Training Salespeople to Succeed by Letting Them Fail

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Go to any bookstore. You will find dozens, maybe even hundreds of books on training employees and team members.

The different strategies and techniques are endless! And no single strategy is going to 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 any training. 

But that’s not realistic. 

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

And selling isn’t like riding a bicycle. You don’t learn once and never forget.

There are always things that can improve. Better conversations, gathering more thorough data, incorporating new marketing strategies, etc. 

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

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

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

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

The beauty of huge companies is that they can afford to hire as many people as they need. The more employees you have, the fewer hats each employee has to wear. There’s a dedicated sales team and a dedicated training team. And they have the ability to spend a lot of time and resources making sure that new hires are well-trained and prepared for success. If they didn’t, there would be outrageous turnover and terrible performance, making the whole company suffer. 

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

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

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

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

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

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

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

I’ve known founders and salespeople who are so good at what they do! But because they have to focus on the business they’ve built, that adds a level of preciousness to their processes and relationships.

There’s a fear that if somebody else steps in, even when they know they need another person to handle the sales side of the business, that they’ll ruin or change what they’ve built. So instead of handing over their established book of business and how they grew it, they give them 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 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.

In business, 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 a lot of the time and patience that should be spent on training and coaching. 

If you’re worried about losing a few clients or prospects because of a new hire, then you may need more resources, (i.e. leads and clients), before even thinking about 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 talk about what happened. Ask them questions to find out how they felt about it, where they think they went wrong, and how they can improve. 

Don’t just give them the answers. If they’re following your process, they have 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 you give up on them.

Many founders and sales managers have to step out of the sales role to train new salespeople. And that’s a hard thing to do. But if you want to train a successful sales team, it’s going to require time, resources, patience, and a strong desire to see them succeed. Think about the gap that your new salesperson is going to fill for that business, and make sure your job description clearly defines that. 

You are going to lose some time initially, but if you document the process the first time, the next 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 very expensive, but proper and continuous training will go a long way towards helping you avoid them.

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