The case for transformation is different for every company and leadership team. I find that most companies know why they should transform, but fewer understand why they need to keep going even after they roll out a new feature or invest in a new technology. 

To quote the Enterprisers Project, “Digital Transformation is the integration of Digital Technology into all areas of a business, fundamentally changing how it operates and delivers value to customers.” 

I cannot underscore the latter part of that sentence enough. If you want to get the return on your investment, you have to fundamentally shift how work gets done. It’s one of the reasons why real transformation is an ongoing process – your customer needs are always changing, which means that the way you deliver value to them should constantly evolve.

So, what happens when some C-suite folks start asking, “when are we going to be done?” You encounter this question more frequently once the charm of the initial momentum has worn off, or after a few new features have been released. 

When you do hear this rumble of doubt, don’t despair. There’s a straightforward way to help the team recalibrate and recommit to the initiative. 

It starts with crafting talking points, and this two-step guide does everything short of writing them for you (believe me, it borders on a Mad Libs exercise).

First, assess what’s true:

Put your transformation progress under a microscope to examine the investment to date against whether or not the org is seeing the anticipated ROI for your transformation. This evaluation is really about pinpointing the gap between where you’re at and where you thought the company would be.

If you’re exceeding goals, that’s great! But I’ll be honest, this scenario is rare (and you probably wouldn’t be reading this post if you found yourself in this position). 

That said, if you’re one of the lucky ones, think about how much further you can push things. Did you set your goals too low, or your outcomes too “safe”? Is there something else needed to sustain or grow that ROI into the future? Is it adding people, or platform enhancements? Pushing into new markets or creating new offerings now that your foundation is strong? Something else? Don’t get complacent just because nothing is overtly wrong.

On the other hand, you may be getting further from your desired outcomes instead of closer. Don't panic. It’s actually pretty common to find a large gap between the investment and the realization of the vision, and to discover that the path you chose was bumpier than planned. 

If you find yourself in this position, consider the barriers or snags that might be limiting your successes and ability to achieve the desired outcomes, including:

• Is your leadership team aligned? Does it agree on the outcomes associated with the ROI? 

• Is everyone on the same page about what “Great” looks like? Has it been communicated to the entire team (could a mid-level manager or an individual contributor articulate outcomes and priorities)?

• Are teams working together efficiently and effectively? Is there friction between tech and business, or between sales and operations?

• Do you have the right roles staffed on teams, and the right people in those roles? Does everyone understand what product, design, and tech roles are accountable for?

• Are there cultural barriers in the way?

Next, synthesize and redefine:

Once you’ve gathered the answers to these questions, define the outcome you think the org can achieve if it doubles down on digital and operating model transformation. If you kept investing, working, trying and talking about it, what would it look like? 

Here are some questions to help steer that exercise:

• “If we had clearer strategy and priorities from the top, we could…..”

• “If we created more consistent and scalable ways for teams to work together effectively, we could….”

• “If we reduced friction and hand offs between business and tech, we could…..”

• “If we brought technology partners into the customer research work, we could….”

• “If we could get our executive team out of the day-to-day logistics of our teams we could….they could….”

This guide will help you quickly identify the struggles the org is facing, and the reasons why the C-Suite has become disillusioned. Most importantly, it will illuminate areas for further investment, focus and planning so you can get your fellow C-suite peers back on the bandwagon (and the transformation train back on the tracks).