Podcast | True Confessions of a Sales Leader

Podcast: True Confessions of a Sales Leader

Grab a cup of coffee and dive into the premiere episode of “True Confessions of a Sales Leader,” the Olsen Group’s new podcast where sales leaders share their secrets of success (and failures) while offering guidance along the way.

Our new podcast helps sales leaders like you and your sales teams develop the skills, systems and culture that leads to sustained and significant results.

Each episode provides listeners with transformational guidance that can be used immediately in your sales organizations.

In our first episode we start with a crucial topic: How to coach an inexperienced sales manager.

Episode 10:
Onboarding your sales team remotely

In this podcast episode of “True Confessions of a Sales Leader,” we discover how sales organizations like yours can successfully onboard a team remotely. Our guest is Tom Whalen, director of inside sales at McKesson, who provides first-hand experience of how his team has accomplished this. Tom joins Scott Olsen, founder of The Olsen Group, and Gary Brashear, managing partner of The Olsen Group.

Key Highlights from the Podcast

‘Walk’ the floor, remotely
Pre-COVID days, many inside sales organization leaders would walk the floor, check-in, or offer advice on sales calls for the day. Tom says his team still does this, virtually. With a simple morning roll call with all reps, new and existing, he offers a fun trivia question to get the conversation rolling that also provides structure. They also discuss any specials or strategy around extra inventory. It’s also a great way to build camaraderie and get to know your new team.

Implement virtual coaching
Virtual coaching lets sales leaders keep their team connected and engaged and ultimately be more effective. So, how do you simulate the presence of a sales leader? Technology helps. Video-based practice and coaching platforms (e.g. rehearsal) support salespeople’s ability to practice and refine “moments-that-matter”, get feedback from their managers, and share best examples across the sales organization. Tom Whalen gathers his teams online through MS Teams on Mondays to discuss the week’s goals, then meet again on Friday to discuss results. These approaches let leaders know what’s happening on their teams but also offers structure.

Create a process for onboarding
For success, have a well-defined process to onboard new team members—recruit, train, and coach—and consider these elements:

Figure out how much time is being spent on coaching.
Develop a high-performance learning journey for your new reps. This will help guide the conversation to where they are today to where you want to get them.
Communicate and pay attention to the details.
After a few weeks ask for feedback and take that feedback to make the next round better.
Track and measure for understanding. What do you want the rep to get out of this? Are they getting it? What can you do better?

Episode 9:
Creating Strategic Partnerships that Work

In this episode of “True Confessions of a Sales Leader,” we explore the steps of creating a successful strategic partnership. Our guest is Geoff Curless, Chief Revenue Officer at Rehearsal—and an actual partner of Level Five Selling.

You know the importance of creating strategic partnerships (and if you don’t, definitely listen to this episode!) but how do you get on the path to creating ones that work for your organization? Listen in as we discuss how we’ve accomplished this and what to look for when considering your own partnerships.

Key Highlights from the Podcast

Define what success is
A successful partnership can be defined in many ways, but most importantly that definition has to meet your own criteria for success. Whether your goal is to reach a bigger market and broader reach or attract new clients, set that definition early. When a new organization approaches you, how will that partnership help you? Know your goals, strategies, and visions of your organization and how a partnership can benefit.

Think upfront
A strategic partnership needs to be valuable for your own organization. Ask yourself the hard questions: Will your partner’s sales team see the value and unique experience you offer? Can the team be coached to successfully sell the product? Will a partnership be critical to your success or will it fall by the wayside? Determine your goals before you set the wheels in motion. Evaluate upfront and make sure this is a strategic move. Spend the extra time before committing. Remember the old saying “measure twice, cut once”? That certainly applies to the research beforehand in building partnerships.

Set your vision and bring it all together
Someone in your organization needs to have the knowledge and the vision of how the various components of a partnership can be brought together. For instance, when Level Five Selling partnered with Rehearsal they needed to go beyond just their technology. They provide video-based practice and coaching to organizations using tech, so how could we leverage that and bring that into our own culture? John Hoskins, founder of Level Five Selling, was able to step back and ask how Rehearsal could complement what he was trying to achieve with clients while helping solve what was missing. It was a win-win for everyone.

Episode 8:
Successfully Creating and Navigating Changer in Your Organization

Organizational changes are hard enough. Add Covid, a dispersed staff, then figuring out how to get everyone on the same page— and keep them there. And if you’re a sales organization, how can you do this seamlessly without client disruption?

In this episode of “True Confessions of a Sales Leader,” we explore how organizations can successfully pivot to change their own culture but also meet client demands and expectations. Our guest is Blackboard vice president Dave McLaren. Dave joins Scott Olsen, founder of the Olsen Group, and Gary Brashear, managing partner of the Olsen Group.

