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How to Future-Proof Your Workforce: 13 Tips from Founders and CEOs

How to Future-Proof Your Workforce: 13 Tips from Founders and CEOs

Posted on 03/23/21 By Brittany K. King

There is no crystal ball to show us what the next year, month, or even week has in store for business. While we don’t know what tomorrow holds, there are proactive steps organizations can take to prepare for the future.

We spoke with 13 founders and CEOs who shared their insights on the best ways to future-proof the workforce with strategic learning and development, proper skills training, and support from leadership. 


Tip 1

“The job market is becoming increasingly expertise-based, rather than position-based. We're moving away from embossed door heads, to looking at what skills you have to offer. This applies to both current and virtual situations.

In retrospect, employers who maintain the position-based systems do a disservice to their employees. Not only does it tie them to the office, but it also leaves out some employee skills.

In order to cultivate a future-proof working group, we invite our own employees to participate in any new projects in the company. This allows us to use their extra skills, and to increase the mobility of employees in the workplace.

In order to have a mobile workforce, you need to facilitate skill-building within the work environment. As a company, we've often felt, and right so that continuous training and retraining our employees in some facets of their jobs provide them with necessary skills for the near future.

That's why we push employees, especially those working in marketing and tech, to engage in continuous training through [online training providers]. We also pay for the training in most cases.

Besides giving them skills to use anywhere they go; the continuous training also gives us a talent pool to draw from whenever we need some expertise.

According to Forbes, on-the-job training has been on a steady decline over the last ten years. In fact, most companies prefer to onboard new employees, rather than use the available talent pools.

Failing to develop a local talent pool is placing your own business, and your workforce by extension at the perils of rapid technological advancement.”

Alina Clark


Tip 2

“Create skills maps, which represent the skills needed to perform any role in the company. Skill mapping helps companies manage flexible networked teams as they change over time.

It also allows the company to adjust to markets and keep up with rapidly evolving technology. By using certain technology, companies can even forecast which skills will be needed for each role in the future.

Engage in continuous learning. Learning shouldn't be just a part of onboarding or one-off solutions. Continuous learning can transform an organization and help it be adaptive and resilient in the face of changes.

Ongoing training also shows employees that they are valued since the company cares about career development.”

Grant Aldrich
Online Degree


Tip 3

“As a business, it's important to focus on the process of continuous development, adaptability, and the openness to change with the technologically trending markets today.

These three factors are crucial because they encompass the assessment and evolution required as economic conditions change.

As a leader, having these core factors as a model in their business will help them encourage their employees to align with these values for an easier transition to digital changes long-term.

Tap into the potential of leadership in employees.

This is another important aspect of growth and future-proofing because employees that are presented with the opportunities to grow in their respective fields are more uplifted and willing to excel in their skills, whether that's related to business ventures or training and upskilling.”

John Li
Co-Founder & CTO
Fig Loans


Tip 4

“Future proofing your workforce requires them to always be ready for new things and have an understanding of changes coming within your industry.

One way that we ensure that our workforce is future proof is through regular training programs.

If there’s new technology that we may want to pick up, we’ll train our staff on that technology, when new security risks present themselves, we’ll train them to understand and deal with those risks.

It’s important to stay on top of the challenges which become apparent to your business. You need to teach your staff how to handle them as well as equip them with the tools they need to do this if you want to survive long-term.

The more knowledgeable your staff are of different situations, the better they’ll be able to handle them. It’ll also mean that they’ll be able to provide suggestions on sustainable changes to the business.”

Teri Shern
Conex Boxes

Tip 5

“We're certainly always conducting training to help our workforce to stay on top of the latest [trends]. However, above all else, the way to future-proof a workforce is to inculcate a mindset of constant learning, including from our peers.

A practice we've seen other companies use and that we could consider is having employees start to teach each other new skills.

Given that information gets outdated quickly in this day and age, we need people to be constantly learning and imparting their knowledge to others in the organization so that the organization can move together quickly. This may include having employees lead training sessions about a topic they know better than others, no matter their position in the company.

Another practice we may consider is giving employees the chance to have a day in another person's job. This gives employees new perspectives and encourages them to take a broader view of the business instead of their own responsibilities.

Upper management and leadership need to lead by example and not be afraid to show vulnerability. They can acknowledge that they don't know all of the answers, but that teams can work together to figure out the right approach in response to changes.

