The Three Signs It’s Time for Your Company to Change

Abby Kearns
4 min readDec 12, 2018


I’ve thought extensively about what it means for non-technical companies to embrace a cloud native mentality and start to acclimate their work culture to these shifts in technology.

But what about before this process even begins? What are the indicators it’s time to seek out new strategies and work models? How do you know when your business needs to make the great leap forward into the cloud?

Reading the T(echnology) leaves

It can be easier to ask these questions than it is to answer them — and it may be easier to recognize the signs that indicate the need for change than to actually embrace them. Sometimes the signs are quite obvious — decreased sales, antiquated applications, recurring mistakes due to miscommunication — but sometimes the signs are incredibly subtle.

To state the obvious, change is hard. It can be easy to ignore the need for change until you absolutely have to. But no business hoping to thrive in our new reality can afford to ignore the new reality — technology is a driving factor in every business across every industry.

While there’s no exact formula, here are the three leading indicators it’s time to start building a comprehensive digital transformation (or digitization) strategy:

  • Your tech teams don’t feel they are adequately equipped to keep up with the (quickly evolving) technology landscape;
  • Your product and development teams aren’t tightly connected with customers (or their feedback);
  • Your organization invested in new cloud native technology solutions, but is struggling to get the efficiency gains you were expecting out of them.

Noticing these symptoms at your company is a good indication it’s time to seek out and embrace change. Yes, it’s going to be hard. But ultimately, it will be worth the effort. I swear.

Preparing for change

Now you’ve recognized the signs and started to put together your strategy for transformation. What can you do to prepare your organization for the process? It may seem like your focus will be on implementing new technology, but I believe the real crux of change for any organization is the culture.

In research we conducted at the Cloud Foundry Foundation in February 2016, nearly 40 percent of respondents reported the technology was a bigger obstacle for their company’s efforts to improve its application development productivity, and just 25 percent cited culture as the bigger obstacle.

In 2018, we saw that number flip. Now, 44 percent believe the bigger problem for their company is the need for culture change, compared to only 33 percent who say selecting and integrating the right tools and technologies is the obstacle.

These findings — which you can read in our new report “The Technology Speaks for Itself: What’s Driving Companies to the Cloud” — suggest that a commitment to culture change across the organization is necessary to maximizing the business opportunity of newly adopted technologies.

Committing to culture change

As parts of your organization get more familiar with working in new cross-functional teams and with new technologies, you need to make sure you prioritize shifting the culture across your entire organization. The most common areas that require focus and investment are:

1) Establishing programs that focus on reskilling/retraining your current employees, like Certification and Training programs.

2) Mapping how communication flows to and within your company. This includes employees across different departments and teams, as well as customers trying to communicate with you.

But how do you get people to collaborate and build communications patterns that have never before existed within your business?

You have to motivate people. A quote that really resonated with me comes from a book by Kelly Palmer and David Blake, The Expertise Economy:

“What today’s employees want is the ability to have an impact in their work, the flexibility of when and where to do their work, to see their work connected to a bigger purpose, and to have the opportunity to learn and grow in their careers.”

The last part of this quote especially hits home for me — the opportunity to learn and grow. For companies undergoing digital transformation, there is a huge opportunity to provide your employees with a path for growth by learning new skills, technologies, and ways of communicating. All of which in turn provides your organization with a new way of working, and offers you the opportunity to take your company into the future with the employees you have today.

Empowering your current employees to learn and grow alongside you is an investment that will pay off in dividends in the long run. Longtime employees with historic knowledge of your business will make your digital transformation journey swifter and smoother.

Continuous learning

Similarly, you’ll need to make sure your business prioritizes continuous learning. Meaning: employees will be primed to train or retrain on new systems or methods. Developing a program that allows people to continually uplevel skills helps people embrace change, and sets up a virtuous cycle for the future. Digital transformation is a journey, not a destination.

You’re investing in your teams who in turn bring those new skills to bear in the workplace, so they’re investing in both themselves and in your business. Your business continues to grow, and you continue to invest in your employees, and they continue to invest their skills back into your business, and so on. This cycle encourages growth across the board.

Companies who are on the path to digitization must face the (even harder) challenge of cultural change. What’s important is to recognize the indicators that it’s time to embrace change so you can embrace the future.



Abby Kearns

Technology Executive | Board Director | Angel Investor