How to Guarantee You Fail in Sales

"All I want to know is where I'm going to die, so I'll never go there."

That line comes from Charlie Munger. He was quoting an old farmer and it’s also some of the most useful sales advice I've come across.

In 1986, Munger gave a graduation speech called “How to Guarantee a Life of Misery.” He didn't tell the class how to be happy. He told them exactly how to be miserable so they could do the opposite.

It’s often a lot easier to think of the wrong thing and the negatives than it is to think of the positives, and that’s why inversion is so powerful.

This edition takes the same idea and points it at sales. Here's how to guarantee you become a terrible rep.

Do the opposite, and you're most of the way to the top 1%.

Let's get into it.

Ask most reps how to become a top performer, and you'll get vague answers like work harder, be confident, find a mentor etc. But none of that is actionable.

So instead ask the opposite question. What would make me a terrible rep?

And it's really easy to figure out what would stop you from hitting quota.

Like if you never prospected or followed up or sold a product that nobody wanted.

That's the power of inversion and how we’ll use it today.

Munger borrowed it from the mathematician Carl Jacobi, whose rule was "invert, always invert," and this idea was echoed by Einstein.

(If it's good enough for Charlie and Einstein. It's good enough for me)

Hard problems get easier when you flip them.

Here's how to use it:

Munger also had a name for what happens when several advantages stack up at once. He called it the “lollapalooza” effect.

Top performers rarely win because of one thing: they have multiple factors working in their favor at the same time.

People ask for the “silver bullet,” the 1 big thing, but it’s actually 100 golden BBs, tons of tiny things that stack up.

Here are the seven that matter most in sales.

Avoiding the obvious mistakes gets you further than chasing the brilliant ideas.

If you wanted to fail, you'd start in the wrong environment.

A rep in a dead territory can do everything right and still miss quota. So before you take a role, ask these questions.

White space or installs: Are you starting from zero, or do you have existing customers to expand from?

Book of business: Are you handed a set of accounts, or building everything from scratch?

Past success: Has anyone hit quota in this patch before? If not, find out why.

Ask in the interview. Ask the reps already on the team. Their answers will tell you more than the job description ever will.

Choosing the right environment is your job.

If I wanted to fail, I would pick a company where it has no product-market fit, provides no value, and is the worst product in the category against competitors.

Now it sounds super obvious when I say it like this, yet it’s still one of the most common reasons I see founding AEs fail.

They join an exciting startup, but it's pre-revenue, and when they try to sell it, they quickly realize the company has no product-market fit

So twelve months later, they're getting blamed for a product problem.

Before you sign, find out:

Who's buying: Are real customers paying for this today, and why?

Retention: Are those customers renewing and expanding?

Revenue: Is money coming in, and where is it coming from?

Even the best rep in the world will struggle to sell a product nobody needs. Check before you join.

The easiest way to be a bad rep is to wait for inbound.

Sit back. Work whatever lands in your lap. Hope marketing has a good quarter.

You'd also become attached to every single deal because you don't have enough, which would destroy your psychology. So we don’t want that.

All the best reps prospect every single day. They dial. They send emails. They reach out in DMs. They go to events.

Your pipeline is air. Without it, nothing else in this list matters.

Block the time in your calendar. Protect it like a meeting with your best customer.

if you don't have pipeline, you'll never get to quota.

Similar to the last point, if you wanted to be really bad, you'd expect everything to fall into your lap.

Send one email. Hear nothing. Assume they're not interested.

Run a great demo. Then wait for them to come back to you.

It's your job to keep top of mind with your prospect, not the other way around. Your prospects are busy.

They have 200 other things on their plate, and you're one of them.

Here's how to fix it:

After every demo: Book the next step on the call and send a recap the same day.

After no reply: Keep them in the sequence and keep following up

Every touch: Add something useful like a case study, article, or insight that would be helpful

The rep who follows up wins the deal the other rep forgot about.

The bad rep brute forces it. They go on vibes and how they feel that week.

They never look at their reply rate, their opportunities created, or their connect-to-conversation rate.

If I go into all of the benchmarks that we teach about in Outbound OS, we'll be here all day so I’ll do 1.

Here are the cold calling benchmarks to know:

Dial to connect: 5% average, 10% good, 13%+ top.

Connect to conversation: 30% average, 40% good, 60%+ top.

Conversation to meeting: 15% average, 25% good, 40%+ top.

If your connect rate drops, check your data.
If your connect-to-conversation rate drops, fix your opener.
If your conversation-to-meeting rate drops, go deeper on your prospect's pains.

Data is everything. It tells you exactly what to fix.

If you wanted to fail, you'd send the same generic message to everyone.

You wouldn't learn their world. You wouldn't know their KPIs. You'd have no idea what their day actually looks like.

Prospects can tell within one sentence.

Here's what caring looks like in practice:

Know their KPIs: What does their boss measure them on?

Know their day: What's slowing them down this week?

Use triggers: A new hire, a funding round, a job change. A real reason you're reaching out to them right now.

This is why we build every email on T.I.P.S. Trigger, Implication, Pain, Soft CTA. You can't write any of those four without understanding their world first.

Care shows up in the specifics.

The last way to guarantee failure is to stay exactly where you are.

Ask basic questions. Never ask for feedback. Never listen back to your calls. Be the same rep in year three that you were in month one.

Munger had a warning for this too. To the man with a hammer, everything looks like a nail.

The rep who only knows how to book meetings sees every problem as a meetings problem. Bad quarter? More dials.

But sales is a full system. Your list, your messaging, your discovery, your follow-up, your deal management, your numbers. They all connect.

That's why you need to become T-shaped. Deep in one skill, with working knowledge across the rest. Munger pulled ideas from psychology, maths, and history. You can pull from copywriting, marketing, and negotiation.

Here's where to start:

Weekly: Listen back to one of your calls.

Weekly: Ask your manager or a peer for one piece of feedback.

Every quarter: Learn one skill outside your lane.

The more tools you carry, the fewer problems look like nails.

And if you want to get one-on-one coaching from the best in the business, you can apply to work with our team here: Apply for Outbound OS

Munger's favourite rule was simple. “Take a simple, basic idea and take it very seriously.”

None of this is new but that's the point

Run the inversion today. Write down five things that would make you a terrible rep this quarter. Circle any you're already doing.

Audit your environment. Look hard at your territory and your product. If either one is broken, fix that first.

Pick your weakest of the other five. Prospecting, follow-up, data, care, or skills. Fix that one this week.

Do the obvious stuff very well. That's it.