Leaders need to lead by example and not dismiss new trends or events that could spark a shift in the industry. Otherwise, employees become complacent as well and the organization can be caught unawares by rapid development.

Leaders also need to empower employees to make decisions and take the initiative to teach others about new information so that the organization can be more agile. A top-down structure in a rapidly developing situation can stifle the agility of the organization.”

Cecilia Hunt



Only 16% of business leaders believe their organization is ready to address the skills gaps they face.



Tip 6

“Future-proofing has taken front and center stage after many organizations realized just how unprepared they were for something like COVID-19.

Since the world went remote, things have changed rapidly, and only those with a strategy and plan to implement are still not only surviving, but thriving. 

There are 3 essential skills needed to be prepared for the future: resiliency, adaptability, and communication.

Providing training for your employees in these 3 areas as well as to management will be essential to make it through this time and anything else that might come our way in the future. 

Leadership also needs to have a strategy in place to implement the best practices around change. Management overall will be responsible for how a team copes with a situation and having a plan in place will ensure the best approach for each company.”

Jana Tulloch, CPHR
Tulloch Consulting


Tip 7

“Technology competence is a skill that future employees should acquire and hone, especially during and after this pandemic. With a large majority of workers at home, logging into Zoom, Microsoft Teams, and other tech platforms at the start of the day has become as normal as making a strong cup of coffee.

These tech platforms, when utilized well, can have a huge impact on managing workflow, collaboration on projects, and effectively communicating.

Not only will those who are comfortable with a range of technology communication platforms be well sought after, but so will those with sophisticated modeling and coding skills.

[DotCom Dollar] provided training that helped our employees be familiarized with the intricacies of these platforms. We are also very open about accepting comments and suggestions (especially about new techs, apps, systems, and AI) that will better aid the business and its people in the future.

Every month, we [conduct] leadership training for our editors and team leaders that will further help them in the management of remote employees.

We believe that through appropriate leadership and employees equipped with the knowledge about new techs, we will be able to secure the future of our workforce.

Bottom line: The success of the company lies in the future of the workforce.”

Allan Borch
Dotcom Dollar


Tip 8

“One way we have had future proof is by considering our security measures. Law firms are at a higher risk for security breaches and hacking so security has always been a high priority for us.

However, with the switch to remote work, securing our network has become even more important. One way we are doing this is by supplying each employee with a high-security VPN.

We also find it important to train all of our employees on cybersecurity; the more everyone is aware of the tricks the more secure our network becomes. With everyone working from home on varying networks and systems, this is a really important part of future-proofing our business. 

The other piece I find imperative for planning for an uncertain future is by prioritizing effective communication amongst the team. […] I find it more important than ever for leadership roles within the company to be available for questions and calls.

I like to check in on a regular basis with each employee individually to ensure that everyone is on the same page and that everyone is doing alright.

Providing that open and available source of communication allows everything within the business to run smoother.”

Andrew Winters
Cohen & Winters


Tip 9

“Future-proofing your business is all about creating an adaptable structure. As many of us learned during COVID, the adaptability of your staff is critical in times of uncertainty and rapid change.

Some companies had to offset falling revenue by laying off staff, others had to shift staff from one set of priorities to another, while others were scrambling to hire new employees to meet growing demand.

Organizations that have a clear set of objectives and a staffing plan with defined roles aligned against those objectives are ready for whatever the future holds. As conditions shift, objectives change, and the staffing plan adapts to meet the future challenges and opportunities.

In the past year, these organizations could clearly identify the roles that should be furloughed, the tasks that could be put on hold while others were prioritized, and which seats they needed to fill.

Getting to that level of adaptability requires an investment from the executive team to create a staffing plan that’s based not only on the people - people are important - but equally on the jobs that need to be done, and how they should get done (SOPs or standard operating procedures).

Organizations must define their objectives, identify the jobs that need to be done in order to meet those objectives, and document how the work will get done.

These foundational pieces will not only help the business as it faces changes in the future, but it will also help with hiring, assigning priorities, and tracking progress across the organization.”

Rachel Honoway
Vice President
We Are Working



67% percent of surveyed workers are willing to retrain for a new job in any situation.



Tip 10

“Upper management and leadership personnel need to guide employees through expected and unexpected changes via:

  • Promotion of the digital native mindset

This means that managers need to know at what level of digital prowess and knowledge their team members have by thoroughly assessing their current skillset and digital capabilities.

