Issue #94

Training the Untrainable: How I Taught Procurement Pros to Sell

Ask a procurement professional to sell, and most will resist the idea outright. Quite a few will actually throw up on your shoes.

It’s not that they’re incapable, it’s because selling feels unnatural. It runs against their very instincts.

They’re trained to question value, not find it. To dismantle a pitch, not build one.

When I was asked to train a group of procurement people to sell their services to heads of NHS procurement, I knew a workshop or playbook wouldn’t be enough.

They didn’t need theory, they would only hide behind it. They needed real, live experience, without risking real deals, or their self respect.

So I ran a war game...

These are not exercises in theory, they’re full simulations of the sale, from first contact to signed contract.

In doing so, I built a model you can adapt and run for your own team, especially when your best experts happen to be your worst salespeople.

Why Experts Often Struggle In Sales

Before I explain how we ran it, it’s worth understanding why these situations are difficult by their nature.

Subject matter experts (like my procurement people) carry three barriers when pushed into sales:

• They’re too reasonable. They identify more with the buyer than the seller, and instinctively take the other side’s view.
• They’re uncomfortable with persuasion. If there’s no absolute logic, they back away, even when emotional leverage is what’s needed.
• They expect the facts to win. Which is fine for compliance reviews. Not fine when convincing someone to change operations and take professional risk.

The problem isn’t confidence or competence, it’s their lived experience. They aren’t anti-sales (so they kept telling me - hmmm), they just haven’t seen a version of sales they respect.

So we built one that made sense to them.

The War Game Setup

Let’s be clear, this wasn’t roleplay, there’s no acting, no theatre.

It was scenario based simulation where each team had a clear mission, a credible opposition, and defined constraints.

Red Team were the sellers, pitching our contract frameworks.

Their objective: win over an NHS trust to adopt our services.

Blue Team were the buyers, the heads of procurement who needed contracts to buy their med devices, pharmaceuticals and indirect spend items.

Typically they are defensive, cautious, and under no obligation to say yes.

I was the facilitator, controlling pace, injecting friction, and pausing for feedback.

We didn’t skip stages or simplify the process. We simulated a full deal cycle:

1. Gaining attention from a reluctant stakeholder
2. Securing a meeting with something worth discussing
3. Demonstrating value in operational, financial, regulatory, medical and political terms
4. Navigating the pilot, an intense data comparison process involving pricing, discounts, and huge spreadsheets
5. Transferring operations cleanly from existing suppliers to ours
6. Getting a referral to grow credibility in the procurement community.

We ran it in real time, with real documents and plausible constraints. No one played nice. That was the point. It was also a little tense at times.

What Worked

Three things made the simulation not just realistic, but transformative.

1. We rehearsed reality

Instead of teaching them what to say, we put them in a version of the situation they’d face anyway, and let them work out where they stumbled.

2. We built in feedback loops

Each stage had a pause point. What worked? What landed? What did the buyer hear vs. what the seller thought they said? We didn’t correct, just reflected and replayed.

3. We treated the buyer side seriously

This wasn’t a straw man exercise. The Blue Team knew they could win by finding fault, staying sceptical, or pushing risk back onto the seller.

They weren’t there to be persuaded. They were there to be convinced, like in real life.

The result was a shift in posture. By the end, the Red Team weren’t apologising for selling, they were building arguments, defending value, and leading the process.

How To Run This Yourself

If you want to apply this in your team, here’s a stripped-back version of the process that works whether you’re selling software, services, or anything with a complex decision path:

1. Set the mission

Pick a real opportunity or common sales scenario. Define success clearly, e.g. get a second meeting, progress to pilot, defend against competitor X.

2. Build a credible buyer team

Have team members play buyer roles with realistic resistance. Include blockers, time-wasters, and genuine power. Sometimes qualifying a prospect out, is the right answer.

3. Assign the sellers

Use your team, in their real roles. Don’t let them rehearse. Let them try it cold. You can always replay sections.

4. Run the meeting live

Start with outreach, move through the pitch, handle objections, push for progression. Let it flow naturally.

5. Pause and debrief

After key moments (a rejected meeting, a failed pilot, a pricing challenge), stop. Ask both sides what happened. Where did things shift? What worked? What didn’t?

6. Replay

Rerun that stage with the learning applied. Then move forward again.

You can do this in a single afternoon or across a sequence of sessions. You don’t need actors, but I have used real customers a few times.

Final Thought

You can’t fix a missing sales instinct with a playbook. But you can grow it with experience, if the stakes feel real enough.

A war game gives your team a chance to see the whole deal from the inside out, without the pressure of live

consequences. That’s how confidence is built.

And sometimes, that’s all a subject matter expert needs to become a seller who actually gets taken seriously.

Let me know if you'd like to know more about the war game process. We're building tools like this into our upcoming programs.

I help founders and enterprise sellers in three ways:

1. My Sales foundations course here gets you and your team up to speed in the basics, which is where it really matters - Personal skills, Pipeline discipline and Value based selling.
2. Drop me an email about coaching you or your team - let me know what particular problems you want to work on. First call free.
3. I'm on LinkedIn everyday, real stories, usable tools and strong opinions. I really appreciate reposts because they spread the word.

Send this edition on to your friends, so they will know you know...

If you run a sales team, and have a go at this then let me know how it goes.