The Long Game

Warm-up: Let's Talk About Long Decisions

4 warm-up questions

• What is the longest you have ever waited for a decision that mattered to you?
• Think of an expensive purchase your organisation made. How many people had to approve it?
• Do you think a slow decision is usually a better decision, or just a more expensive one?
• How would you keep someone interested in your idea for six months without annoying them?

Reading: Two Deals, Two Timescales

Read a 324-word text about Two Deals, Two Timescales

Two Deals, Two Timescales Selling software to a small business and selling it to a large organisation are not the same job, even when the product is identical. The small deal A café owner watches a demonstration on Tuesday, thinks about it overnight, and pays with a card on Wednesday. One person decides. The sales cycle lasts two days. If the software disappoints her, she cancels and loses very little. The enterprise deal Now imagine the same software being sold to Northwind Logistics, a company with four thousand employees across nine countries. Nobody there can simply buy it. The operations manager who loves the idea has no budget. The finance director has budget but has never heard of your company. The IT team must confirm that the system is secure. Procurement must run a fair process, sometimes by publishing an RFP and inviting three suppliers to compete. Legal must approve the contract. Somewhere in that structure, an executive has to give final sign-off. That is not two days. That is seven to eighteen months, and during those months your contact may change job, the budget may be frozen, and a competitor may appear. What actually moves it forward Experienced sellers describe an enterprise deal as a relationship, not a transaction. Three habits separate the sellers who close from the sellers who wait: They find a champion — an insider who wants the change to happen and who will argue for it in meetings you will never attend. They map every stakeholder early, because the person who blocks the deal in month eight was usually visible in month one. They propose a small, measurable pilot rather than asking for a large commitment nobody is ready to make. The uncomfortable truth is that you cannot make a large organisation move faster than it wants to. What you can do is make it easy for the people inside it to say yes when they are finally ready.

Vocabulary: The Language of Long Deals

10 items

Framework: The Five Stages of an Enterprise Deal

Qualify – Map – Prove – Approve – Close, 5 steps

Qualify – Map – Prove – Approve – Close: A shared language for describing where a long deal currently stands, and what has to happen next.

Practice: Describe Where the Deal Stands

Gap-fill exercise, 10 items

• Our average sales ____ in this sector is close to eleven months.
• We have identified nine ____ across three different departments.
• The deal stalled because we never found a genuine ____ inside the company.
• Once ____ got involved, the negotiation became far more formal.
• They have invited four suppliers to respond to the ____ by the end of the month.
• Rather than a full contract, we proposed a limited ____ at a single site.
• Everything had been agreed, but final ____ took another six weeks.
• If the results are convincing, they intend to ____ the system out globally.
• We are still in ____ , so no decision has been made yet.
• Selling to ____ customers requires more patience than we expected.

Practice: Cause and Consequence in a Long Deal

Matching exercise, 7 items

• Your champion changes job in month five
• You never asked about the approval process
• The pilot had no agreed success criteria
• Procurement receives your proposal late
• You send the security documents unprompted
• You push for a signature every week
• You map the stakeholders in the first month

Dialogue: Explaining the Timeline to Your Own Manager

Role-play: A weekly pipeline review with your sales director, who wants the Northwind deal closed this quarter. (4 lines)

• Give me the situation on Northwind in one minute. Use the five-stage framework as your structure. Name the stage the deal is in, and give evidence for each claim rather than opinions.
• Can you get it signed by the end of the quarter? Disagree without sounding defensive. Acknowledge the pressure, give the concrete blocker, then offer what you can realistically commit to.
• What could still kill this deal? Name real risks and pair each one with the action you are already taking. Use conditional structures.
• What do you need from me? Make one specific, easy-to-approve request, and explain the return on it.

Discussion: Let's Discuss

5 discussion questions

• Tell me about a decision at your organisation that took much longer than anyone expected. What caused the delay?
• Do you think long approval processes protect organisations, or simply slow them down?
• If you had to keep a customer engaged for a year, what would you actually do each month?
• How is the way large organisations buy different in your country compared with what you have read here?
• Which is harder: finding a customer, or keeping one interested until they are ready?