Issue #105

When the Past Trips the Sale

Enterprise sales looks like a straight line when you see it in a training deck.

Prospect. Discover. Engage stakeholders. Negotiate. Sign.

Easy, right?

Except it never runs in a straight line. And half the time, the detours aren’t coming from the client at all. They’re coming from you.

I’m not talking about skill gaps or lack of product knowledge.

I’m talking about the stuff that lives under the surface.

Old wiring from when you were a kid. Rules you didn’t choose, but learned early because they kept you safe. Rules that now cost you deals.

Prospecting

You know you should be aiming high, the decision makers, budget holders, the people who can say yes. But instead you’re sending safe emails to mid-level contacts who’ll happily chat but can’t sign a thing.

That’s not laziness.

That’s avoidance dressed up as activity. If you grew up in a house where rejection was brutal or constant, your brain still treats it like a threat.

So you stay where the stakes are low.

I’ve seen this kill careers. One rep I coached had every reason to connect with a CEO, but kept “waiting for the right moment.”

Three months later, procurement issued an RFP to his competitor. The right moment was long gone.

​

Discovery

This is where you’re meant to find the truth about the client’s problem. But you keep the questions polite, shallow, safe.

Why?

Because you learned that asking the wrong thing gets you hurt.

A rep I knew grew up in a house where “don’t rock the boat” was the survival plan.

On calls, she’d skip over anything that might sound challenging. She’d leave with pages of notes and nothing of value.

It’s not just learning better questioning (click here to get a video on that). It’s building the courage to go where the conversation actually matters.

Stakeholder Engagement

In enterprise, you have to pull a group into alignment. It’s political, messy, and often uncomfortable. If your early encounters with authority figures meant humiliation or punishment, your instinct will be to keep your head down.

I’ve watched reps vanish from the internal politics of a deal because sitting in a room full of senior people feels like walking back into the headmaster’s office.

One guy I worked with let his champion handle the senior team alone. He thought he was being respectful. He was giving away control of the deal and ultimately the deal itself.

​Click here to read about how to pitch to the C suite so that they listen.

Negotiation

This is the stage where childhood perfectionism comes out to play. I grew up in a hypercritical house where nothing was ever good enough. That conditioning followed me into sales. Every objection felt like proof I’d failed.

My reflex?

Concede too soon, trim the price, agree to extras, just to make it go away.

The shift came when I learned to say (internally!), “Fuck it, the price is the price.”

I wasn’t being stroppy, I was refusing to give my “people pleaser” reflex the wheel.

If you want a strong negotiating position (and who doesn't?) then you have to know your value equation, read about it here.​

Closing

Even here, the past can take over. Some reps delay sending the final paperwork, making “one last tweak” before the client signs.

On paper, it looks like diligence. In reality, it’s fear of losing the win at the last second. It’s the fear you get if you’ve had things taken away right when they were finally yours.

I had a colleague who let a signed contract sit in his inbox for two days. By the time he sent it back, procurement had found another problem, the one they used to kill the deal.

All because he couldn’t bear to call it done.

The point is that every stage of the process offers a place to hide.

If you’ve got old scars, you’ll hide in the same kinds of moments again and again.

The client won’t know why the deal went cold. You might not know either, unless you start looking at your own patterns.

Find out more about getting things done - click here.​

What You Actually Do

If you see yourself in any of this, pick one stage where you regularly stall. Name the exact moment it happens. Then get someone (a peer, a manager, a coach) to hold you in the moment until you act.

You don’t need to solve the past right now. You just need to stop it destroying the present. Get past the blockage in front of you.

Enterprise sales is hard enough without you playing defence against yourself.

See the pattern, name it, and start pushing through it. That’s how you keep the past from tripping the deal.

More about overcoming internal blockers, click here, from last week's post.

---

If you want to know more about how I help people succeed in sales and sales team management, drop me an email.

If you want to get your team trained up in the basics of enterprise sales click here.

My course is a full suite of punchy, 10 minute videos.

You can integrate them into your team meetings to coach your team to excellence, step by step.

Never be stuck for an agenda again as you watch your team grow into experts.

Reply to this email if you want to discuss coaching or consultancy for you or your team.