Costello joins SalesLoft, the #1 Sales Engagement Platform.
Life just got better for all sellers | Learn More

An Interview With Scott Leese: How to Weather the ‘Ups and Downs’ of Sales While Building Your Career

By: Teresa Weirich

January 15, 2019

Scott Leese, SVP Sales, Qualia

As anyone in sales knows, the disparity between the good days and bad days can quickly eat away at your resolve until it seems like you’re hanging on by a thread. For Scott Leese, SVP of Sales at Qualia, it’s these ups and downs that have given him a unique perspective on what a successful sales career means.

“Sales is not your typical 9-5 job with punch-in punch-out hours,” Scott said. “You can end up logging very long or very strange hours which can be disruptive to daily life. For example, it can interrupt dinner time with your family or disrupt your self-care routine. Not solving or addressing any issues this causes can add stress to what is an already stressful position.”

Scott knows just how important managing this delicate balance is because of his own personal experiences.

“In my early 20s, I was very ill and spent 4 years in the hospital. I became addicted to opioids during this time and while I am now recovered, I still function differently than normal people. I have challenges every single day with my health that test my resolve and commitment, which can mirror the experience of people in sales. It’s like flexing a muscle to become stronger every single day.”

In his first conversation with Costello, Scott discussed how salespeople can overcome obstacles and how sales leaders can use psychological elements to help shape the careers of future leaders. In this article, he shares how sales leaders can weather rough patches in their career without losing sight of professional development.

What advice do you have for sales reps going through a rough patch in their careers?

If you’re struggling in the moment, just remember that you’ve gone through harder things than worrying about whether or not you’re hitting your quota. It’s important to pause and give yourself a pat on the back and say ‘Look where I am! I’m killing it!’. Your attitude defines you, and presumably, we’ve chosen to make the most out of it. People don’t do this enough – just pause and be complimentary. It’s much easier to be critical of yourself than to be complimentary.

It comes down to perspective and asking yourself what is the actual worst thing that could happen. Like right now, the worst possible thing that could happen is that you might lose your job, but everyone needs to have things sold, so in reality, salespeople have great job security. It’s important to realize that there is always something else or somewhere else you could be. People worry so much about finding another job if they lose their current one, but that shouldn’t be your main focus.

As a sales leader, how do you help coach reps who are going through a hard time?

It’s my job to help remove obstacles from my team’s path while they’re trying to do their job. This could mean greenlighting a contract or streamlining a process, or it could mean helping to clear up issues in their personal life so they can focus on work. A lot of times the reason people are struggling has nothing to do with their job. If I can create the right environment and a strong sense of trust between my team and I, then I can help them in small but meaningful ways.

In leading and being around people, you learn to ask the right questions that encourage people to share and that in turn allows you to help them on a deeper level. If they feel like they’re in a safe environment with you as a leader, then you can have those kinds of conversations. About kids, family, finances, medical questions – it doesn’t matter. It’s about the sense of trust and community you’ve created.

What are some boundaries that you have in place to encourage a positive work/life blend?

For myself personally, I don’t have any formal boundaries. If someone sends me a question at 8:30 PM, I’m going to respond. I’m going to find a way to help out because that is part of my job and not responding would be letting someone on my team down. If I’m out on vacation somewhere for a week, I’m not going to be tied to my phone, but I might be checking emails a few times. When I first started out in my career I was terrified about not responding in real-time, but now I realize that is how a negative work/life blend gets started.

For my team, I model the boundaries I think they should follow. If I create a space that I think is okay and scalable, they will become more comfortable with their own work/life blend. If someone isn’t feeling well, I tell them to go home. It’s okay to rest. It’s okay to handle your personal business and schedule your work around your personal issues and not the other way around.

How does taking care of yourself and advancing your career go hand in hand?

First, you have to believe that the two are not independent of each other. You don’t have to sacrifice your career to stay healthy or vice versa. It’s about building a balance of the two. Second, don’t go to work for people who make you choose between the two. Find a leadership team who inspires happiness and who will foster a balance between your health and your career.

What advice do you have for sales reps who are going through a tough time about seeking out advice or guidance?

You have to find someone to talk to. It doesn’t matter who it is but it needs to be productive, positive, and deliver value. Also, you have to be the one to go seek out help. It’s a poor excuse to say ‘I don’t have anyone to talk to’. Go find someone in the same role and just ask them. Sure, you might be ignored, but it’s no different than building a sales pipeline, right? If you ask enough people to listen, someone eventually will.

What advice or resources can you share?

My own book is called Addicted to the Process and I wrote this specifically for those who are just starting out in their career. I also have an essay included in the book Standing O by Scott MacGregor. This is a collection of essays from successful people including business owners, CEOs, and athletes on people who inspired them, events that shaped their lives, and more.

My past has made me who I am and has given me a unique outlook on life, but it has also made me empathetic with those I work with and those who work for me. It’s not easy and I certainly don’t have all the answers, but I have learned to prioritize myself to stay healthy and I want to help others do the same.


  • Teresa Weirich's Headshot
    Teresa Weirich

Ready to Learn More?

For more information on best practices of great sales leaders, check out the Costello resources below. If you’d like to see Costello in action, request a personalized demo of our real-time sales playbook software.

Related Posts: