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Courtney Underwood: “Pay attention to the warning signs”

Focus on outcomes. The goal of effective delegation is the outcome — work done that meets or exceeds expectations. If you delegate the “what”, but micromanage the “how”, then how much time, money and effort are you really saving?For example, many of my clients point to graphic design as a great delegation opportunity. However, if they’re dictating […]

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Focus on outcomes. The goal of effective delegation is the outcome — work done that meets or exceeds expectations. If you delegate the “what”, but micromanage the “how”, then how much time, money and effort are you really saving?For example, many of my clients point to graphic design as a great delegation opportunity. However, if they’re dictating the programs and the methods to use to arrive at the final product, then they might as well continue to do it themselves. As long as the final design meets expectations and can be used correctly, nitpicking the creation process is not the best use of time. Focus on outcomes.


As part of my series about the “How To Delegate Effectively and Be Completely Satisfied With the Results”, I had the pleasure of interviewing Courtney Underwood.

With over 18 years of experience in Human Resources and Leadership Development, Courtney Underwood understands the unique challenges that companies face when hiring and managing their talent. As an HR Alignment Strategist, she helps her clients understand the importance of an effective team and how it impacts the growth and profitability of their business.

After spending more than a decade in corporate America, serving companies across several different industries, Courtney knew that she had to bring the proven corporate strategies she created to the audience that needed them the most: entrepreneurs that want a strong foundation from the start. Utilizing her signature systems, tools and resources, Courtney founded Kassar Consulting to help entrepreneurs and leaders navigate the business of people and increase their bottom line.

Her favorite quote? “You cannot dominate the marketplace without first mastering the workplace.”


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?

Thank you for this opportunity — I’m excited to share more about the business of people! I majored in Organizational Communication in college, where I was introduced to the connections between healthy communication and thriving companies. Those concepts drew me to the field of Human Resources and Leadership Development, and I dedicated my career to helping people feel understood and empowered in the workplace. The field of Human Resources is vast, and I’ve held roles that span the breadth of what it covers: Recruiting, Onboarding, Performance Management, Engagement and Retention, and Policies and Procedures. After spending 18 years in the industry, I founded Kassar Consulting to serve on a larger level, providing companies with the resources, tools and strategies I developed to effectively build and manage their teams.

Can you tell us a story about the hard times that you faced when you first started your journey? Did you ever consider giving up? Where did you get the drive to continue even though things were so hard?

When I first founded Kassar Consulting, I spent too much time working with entrepreneurs who only cared about filling gaps in their business. They only saw staff as a means to an end, and I quickly discovered that it wasn’t the right fit for my philosophy. I had to make the difficult decision to end those working relationships, and stand firm in my people-centric approach.

I never considered giving up, because I knew that the cost of quitting was too great. My drive was fueled by knowing that I had a solid team that supported our work, and incredible client success stories that demonstrated our impact. This motivated us to push through.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lessons or ‘takeaways’ you learned from that?

When I first started out, I conducted an HR Audit for a large client, diving deep into their culture and policies to assess their organizational health. Part of this audit included interviewing current staff members. There was one staff member in particular that was so eager to conduct our interview, she arrived to the meeting half an hour early! Before we even got acquainted, she went straight into listing her grievances with leadership, some over a year old. After covering everything from the CEO failing to return a borrowed pen to not having an office with east-facing windows, I politely asked her if she ever brought up these issues to anyone prior to our session. She was silent for a while, then quietly responded, “I didn’t know that I could. Before you came, I didn’t think anyone cared”. The major takeaway from that conversation was that by listening to what most would consider to be a list of petty and spiteful grudges, I was able to uncover a huge red flag that was later echoed by others within the organization. That meeting definitely went over our scheduled time, and I later learned to set boundaries, but it taught me the power of paying attention.

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

Kassar Consulting stands out because we approach HR and Leadership Development from a very unique perspective. Not only do I have close to 20 years of experience in the industry, but I am also an entrepreneur myself. Therefore, I am keenly aware of the challenges that leaders face when building their companies from the ground up. I have walked in their shoes and I lead with that knowledge to get my clients to see that transformation is possible. My signature course, Put Down The Cape, speaks to this mindset shift directly.

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”? To avoid burnout, I would recommend the following three tips:

  1. Audit your day. Over the course of a week, take an inventory to figure out where your time is going. Are you stuck in social media posts? Responding to customers? Learning Quickbooks? By paying attention to patterns, you will be able to make the shift from busy to productive.
  2. Set boundaries. An alarming number of entrepreneurs and leaders work long nights and weekends in the name of building their businesses. After a while, they find themselves deeply unsatisfied with the lives that they’ve built, even after becoming profitable. If you don’t set boundaries early on, chasing your vision will feel like a burden instead of a passion.
  3. Pay attention to the warning signs. Missed deadlines, poor quality products or services, and stagnant business are all warning signs that burnout is approaching. Responding proactively instead of reactively can stop a problem from growing into a costly mistake.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

The first person that comes to mind is my Consultant and Launch Strategist, Jessica Brown. Not only have her insight and expertise helped grow Kassar Consulting to where it is today, she’s also phenomenal at keeping me accountable for practicing what I preach. Jessica was the first to tell me when it was time to hire a team of my own, and I can directly attribute my success to her vision and foresight. She does of all this gracefully and with compassion, pushing my limits while making sure I don’t lose myself in the process. Her support and wisdom are absolutely essential, and I’m grateful that we’re connected.

