Cultivating Confidence: How to Coach, Develop and Inspire Your Reps

Whether you’re an entrepreneur, sales leader, or frontline rep (or all of the above), you’ve likely spent a lot of time thinking about the in-the-trenches tactics that will improve your job.

And why wouldn’t you? Every new tip and trick that helps you succeed is worth investigating and, if possible, incorporating into your daily routine.

But what about the more esoteric elements of sales? You know, emotional pillars such as confidence that underpins each thing you do at work. What do we do to cultivate those critical concepts?

Not enough, says Factor 8 and #GirlsClub founder Lauren Bailey, on a recent edition of The Predictable Revenue Podcast. But it doesn’t have to be that way – there are ways to foster confidence in your sales teams that will, over time, produce both personal and professional benefits for everyone.

All it takes is consistency from leadership and maintaining a mindful interest in your reps as people, not just deal-closers.

“Sales is a confidence sport. Life, in fact, is a confidence sport. It wasn’t until I founded #GirlsClub that I realized this,” says Bailey.

Confidence vs. bravery

Defining confidence, adds Bailey, can be a tricky thing. It’s a feeling…a feeling rooted in a firm inner knowing that you believe fully in who you are and what you’re doing. There’s no second guessing, no worrying, no sweating the small stuff. Do you need some help coaching your sales team? We can help you get it right.

To use a sports analogy, you’re in the zone.

According to Bailey, a good way of understanding and defining confidence is to examine bravery – a related concept, sure, but one that far too often gets confused for confidence. For example, Bailey says that bravery is when you feel nervous about a task, but you do it anyway.

Bravery, she adds, can be the beginning of confidence, but it is a more negative feeling, often fraught with worry.

“The difference is: confidence is knowing you deserve what you want. Nerves, of course, don’t totally go away, but there is a drastic reduction,” says Bailey.

“It’s like getting an extra 10 hours per day. When you’re confident, it isn’t draining. Bravery, however, burns out.”

Confidence killers

Before we look at how to cultivate confidence, it’s instructive to look at some of the ways we routinely kill confidence in our sales reps. 

Chief among those confidence killers, says Bailey, is scripting their actions – from call scripts to rigid email templates (the list goes on).

“We, as an industry, have adopted a rigorous interview process to find the right people. Are they curious? Have they played sports? We learn a lot about candidates over the course of hiring. We work our butts off to find great talent,” says Bailey.

“And then when we hire them we tell to just say what we have prepared. I think that’s a killer. It tells your team you don’t trust them, you don’t want them to use their own words.”

Another confidence killer, adds Bailey, is the regular promotion of inexperienced reps to managerial roles. To be fair, the practice of inside sales is growing so fast in so many industries that elevating reps to leadership roles can be unavoidable at times. The problem with that trend, however, is that reps who have had potentially subpar training themselves – scripting every element of the job, for instance – are now in charge of training new reps.

“If you’re a manager that was a rep five minutes ago then you aren’t sure how to train properly either. Managers just treat reps how they were treated,” says Bailey.

“If you got poor training and it turned out okay for you, that will likely end up in you doing the same. This is a hard one to get rid of, we hold on to this feeling regularly, but training keeps your team together longer and reps will make more money.”

Confidence builders

So…what about building confidence? What are the things managers can do to propel their teams?

Bailey says reps need to be taught “first base skills” such as how to execute an outbound cadence, leave effective voicemails, and master introductions to ensure prospects stay on the phone.

“We have to celebrate the people who can get the conversations, not just the closers. So, teach your reps how to leave a great voicemail. People have stopped leaving voicemails, but they work. You can get an extra 5-10 calls per week from returned phone calls, if you do it right,” says Bailey.

“The chance to sell is first base and these skills build happiness and success.”

For more tenured reps, Bailey suggests teaching them important concepts such as business acumen. For example, it is important for a rep to know the difference between the responsibilities of a CFO and CEO. This knowledge will make for better conversations.

A nuanced sales skill such as understanding wallet share, adds Bailey, is another important concept for senior reps to understand. 

“I’ve seen very tenured reps that don’t know what percentage of the wallet they are getting. They build great relationships, but they don’t have fundamental business acumen,” says Bailey.

“This takes time – you need to build a relationship, grow that relationship, and then work on this. But you have to understand where customers are spending other bits of their money.”

(Editor’s note: we had Margaret Weniger, former Executive Director of #GirlsClub, on the podcast a while back to discuss how to develop diversity on sales teams. You can read about our chat here, or listen to the whole podcast here)

How frontline managers can inspire confidence

The final piece of the puzzle is establishing clear, regular channels to help cultivate confidence in your reps. Each company and each rep is different, of course, so each rep deserves a tailored process that helps them feel empowered.

For example, weekly call coaching is an important piece of training that every rep needs. But, too often the focus of call coaching becomes deal coaching or a focus on why certain deals didn’t close. That narrow focus can be deflating to a rep, says Bailey. It’s better to hone in on what elements of a call can be improved, rather than focus on the undesirable end.

“Make sure you don’t care if the rep gets the deal. It’s about making them better, not just about closing. They should leave feeling like a superhero, not just like they lost,” says Bailey.

“So be consistent, meet with your reps regularly to help them, and let the rep choose what they want to work on.”

For more on Bailey’s thoughts on cultivating confidence – including a fascinating discussion on the role personality plays in developing sales reps – check out the rest of her interview on The Predictable Revenue Podcast.




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