Training Salespeople to Succeed by Letting Them Fail

Training salespeople is a vital part of owning or running a business, and letting them fail is one of the best ways for them to learn. — Photo by the blowup on Unsplash

Go to any bookstore. You will find dozens, maybe even hundreds, of books on training employees and team members. Do you know what you don’t see as often? Books on training salespeople.

Since too many people believe selling is an inherent trait or natural talent, businesses primarily focus on sales training for their products and policies. They don’t often train them on how to actually sell.

The reason for that (other than the one just mentioned) is that the different training strategies and techniques are endless! No single approach will be far and away better than others for every employee.

That’s why most sales managers want to try to hire salespeople who already know their stuff and don’t need training.

But that’s not realistic.

Training Salespeople is an Ongoing Process

Even when you hire the best salespeople for your team, plenty of new and ongoing training should still be involved. You want to know that they can sell your product and do it with company values and your target market in mind.

Training salespeople doesn’t stop six weeks after you hire them. Selling isn’t like riding a bicycle; you don’t learn once and never forget.

There are always things that can improve—better conversations, more detailed data, new marketing strategies, etc.

Even the best salespeople in the world will do better with training and coaching.

However, the best salespeople or founders do not always make the best trainers.

Doing Does Not Equal Teaching

Most people would assume that anybody who is crushing it at sales will be able to teach the newbie to be just as good. Sadly, that is often not true, primarily if they have never taught or trained others.

Over time and with enough practice, everybody gets to a level of unconscious competence in almost anything they do. That means you don’t have to think about all the small things you do to accomplish the bigger goal. And that level of ability is excellent for the company’s success, but it might not translate into helping others very well.

Training salespeople, or anybody in anything for that matter, involves patience, dedication, and empathy on top of actionable knowledge. These are all things great managers can gain over time, but not everybody starts with it.

That means that smaller companies, where the manager/owner has to wear different hats, struggle to train sales reps and put them on a short path to success.

On the other hand, huge companies can afford to hire as many people as needed. The more employees you have, the fewer roles each person has to fill. Large, well-established businesses typically have a dedicated training team that can spend a lot of time and resources ensuring that new hires are well-trained and prepared for success.

And not only that, but they have years of experience and progress to utilize when hiring new people.

These benefits usually don’t apply to newer or smaller businesses. Every person has to fill several roles. Practices, processes, and knowledge typically grow with the company.

So what do you do when you’re the founder, lead salesperson, and trainer to new hires?

Training Salespeople the Right Way

First and foremost, document your process as much as you can. We’ve talked before about how important building and writing processes are so that you can ensure new employees have the blueprints and guidelines for your specific company.

Second, as mentioned above, learn how to hire well and ensure every salesperson has taken a personality assessment. That will help you so much in your ability to train, coach, and motivate each team member.

And third, give them all the knowledge and time you can, and then let them fail.

But Don’t Let Them Hang Out to Dry!

This two-part step sounds obvious, but it isn’t as easy for many small business owners or managers as you’d think.

I’ve known founders and salespeople who are so good at what they do! But they must focus on their business, so their processes and relationships are vital.

There’s a fear that if somebody else steps in, even when necessary, they’ll ruin or change what they’ve built. So instead of handing over their established book of business and how they grew it, founders give salespeople a quota and let them go.

That’s the wrong kind of ‘letting them fail.’ But it happens all the time.

If your business’s growth has made it impossible to continue wearing the hat of the founder, manager, and salesperson, give your new salesperson everything they need. All of your processes, all of your knowledge, everything. Including as much time as you can spare.

And then, when you’ve given them all the ingredients to succeed, step back and let them fail.

Children will never learn to tie their shoes if their parents always do it for them. They’ll never ride a bicycle if you never take off the training wheels and let them fall a few times.

The same thing applies to training employees. In any department, not just sales.

Training Salespeople With Guidance and Patience

Too many trainers or managers step in during a bad sales conversation or with an upset client. Or, they don’t let new hires take over established accounts at all.

This takes up much of the time and patience managers should spend on training and coaching.

If you’re worried about losing a few clients or prospects because of a new hire, you may need more resources (i.e., leads and clients) before even considering hiring a salesperson. The fewer you have, the more attached to the outcome of every interaction you’ll be. And it will be a lot harder to work on training and improvement in that situation.

With an abundance of leads or a large book of business, you can give your salespeople the freedom to work out the kinks in their sales conversations.

After any failed or less-than-satisfactory interaction, sit down with them and discuss what happened. Ask new salespeople questions to find out how they felt about it, where they think it went wrong, and how they can improve.

Let your process do the training!

Don’t just give them the answers. If they’re following your process, they need to figure out how to make it work for them. Otherwise, you’ll always have to look over their shoulder.

Then, when you’ve talked them through the issues, roleplay the same conversation to let them try out their new ideas or correct their mistakes.

Obviously, if they’re not improving after many failed attempts and training or roleplaying sessions, maybe they just weren’t as good as you’d hoped.

But they have to be given the resources and knowledge to try before giving up on them.

Building a Successful Sales Team

Many founders and sales managers must step out of the sales role to train new salespeople. And that’s a hard thing to do.

But if you want to prepare a successful sales team, it will require time, resources, patience, and a strong desire to see them succeed. Think about the gap your new salesperson will fill for that business, and ensure your job description clearly defines that.

You will lose some time initially, but if you document the process the first time, the following hire will be easier, and so on. Or, if you know you won’t have the time or ability to train someone to the level that you expect, then hiring a sales trainer may have to come first.

Hiring mistakes are pretty costly, but proper and continuous training will go a long way toward helping you avoid them.