Episode Twenty-seven

How to Build a Coaching Culture in Your Business

Guest: Chad Dyar, Director of Sales Enablement at OnDeck

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Chad Dyar Coaching Culture Sales Engagement

About This Episode


Sales is hard to stay on top of. When the industry, and the technology that pushes it forward, is constantly changing, it’s natural to want to keep up and change with it.  

Big, sweeping changes feel exciting and innovative, but have you stopped to consider whether you’ve mastered (or even tested) the art of change management? Or do you tend to just announce a change with the expectation that everyone will buy-in? It’s an important question to ask yourself as a business leader.

We sat down with Chad Dyar, Director of Sales Enablement at OnDeck. As the leader of the sales enablement team, his focus is on driving sales productivity and efficiency through performance management, process improvement, technology implementation, new tool adoption, and creating career opportunities.  

Rather than being focused on the everyday operations of the team, his job is to take a step back and see the bigger picture of where the organization is headed. This allows him to build strong, long-term strategies for their tools and coaching program.

Four Steps to Build a Coaching Culture

1. Simple to Scale

Simple to scale simply means doing one thing at a time. Doing too many things at the same time makes it difficult to know whether any one of those things is actually happening. Start with one thing and make sure everyone is bought into it.

Once they’re doing that one thing, ask for a lot of feedback so that you can continuously iterate to get it where it needs to be.

Chad’s team started with coaching. No tools, just coaching. Focusing on one thing helped them get 100% adoption early on and built the important foundational mentality of coaching.

We built a scorecard so that people knew what to listen for, how to identify who was in what level, and how to move them up the ranks based on where the sales people were in their calls

2. Complexity

This happens over time once you build a simple process. At OnDeck, once they had coaching down, they started looking into the best tools to help them keep track of progress; that’s when they found ExecVision.

They brought a trainer into the office to spend a few days working with the entire team while ensuring everyone else was using ExecVision in their day-to-day. Thanks to the new tool, managers were doing two coaching sessions per person every single week. All of a sudden, a coaching culture was born.

3. Focus on leadership

OnDeck put a lot of training and development focus on their managers because they have the most impact. Large teams would learn from these leaders, so Chad invested the most development in them.

One way they did that was by setting up manager effectiveness training and various workshops. During one of the first training sessions, they realized, while they were all coaching their teams, many of them were doing it differently. So they gathered all of the feedback and best practices from each manager in order to teach others what was working and what wasn’t.

They also held a Coaching Olympics, where each manager would coach someone that was not on their team. A panel of business experts spent a full day watching each manager’s coaching style. A winner was recognized, and Chad’s team added the insights into the coaching curriculum.

4. Continuity

How do you keep a team from getting off track after the excitement dwindles? It might sound too simple, but Chad says it’s by checking in all the time.

His team does what they call a monthly touchback. He gathers all the managers once a month and has two of them present on something interesting they’re doing in coaching, what’s working, and what’s not.

Chad Dyar Coaching Culture Sales Engagement

Chad also spends intentional time looking at the notes in their coaching tool to see what people are trying. This creates accountability and keeps coaching fresh on their minds. He also does regular drive-bys where he checks in on people to ask them what they’re working on, how it’s working, who’s making progress, who’s not, etc. Managers are usually excited about this so Chad’s job becomes keeping that excitement up.

Get Started Today

Improving the training and enablement of your team doesn’t have to be complicated. Remember, start simply and then scale.

Chad recommends starting by surveying your team. When you have an idea for a new initiative, start with the team you’re already working with. Grab a couple people on the floor who you trust and who will give really good feedback.

Getting buy-in is crucial, so meeting with a small group first will help you strategize on how you will explain why you’re doing this to the larger organization. This will also help you ensure you’re fully prepared before bringing this idea to your leadership team.

A coaching culture will look different in every organization, but they will all start the same. How are you building yours?

This post is based on a podcast interview with Chad Dyar. To hear this episode, and many more like it, you can subscribe to The Sales Engagement Podcast.

If you don’t use iTunes, you can listen to every episode here.

About The Podcast

The Sales Engagement podcast is the #1 podcast focused on engaging your customers and prospects in the modern sales era. This show features real life stories and best practices from revenue leaders doing the job day in and day out, in a casual, radio-like talk show.

Each episode features modern tactics, strategies, hacks, and tips to get the most out of your sales engagement strategy and help you navigate the next generation of sales. You’ll find an energetic talks that will provide you with real actionable value around building meaningful connections and creating a better selling experience through authentic conversations that you can measure.

The Sales Engagement podcast is here to help B2B sales leaders, customer success leaders, and marketing leaders innovate and usher in the next era of modern sales by building pipeline, up-selling customers, and ultimately generating more revenue with more efficiency.

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