4 types of employees you'll need to manage carefully during digital transformation

July 10, 2019 Becki Hyde

By Becki Hyde and Sean Olszewski

You’re nine months into having transformed a small part of your organization, and you’re beginning to see the benefits of your investment. Teams are making decisions–and acting on them–faster than they have in the past. As a result, your products are being delivered to users faster, and employee morale is on the rise. Operational costs are decreasing as a result of having adopted a cloud platform, and legacy systems are being sunset at a cadence that far outpaces your initial projections.

Sitting back in your chair with your morning coffee in hand, you’re beginning to believe that your company is going to transform, even if it takes the better part of a decade. As you bask in the wondrous potential of the operation, a key employee walks into your office and announces their resignation, effective two weeks from today.

A situation like this will certainly come as a surprise, and is never ideal. Yet it is inevitable when introducing change into an organization. 

Change breeds concern

Once change gets into full swing, it’s typical to see some employees begin to question their roles in the company, or whether they want to remain at the company at all. Things are changing fast—technologies, processes, expectations—and that can make for a difficult adjustment. It’s unavoidable, but not entirely negative. Think about it as an opportunity to reassess roles and put people in the right places, and to part amicably with folks who do not want to be part of the journey.

However, understanding why your employees feel the way they do is crucial–not just so you can keep great people, but so you can understand if you’re transforming into the organization you aspire to be. 

We spend our days helping organizations navigate change, and manage challenging growing pains. In our work, we’ve observed four common types of employees who are at risk of becoming alienated or otherwise unhappy inside transforming organizations. Here are some of the traits to look out for, and some advice for keeping those people not just around, but also happy.

Frustrated Converts

The Frustrated Convert gets exposure to a new way of working, and is then forced to go back to the old way–to what is often perceived as cumbersome process, wasted time, dead ends, and a lack of autonomy. 

There are two primary reasons someone becomes a Frustrated Convert. Perhaps they were assigned to try something new, then after some time, told to go back to the old way. Alternatively, they are still working in the new way, but they face roadblocks and detractors who undermine the process. Perhaps their direct manager has bought in to agile, but someone else up the chain–or in another team–has not, and those people are acting as blockers.

These blockers often occur due to senior leadership being bought into an effort, but failing to cascade the intent and importance of this to middle-management. Because of this breakdown in communication, middle-management doesn’t allow individual contributors the flexibility they need to deliver effectively, creating frustration and ultimately causing them to leave. This lack of control frustrates employees and leads to them leaving for a role where they can work more like the new way they experienced.

How to help

A key challenge of modernizing your software delivery process is ensuring those who undergo and facilitate the change can continue to work in the new way, and have support in dealing with teams and leaders who are not yet convinced of the value of the changes being implemented. To prevent turnover of otherwise engaged and excited employees, work toward support for the change at all levels of your organization, and provide air cover until that is achieved. 

This need not happen all at once. Having one or two key allies at the manager, director, and vice president levels goes a long way toward preventing Converts from ever becoming Frustrated. These leaders can support, advise, and unblock individual practitioners who are running into challenges from traditional process. By knowing they have direct leadership support, employees will be able to weather the challenges of introducing change for much longer than if they feel they are doing it alone.

High achievers

High Achievers are employees who thrive in an agile environment, becoming so effective at what they do that they begin to be courted by other companies, or seek promotion opportunities elsewhere. If they do move on, it’s often because they are not being utilized or compensated appropriately. People who know how to deliver modern, user-centered, cloud-native software on interdisciplinary teams are highly valuable talent.

High Achievers, having been trained in practices like extreme programming, lean product management, and user-centered design, have a strong desire to apply these skills and be challenged and rewarded for being able to apply them effectively. If the High Achiever finds their compensation is low relative to the market, or if their work environment is not supportive or trusting of their capabilities, they’ll be easily recruited away. Time and time again, we see this issue come up as companies undergo change, and the strongest way to combat it is to have a strong, protected culture of learning, with a fair and competitive compensation structure.

