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Ashley Dellinger of OneRail: “Provide feedback, both positive and negative”

Provide feedback, both positive and negative. When an employee or coworker does a great job with the delegated task, tell them what made it great. Positive: “The new report that you included was incredibly helpful to showcase to the client how we’ve grown their business, and it had a very positive impact on the meeting.” […]

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Provide feedback, both positive and negative. When an employee or coworker does a great job with the delegated task, tell them what made it great. Positive: “The new report that you included was incredibly helpful to showcase to the client how we’ve grown their business, and it had a very positive impact on the meeting.” Negative: “The new report that you included was a nice touch, but my concern is that showing that report will potentially derail the meeting into focusing on a few minor details that aren’t the goal of the meeting. In the future, please exclude reporting that isn’t directly relevant to the topic at hand.” Feedback, positive or negative, allows for continued growth and success!


As part of my series about the “How To Delegate Effectively and Be Completely Satisfied With the Results”, I had the pleasure of interviewing Ashley Dellinger, Vice President of Sales for OneRail, a two-year old, rapidly growing SaaS tech startup, connecting retailers to over 4.5 million contracted logistics partners, simplifying shipping and delivery solutions in real time. In 2019, after over a decade of success in advertising and marketing technologies, she made a career transition into supply chain logistics software. The move came at a time where final mile and supply chain were already broken, then Covid-19 shattered them.

Dellinger’s experience in multiple successful tech startups — consistently bringing on seven-figure clients — landed her in an executive leadership position at OneRail to disrupt the antiquated logistics models of the past. Her prior experiences include companies like UberMedia, SpotX, Sinclair Broadcast Group, and the former Raycom Media (now Gray Television). She graduated from the University of Georgia in 2008 and currently lives on Lake Norman, just outside of Charlotte, North Carolina.


Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

I graduated from the University of Georgia in 2008, which if you recall, was not a great time to be entering the job market. I had degrees in Political Science and International Affairs, and the plan was to get out into the professional world and work for a couple of years before going to law school. Like so many that set out on that path, I never ended up in law school. Instead, the “sales bug” bit me after I found myself in digital media sales for a local television station in my hometown. I was promoted by the parent company a couple of times and moved to Louisville, then Savannah. From there, I entered the world of AdTech and MarTech sales and never looked back. I moved from Savannah to Milwaukee to Los Angeles and eventually settled in North Carolina… for now.

In 2019 I was approached by a recruiter for an AdTech SaaS position in the fashion retail industry. I wasn’t interested in that role, but he casually mentioned that he had an opening in Supply Chain Logistics SaaS. I jumped right on it. Coming from the AdTech world, I watched Uber, Netflix, and Amazon disrupt their industries. Considering my firsthand experience and understanding how behind the logistics world was, and now, here we are!

What do you think makes your company stand out? Can you share a story?

I think the best companies are created when the founders have intentionally created a company that solves for a problem that they have personally experienced. That is exactly what our CEO and Founder, Bill Catania, did with OneRail. What makes OneRail stand out is that we are solving an incredibly complex set of problems, simply. We are connecting supply and demand. Companies have items that need to be delivered, and we connect those deliveries to drivers willing to deliver them. Of course, there is highly complex tech stack behind it, but the solution to the problem was right there all along. Bill had to vision to harness it and turn it into a business.

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

The starting point is to determine the cause of the burnout. If you are experiencing burnout, you are either not in the right position or you need to ask for help or for more resources… which is timely for our chat today about delegating. That said, there will always be periods that are more stressful that normal and longer hours are required, but if it is nonstop, that is not sustainable for anyone. Find the source and start there. Those periods of stress should not be frequent enough to cause burnout. Dedicate time to take a breather using take your vacation days. Stepping away is healthy!.

Ok thank you for all that. Now let’s shift to the main focus of this interview. Delegating effectively is a challenge for many leaders. Let’s put first things first. Can you help articulate to our readers a few reasons why delegating is such an important skill for a leader or a business owner to develop?

Of course. First, if you’re not delegating you are missing out on valuable input and ideas from others. Repeating the same process, the same way that you’ve always done, won’t allow for improvement or fresh points of view that could be beneficial for your company.

Second, delegation is necessary to develop your team. How many times have we seen this scenario or heard this: “I’ll send it to Todd. He’ll be able to get it to about 80%, and then I’ll finish the rest.” Instead of accepting Todd’s 80%, we should be coaching Todd on how to get it to 100% to improve his development. Added bonus: Now every time you delegate that task to Todd, he knows how to do it, and you’ll get back that 20% of your time over and over again.

Third, in any position, especially a leadership position, you should focus your productivity on your main objective is. If your job is to generate revenue, the vast majority of your time should be spent doing that. If you need Marketing collateral, don’t try to build your own. Reach out to Marketing and explain what you need, and why it is important to reaching your revenue goals. Focus your time on your objectives. Delegating is a great start to that.

Can you help articulate a few of the reasons why delegating is such a challenge for so many people?

It’s difficult for a several reasons, generally specific to the individual. I think the most common is fear. Many leaders are naturally control freaks. They have gotten to where they are because they are good at what they do. It can be hard to let someone else contribute. There are risks associated with delegation. The risks create fear. What if we aren’t in full control of every piece of the process and the subsequent desired goal is not achieved? That outcome may leave us thinking after the fact, “If I had just done all of this myself, would the outcome have been the same?”.

