I’ve been doing this for a long time. Over that time, I’ve struggled with teaching others to sell. I haven’t figured it out.

I always did reasonably well at selling stuff myself. I sold radishes (yes, radishes) from my garden when I was a kid. Who even eats radishes?

As a 10-year-old, I sold holiday cards door to door from a catalog I got by responding to an ad in the back of a comic book. I moved some cards in my neighborhood. That’s where I learned how seriously people take the spelling of their own names (the cards were imprinted).

I sold subscriptions to the North Dade Journal and the Miami News during those years, and I sold cameras in a camera store as a teenager.

Selling stuff comes naturally to me. I’m moderately full of crap and can have a conversation with lots of different kinds of people (including the naked couple who answered the door one day when I was selling newspapers).

But I’ve never had much luck teaching others to sell stuff. And it’s not like I haven’t tried.

Can Sales Skills Be Taught?

I’ve tried to teach it one-to-one. I’ve tried making videos. I’ve enrolled my team in sales training programs. I’ve brought sales trainers into the firm.

If teaching people to sell stuff works, then I’ve missed the boat. Nothing I’ve tried has made much, if any, difference.

The people I’ve hired who are good at sales were good from the first moment. The people I’ve hired who aren’t very good don’t really change. Of course, the not-so-good people have their moments. They get decent numbers once in a while and then they fade. They can’t sustain it.

Some people seem to have it, and some don’t. It doesn’t appear to me that anything I’ve ever done has had much of any impact on changing those people. They can sell or they can’t.

Maybe some others are good at teaching people to sell. I haven’t met them yet. In fact, the only people I’ve met who claim to be good at teaching people to sell are people selling programs to teach people to sell. I’ve never met a business owner who advocates for these sales training programs. And I’ve never met a business owner who tells me that she’s good at teaching her own people to sell.

Most business owners I know talk about giving people a shot at selling and keeping those who turn out to be good at it. They aren’t turning nonsalespeople into salespeople. Of course, it’s certainly possible that I’m missing something. Maybe I’m wrong, but I’m just not seeing any particularly effective ideas for turning people into salespeople. That makes me sad, but I’m increasingly accepting of that reality.

Of course, you’ll need to learn this for yourself. You’ll need to give your ideas a try and see whether you can teach your people to sell. Go for it. I wish you success. But maybe our discussion here today will help you short-cut your process. Maybe you’ll trust your numbers and not get lulled into believing that a sudden bump up is significant; it’s not. The good ones start strong and stay strong. Sure, they have the occasional slump, but the others have mostly slumps punctuated by brief success.

5 Steps to Teaching Lawyers to Sell

There are a few things I’ve done with teaching lawyers to sell that have helped. They won’t change the lawyer from being unable to sell into being a magical salesperson, but they’ll allow the inner salesperson to come out.

1. Shut Them Up

Lawyers think the solution to every problem is more talking. Selling works better when they close their mouths and open their ears (you know, that whole God, two ears, one mouth thing). Convince them to listen. I wish I could require a shock collar for them to wear during consultations that would go off each time they speak. Lawyers who happen to be good at sales often fail to realize it because they can’t stop talking. This requires persistent force to teach.

2. Turn Off the Professional

Get them to take that stick out of their ass. They need to relax and be human. I wish I could trip them as they escort the client down the hall so they’d loosen up. Falling down instantly makes you more human. The lawyers put barriers between themselves and others that make it harder for the client to say yes. The lawyers need to relax, admit to having their own problems, be human and actually let others connect with them. Again, it’s mostly about helping lawyers who are otherwise good at sales get out of their own way.

3. Speak Against Their Interest

Convince them to let some clients go. Help them see that turning a client away is good for the client, for themselves, and for their reputation. Tell them not to sell. Teach them to explain the downside of hiring the firm. They have a tendency, mostly because they can’t stop talking, to oversell. Sell less, listen more, and act like a normal person. That’s what I try to convince them to do.

4. Positivity

They’re cynical, bitter, and hostile, and they largely believe people will be forever unhappy. But they need to be able to draw a picture of light at the end of the tunnel in order to sell services. They need to believe that some people will have moments of happiness. They can’t let their cynical, pessimistic perspective permeate the process. Regardless of whether they believe it, they’ve got to be able to describe the pot of gold at the end of the rainbow in terms so vivid that others can see it. No client buys a dreary, sad, depressing outcome.

5. Give Them Small Wins

They’ll get into slumps. They’ll have down times. Mostly the slumps will just be a coincidence, but some will see the slump as evidence that they’ve lost it. They can talk themselves into believing most anything, so they’ll do as much harm as good with that skill set. When they’re down and the slump is continuing, it’s important that they get a win. It can be tiny. They just need to see that the course has changed. A happy e-mail from a client might be sufficient. A small sale will help. A victory on a case has an impact. The fast way back to winning is winning.

How to Build a Selling Team

My experience is that those who can sell will sell. Those who can’t sell won’t sell. Obviously, you need a plan for ferreting out those who can sell if you’re to grow your business. The bigger you aspire to be, the more critical your sales team. You can help them grow the business and improve their skills, but you’ll need a systematic approach for finding those who can close the deal.

I haven’t figured out how to teach them to sell. I hope you can. In the meantime, give your lawyers a shot. Some can do it. Keep those folks. Some can’t do it. Let those folks handle other things. Keep trying new people and, eventually, you’ll end up with a team who can sell radishes, newspapers, or legal services.