When Dave’s team recognized that clients were increasingly moving to the cloud and SaaS and away from on-premise hosting and meetings they’ve been on a journey to meet these new requirements through their own changes. Listen to how they’re accomplishing this.

Key Highlights from the Podcast

Never forget the client
This is important: Focus on the client journey, too. Help define your change from a client’s perspective so they can come along on the journey. Interview and record your best clients and not-so-satisfied clients and play the interviews for team members responsible for the journey. This helps them become empathic because they’re hearing real feedback from an actual client. Changes won’t matter unless everyone in the organization is running with the same client heartbeat and thinking of the client first.

Remember individual sales team members
Don’t get lost in the big picture of organizational change. Build on what you’re doing right, then recognize the gaps in the group plan and individual plans. Convey to your team along the way to help them understand the “why” so everyone buys in.

It’s about coaching, too
The shortcut? Just tell your sales team what to do. The hard, but better option? Ask tough questions. This helps create a discovery moment so they come to their own conclusion for a resolution, and why it makes sense because they figured it out. It sounds simple but you need to coach people to think differently on an individual level and create an environment with trust so you can get buy-in into the organizational change.

Keep your eyes on the prize
Changing your organization in any scenario but especially in the midst of a pandemic is stressful. Remember this: Go back to the “why” the decision was made to change and why it’s important to the client. What are the values and tenets you agreed upon? What do you want it to look like? Make the commitment as a team to work toward that.

Episode 7:
Conversation Intelligence: Capturing Sales Call Success

More times than not, when asked about how a sales call went many salespeople respond with “it went great!” Conversation Intelligence is changing how these calls are recorded, listened to and how you can respond to them. It lets you be more precise about your coaching, and during our current working-from-home environment, it’s a powerful way to coach while we can’t be in the same spaces together.

In this episode, Gary Brashear, managing partner of the Olsen Group and Scott Olsen are joined by Jim Benton, CEO of Chorus, a Conversation Intelligence platform. Listen in as we discuss how Chorus and artificial Intelligence (AI) technology are helping capture conversations, make real connections, and allow sales leaders to train and coach like never before.

Key Highlights from the Podcast

Capture intelligent conversations
Part of the magic of capturing conversations is the ability to understand what happens in calls between your sales reps and customers. AI and Conversation Intelligence highlights key moments like pricing questions or a customer mentioning your competitor. It allows sales teams to hear key moments of a conversation so they can evaluate call quality.

Use the gathered information
Let’s say you use technology like AI and a platform like Chorus and you’ve captured a sales/customer conversation. Now what? For starters, sales leaders have access to these conversations and often don’t have time to listen to 30-minute calls. Conversation Intelligence provides small snippets of important information, lets sales leaders hear a lot of data quickly, drill down to the specifics, and then lets them coach on those small emotional pieces of information versus just an overview of how a call went. It goes beyond “hey, great call.” It lets you be more precise about the feedback and coaching you provide.

Coach from these ‘crucial’ conversations
By capturing conversations you can hear and analyze conversations between your salesperson and customer. Is it one way or a conversation with a connection? Platforms like Chorus allow you to go back and pinpoint areas with a timestamp and re-listen, then work with your salesperson on what they did or didn't ask. You can listen to the flow, and you can suggest positive changes. It’s not calling out a sales rep, it’s helping them improve. We’re even using these recordings in all interactions and meetings we’re having at the Olsen Group.

Episode 6:
The Keys to Effective Sales Coaching - Part 2

Part 2 of our dual episode of “True Confessions of a Sales Leader” continues with a discussion with Dr. Richard “Dick” Ruff and John Hoskins, respected experts in sales coaching, founders of The Level Five Selling Coaching System, and authors of the book, Level Five Selling: The Anatomy of a Quality Sales Call Revealed (click here for a complimentary copy).

In the first episode, Scott Olsen, founder of the Olsen Group and Gary Brashear, managing partner of the Olsen Group, joined them to discuss why sales coaching is so important to an organization, especially in these times. If you don’t think your sales organization or team needs a coaching program, listen to part 1.
After you’ve listened to part 1, then come back as we share insights and some real-world tactics on how you can get started on a coaching plan immediately.

Here are four key takeaways from this Podcast:

Start at the top
Want to launch a coaching program? Most companies like yours probably have some previous history of coaching. Maybe it was intermittent or only done by a few people instead of a systematic way throughout the whole organization. So, how do you successfully get started or get re-started?
Start with your top management and top sales management. You’ll need an institutional commitment from them to establish a sales culture. Then, set the direction and focus for a coaching program before executing.

Establish expectations
Conduct a quarterly business review by having your frontline leaders report on what they worked on and who they worked with. Review that plan and ask how the sales leader executed that plan. Prepare for some pushback, too. Pulling a sales member off of the time they’re spending making sales to coach them? Tough sell. However, it might also let you discover what the sales team is actually working on. Tasks that aren’t revenue-driving can be assigned to a non-sales member.

