Let Them Fail - Lessons in Sales Management

Let Them Fail - Lessons in Sales Management


This past November was my 13 month in Sales Management. It has been the most challenging role of my career and there are some lessons I wish I would have known. If you’re in management and find yourself struggling, or are starting out and want to avoid systemic mistakes, this series will be for you.

I am about to end the year at >105% to goal and these are the principles that helped me get there. Know that I continue to struggle with this. We can all get better. Strap in.

Lesson 1: Let Them Fail

So you got the job, got hired, or were so star-spangled awesome as a salesperson you got promoted and are now a manager.

Congratulations and fuck off. This isn’t about you. Your priorities are now to provide and fight for your team. Which is why this first lesson is so difficult to swallow.

You need to let them fail.

I don’t mean you need to check out. You must be 100% there all the time (because why the fuck would you half-ass this game). Show up early. Stay late. Take every lunch at your desk. Listen to calls when you get home. The workday no longer ends when you leave. If you want to be great in this role it will take all your time.

There will come a moment on the first day, week, or month when each of your reps is struggling. They can flounder on a call, get nowhere on the front end, struggle to communicate a core concept on a demo, have a close fall apart, or fall behind on their daily metrics.

Let them fail.


I understand you think this is stupid. That you got here because you know what to do in this situation. You know how to fix it. You’re a mechanic, your team is an engine, and you apply oil where you see it’s needed. If anyone ever tells you this analogy call them an idiot and send them this article. There will be squeaky problems you must ignore

A sales team isn’t an engine. It’s a group of people. Your job is to cultivate confidence and self-reliance. A great sales team is one where you don’t see the need for a manager. You can parrot lines until you’re blue in the face but then no one learns.

Learning, true learning, is always a painful process. Your true job is to make yourself obsolete. This cannot happen if you jump in to put out a fire every time a rep cries out for help.

Call this “Learned Helplessness”. It creates job security. It doesn’t create success.

Why It’s Hard to Do This

You’re insecure.

Yes, you are. You feel the need to voice your opinion in meetings on how you would have handled a situation, how you have trained your reps to do your process, how you and your team are attacking a situation, blah blah blah. You create sheep in need of a savior to please your own vanity instead of training future managers who happen to be rock star salespeople.

It’s also hard because their performance is your quota and paycheck. You mean I have to put my paycheck on the line in hopes of them being better in the future? Yes. All this job is is sacrifice, risk, and trust. If that’s too difficult, go back to being an individual contributor where you can control everything.

After They Fail — Discovering the Solution

When they fail they’re frustrated, angry, and feel abandoned. Be careful because you can waste the learning environment you’ve crafted. How do you ruin it?

Come into their failure and tell them exactly what they should have done.

I see this a lot (with myself). A manager swoops in after a call. Rep asks “what should I have done”. The manager tells them how they would have handled the situation. The manager walks away feeling validated in their process because, in the hypothetical scenario, they were the perfect rep. The rep feels inadequate. They wonder why they didn’t do it that way. They question if they can ever get to the level you described. And they browse Instagram or LinkedIn looking for job inspiration or openings.

You cannot provide the solution. You must help them discover the solution.

Here’s how.

After a call, you sit down with the rep. They’re frustrated. You likely heard 17,000 issues with the call but identified one central, upstream issue. They want to talk about why the close fell apart but instead you ask,

“In your needs analysis section, what did he say was his big problem?”
“He hasn’t gotten the number of jobs per week to where he wants it to be.”
“Gotcha. And what has he done to try and solve that?”
“Well, he paid for leads for a while but their quality was pretty bad so that was a major point of frustration and something I hit on a lot in the close.”
“I heard that and it was good. But why do you think it’s frustrating for him?”

Your goal here is to help the rep understand the why. In this hypothetical B2B scenario, a business owner is feeling frustrated at their lack of control over their own business. They feel inadequate that they couldn’t achieve their goal of increasing the number of jobs. They’re now skeptical of everything because there’s no guarantee. They’re confused because they tried something and aren’t sure why it didn’t work. And (depending on how the rep reminded him of his mistake during the close attempt) they’re now annoyed.

It’s important that you continue asking questions until the rep gets at least 80% of the above pain on their own. Filling in the last 20% yourself is fine. You’re helping them analyze their own process (which builds self-reliance). They’re building an understanding of all angles of a scenario (which builds confidence). They’re feeling what the potential sale feels (which builds empathy — the foundation of sales). This conversation could take 30 minutes during your “busy” day.

Once the rep is on the same page with the context, then it’s time to ask the magic question.

“So I noticed that you moved straight from this part into trying to close him. But in light of the guy’s situation what do you think would have been a better to do?”

You’ve taken the time to build context and help the rep discover their own solution. They’ll have an answer.

This is where all the magic happens.

Even if their solution isn’t what you would do or it’s not quite right, you say the following,


There will be further lessons. You’re in management. You’re not going to create perfect performers with one conversation. It’s about the long game.

What to Change When Nothing’s Working

What to Change When Nothing’s Working