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?

In today’s society, entrepreneurs are consistently told that they have to stretch themselves beyond measure in order to be successful. They have to be everything to everyone, wear every hat in their business, and still find time to eat, sleep and live. Many buy into this narrative without questioning the logic behind it.

Actually, the opposite is true. The key to success is doing less with more focus. Delegating tasks and building a team is the only way to scale your business effectively. Otherwise, your growth will be limited by your capacity. Buying into the toxic “hustle” mentality will stifle both your business and your quality of life. Mastering the art of delegation is a critical leadership skill.

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

Delegating is a challenge for many people for three reasons:

  1. Deception. People tend to think that they already know how to communicate effectively, when the truth is that good leaders and good managers are not the same thing. Management is a skill that has to be studied and applied like anything else.
  2. Mindset. Most people haven’t made the proper mindset shift to truly let tasks go. They may ask a team member to complete a task or project, but haven’t overcome the mental roadblocks that stand in the way of handing it over to someone else entirely.
  3. Comfort. If someone is used to doing everything themselves, delegation can be intimidating.

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?

People need to honestly acknowledge and conquer their trust and control issues that are standing in the way of the growth of their business. Whether they acknowledge it or not, a lot of people tend to see their business as their “baby” and usually put up a ton of resistance to handing over tasks for fear of being disappointed.

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.

My recommendations are below:

  1. Be selective. When delegating, choose the person that is actually skilled enough to do it. Sounds simple, right? That’s not what usually happens. Most often, leaders delegate to whoever has the free time or whoever they have an established rapport with. These characteristics are all secondary to who is actually qualified to take on the task.
  2. Provide context. Make sure that you take time to explain how the task or project fits into the overall big picture, why the outcome matters, and why they were chosen to complete it. Quite often, the end result is better than expected because the person completing the task now knows exactly what you need, and can use the full breadth of their talents to provide it to you.
  3. Confirm and review. When delegating a task or project, you should come to the meeting prepared with an idea of the resources they need to get it done, a clear picture of the end result, and a deadline. After reviewing all of that information, the natural conclusion is to ask the team member, “Do you have any questions?”. Practically every employee will tell you that there aren’t any questions, even if they are still confused or unsure. No one wants to appear as if they weren’t paying attention or as if they’re incompetent. A better way to address this issue is to ask the team member to share a summary of the meeting in their words. That way, you can discover any knowledge gaps before they become bigger problems.
  4. Focus on outcomes. The goal of effective delegation is the outcome — work done that meets or exceeds expectations. If you delegate the “what”, but micromanage the “how”, then how much time, money and effort are you really saving?For example, many of my clients point to graphic design as a great delegation opportunity. However, if they’re dictating the programs and the methods to use to arrive at the final product, then they might as well continue to do it themselves. As long as the final design meets expectations and can be used correctly, nitpicking the creation process is not the best use of time. Focus on outcomes.
  5. Get feedback. Sincerely expressing appreciation for a job well done is just as important as identifying opportunities for improvement. Of course, feedback should not just flow in one direction. This is a prime opportunity to learn if you provided enough context, resources, support and information to paint a picture of what successful task completion looked like. Additionally, you will be able to quickly find out if you’re assigning items to the right members of the team.

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?

This saying is absolutely false because it diminishes the contributions of the experts that are positioned to serve and scale your business. The truth is that there are others that can do many of the things you do better, thereby freeing you to work on the thing that you do best. If you’re blind to that, you will never let go of the good in order to be great.

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. 🙂

The movement that I would start is exactly the one that I’m working on: “Hire for attitude, train for aptitude”. Hiring good people that are willing and quick learners will lead to greater success when compared with hiring applicants that have the required technical skills but not the right attitude. You can train someone on the requirements for the role, but you cannot train them to be a good person. At Kassar Consulting, we teach our clients this fundamental hiring principle, resulting in increased productivity, profits and peace.

How can our readers further follow you online?

You can find me at www.kassarconsulting.com where I share further details on how to work with me, articles to support leadership development, and resources to thrive in these newly challenging times.

You can also follow me on Facebook or Instagram at @kassarconsulting where I share regular live broadcasts, Q & A sessions and content on effective hiring best practices.

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

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