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Digital transformation: 5 types of leaders who can get in the way

Successful digital transformations require support from almost everyone in the company and in particular, from other leaders. You can have the best playbook ever produced, but it won’t matter, if you still lack that leadership support.

Leaders are so critical because they influence the attitudes and perceptions of the people on their teams. When they resist the change, their people will resist – and that paves a long and difficult road for the transformation. If they’re excited about the transformation, their support enhances your efforts and builds the momentum you need to succeed.

CIOs who navigate their colleagues’ different leadership styles and give the struggling leader what they need, without compromising the core goals of the transformation, will clear the path to a successful transformation.

In practice, we see five types of leaders who can stand in the way. Navigate their personalities and push back to move the transformation forward and (hopefully) bring them along with you.

[ Culture change is the hardest part of digital transformation. Get the digital transformation eBook: Teaching an elephant to dance. ]

The Saboteur

Every good spy movie includes a saboteur. Saboteurs appear to be on the team, which gives them access to information: But in reality, they work to subvert good efforts by collaborating with the villain. The hero of the movie eventually finds them out and “eliminates” them. 

Identifying the saboteur and guiding them to support the mission requires more finesse in the real world. They resist behind the scenes, in conversations with the people they lead, and in everyday decisions. However they appear supportive in conversations with you.

[ Is your digital transformation stalled? Maybe it’s an unhealthy IT culture. Read: 4 early warning signs your culture is starting to crack. ]

To spot them, do some sensing in their organizations. Leaders reproduce their attitudes in their organizations and saboteurs betray themselves through their team(s). While you do your sensing, ensure you remain respectful and avoid becoming a saboteur yourself when discussing the situation with people on their team.

Be mindful that not every saboteur sabotages intentionally.

Be mindful that not every saboteur sabotages intentionally. They may not realize their own resistance and certainly, most lack malice. However they still resist the effort. Your mission: Discover why they resist and eliminate that challenge for them.

The HiPPO

HiPPO stands for “Highest Paid Person with an Opinion.” HiPPOs share their opinion with anyone willing to listen. They announce it in lead team meetings and they declare it to their team. Each moment offers an opportunity to actively resist transformation efforts.

HiPPOs may be intimidating, but winning them over is often critical to your efforts.

Identifying a HiPPO is easy. They know they resist and probably already told you 10 frustrating aspects of the transformation that are “wrong” or “doomed to fail.” However they create collateral damage for the transformation very quickly, so get ahead of them as soon as you see one coming.

HiPPOs may be intimidating, but winning them over is often critical to your efforts. To resolve their concerns, sit down with them in a one-to-one meeting with an intent to learn. They probably have valid concerns and adjusting your transformation strategy to alleviate those concerns will not only win their support, it will strengthen your transformation strategy.

One other reason to win a HiPPO’s support for the effort: HiPPOs who support the effort can evangelize the transformation effort. In fact, winning the support of a HiPPO in early stages bolsters support for the rest of the transformation.

The Eeyore

Remember Eeyore from “Winnie the Pooh?” The pessimistic donkey dragged his feet on adventures and shuddered with fear during storms. Change scares him simply because it means something will be different.

Your digital transformation requires changes that frighten the tail off Eeyore. You stand in front of the room excitedly casting vision while they sit in the corner making a list of reasons the transformation will fail. At the top of that list? “It’s different than how we do it today.”

Winning the support of an Eeyore requires empathy.

If Eeyore’s people are onboard, you can maintain the course. However, if they remain reticent, you need to win them over directly or win Eeyore’s support, which will help secure everyone’s buy-in.

Winning the support of an Eeyore requires empathy. As an IT leader, change drives your entire world and you adjust quite easily. However, Eeyore sees the flood of new information coming at them and turns away in fear. Spending time viewing the world from their standpoint and feeling the pressure and fear they feel provides perspective to ensure you capture important details, while showing Eeyore you care about their ability to make the change.

In reality, Eeyore rarely derails a transformation because everyone already knows they lag behind, which sadly causes their opinion to be dismissed by others more easily. 

The Lukewarm Buzzkill

Some leaders (even visionaries) cannot see the vision you cast for them. You stand in front of the room, cast vision for the transformation (you nail it!)  and everyone is onboard, except one person who just doesn’t seem to get it. They’re lukewarm at best and they can drain the excitement from the room.

They can drain the excitement from the room.

You can spot a Lukewarm Buzzkill by their lack of support. In normal circumstances, they voice support and cast their own vision for new initiatives. In this case, they disengage or they quietly wait for more information because they’ve heard the buzzwords and they’ve heard the theory, but it’s not real to them. They’re not afraid of change. They just can’t see where you’re headed. Gain their support and you get a teammate that naturally casts vision to everyone around them. 

To help them, change the way you communicate. Instead of using charts and diagrams, make it tangible for them. They must see it to grab hold of it and become ardent supporters. Consider enrolling a designer to bring the transformation to life (app mockups, tool designs, etc).

A note of caution: When you show how an app might work or what the new customer interaction will look like, you create a risk. If they disagree with your theoretical execution, you create an uphill battle for yourself. To mitigate the risk, tell them the mockups represent ideas and then invite them into the brainstorming and more fully enroll them in the transformation process.

The Capacity Monster

Some leaders and their organizations lack capacity to play a key role in the transformation. 

When you ask for their help these “capacity monsters” push back, talking about other priorities. Sometimes those priorities represent an unwillingness to change, in which case you need to address them as an Eeyore. Other times, those priorities build the business, and respecting them produces better business results. 

When you ask for their help these “capacity monsters” push back, talking about other priorities.

When their reasons are truly mission-critical, win their support by investing transformation efforts more heavily in their direction. Consider addressing their current bottlenecks or finding tangential opportunities to help them create capacity. Either way, give them support in their mission-critical work.

While you’re helping them, strive to over-deliver and develop a case study. Eliminating their bottlenecks and helping their high-profile work succeed gives you an easy success to share, which can win support from other leaders for the transformation.

Enrolling these five types of leaders builds a critical front for pushing the transformation forward.  Doing it well multiplies your efforts across the entire organization, enrolling not just the leaders, but the people they influence. When you do that, the entire company will soon be bought-into the transformation, setting it up for success and building the organization’s capacity to tackle future change efforts more eagerly. 

[ Get answers to key digital transformation questions and lessons from top CIOs: Download our digital transformation cheat sheet. ]

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Two employees playing tug of war with pie chart

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From the saboteur to the capacity monster, these personalities can hurt grassroots support for your digital transformation. Here’s how to deal with the challenges

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