Thoughtful Transformation

10 tips from the trenches to successfully lead a major digital transformation

Fred Santarpia
Mission.org
Published in
8 min readSep 5, 2019

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The core skill of a transformation leader is a deep understanding of how technology is changing the ability of companies to build, serve, and monetize communities of people who share specific wants and needs. That understanding drives the evolution of your business model, your key investment decisions and your customer acquisition tactics.

But despite the obvious need for an expert level grasp of rapidly changing consumer behavior, the challenge to drive even the most well thought out transformation agenda through the established culture of a large organization is often overlooked.

The successful transformation executive must be both an educator and an evangelist. Operator and strategist. Investor and pragmatist. And above all else, human.

Informed by years of direct experience in the trenches at companies navigating the digital disruption of their core business models, here are my best tips for avoiding the pitfalls and successfully leading a thoughtful transformation agenda through your company.

1. Establish expectations early

It’s important to acknowledge that your role and responsibilities may be ambiguous. Don’t assume that people understand your role. Be clear why you’re there and what you’re specifically measuring yourself against to make it clear that you are not afraid of accountability.

Regardless of your end goal, be thoughtful and explain how you plan to start. Are you going to overhaul technology? Will it require shifting the org chart? Take the time to talk through “what” you’re going to do, the “why” and most importantly “how.” The “how” is where all the uncertainty usually lies in who it will impact and what exactly will change.

An underlying current of uncertainty in an organization can be especially damaging as it distracts your people from focusing on the hard work ahead. It’s up to you as the leader of the transformation to be seen as the calm, steady hand on the wheel to ease fears and reduce tensions.

2. Talk like a human being and go door to door

Sure, it can be helpful to put on your nicest suit and present in front of everyone on the benefits of your grand vision, but those settings aren’t conducive to open, vulnerable, and honest discussion.

Many folks will hesitate to ask you important questions in large forums. Moreover, you’ll lose the opportunity to really connect and ensure that key stakeholders truly understand your plans, grasp your sincerity, and ultimately want to support your efforts organically vs a top-down corporate mandate.

Be prepared to take the time to go door to door to explain your role. And be prepared to do it often to build your relationships and establish trust.

Part of really connecting successfully is losing the MBA and consultant speak. Talk like a human being. If you’re explaining a complex topic to someone who does not share your background or expertise, try explaining it as you would to a friend or a spouse, not in your industry. It’s not realistic to expect your stakeholders to always learn what you want them to know. It’s on you to make your strategy understandable, tangible and manageable for the individuals you need to align to your efforts.

And finally, do what you say you’re going to do. Don’t make promises you can’t keep. As a transformation executive, your credibility that you back up your words is critical to offset the natural skepticism that occurs in any big shift in status quo operations.

3. Walk the talk…AND walk the FLOOR

As a newly appointed transformation leader, there may be a well-intentioned temptation to be out in the market doing PR or attending conferences & panels in the service of positioning yourself & the company as “innovators” and “thought leaders”.

My advice is to stay inside the building and focus on being available.

The more visibly engaged you are in the day to day operations of the business, the more important the work will be perceived by the people inside the organization. A team that knows its leader backs up their talk in presentations by personally getting in the mix to solve problems as a member of that team will rally around that leader.

Being available also gives you the opportunity to sense uncertainty early and address concerns before they take deep root. So always be willing to get your hands dirty. You’ll learn more about what’s actually happening in the business from circulating with your people on the floor then you’ll ever learn in a weekly staff meeting or all-hands.

4. Galvanize the organization with a clear north star tied to individual KPIs

Lead with a big, bold, audacious goal for your overall transformation effort. Articulating an inspiring vision for the entire organization clears the road for the company’s future.

It paints a bit of a target on your back but it also creates a visualization of what success looks like for the company. When everyone knows what success is, you can create broad alignment across divisions.

It’s important that every division, department, and individual has some tie to this larger goal through KPIs. Obsess about keeping those KPIs simple. The easier they are for people to understand how to impact the better.

Most importantly, avoid the temptation of having too many KPIs driven by the perceived need to serve internal politics and power structures.

The more KPI’s you have, the less likely you are to hit any of them. Once everything is a priority, nothing gets accomplished.

5. Tie your goals to meaningful incentives

As a transformation agent, especially in highly matrixed organizations, you may not have direct management authority over many of the company’s most important operating departments. Yet they may play a critical role in your overall success.

One helpful tool in the tool belt is a discretionary incentive pool that allows you to reward those departments that you envision will be instrumental in your change effort.

An important nuance is to ensure that you aren’t just rewarding the “digital” lead or the “transformation” lead, but that all leadership gets rewarded. The goal is to ensure that you are able to smooth over the gaps where change agents may run into resistance from pockets of obstruction throughout the organization by strategically deploying financial rewards.