Also, many leaders, especially new leaders, can feel like they are “dumping” work onto someone else by delegating. That is where the five points which we are going to talk about later come into play. If you delegate efficiently, ensuring that everyone understands their role in the business and the expected outcome, then it isn’t “dumping”; it’s collaboration and teamwork towards a common goal. Delegation should show your teammates that you trust and value them, which is what will set the standard for your company’s culture.

In your opinion, what pivots need to be made, either in perspective or in work habits, to help alleviate some of the challenges you mentioned?

Your perspective has to change from a “me-centric” standpoint to a team-oriented standpoint. Focusing on effective delegation will lead to the development of your team and your business. Many people have the viewpoint of wanting to be indispensable in their organizations. In my opinion, we should be doing the opposite. If you step away from the business for a vacation and the wheels DON’T fall off, THAT is the sign of a successful leader.

Quite frequently, those who experience that burnout are those who haven’t given their people the authority and the tools that they need to be successful without them. Your goal should not be to be indispensable; it should be to empower and develop those around you to make decisions and act with autonomy and confidence. If you think you are great at what you do, wouldn’t it be even better to have more “you”s in the company? Imagine your business’s trajectory from there.

Can you please share your “Five Things You Need To Know To Delegate Effectively and Be Completely Satisfied With the Results?” Please share a story or an example for each.

To delegate effectively, we need to focus on 5 key factors.

1 — Clear instructions of the task at hand.

Executives move quickly, and they tend to expect everyone to move quickly with them, without always pausing to make sure everyone is on the same page. The best way to do this is to “show” first. If I were to delegate, say, the task of creating a sales presentation — rather than saying, “Please build me a deck for Client X,” I would say, “I need you to build a presentation for Client X. Here are the key points that need to be highlighted. The structure should be similar to what we did for Client Y, and you can find that information in DropBox from May of 2020.”

2 — Be sure to set benchmarks and deadlines.

When delegating a task, always ensure the recipient understands a clear, precise deadline and check-in along the way. For example, “I’d like to see a rough draft by Wednesday at 5 pm and the final version will need to be completed by 5 pm on Friday.” That allows for several key factors. One, it allows the delegator to check in on the task to ensure that their expectation was clearly communicated before we have “surprises” on Friday at 5 pm. Two, it presents the opportunity to give feedback on the feasibility of the task. If I didn’t give a timeline, they may assume low priority of the task, accomplishing it later in the week or over prioritize, ignoring more urgent duties.

3 — Provide feedback, both positive and negative.

When an employee or coworker does a great job with the delegated task, tell them what made it great. Positive: “The new report that you included was incredibly helpful to showcase to the client how we’ve grown their business, and it had a very positive impact on the meeting.” Negative: “The new report that you included was a nice touch, but my concern is that showing that report will potentially derail the meeting into focusing on a few minor details that aren’t the goal of the meeting. In the future, please exclude reporting that isn’t directly relevant to the topic at hand.” Feedback, positive or negative, allows for continued growth and success!

4 — Share changes or re-delegate them.

For example, if only 8 of the 10 reports provided met expectations, you have two options. One, send it back, provide feedback explaining the needed changes and why. Two, if it’s a quick fix, you can make the updates yourself. However, share it back with an explanation of what you did and, why. “Reports 1–8 were perfect, but on 9 and 10, the terms you used weren’t accurate. I’ve updated the reports, but I’d also like for you to review them so you have a reference for next time.” This allows the other person to more effectively complete the task in the future, saving time for everyone.

5 — Step back.

Once you have given instructions, provided guidelines and deadlines, step back. Allow that person to do the task. It’s okay to have checkpoints and give feedback, but if you can’t give clear enough directions on an assignment and step away, don’t delegate it. You’ll end up either wasting your time trying to change everything or their time micromanaging them for something you are going to end up doing anyway.

One of the obstacles to proper delegating is the oft quoted cliche “If you want something done right do it yourself.” Is this saying true? Is it false? Is there a way to reconcile it with the importance of delegating?

I think there are times in which that statement is true. But is your backup plan just as or almost as good? Let’s say there is a speaking session at a conference that will have every major current and potential client in the room. As the CEO, you may feel it is imperative that you be the face of your company and control that narrative. That is perfectly acceptable. But what if you wake up with the flu that morning? If you have done your job leading up to that moment, you will have someone ready to step in for you, and you’ll still be satisfied with the results.

Thank you for all of that. We are nearly done. You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

I would love to see more business leaders take time to focus on at-risk youth, earlier — before they’re at-risk. After college, I spent a few months volunteering in a mostly low-income elementary school. What I saw would break your heart. Teachers can’t do it all, and kids expect to hear encouragement from their teachers. What they don’t expect is to have the CEO of a company tell them that they can do it and take an interest in their future and success. I would love to see more businesses step up in that area. Businesses are generally great at donating money to organizations, but I would love to see more of us donate our time as well.

How can our readers further follow you online?

I can be followed directly on LinkedIn at https://www.linkedin.com/in/ashdellinger/ or OneRail’s page at https://www.linkedin.com/company/onerail-finalmile/

This was very inspiring. Thank you so much for the time you spent with this!


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