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What Every Founder Needs to Know About Reskilling

Prashant Srivastava July 23, 2019

This article originally appeared in Forbes. View it here.

Entrepreneurs are typically the visionaries for a company, and they carefully hire a few key people to stand alongside them as they let that vision grow. As that visionary, you have an opportunity to get ahead of a massive talent challenge that even the most experienced entrepreneurs have difficulty grappling with: recognizing when to establish new skill sets for both themselves and their team members.

For the traditionalists, this is known as retraining. But you’ll also hear upskilling, new-skilling and my preferred term, reskilling. As a founder myself, I believe starting your business with a plan to reskill workers at each stage of the company will not only keep your organization competitive, but it will also make your company a destination to work—especially for those seeking career growth.

Furthermore, there’s the red-hot job market that shows no immediate sign of slowing. Second, and more importantly, I’ve observed some required skill sets are changing so quickly with the evolution of service capabilities, such as cloud computing and AI as a service (AIaaS) that your skill needs will rapidly evolve as you scale.

So why not develop an ongoing strategy from day one to predict future skill needs and to reskill your existing employees accordingly?

Develop a plan for success

Think about what your organization will look like three to five years down the road. Then, start filling in the roles you see in a strategic way. For example, when hiring a person to lead your finance team, define the role that is needed now, and correctly identify it on the organization chart. In this case, you might hire a director of finance who knows there is room to grow into a vice president or C-level position (or at least, that as the organization grows, there will be others above him or her).

This approach not only ensures you set the right expectations for your hires, but also that your employees have the opportunity to aspire to bigger responsibilities. Moreover, they’ll be prepared for others to enter the organization between you and them, which is important in the early stages of a company.

Find mentors who can help you learn about learning

Whether it’s someone you hire, someone you know or someone you want to add to your advisory committee, find a mentor who has successfully scaled a business before and can advise you on creating a reskilling philosophy for your own company. (This goes along with creating a learning culture for yourself, as a founder, in order to create one for others.) In addition to mentors, talk to your employees, as they might have valuable insights into what will best shape this philosophy as well.

Constantly reinforce a learning culture

Encouraging continuous learning throughout your organization provides a support system for all the types of skills your employees need to excel. If your team is encouraged to develop skills that will help build their careers, their perception of skill gaps might help you spot new opportunities for the business. Also, keep in mind that building a continuous learning culture isn’t always a sizable investment. Depending on your industry and corporate environment, it might be as simple as allowing your employees to direct their own training and to possibly teach others.

Encourage specialization

In the beginning, you start out with people who can wear multiple hats. But as the organization grows, you will need individuals who are more specialized in narrower roles. You can empower generalists to identify where they can contribute (i.e., what they are really good at and passionate about), and then bring in specialists to fill other gaps where necessary.

Expect hard conversations

Founders learn to depend on that first group of employees to get their company off the ground. Unavoidably, the reskilling discussion involves changing the roles of people who were with you at the start, both in the highest and lowest ranks of your organization. But creating a reskilling culture early can develop a more flexible workforce that’s open to change and learning.

As the business grows, there may be people who were part of the original team who struggle to make the transition. An open dialogue about the organizational needs in the future and a reskilling culture will help these conversations. Nonetheless, they are still difficult given the closeness and personal relationships that are born in the initial foundation of the company. Knowing these transitions are inevitable helps you and the team prepare to have them at the right times. In the best case, methodical planning will give each individual ample time to learn, grow and succeed.

So how’s your culture? Are you building a company where employees know what the next stage asks of them? Are they actively engaged in a dialogue about reskilling? Do you know when to start looking for talent for that next level?

Now it’s time to get to work discovering what you need now and what you will need in the future. It can define your success.