I walked into a cozy coffee shop nestled in the heart of my alma mater (Georgia Tech) to spot a well-dressed gentleman patiently waiting for me across the room. Timely as ever, Ryan Gottlieb’s presence exceeds his years.

Ryan Gottlieb is a Director at The Aspire Group and oversees a team of 2 managers and 11 Sales & Service Consultants. The Aspire Group has represented 130 sports and entertainment properties who have trusted their team with revenue enhancements through sales and marketing.

It’s rare these days to find a manager as classic as Ryan. He believes in punctuality, hustle, loyalty, and respect – all things you’d expect to find in a manager twice his age. But age has rarely ever been a consideration for Ryan. Having managed a sales team since the ripe age of 23, he has the experience of a seasoned vet and can show you the results to prove it.

He’s the kind of guy that doesn’t demand respect; he simply exudes it. And as someone I have admired since my first day at WideAngle, he has definitely earned mine. All of this ran through my mind as I hurriedly walked over to the table he had chosen for our interview. I sat down, we ordered two espressos, and for the next hour or so, Ryan and I spoke about how he runs his One on Ones. Here’s what I learned.

For Ryan, his One on Ones are a mix of several things.

Constantly Fresh Training Sessions.

Training sessions are extremely important to The Aspire Group. Each season has different sales processes which places an emphasis on an agile training methodology. These can range anywhere from 10 to 30 minutes. He sees this as a tactical effort – time spent working on the fundamentals of sales. In his WideAngle Brief Ryan asks if there is anything his reps want to cover during the next week’s training sessions, giving each Sales Consultant a chance to ask for help or even to teach the group something they learned over the past week (we all know how much sales reps love to show off). This not only helps each rep to hone and develop their skills, but Ryan has also noticed that it works to create bonds amongst the team.

Spend Individual Time with Each Rep.

Ryan asks each rep to set the agenda for their sit-downs & must come prepared. This helps him better understand what it is that personally motivates his reps and how to cater his coaching style accordingly. If a rep wants more responsibility, for example, Ryan can sit down and set specific goals to make sure they’re on track to working their way up. By guiding the conversation based on what he knows motivates them, it keeps everyone engaged and drives the reps to do better work.

He likes to keep these meetings rather informal. While metrics are a huge factor in every sales organization, he makes sure that it doesn’t monopolize the entire conversation. He has more formal reviews dedicated to metrics (more about these in just a few), but sit-downs are mostly about building professional relationships.

Maintain a Metrics-Based Coaching Rhythm

Sales is a very metrics-focused profession and it must stay top of mind for every great sales leader. Ryan asks his reps to prepare a metrics overview, encouraging them to self-assess their own performance before he interjects what’s on his mind. Most of the metrics are pulled straight from Salesforce.com and displayed simply in WideAngle, saving the reps countless hours. Even in the metrics-focused One on One, Ryan sticks to the 80/20 rule: even when you want to speak up and be critical, wait. It is important that he lets the rep make discoveries on their own terms. Otherwise, they become too dependent on management. Ryan is well aware that ticket sales can be a tough job and wants his reps to have a quality experience while producing the numbers necessary to fill the stadium. As a Georgia Tech season ticket holder, I can confidently say that the bar he’s set for them has paid off.

Even in a world driven by numbers, relationships matter most; Ryan exemplifies this in appearance and action. We’re proud to have Ryan and The Aspire Group as a customer for over a year now.  

Interested in how more managers conduct their One on Ones? Read more here.


WideAngle is One on One meeting software used by companies including General Electric, IBM, AT&T, Google, and many more to make sure One on Ones happen, are productive, and documented.

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