Digital transformations require empathy

Digital transformations often leave employees feeling overwhelmed, but strong people skills can support team members.

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Agility, experimentation and empathy are key to successful digital transformations, says Isaac Sacolick, president of StarCIO, in his book Digital Trailblazer: Essential Lessons to Jumpstart Transformation and Accelerate Your Technology Leadership. And leaders who develop these people skills have the upper hand. Digital transformation initiatives require a balance between discipline and innovation. To cultivate the latter, IT leaders should encourage employees to build time into their schedules to experiment. That experimentation is key to gaining valuable insights that can lead to success.

Here, Sacolick offers tips on how to support agility with feedback, encourage experimentation and build empathy.

How can IT leaders ensure their digital transformation strategies are agile?

Isaac Sacolick: It starts with communications and making sure your team, your stakeholders -- people who are funding what you're working on -- understand what your objective is.

I think a lot in terms of the terminology we use for software.

I think about putting something out as quickly as I can so that I can get feedback. Feedback gives me the room to realign priorities. It gives me the room to realize that I've underinvested in a feature, or I have to invest more in a feature, or I implemented something the wrong way.

I'm using that as a way to get feedback to say:

• Am I heading in the right direction?
• Do I need to change my vision?
• Do I need to change my priorities or my requirements?

I bring that all the way to the sprint level. I go to every single team -- regardless of how Agile or how Scrum-like they are -- and I say to them: What do we think we can get done over the next sprint? I'm going to get to the end of the sprint. I'm going to do my retrospective. I'm going to readjust and pivot what my expectations are for the next sprint.

I could do it at the macro-vision level. We could do it at release level, based on customer feedback. I could do it at the sprint level, based on how well the team is performing and whether we're making our commitments.

The heart of being agile is being able to do it at [all] levels.

What can an IT leader do to create an environment of safety and trust that encourages experimentation?

Isaac Sacolick

Sacolick: The universal thing I'm looking for is room in people's calendar to be able to experiment. That's one of the issues when we talk about how we measure somebody's performance today.

One of the things I'm going to look at is: Did you experiment? What did you do that was a reasonable question around what you're experimenting with, that you take reasonable risk precautions when you designed that experiment.

I think we want to experiment frequently. I think we want feedback frequently. What we're trying to ask people is: What did you learn from your experiment?

That's the culture leaders have to bring in:

• Are you giving time for people to experiment?
• Are they designing reasonable experiments?
• What did they learn from that?

What can IT leaders do to encourage empathy within their teams?

Sacolick: I honestly don't think any of us put enough attention to this until COVID-19 hit -- the side of empathy and realizing what it means to work with individuals. How people on your team are showing up today, versus yesterday, versus next week, and being able to understand that they have things that are going on in their lives.

Empathy is realizing that someone on your team is going to look at what you're trying to accomplish from a different set of principles and values.

[Recognize that] there isn't one right answer. There are lots of different ways to look at a problem.

Empathy is realizing that someone on your team is going to look at what you're trying to accomplish from a different set of principles and values. Some will be vocal about it to the point where they're perceived as detractors. Some are going to sit and not say anything until something's too late, and then start asking questions.

An empathetic, diverse leader is going to realize that there's a time when I need to bring my team together to listen and learn. I need them to hear that we're going to make some decisions going forward.

But those decisions are never final or written in stone.

Editor's note: Responses were edited for length and clarity.

Guilliean Pacheco is an associate site editor covering CIO strategy, digital transformation and sustainability in tech. Before joining TechTarget, she was a freelance writer and copy editor.