Issue #92

Enterprise Sales - Mindset Primer

Nine thoughts you need to keep in your head, and questions you can ask, for moving high-stakes sales conversations forward.

I learnt five of these from a colleague who spent years in British Intelligence, negotiating hostage situations.

I can’t say which ones because he would have me disappeared.

1. Recognise the emotional pressure they’re under

Buyers carry personal risk. They’re expected to deliver results but don’t want any added exposure. Before they’ll talk freely, they need to know you understand what’s at stake for them.

How to do it: Make a clear, honest statement that shows you understand the pressure they’re under.

Example: “You’re being asked to make a big call here, so we will be sure to cover off risks as we go..”

When they feel understood, the conversation opens up.

2. Don’t soften or solve the problem too early

When you spot what’s getting in the way, say it plainly. Don’t pitch and don’t fix it immediately. Just confirm that you see what they see.

How to do it: Call out the issue and stop talking. Give them space to confirm it or correct it.

Example: “This deal isn’t moving because no one wants to bring it to procurement yet.”

You’re not arguing. You’re aligning. They will probably start coming up with solutions, if not then you can.

3. Surface what isn’t being said

Important blockers often stay buried. You can bring them up gently when you suspect they are at work, without sounding like an accusation.

How to do it: Use a calm observation to give them a safe way to speak honestly.

Example: “Seems like there’s still some internal doubt about timing.”

Let the silence do the rest.

4. Share experience that’s useful to them

You’ve probably seen their situation before. That knowledge is valuable, but only if it’s brief, relevant, and focused on them (not a story about how great you are).

How to do it: Offer one line of insight, check it applies to their context. Then tell the full story.

Example: “I’ve seen strong deals fail when IT was brought in too late. Would that be a risk here?”

You’re helping them see ahead.

5. Guide the mood through how you behave

Your tone and body language influence how the conversation feels. Match their energy at the start, then guide it toward calm clarity.

How to do it: Slow your pace slightly. Speak clearly. Hold still when it matters. Let silence land.

They will follow your state if they trust you.

6. Earn the right to offer a different view

You must not challenge someone until they know you’ve understood them. Once they feel seen, you can offer a new perspective with low likelihood of pushback.

How to do it: Show them their own problem clearly, then offer a better way to think about it.

Example: “You’re caught between speed and certainty. What I’ve found is that slowing down one week now often saves four weeks later.”

They’ll only hear it if they trust where it’s coming from.

7. Don’t ask them to fix your constraints

If they ask for something difficult, don’t push back. Ask them how they’d handle that kind of tension if they were in your seat.

How to do it: Describe the pressure clearly and invite their input without complaint.

Example: “You want to cut implementation time in half. How do you think we could manage that without hurting quality?”

Now you’re on the same side of the problem.

8. Make them feel safe telling the truth

The best information only comes when people stop performing. If you show that you’re not there to trap them, they’ll start to say what matters.

How to do it: Ask honest questions. Use language that respects the pressure they’re under.

Example: “If this stalls, what’s in the most likely top three reasons?”

No tricks. No framing. Just clarity.

9. Focus on what they need to decide

Enterprise buyers don’t need to be aggressively closed. They need help making a good decision under pressure. That’s the real job.

How to do it: Ask yourself before every meeting, “If I had their goals and risks, what would I need to be confident right now?”

Then help them get there.

Here’s a downloadable PDF you can keep on your phone to act as a reminder before sales conversations.

​Enterprise Sales Boot Up Sheet.pdf​

I made this for one of my clients, who uses it as part of his boot up process every day, whilst he has his Espresso and some deep breathing.

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Do you like the downloads I include every week? Yes, they are tasty, thanks Prefer videos, tbh Never click them, I wouldn't bother, mate...

I help founders and enterprise sellers in three ways:

1. You can get my Sales foundations course here
2. Drop me an email or DM about coaching you or your team
3. I'm on LinkedIn everyday, real stories, usable tools and strong opinions.

Send this edition on to your friends, so they can use the mindset boot up tool too.

If you run a sales team, then share it with them and let me know how they get on - I always welcome feedback.