The Workforce Therapy Files Podcast Show Notes – Workforce Development and the Skills Gap

March 26, 2025 workforce podcast show notes

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File 22: In today’s file, the team welcomes Amy Rudy, the Founder of Impact Sales Systems, to discuss the challenge of staying relevant in your industry or field and growing your knowledge, skills and abilities. It’s also going to require a level of resilience to remain agile in the future of work.

In case you missed them, the previous 2 episodes focused on The Future of Work.
The Future of Work (Part 1)
The Future of Work (Part 2)

Meet Amy Rudy

Amy is a sales and sales management coach. She works with business owners and sales teams on the behaviors behind selling. She often works with solely-owned and closely-owned businesses. Prior to launching Impact Sales Solutions, Amy founded a software development firm that built custom solutions for specialized challenges facing both small businesses and Fortune 500 companies.

The Gap Left when a Founder Leaves the Organization

Amy explains that a successful business will often outgrow the skill set that enabled it to launch and grow, in the early days. This is especially true of a business that had a sole owner/founder. It works for a while, but because so much of what makes the organization unique is tied to the knowledge, skills and relationships of that individual, it may be difficult to export that talent to a larger team.

As the team attempts to take shape, the initial inertia can slow and leave the team wondering how it can regain the momentum and direction.

Managing the Transition

It may be a case of the leader wanting to retire or exit in 15 years, or so. However, when Amy is approached with the idea of accelerating that exit to 18 months or less, it’s virtually impossible. Now the exit can definitely take place, but it’s a question of how stable the company was built to withstand the event.

It’s a matter of being strategic with the decision. If new leaders are beginning to surface and take on some of the responsibilities, they may be willing to do even more. There’s already a sense of forward motion occurring. The reality is often smaller companies are managed and controlled (along with the decision-making). This environment may work well for the leader, but the rest of the organization is underprepared to move beyond that individual; even to survive after the exit. Is the organization ready to operate with a business-mindset, rather than as a personal checkbook?

Amy recommends planning for succession much earlier that people often assume is necessary.

The Importance of Creating Succession Plans

Jason asks about how this is initiated and developed. Amy comments that it’s a question of whether the organization needs “more of same” or needs to pivot. If the company needs more of the same approach, then documenting work processes and operations would make sense.

Amy prefers to begin by asking the client(s) to describe their future. What does FutureCo look like? How much revenue will it produce? How much volume will be required to generate that revenue? Is it truly more of same or is it different? Will it need to move faster? Will the problems be more complex?

She also challenges the client(s) to consider the required capabilities. Describe the necessary skills to operate at those levels and in those areas. How much cash will FutureCo require to operate at those levels? It’s a matter of really attempting to define what the intended future will look like.

Once you have that vision defined, Amy notes that the business needs to measure where they are today, using the same metrics, for CurrentCo. When accurately performed, a true gap-analysis provides valuable insights. Leaders should then involve the people around them to figure out what needs to be done differently to become FutureCo, as envisioned.

One of the underlying challenges becomes reality when the new leader steps into the role, but the insight and resulting roadmap doesn’t exist, because it walked out the door inside the previous leader’s head. This can echo throughout company leadership as people begin to protect what they know. There’s no real knowledge transfer and the organization becomes stuck, or worse yet, begins to regress.

It may not be a question of who the organization replaces “Steve” with another Steve (e.g. more of same). Maybe Steve hit his performance ceiling. It’s it possible that moving forward will require a different kind of leader who can take what Steve began and effectively navigate into the future?

Jason and Amy discuss the view that, “It worked, so why change it?” Assessing whether it’s still working and will it work in the future are importantly different questions. While this is a difficult conversation to have, Amy observes that there are people at the table who want to be part of the conversation, but unfortunately are not always given the opportunity to contribute their ideas, perspectives and innovation to the situation.

Having a level of transparency among all leadership roles should mean that everyone can contribute. Unfortunately, people become accustomed to waiting to be told what to do next, rather than helping to define what actually needs to be done next.

However, if a business owner can adopt that mindset and begin encouraging those additional points of views, true progress can be made toward actively planning and preparing for FutureCo.

Planning Remains Important

Amy reinforces the need to have solid roles and responsibilities enabling people to communicate what and how they’re going to proceed, while enabling the organization to measure that progress is important. It’s about accountability and results. This is especially true in sales. Enable to individuals to own the role and own the goal.

Are there Trends in the Skills Gaps?

Jason asks Amy if there seem to be a set of trends she notices in the workforce? Technology is advancing incredibly quickly. Technical skills involving office tools, such as spreadsheets, could enable people to analyze large data sets on their own. There seems to be a gap in this area.

Additionally, Amy recognizes gaps are apparent in:

• Negotiating
• Forecasting & Planning
• Accounting
• Account-level Planning
• Questioning
• Navigating the Way Forward

Are your sales people neglecting the sales tools and simply waiting for leads to be generated for them? Are they consistently initiating contacts and cultivating referral-relationships? Even an excellent marketing machine will only generate a certain percentage of leads. The individual network a professional can cultivate could generally exceed that. Is it being developed, effectively and consistently?

Amy points out that while marketing can plant seeds in the minds of a target audience, sales has to be there exploring those opportunities with those prospective clients. That requires an understanding of the prospect’s business, as well as their own. This is a definite skills gap.

