Understanding the dynamics of business transformation: Why great directors speak truth to power

By Alex Shootman, CEO

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This article originally appeared on Forbes, where Alex Shootman is a guest author and member of the Forbes Technology Council.

One of the best questions a director can ask their boss is also one of the toughest: "Do you really want me to tell you the truth?"

Director-level is the point in the organizational chart in which C-suite visions of transformational change meet the hard reality of how it will be delivered. By virtue of being close to front-line teams, directors are likely to know better than their bosses what is possible and how decisions taken higher up the chain are likely to play out.

If directors hide the truth, they are responsible for the failure. But speaking truth to power is a hard ask of anyone; inevitably, it's accompanied by a sense of professional jeopardy. Directors put their reputations on the line when they point out that the emperor isn't wearing any clothes.

Back in the days before Workfront, I recall working as a director running services in a tech firm and having lunch one day with the newly appointed CEO, and I was asked what I'd learned in my role and what my team did.

I said that customers were actually paying us to turn stuff off in the product. We would ship the product, it would monitor the customers' environments, and then it would light up like a Christmas tree to the point where the customers started to ignore it. I said we had a value proposition that customers were asking us to switch off.

Uncomfortable conversations followed with colleagues around the business, but we started to work on reconfiguring the product. Would it have been easier to say something less honest? Varnish the truth a little? Sure, but would it have served my team, the organization and our customers if I'd held back?

In The Book of Five Rings, legendary 17th-century samurai Miyamoto Musashi wrote: "To win any battle, you must fight as if you are already dead." At the right moment, directors must put aside any fear of saying what needs to be said and speak with the candor of someone who has already been fired.

An organizational lesson

One lesson for organizations is that directors need to own the transformation message. While feeding truth back up the organizational chart, directors need to be able to translate the message to their teams in a way that shows they believe in it while retaining a vital sense of realism and acknowledging any part of the plan that doesn't quite ring true at the front line. Teams need to have trust that their director is having those tough conversations behind closed doors.

It's also vital that directors build strong peer-to-peer relationships across the organization. Directors drive seamwork: the collaborative efforts across business units — from product engineering to sales and marketing, for example — to deliver the right outcomes for customers.

It's no secret nor surprise that innovation often happens when practitioners from different disciplines bring their expertise to bear on the same problem at the same time. Directors can be instrumental in making innovation happen at those seams between teams if they have invested in director-level relationships across the business.

The unavoidable challenge

No one should underestimate the scale of the challenge transformation poses to any business. However, it's not a challenge any of us can ignore.

Notwithstanding the economic shock of the COVID-19 pandemic, only 8% of CEOs believe their business model will remain viable if the current pace of digitization of their industry continues, according to McKinsey. At times of crisis, innovation and change tend to accelerate as a necessity rather than a choice.

In our exploration of the dynamics of transformation, we've charted the three front-of-mind questions for CEOs:

1. How do I get our strategy to the last mile?

2. How can I tell if the right work is happening?

3. Are there enough resources to deliver the strategy?

Shifting down a level, we've looked at how senior vice presidents (SVPs) need to ensure that work to run the business and change the business happens simultaneously. SVPs don't get to choose between run or change — they are paid to do the hard things.

Finally, we looked at how directors need to approach their role with courage and say what needs to be said up, down and across the organization.

What I've tried to achieve across this trio of articles is empathy for the different roles as they grapple with this common challenge of transforming an organization. What should be clear is the interdependency between roles in a chain of command but also how thought and action need to break out of departmental silos and function more as a network.

Your organization can be in McKinsey's fabled 30% that succeed at transformation. It starts with understanding the organizational dynamics as soon as the call to action leaves the C-suite.