Issue #89

Building Sales Mastery

At 61 years of age I can safely say that experience is overrated.

People talk about their “years in the game” as if that means anything. It doesn’t unless that experience is dissected, systemised and practised.

Unexamined experience is just repetition.

And repetition without reflection leads to boredom, burnout, and bugger all results.

If you want to get better at enterprise sales (or anything complex) you need two things:

1. The courage to go out and get experience while knowing you’re not very good yet.
2. The wisdom to examine that experience without flinching, knowing it’s going to hurt.

That second bit is where most people fail.

• They protect their ego.
• They blame the client.
• They get busy and move on.

That is how you end up stuck five years into a job you’ve technically done for one.

And you know that feeling, we all do. I read it everyday in my DMs. I posted about this on Linkedin recently, read it here.

So here are five questions that will improve your outcomes - if you’re willing to answer them honestly.

1. Can you name the last 3 sales meetings that ended with the buyer doing more work than you?

Most sellers do all the lifting, we are told to. We follow up, chase, send decks, "circle back."

But in enterprise sales, real buying looks like work; internal pitching, escalation, planning.

If none of that is happening then all our following up is wasted.

Example: One founder I worked with started ending meetings by assigning small but strategic tasks to buyers: “Can you map out who else would need to approve this?”

Buyers who didn’t do it? Disqualified.

Buyers who did? They closed faster. Clear line.

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2. How many of your open deals have a next meeting booked with someone more senior than last time?

You don’t climb inside the buyer’s org unless someone pulls you up. If your deals stay flat - same people, same level - they’re already dying.

You have to call it out or else you’re wasting time - and we know that is the only sin in sales, don’t we?

Example: A head of sales I coached built a “ladder or leave” rule. If no new stakeholder appeared in two meetings, the deal was deprioritised. It saved 15 hours a week and increased close rates by 22%.

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3. When a deal goes quiet, do you know why or do you just move on?

Silence isn’t golden, it’s rejection in slow motion. But most people don’t chase the truth. It’s easier to call it bad timing or budget review or competitor ambush.

If you start getting ghosted, escalate until you find out why. You literally have nothing to lose, but might have a vital lesson to learn.

Piece of advice here - get the customer’s holiday timetable before you start panicking.

Example: A BDM I advised added one line to her follow-up:

“Even if it’s a no, I’d value the reason.”

One reply: “Legal blocked us. Can you speak with our ops lead?”

That deal closed three weeks later. “No” would’ve been the end, but asking made it the middle.

4. What’s the last deal you walked away from - on purpose?

If you never walk away, you’re not in control. What you think of as your sales strategy is just a vague bit of targeting and a load of exceptions.
Desperation is invisible to you, but obvious to buyers. You are also not building valuable reputation and expertise in your niche.

Example: I turned down a seven-figure deal because the procurement terms were unworkable. I knew my own board would laugh me out of the room.

Three weeks later, the buyer CEO came back with a new procurement VP and a revised path. Never did find out what happened to the old guy.

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5. How often do buyers escalate your proposal internally without being pushed?

If that’s not happening, they’re not invested. It is a harsh truth, but still a truth.

They might like you. But they won’t fight for you.

Find a way to get them personally and professionally involved or qualify them out now before you make a fool of yourself.

Example: I coached a seller to reframe their offer using the client’s board metrics instead of product features.

The operational lead took that deck and presented it internally. That brought three new stakeholders into the deal. The seller didn’t “drive urgency”, they made it easier for someone else to do it for them.

Each of these questions hurts a little. That’s the point.

It’s not the experience that makes you good. It’s your willingness to look at it clearly.

And drag out every ounce of value. It saves you having to learn it twice (or in my case about five times…)

Want to do more of that? Get a coach.

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I help founders and enterprise sellers in three ways:

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

Tell your friends about "One Step Up", they will immediately make a note in their gratitude journal with your name next to it.

I want to reach my goal of helping another 1500 salespeople succeed, starting this year.

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