  • Provision of reskilling or upskilling opportunities

[This helps] bridge the gap between each employee's current capabilities and make all employees "digitally-in-the-know". This means providing specific trainings designed to develop more digital natives in the organization

  • Promotion of an open and collaborative environment within the company.

Opening up the lines of communication through collaborative software like Slack, group chat, and closed Facebook group promotes creativity and an abundance of constructive feedback.”

Tehsin Bhayani
CEO & Founder


Tip 11

“The business industry is a volatile field; the future is uncertain which can be scary for both employers and employees.

It is the employer's obligation, however, to help their workforce prepare for the future. Achieving this goes beyond financially investing in employees — it's crucial for businesses to prioritize their employees so their employees can properly take care of the clients.

Skills training and development is the most optimal way of increasing the business's value through improving the workforce's skills. The world has been technologically driven and more innovations that can elevate business processes will not stop popping up.

For this reason alone, employers must make a move on equipping their employees with adequate knowledge to increase their competence and dexterity.

This preserves the role they play in contributing to the growth of the business as it will increase their satisfaction, leading to higher employee retention. Re-training and re-skilling also ensure that the business remains afloat in a sea of a highly competitive market.

All training should emphasize the shaping of each employee's leadership skills — when a company aims to develop future leaders, the whole business's standards and merit ultimately becomes elevated.”

Solomon Thimothy


Tip 12

“Future-proofing has transcended beyond functional support provided to employees, to a point where our organization needs to be holistic in our approach to people care. When the pandemic lockdowns first-occurred, the most immediate impact was our 1-day a week remote policy shifted to 5-days a week.

As a department head, my primary concern was burnout and productivity: two aspects that go hand in hand.

The implementation of daily stand-ups was critical with a difference: most of the meetings allowed my team to share their mood & morale, rather than tasks. I trusted them to get the work done and use these stand-ups for an emotional well-being check-in as well as helping remove blockers from their success.

This daily stand-up experiment has worked so well we are continuing to use it to this day and rolling it out to the other departments as a 'future-proofing' measure — it's critical to keeping our team of distributed employees engaged and motivated.

[We] are implementing more frequent performance review check-ins with the goal of career development. COVID-19's big impact on the tech industry was getting organizations comfortable with the idea of hiring the best talent from anywhere, regardless of location. This has put our organization on high alert to ensuring we can retain talent by helping them achieve their personal and professional goals.

Beyond that, we continue to formalize our knowledge sharing endeavors between different functional teams, tentatively named Rootstrap University, to keep abreast of the latest in emerging technologies. Not only does this help our organization 'future-proof' itself with latest in solutions that we can provide to our clients, it helps employees build skill-sets in highly-demanded fields.

Finally, we are creating more flexibility in our real-estate footprint to alleviate future fixed costs. While we still maintain offices across three countries, the real estate footprint is substantially smaller as we move towards flexible, month-to-month arrangements with co-working spaces for temporary office needs — all the while extending our remote work policy for the foreseeable future.”

Patrick Ward


Tip 13

“In my mind, 'future-proofing' is synonymous with improving your team’s agility. Even the best predictive minds can’t be certain what changes the future will bring, so to be future-proof you need a team that’s prepared for anything and adapts well to change.

With that in mind, here are the 2 main skills a workforce needs to become more adaptable:

  1. Data analysis.

One side-effect of an increasingly digital world is an explosion of available data. The sheer volume of available information can make it difficult to even identify the potentially useful data from the rest.

A workforce that is able to do this, and to analyze that data effectively, will be better able to understand and respond to changes in the industry.

2. Continuous learning.

You can train your workforce to have the skills you know they need, but times of quick change often bring the need for new skills before you have time as a company to institute training programs.

This makes it critical that key members of your workforce are in a constant state of learning and growth, identifying and acquiring new skills as they work rather than waiting for the company’s leadership to teach them.

[Upper management needs to] provide as many cross-training, up-skilling, and professional development options as you realistically can, and encourage your workforce to take advantage of them.

It's impossible to know which skills will become important in the future. Having a multitude of different skills and knowledge at your disposal is the best way to stay agile and adaptable in a quickly changing landscape.

Establish a learning-oriented culture that encourages the team to keep acquiring new skills at every stage of their career. Leadership can also help this by 'walking the walk' and continuing to expand their skill set, as well (which will in turn help to future-proof management and leadership, too)."

Darrell Rosenstein
The Rosenstein Group



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