How to help

Supporting High Achievers isn’t just about salary and benefits. The most engaged and motivated participants in change can become disengaged if they aren’t given opportunities that align to their interests and professional development–and have a measurable impact on the business. After seeing success on their teams, some employees naturally want to spread the principles and practices they’ve become so passionate about. This gives them an opportunity to grow professionally, and to have a larger positive influence on company culture. 

If these High Achievers–highly-engaged, high-performing employees–are not given opportunities to grow professionally and have more influence, they will seek those opportunities elsewhere. Managers should identify these employees early, and stay engaged with them, so that they aren’t overlooked on the assumption that because they’re doing well, they are satisfied. Consider internal career paths, seeding new teams, and mentorship or teaching opportunities.

Ultimately, you won’t be able to prevent some High Achievers from leaving. Celebrate their achievements with the team, and welcome them into your alumni network. They may come back in the future, and as they move on and extend their network, they can be advocates for the organization, potentially sending others like them your way. 


When people are asked–or told–to change the way they work, some will self-select out. This is especially likely in companies where employees stay in roles long-term, and develop well-understood processes over years of experience. 

An Opt-Out may see their management invested in a new–and sometimes radically different–way of working and don’t want to be a part of it. They don’t like or aren’t convinced of how effective this new way of working will be. It’s not uncommon for people to have seen many attempts at changing their enterprise, and this can create cynicism. If they believe that the new way of working will never be sustainable in their company’s environment, then rather than seeing this new way of working pan out, they leave.

How to help

It’s okay and in fact natural to have a number of Opt-Outs. A harsh reality is that if someone doesn’t want to be part of a change, they won’t be an effective contributor. The trick is figuring out the course of their opting out—some might prefer to leave the company entirely, while you might be able to find valuable roles in other parts of the organization for those who wish to stay. 

As you introduce change, think ahead to how you can support these potential Opt-outs. Perhaps they can be effective advisors in their area of expertise, or perhaps there are other teams in the company that could benefit from their experience and knowledge. Regardless, if you don’t consider these employees’ concerns and manage their transitions, they can poison others who are interested–but nervous about–the change. 

Some employees who seem like Opt-Outs might just need more time. Don’t assume that someone’s first reaction to change will be their continued reaction. Reach out and revisit individuals who have seemed resistant in the past, and keep them engaged in understanding the change for as long as possible. 


Some of your best team members will get promoted–perhaps onto a different team, or into a new business unit. On the surface, this is good news; it speaks highly of both those team members and the team as a whole. However, if people leave early, or several leave in quick succession, the team leading the change may struggle to maintain maturity and momentum in their absence. 

Too many graduates, too soon, can stall out your efforts. Those moving into new roles become focused on their new team, and the team they’ve left lacks leadership. What’s worse, it’s possible that the Graduate has joined a team where they lack social or political capital to influence change, essentially putting them back to square one. 

How to help

Because it is important to keep teams intact until there are people ready to backfill leadership roles, start succession-planning early—even down to the individual team level. While you can encourage people to stay in place for a period of time by providing them with interesting work and fair compensation, prepare for the future early ensures your efforts won’t stall out. When you are ready for people to move on, consider planning for Graduates to seed new teams in pairs or small groups, so that they can support one another and have greater influence on others. 

For teams with a deep bench, Graduates can be advantageous. Internal promotions should be something to celebrate! If the team is healthy and has people ready to step into new roles, then the core team continues to thrive, and now has an ally on another team. This shows that your organization is welcoming change and adaptation, and by seeding leaders in other teams, you can accelerate more easily than you can by changing minds from the outside. 

You’re on the right track

While higher turnover feels alarming, it can be a good sign. It’s evidence that you’re effecting change. Instead of feeling powerless, proactively preparing for and guiding changes in staffing can keep your transformation on track. When staff do leave, strive to understand the motivations of the people who are leaving through genuine exit interviews. 

While you may not prevent people from leaving–or even want to–you can learn valuable lessons from the reasons they leave, which you can then leverage into actionable insights that help you on your journey.

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