Use the right tools
Hire a coaching planner to help you get a good view of what the managers are focusing on and dealing with. Consider workshops that will help get everyone on the same page by using common language, a common framework, and the definition of what quality looks like. Employ—especially in these times—a virtual coaching platform. This technology, for instance, can provide videos with exercises that let the sales team “respond” on how they’re applying and responding to their current accounts. Then, the sales leader can view that and provide feedback.

When do you know you’re finished with coaching?
You never are. Coaching isn’t an extended exercise, it continuously needs to be done. Sales team members need to learn new skills, especially in our current environment. Those skills are constantly changing so coaching doesn’t have a beginning and an end. That said, don’t over-invest in people that aren’t performing. If you do, you have to cut your losses early. Don’t let your ego hold on to someone you think you’ll turn around. Other team members will suffer and might not get the level of coaching they need.

Episode 5:
The Keys to Effective Sales Coaching - Part 1

Welcome to this special two-part episode of “True Confessions of a Sales Leader.” We are honored to have on two guests: Dr. Richard “Dick” Ruff and John Hoskins, respected experts in sales coaching, founders of The Level Five Selling Coaching System, and authors of the book, Level Five Selling: The Anatomy Of A Quality Sales Call Revealed (click here for a complimentary copy).

Before we dive in, a quick bit about our guests. Dick has spent the last 35 years helping large corporations develop sales teams in the B2B market in the high-tech (yes, that includes Apple) and medical devices spaces. John began his career in the corporate world in a variety of sales and sales leadership positions and founded his own company. The two then combined forces and founded The Level Five Selling Coaching System, the only sales coaching system to master call planning and execution skills that helps salespeople deliver top-line revenue growth.

Joining Dick and John are Scott Olsen, founder of the Olsen Group and Gary Brashear, managing partner of the Olsen Group. Listen in as this virtual table of sales experts discuss why sales coaching is so important to an organization, especially in these times.

Here are four key takeaways from the Podcast:

Sales coaching, defined
We’ve all heard the term but what exactly is it? It’s a formal process for helping a salesperson develop their full potential. The key is helping somebody learn versus just teaching them. You might be talented in sales but it’s hard to reach your potential without some kind of coaching. The challenges of coaching can go deeper, too, such as changing the behavior of a high-performing salesperson who brings a toxic environment to the team, or improving performance of those who don’t perform well, or getting people to change habits like those who don’t do the basics like submitting expense reports. These behaviors require a whole different skillset of coaching.

Set milestones for coaching
Sure, there are regular sales meetings between directors or the first-line sales team but what’s often missing is a standard format for coaching. Without that framework, it’s hard to tell if coaching is working and hard to adjust if it’s not. Coaching can be inconsistent even within organizations. Some teams will do it well about 20% of the time, while others may not spend much time coaching because of confusion or clear roles and responsibilities. Set objectives. Spend the time to do it effectively.

Coaching, virtually
A personal connection is important when selling and when coaching. How do we connect —and coach or get coached—in a virtual world? In a nutshell, plan. Many successful programs will have a 90-day plan, including who the salesperson will be working with and a mutual agreement on a plan by all parties. This enables measurement when coaching online, whether it’s effective, and provides an overall ROI.

Decide if you need coaching
If an organization says they don’t need coaching, that’s a good sign they probably do. Every company needs a coaching regiment in place, especially in a transitional period as we are experiencing now. There’s no question that companies are changing what they buy, and how they buy. When customers change how they buy, sellers need to change how they sell. Short answer? Your organization needs coaching.

Episode 4:
Transforming an Inside Sales Team

Picture this: You’re new to a sales organization and have been hired to transform it. The reasons for this needed transformation can be many, one of the most common being that the market has changed, forcing the business strategy to also change.

How do you start organizing your new team to meet this transformation?

In this episode of “True Confessions of a Sales Leader” we discuss ways sales leaders can transform their inside sales organizations.

John Belle, global head of inside sales at PayPal joins Scott Olsen, founder of the Olsen Group and Gary Brashear, managing partner of the Olsen Group, as they discuss the path to take.

Here are three key takeaways from this Podcast:

Get aligned early
A successful leader should always know what they’re walking into. Remember: There’s a reason you’ve been hired. However, before this can occur, you need to be aligned with the team or stakeholders, whether that’s marketing, finance, and certainly HR. Getting alignment at the executive level is crucial—long before you share your vision or transformation with your new team.

Be empathetic but also prepared
How do you prepare for team members worried about inevitable change? If you've aligned with the leadership team, and you have a clear definition of success, articulate it to your team in a simple but organized way by breaking your mission down in the first moments with them. Help them get their head around your vision and set the stage where key initiatives need to be taken. There are four focal areas to help explain your point of view and define what “good” looks like:

Business results. This is a given and will drive your team.
Operational excellence. Create results in a thoughtful way.
Employee engagement. Everyone needs to contribute and provide full engagement.
Customer and partner loyalty. All of this is moot if you don't build the systematic practices to ensure our partners and customers stay with you!

