How to Unlock the Growth Potential in Your Account Executives

For years, I struggled with being myself at work. There were two different Collins: the laidback one that hung out with his friends and family, and the one that came into the office keenly focused on crushing his numbers.

I thought, back then, that having those two identities was positive: it showed I took my work seriously, and when the grind was done I was free to relax. What I came to realize over time, however, was that dual personality was actually hindering my job. 

Sales are all about building genuine connections with customers – really getting to know their needs and wants – but my attempt at being serious in the office was rendering my calls…bland. That all changed when I stopped splitting up work Collin and “regular” Collin. I decided to start bringing my whole self to my job and it’s helped my career in more ways than I can describe.

That same project – the quest for authenticity and empowering salespeople to be their genuine selves – is what Justin Clifford, Director of Sales at Lessonly, is also working towards at his company. According to Clifford, unlocking the potential in your sales team starts with understanding them as individuals, and giving them space to just be themselves.

“It’s up to us to set them up for success. It’s not just about enablement and sales skills, but understanding them as people,” says Clifford, on a recent edition of The Predictable Revenue Podcast.


“It is really hard to separate work and life – so we want to understand who they are, what drives them. We have to pay attention to the whole person, not just the person in sales.”

Click here to Tweet: “It is really hard to separate work and life – so we want to understand who they are, what drives them. We have to pay attention to the whole person, not just the person in sales.” @CollinYVR


Displaying vulnerability

Chief among the ways Clifford helps his sales team show their full personality is to give them the space to be vulnerable at work.

No one, of course, has it all figured out – we all know this to be true. Yet, for some reason, we rarely show that vulnerability at work. We’re trained, often from childhood, to show that we have all the answers and that we’re masters of our chosen field.

What that false sense of mastery results in, however, is an unnecessarily tense environment often with less collaboration. 

“If you just start saying ‘hey, I don’t know’ or ‘I’ve never seen this before’ or asking ‘what do you think?’ you give people the space to collaborate, think of new answers, and be free to be themselves,” says Clifford.

“And that results in more creativity, more autonomy, and more collaboration.”

A good example of this vulnerability was Lessonly’s alterations to its sales territory breakdown. According to Clifford, the model was creating some inequity amongst the reps – everyone had the same quota, but not the same territories to support that goal – and it needed to be fixed.

“Some really good reps weren’t being successful and the territory model was behind that. So, we made adjustments and reps said that it created a 180 degree change,” says Clifford.

“I had to stand in front of our AEs, tell them we made a mistake, and that we were changing things. We let them know what we’re thinking and we asked them what they think we should do. Now every rep has the chance to be successful.”

(Editor’s note: we had Kyle Roach, also from Lessonly, on the podcast a while back to discuss how he teaches his team to “sell the dream.” You can read about our chat here, or listen to the whole interview here).

The autonomy to get your teeth kicked in

Despite its eye-catching tagline, what Clifford means when he discusses “the autonomy to get your teeth kicked in” is the space to learn and grow as a sales rep.

For example, during Lessonly’s onboarding process, which includes plenty of role playing, new reps are also given a few real opportunities to handle. Although it’s early in their tenure at the company, working real opportunities gives Account Executives that chance to ease into a fully ramped schedule and find themselves as an AE at Lessonly.

“Even if you are a seasoned rep, you’re learning at this point to be a Lessonly rep and get used to things like our sales cycle,” says Clifford.

“I want new reps to have space to do their thing, become themselves, and develop their style. It’s really important.”

This period in a Lessonly AE’s development is also about celebrating what goes well, adds Clifford. Sure, you’re learning a lot at this point, but many reps contribute right away. And that should be recognized.

One of our values is to highlight what’s working. Too often we give space to what is annoying or anger inducing, but it’s much better to give credence to something that is awesome or enjoyable.


There is plenty right in front of you that you should give energy to doing more of.

 The subtle art of 1:1s

Finally, Clifford uses his weekly 1:1s with his team as yet another avenue to ensure Lessonly reps have space to, again, be themselves. 

But getting to that point, admits Clifford, took some time. He’s volleyed back and forth over the years about what the focus of 1:1s should be. Should we talk about deals? Forecasting? Feelings? These are tough questions, to be sure, but after some time experimenting, Clifford settled on focusing the 1:1s on “whatever is on his team’s mind.”

“I sucked at 1:1s. So, I called a lot of people to really understand them – ‘what makes a good 1:1?’ Without a doubt, 1:1s can be very powerful,” says Clifford.

“A major factor in their effectiveness is the way you open the meeting. It sets the tone for what happens over the next 30 mins. So I always start with ‘what’s on your mind?’ It could be deals, prospecting, territory development, but it also might be about bad news in the family this week. It really allows us to connect as people.”

But don’t forget, adds Clifford, the first step to effective 1:1s is simple: make sure they happen. So, get the meetings on the schedule and make sure they are recurring. You need to carve out repeatable time with your team because as everyone settles into a routine, these meetings grow in importance and will yield more personal results.

“This is the power of the 1:1. It has helped me develop a lot of empathy,” says Clifford.

“We just do whatever is on their mind. It is not a focused thing that they have to prepare for. They are all about connection.”

For more Clifford’s thoughts on team connection and growth – including his thoughts on effective forecasting and avenues to add value as a manager – check out his full interview on The Predictable Revenue Podcast.



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