Is This the Greatest Gaps Amy Sees in Her Client Base?

Amy begins by confirming it’s fixable. Understanding how a business makes money and where the problems typically exist is vital. It’ll help to identify the problem you solve and how that impacts the prospect’s P&L.

One of the issues is that business owners may not be focused on developing that talent within their respective staffs. Do those sales professionals know how to think like a business owner? Does the business owner share their own P&L to provide insights and to demonstrate the relationships between the line items? Is the business owner training them to make decisions like a business owner?

How to Improve the Job Description and/or Interview Process to Identify those Gaps

Having worked with Molley and Jamie, Amy is confident business owners may not know the skills they need or what will need to be different to move them toward FutureCo. Often the descriptions are copied from previous versions.

Amy leads clients through an assessment of the specific skill sets the company needs. The list could be extensive. It’s critical to understand the skills and why they’re important to the specific role in question. Does the candidate have the proper mindset to sell into a C-Suite verses a different client base? This may be a key, differentiating factor.

Can Companies Define What Success Looks Like for Their New Hires?

Jamie asks this question based on the premise that it’s easier to identify the skills that are needed rather than what those skills are meant to deliver. Amy recommends including interview questions focused on how the candidate can demonstrate their skills to a prospective employer.

Amy goes on to explain that if the leader’s goals for the organization are overly general, or vague, they haven’t broken down what it would actually take to be successful in that role. An overreliance on the dashboard may mask specific behaviors that ultimately result in the metrics that show up on the dashboard. For instance, how does a sales professional plan his/her weekly activities, how they conduct their conversations, do they sound like a traditional sales rep or more like an advisor who is equipped with insights and knowledge to help the prospective client?

Jason comments on the talent and skills an effective sales professional brings to the role. He admits that he’s challenged during interviews with prospective sales candidates, because he leads them too much with his questioning. Many business owners and managers often get sold during the interview, only to discover that individual isn’t exactly what they thought, before hiring them.

The other challenge, Jason observes, is that the owner or manager fails to manage their new sales hire through the gaps.

Advice to Prepare to Interview Someone for a Sales Role

Amy leads with an admonition to stop validating yourself and force them to validate themselves. You should be transparent, but you still need to test for fit instead of focusing on selling the candidate on the job opportunity.

The hiring process should result in a mutual selection. Again, be transparent about the current situation within the company and its market environment. Is your organization anticipating a period of significant changes? Is your market leadership making you a target for your competitors? Define the necessary skills for the company to be successful and then provide the candidate an opportunity to demonstrate those specific skills and aptitudes.

It’s not inappropriate to ask them to bring examples of how they’d plan their week. This is especially important for remote work.

Undertraining, even a seasoned sales professional, is a key reason they may be looking for a new opportunity. Simply dumping that individual into a situation and requiring them to figure it out (e.g. sink or swim) is a recipe for failure. As the team discussed in File 8, there’s a value to a well-designed and executed on-boarding program.

Jason points out that often the person hiring for the role may not have direct experience having been in that role, so they don’t know what they should ask and how to respond to the answers provided.

Amy describes her surprise with how long it takes for an owner to begin discussing the earnings potential, during the interview. A typical sales professional is going to key in on that aspect of the discussion. At the same time, has the leader developed a solid understanding relationship between the compensation and the cost of the product or service. This topic should be covered very early in the engagement.

What Do the Skill Sets of Successful Sale Professionals Look Like in the Future?

Molley asks what should be expected as we continue to look forward. It’s imperative that sales professionals have and continue to develop strategic mindset activities. The sales team should evolve into an advisory resource for company leadership. The resulting collaborative approach can help to identify deficits in features/capabilities. It can also provide insights into the profitability of what’s actually being sold. A trusted feedback loop will also provide information on how the competition is adjusting to your offering.

In reality, Amy often observes the skills gap may actually be in the leadership seats. It goes back to whether the owner or leader knows how to build a cohesive team who know how to properly define where the organization needs to go, how it’s going to get there and the resource required for the journey.

Relying too much on the automation, to the detriment of actually knowing what the detailed activities truly are, is a challenge for some leaders. Automation is a tool; not an answer.

The pace of change is accelerating. Focus your leadership team on finding ways to look further down the road that your competition my currently be doing. Challenge them to develop the most effective plan to get there and hold people accountable for the results.

Would You Like to Contact Amy Rudy?

Website: impactsalessystems.com
Phone: (502) 589-2139

That’s where we’ll leave the conversation for today.  Before we close the file, we invite you to reach out to us with questions, suggestions or other comments. We’d love to hear from you.

Did You Enjoy Today’s Conversation?

Visit WorkforceTherapyFiles.com to listen to additional WTF files or to let us know you’d like to be a guest on an upcoming file.

Need Help Supporting Your Company’s Recruiting and Staffing Goals?

We’re here to help.  You can contact us via our individual websites, depending on your specific needs or questions:

• Jamie Swaim, SPHR – www.ParcelKnows.com
• Molley Ricketts – www.IncipioWorks.com
• Jason Heflin – www.CrowdSouth.com

We hope you found this file insightful and helpful.  Thank you for listening!