6. Think holistically regardless of your title and responsibilities

Executives approaching transformation correctly don’t think about “digital” transformation. They think about holistic transformation, of the end-to-end consumer experience in the online and offline world, with digital capabilities and technology playing a leading role in seamlessly integrating the two.

Siloed thinking artificially limits the growth of many organizations. Companies should look at the most important points of interconnectivity between platforms to understand their synergies. Digital investment efforts are often additive in driving traditional gains. More importantly, parts of traditional operations are almost always critical elements to fully realizing digital potential. Traditional and Digital organizations should share a common goal: the growth and success of the combined organization.

If not thoughtfully managed, however, you may inadvertently create a culture of “haves” and “have-nots”. If you are spending while others are cutting, it can create the appearance of one side “paying” for the other, leaving folks resentful, and resistant to further change.

As the “transformation leader, you must be extra vigilant in being the visible leader in bridging the old world and the new. You must always represent the entire organization, not just for the areas you are directly leading, but the company as a whole.

7. Optimize for consumers, shift the employee experience in parallel

One of the best ways to fulfill the needs of your consumers is by building a common framework that puts people first internally and externally.

It’s important to think about your team as a community and establish your values, beliefs, and behaviors. If a culture is truly built around its people, it won’t sacrifice its’ values for revenue (or something else) at any cost. Strong, transformative cultures enforce this rigorously.

Like in most communities, people want to feel safe to participate without judgment and connect with one another. This is true of consumers on a social platform discussing a lifestyle passion and it’s true of people contributing in the workplace against a team goal. People want to belong to something and participate in a cause or a mission. They want to know that their work is meaningful and connected with a purpose beyond a title or a paycheck.

So, when you’re thinking about your business goals, keep your culture top of mind. A culture of highly engaged believers in the inside of the company will often lead to highly engaged consumers and brand advocates on the outside as well.

8. Learn to go “bottoms-up”

One of the fastest ways to transform a company culture is to flip from top-down to bottoms-up thinking.

The people closest to the work almost always have the most creative ideas on how to solve the problems. The role of management is to remove the blockers, get out of the way, and let the talent lead.

This doesn’t mean you can create a free-for-all. Rather, this only works when you’ve communicated a clear vision and reinforced that vision with clear goals for the organization.

Done well, it raises expectations, increases personal accountability, and reduces churn.

This can be one of the hardest changes for traditional hierarchal organizations to grasp but it almost always accelerates the pace of change relative to the degree of freedom the individuals on the ground have to execute with speed and creativity.

9. Go for the hard stuff first

Real transformation takes time, yet everyone needs results now.

Starting with the “low hanging fruit” sounds sensible, when in reality, it’s short-term thinking. Speaking as someone who’s taken that approach myself, it may seem like a safe way to begin. I can tell you it’s the exact opposite of what you should do.

As a new transformational executive, you’ve likely been brought in or promoted based on the clearly identified need for change. Because of that, you are most likely to have your strongest mandate to drive that change at the start.

Be bold and go for the hard stuff first, otherwise, you may never get that far. Timing is critical and your competitors are moving with speed. The true cost of starting something too late, or perhaps never getting the opportunity to transform something at all will greatly overshadow the easy wins gained from picking the low hanging fruit.

10. Celebrate what the company is doing well without you

Here’s something that should be obvious. You don’t have to change everything. In fact, there’s a lot that you probably should just leave alone.

There’s only so much change an organization can absorb at one time. You need to balance the need for results with an understanding of how much change the company is able to handle. This will help you create realistic goals and more importantly, plans that are achievable and set up for success.

At the same time, assess what the company is doing right and calculate how you can redirect resources to do more of what’s working. It’s a powerful statement for a transformation executive — expected to drive vast change — to declare that parts of the business are doing it just right and to bolster with more resources. It’s a highly visible signal to the organization that you are not here to simply break things, and that you’ve taken the time to understand and respect the value of things the company does well.

In Closing …

It goes without saying that you can’t be an effective transformation executive without expertise in how the evolution of technology is impacting our world both online and offline.

You can’t rely on those skills alone, however.

Real transformation requires thoughtfulness. It’s about building relationships, addressing fears, mitigating uncertainty, and keeping your promises.

Put these tips to work and you may be surprised to find that bringing those principles into the core operations of a company can drive more value creation for a business than the shift to digital ever could.

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Fred Santarpia
Mission.org

Former Chief Digital Officer @CondeNast. Former @VEVO GM. 2018 CDO of the year. Perpetual work in progress. Make big promises and keep them!