Transforming at scale
Once your mission and vision have been determined, how do you execute and support? Work with your front line sales team to build a coaching culture. Help them understand how to do that effectively. Assess the sales team, benchmark, then build on what’s working and work on areas where there can be improvement. Remember: It’s just not working on making a salesperson better, it's how you are affecting the quality and productivity of conversations with your customers.

Episode 3:
The Power of Sales Mentorship

Have you ever had a sales mentor? Have you ever been a sales mentor? Looking for ways to integrate a mentorship program into your own sales organization but don't know how to start?

In this episode of “True Confessions of a Sales Leader” we discuss the power of mentorship in sales orgs and teams and how successful companies can use mentorship to ramp up sales, build confidence, and create success.

Scott Olsen, founder of the Olsen Group, Gary Brashear of the Olsen Group, and Konnor Martin, VP of Sales, rfpio, discuss the importance of mentorship but also share their own personal stories on how it has affected their careers.

Here are four key takeaways from this Podcast:

Mentorship, defined
Mentorship is about imparting wisdom that comes with experience. It helps keep things running and fulfills a leadership and coaching capacity that one individual can’t do on their own. It’s also about sharing knowledge, wisdom and advice—a relationship that benefits both the mentor and mentee.

Get introspective
Ask yourself how mentors have helped you to get you to where you are. This can add clarity to the why and purpose of a program, based on its impact on you. Use that experience.

Exercise humility
Being a mentor is more than what you know and telling your mentee how to do it. Ask questions. Prod and probe. Try to understand where your mentee is at in their career. Mentorship involves heart, your mentee’s best interests, and encouragement from you. Put your ego aside.

Integrating a mentorship program into your organization
If you want to start integrating a mentorship program, establish clear expectations on what the boundaries and parameters are for mentors and mentees before getting team members involved. Start with coaching—it’s short term and simpler and may evolve into mentorship.

Episode 2:
Navigating While Managing a Sales Team During COVID-19?

Navigating while managing a sales team during COVID-19?

You’ll want to listen to our new episode of “True Confessions of a Sales Leader,” The Olsen Group’s podcast where sales leaders share their secrets of success, insight, and guidance.

For this crucial episode, we interviewed our own Gary Brashear, Managing Partner, The Olsen Group, and Matt Greene, head of sales for Fetch, a company that offers direct-to-door package delivery for apartment and multi-family buildings. Gary and Matt share how they are coping with the disruption, how they are motivating their sales team, and what they see on the horizon.

Here are three key takeaways from this Podcast:

Empathy is imperative
Practice empathy with your sales staff and share your concerns and your own fears with staff. Salespeople tend to be extroverted. They’re stuck at home, they’re not face-to-face with clients, sales are down. A status check can reveal who’s having a rough time or needs more guidance. It’s about more than the numbers right now.

Use past experiences
Is there a past experience that emulates what we’re going through now? It’s like a combination of 9/11, the 2008 recession, and the dot-com boom and bust all wrapped together. Take things day to day, try to navigate through information (or misinformation), and as a leader show up, represent, and listen to your team. If we learned anything from past experiences it’s that being transparent is key.

To pivot or not to pivot
“Pivot” is the word du jour for our current crisis. So do you stay the course or pivot? Ask questions of your team that may lead them to look at a challenge a different way. Talk to your customers and find out what has changed with them. As a sales leader it’s your job to serve customers, help them achieve their goals and if those goals have changed, (and they indeed have) you have to realign your strategy and goals for you—and for them.

Episode 1:
How to Coach Inexperienced Sales Managers

Let’s say you’ve hired a new sales team leader. They bring the chops, the energy, and the enthusiasm. But, what if they don’t have the experience your organization needs? They might be new to your organization, maybe they’ve recently been promoted or have moved over into that role from another one.

Our three experts— Scott Olsen, founder of the Olsen Group, Gary Brashear of the Olsen Group, and Tony Esposito, a chief revenue officer and head of sales—offer crucial advice on how to coach, make the right decisions, and ensure your new sales manager is embedded into your organizations’ DNA.

Here are three key takeaways from this Podcast.

Your new front line leader needs to be more than a manager. They need to be a colleague to the sales team and understand the strengths and weaknesses of their team.
You need to develop a unique coaching plan for your new hire. Training is an investment in both time and money and you need to ensure they know how to perform without being micromanaged. You truly want them to be successful, not just force something on them.
Interviews are still important. They allow you to uncover what their prime motivation is of getting into sales management. (Hint: If it's not based on truly wanting to help others succeed it’s the wrong role for them.)