People walking through a doorway into a digital world, signifying digital transformation

5-second summary
  • Research shows that culture is a key indicator of success during a digital transformation.
  • Employee attrition, burnout, or a lack of progress towards your goals could signal that silos are preventing teams from working together efficiently.
  • Getting buy-in at every level of the organization is key, otherwise teams will be constantly sidetracked with other priorities.
  • Listen to the concerns of people who might be resistant. Involving them throughout the process may convert them into champions.
  • The best technology in the world won’t achieve maximum ROI if the people using it aren’t bought in. Proof: A Boston Consulting Group study of 40 digital transformations showed that companies that focused on culture instead of just implementing new technology were five times more likely to achieve breakthrough performance than companies that didn’t.

    “I think the organizations that just assume people will fall in line are missing the opportunity to get their staff to become advocates for the change,” says Ken France, VP of scaled agility at consulting firm Cprime. “That’s why, from the very beginning of [a digital transformation], we identify who our key champions are across the business because they are ultimately going to take ownership of the evolution going forward.”

    That early buy-in has another substantial benefit as well. It can feed into a cycle that creates lasting, positive changes that empower a growth mindset within the organization.  “Culture is an output of a transformation because you’re showing people a new way to be successful,” says  Mark Schwartz, an enterprise strategist at AWS who meets with hundreds of executives a year to advise them on their transformations.

    Unblurring the lines of a digital transformation

    Whether you’re moving to the cloud or adopting new collaboration technology, it’s clear that putting people first is an essential ingredient for success. Employee attrition, burnout, or a lack of progress towards your transformation goals could all be signs that it’s time to zoom in on how your teams are working together. 

    Through conversations with five tech leaders – all with deep expertise in overseeing successful transformations – we identified four themes for handling the human side of your company’s digitization.

    1. Have a common vision and communicate it to your employees

    Change is hard, but it’s even harder when it’s not clear why change is happening. Before you take any action, spell out what you think the business can gain by transforming, then connect that vision to every person, team, and department in the organization. “I find in a lot of cases that [companies] are stuck in their traditional ways of thinking that are too tactical,” says France. “They don’t have a vision [for the transformation] that is tied to the business outcomes they’re trying to achieve.”

    While a transformation can start from anywhere in the business, it’s important to make sure that the C-suite is bought in and champions it. “Employees need to see clearly where they’re headed and in order to get there, I find leadership needs to keep reinforcing consistent messages,” says Schwartz.

    Once you have executive buy-in, make sure their messages reach every level of the business. “The most successful customers we work with bring their employees along with the changes they are making so that everyone becomes a passionate, engaged, and open-minded part of the transformation,” believes Samit Mehta, a digital transformation consultant for 321 Gang.

    Dan Radigan, a Technical Account Manager at Atlassian agrees. “Digital transformation is really about culture and empowering the right people at the right levels of the organization to make consistent, effective and evolving decisions.”

    Employees who are bought into the vision for a transformation become champions for change. To successfully communicate your vision for a digital transformation, try these plays from Atlassian’s Team Playbook.


    How to kick off the change management process – Lead your team through the change management process, from “change approved” to “change completed!”


    How to create a stakeholder communications plan – Spell out how you’ll provide stakeholders with the right information at the right time and via the right channels.


    Team health monitors for building high-performing teams – The Health Monitor is your team’s chance to take an honest look in the mirror. You’ll assess your team against the eight attributes most commonly found among healthy teams. At the end of the Health Monitor session, you’ll identify strengths to exploit as well as challenge areas to grow.

    2. Connect performance metrics to the big picture

    To build greater buy-in for your transformation, connect it to individual performance metrics that determine raises, bonuses, and stock options. “I often suggest getting human resources involved early and often so that they can change how people are measured and compensated to align with the vision for the company’s transformation,” says Bryan Smith, scaled Agile framework lead at 321 Gang. “Because often, individuals are measured by metrics that don’t apply to the new ways of working that a digital transformation requires,” such as the delivery of a finished product instead of an improved customer CSAT score or increased speed to market.

    When you connect individual performance to your transformation, it can result in a groundswell of transformations across the business. “When you’re an individual contributing to company transformation, you can actually implement hands-on change,” says Schwartz. “In many cases, you can implement change without asking permission because you’re often reducing risk and producing good outcomes. For example, if one of my goals as CIO was to automate everything and an engineer came to me and said ‘By the way, I’ve automated everything,’ I would be thrilled that they took the initiative.”

    How to fail-proof your digital transformation

    But don’t just focus on individual performance metrics; measure your executives, too! When your executives and board are bought in on the transformation and understand how it connects to business performance, they’ll be more likely to invest in it. “Create success metrics that speak to the language of money for leadership so that they can quantify the returns on their investments for the digital transformation,” says Smith.

    Schwartz agrees. “I’ll be working with a customer and there will be complaints that things are moving too slowly, and when you look at it, you can see there’s very little urgency in the transformation because it’s not connected to what the CEO or the board cares about,” he says.

    3. Empower managers

    Let’s face it – managers are the reasons why people stay at or leave a company. So, empower middle management to lead your transformation. 

    “Many customers tell me ‘We’re undergoing a big transformation on the ground and have technologists who are learning all kinds of new things but middle management is somehow getting in the way,’” says Schwartz. “But I almost always find that is not their problem.”

    Instead, managers’ roles need to be redefined so that they’re given the autonomy to decide how their teams should work. Schwartz shares an example. “A QA-team lead I used to manage originally thought our approach to transforming QA was insane because I wanted to take a DevOps approach, where teams would constantly be deploying new stuff. He was worried that the quality would be terrible [so that] was getting in the way of our transformation. But then we redefined his job to make sure everything was produced at a high level of quality throughout the development process instead of at the end. Once we did that, he was so engaged that he was coming up with incredible ideas and solutions that I never could have thought up myself!”

    Because a transformation often requires shifts to team structure and how teams work, managers can be crucial in leading change management with their teams. “In a transformation it’s easy to say ‘I just need to send my developers to agile class.’ But if we leave managers behind, we’re handicapping our organization in some really critical ways,” says Radigan.

    “A role like a developer-manager is somebody who’s out recruiting, hiring, and building growth plans for their engineers,” he adds. “They’re working with various teams to set coding standards and make sure that the technical health of the projects across different Agile teams is remaining [healthy].”

    4. Lead with empathy

    Finally, remember that your employees are human and that a change in how they’re working may not be the only change they’re experiencing in their lives. “It’s easy to talk about work deliverables and performance metrics,” says Radigan, “but we’ve collectively experienced 18+ months of hard, and hard looks different for different people in different ways.” Put in the effort to meet people where they are at. Everyone is going to have their ups and downs – especially in this season. Be agile to help your teams be the best that they can be.

    Lead with empathy. Show compassion. Always remember that any successful digital transformation starts with – and is powered by – people.


    As your team adapts to remote work, use the Work Life Impact workshop to build empathy and identify the right support.

    Learn more about how to achieve digital transformation at the enterprise level.

    Why a successful digital transformation is more about people than tech