but you are presenting it in marketing's language to people who do not think in that language. They hear a marketing project competing for their time, not a shared goal. The work is to learn what each team measures and worries about, then say the same true thing in their terms.

  1. 1Pick the one stakeholder most likely to block your current initiative: IT, legal, finance, or an executive. Write three sentences in their voice about what would make this project a headache for them. If you cannot fill three, that is your sign you do not yet know their world well enough.
  2. 2Take your initiative and write a one-paragraph version of it for that single stakeholder. Use their measures of success, not yours. Finance hears payback period and total cost, IT hears integration and maintenance, legal hears compliance and contracts, executives hear competitive position and capability.
  3. 3Test it. Read your paragraph to one person who actually sits in that function, or someone close to it, and ask: does this sound like it was written for you, or at you? Adjust until they say for.

If Coalition is your lowest:

Your gap is coalition

You may be making good arguments to the wrong-sized audience. A single polished presentation rarely moves an organization. Support builds when a small first win earns trust, when the right people feel ownership, and when momentum makes resistance irrelevant rather than defeated. You are likely trying to win the whole room at once.

  1. 1Shrink your initiative to one keystone project: concrete, finishable, valuable to more than one team, and a stepping stone to the bigger thing. Write it as a single sentence with a real first segment or use case, not a vague intent.
  2. 2List the people your initiative touches and sort each into one of five buckets: backs it actively, supports it quietly, undecided, quietly resists, actively blocks. Be honest, not hopeful. The undecided group is usually your largest and your best opportunity.
  3. 3Give one undecided or quietly supportive person a genuine role in shaping the work: a seat in vendor evaluation, a say in requirements, a pilot advisory slot. People defend what they helped build. Do not assume the blocker is the loud opponent, it is often the absence of any owner besides you.

If Credibility is your lowest:

Your gap is credibility

Your logic may be sound and your coalition mapped, but stakeholders are not yet sure they can trust you to deliver, or to tell them the truth when things go wrong. Credibility is earned in small moments before the big meeting: admitting what you do not know, keeping minor commitments, and hearing concerns without defending. Without it, the best case still stalls.

  1. 1Find the most skeptical stakeholder on your initiative and ask yourself why they are skeptical. If you do not know, that is the problem. Book a private, low-stakes conversation and ask two questions: what would success look like from your side, and what concern have we not addressed yet? Then listen without selling.
  2. 2Make one small, visible commitment this week and keep it exactly: a follow-up document, a meeting you said you would set, an answer you said you would find. Trust on the large ask is built from a track record on the small ones.
  3. 3Name one thing about your initiative you do not actually know yet, and say it out loud to a stakeholder before they catch it. Admitting a gap on purpose buys more credibility than being caught hiding one. If most resistance you face is about past failures rather than your plan, your first job is acknowledgement, not persuasion.

If every area scored 4 or higher:

You are ahead of most

You translate across functions, you build coalitions instead of pitching at people, and you have earned the trust to be heard. The engagement work that sinks most marketing technology projects is already your strength. Your risk now is not a gap, it is complacency: the coalition you built for the last initiative does not automatically carry to the next, and trust decays when it is not maintained.

  1. 1Pressure-test your strongest zone. Pick the statement you rated a 5 and find one stakeholder who would rate your performance a 3. The distance between your self-assessment and their experience is where your blind spot lives.
  2. 2Move your attention to where engagement actually breaks down next: turning one-time approval into a standing working relationship. That is the Exchange work in Chapter 3. Skim it now, because buy-in that is not maintained quietly expires.
  3. 3Document how you built support this time, while you remember it: who you talked to first, what won the skeptic over, which keystone project unlocked the rest. When the next initiative needs a coalition, you will have a playbook instead of a memory.
Section 3

Prompt Pack

Always open. No unlock. Three exercises that build on each other — each has a goal, steps, write-in fields, and a grey optional-AI box.

These three exercises build on each other. By the end you will have an engagement plan you can act on Monday morning: a map of who matters and where they stand, a version of your case written in each key stakeholder's own language, and a sequenced first move that earns trust before it asks for commitment. Work them in order. You can do every step with pen and paper. If you want an AI assistant to speed up the thinking, the grey box under each exercise shows you how to hand it over. The AI is optional. The thinking is not.

1

Map the room

Goal

Produce a written map of every stakeholder your initiative touches, what each one cares about, and where each currently stands, so your plan rests on the real terrain instead of your hopes about it.

Do this
  1. 1.Name your initiative in one concrete sentence. Then list every person or team whose support, approval, or cooperation you need: IT, legal, finance, executives, and anyone else who can speed it up or stop it.
  2. 2.Next to each, write one or two words for what they actually care about (uptime, compliance, payback, competitive position) and one real worry they have about this kind of project.
  3. 3.Sort each into one bucket: backs it actively, supports it quietly, undecided, quietly resists, actively blocks. Resist the urge to round everyone up to supportive.
  4. 4.Circle the single undecided or quietly resistant person whose shift would most change your odds. That circled name is the focus of the next two exercises.
If you want an AI to help

Type your stakeholder list into an AI assistant and ask: “Here are the stakeholders for a marketing technology initiative and what I think each cares about: [your list]. For each one, what concerns do people in that role usually raise about projects like this that I might have missed? Keep it specific to their function.” Use its answer to sharpen the worries you wrote down.

2

Translate the case

Goal

Write your initiative in the language of the person you circled, so the version they hear is built from what they measure and worry about, not from your marketing goals. A translation, not a new project.

Do this
  1. 1.Take your circled stakeholder. Write down the two or three things they measure success by, and the one past experience that might make them skeptical of you.
  2. 2.Now write a single paragraph describing your initiative entirely in those terms. Lead with what they care about, name the worry directly, and say how you will handle it. Keep every claim true; you are revealing a real facet, not inventing one.
  3. 3.Read it back and strike any sentence that is really about marketing's benefit. If a line does not connect to their world, it does not belong in their version.
  4. 4.Write the one question you will open the conversation with: usually what would make this a win for you, rather than here is my plan.
If you want an AI to help

Give an AI assistant the stakeholder and your draft and ask: “I am presenting this marketing technology initiative to [role]. Here is my paragraph: [draft]. Rewrite it so it leads with what this role actually cares about, names their likely objection, and stays honest. Flag any claim that sounds like a stretch.” Keep what rings true, discard what does not.

3

Sequence the first move

Goal

Turn the map and the translated case into one specific, trust-earning first step you will take this week, small enough that it asks for participation before it asks for commitment. This becomes your input to Chapter 3.

Do this
  1. 1.Define your keystone: the smallest version of your initiative that still delivers visible value, touches more than one team, and opens the door to the larger plan. Write it as one sentence with a real first segment, channel, or use case.
  2. 2.Decide the single first conversation that earns trust rather than spends it. Usually this is a private, one-on-one with the stakeholder you circled, where you listen more than you pitch.
  3. 3.Write what you will ask them to shape, not just approve: a role in vendor evaluation, a say in success criteria, a seat on the pilot. Ownership is what converts a skeptic.
  4. 4.Put a date on it. Name the one early result you could show within weeks that would move an undecided stakeholder toward support. A coalition without a first date stays theoretical.
If you want an AI to help

Hand the keystone to an AI assistant and ask: “Turn this into a 60 to 90 day sequence for building stakeholder support: the first conversation, who to involve early, the early win to aim for, and the order to bring people in. My keystone: [your answer].” Carry the result into the Chapter 3 companion.

→Your keystone project and stakeholder map from Exercise 3 become the raw material for Chapter 3: Exchange, where one-time buy-in turns into a standing working relationship.