Tech talent development rests on DEI, upskilling, teamwork

Monica Caldas knows a thing or two about creative approaches to tech talent development -- and their importance.

Caldas is currently deputy CIO of global insurance company Liberty Mutual Insurance, headquartered in Boston. In January 2023, she will become the company's CIO, when its current CIO James McGlennon retires. Caldas is looking forward to continuing the global insurer's digital transformation and using the creativity those projects demand. But the CIO role also gives her an even bigger platform to lead in and advocate for new ways to approach tech talent development.

As a person who identifies as both female and Hispanic, Caldas is in the decided minority as an IT leader and technologist in the largely white and male-dominated tech industry. Many personal factors have supported Caldas' success, including grit and an outcomes-based mindset. But what has also been crucial is Liberty Mutual's support of diversity, equity and inclusion (DEI) and, before that, the support of her previous employer, General Electric. In turn, Caldas is passionate about DEI and creative approaches to talent development.

Here, Caldas shares advice on how IT professionals can look for upskilling opportunities, steps leaders can use to address the tech talent shortage and ways change management can support IT project success.

This interview has been edited for clarity and length. To hear a more expansive interview with Caldas, click on the video.

How to develop IT leadership and solve the tech talent gap

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Why do today's IT leaders need to broaden their skill set beyond tech skills and think about soft skills?

Monica Caldas: Today's IT leaders have to be comfortable wearing various hats, from being technical -- and able to weigh in on technology stacks and architecture and data choices -- but then able to put on a different hat, sometimes simultaneously. You have to understand the relationship with the technology solution with the business problem you're solving. You have to have engagement with all the different stakeholders and at different levels of the organization.

How should IT professionals think about balancing tech skills and soft skills?

Caldas: The table stakes are technical skills. You always start with those. You build up from there.

How can IT professionals -- especially from non-dominant groups -- view leadership and change management to better develop those top soft skills?

Caldas: When it comes to leadership, focus on: How do you show up as a peer? How do you collaborate? How do you have tough conversations in a meaningfully constructive way? And can you do that so that you can bring out the best in everybody at the table? You can hone those leadership skills anywhere.

Affinity groups [such as women in tech resource groups] are also great places to develop those muscles. And perhaps you feel that these may be safer places because you're not connected to a particular [work] outcome. They give more space for developing [soft skills]. When I was at GE, I leveraged women in tech circles and other allies. We had a buddy system to say, 'Here's how I want to show up. How do you see me? How is this actually coming across?'

Figure out what pieces of your competency you need to home in on, and then find different avenues and channels to do that. Have allies and a system to give you some real-time feedback.

For change management: Transformation is on everybody's agenda. What people sometimes miss is understanding the environment they're in and how ready that unit or team is for the change.

I like to say that massive transformations are like heart surgery. Before you put the patient on the table to operate, you have to make sure they're healthy enough to be able to withstand that change.

And although leadership and change management are some top soft skills that people should focus on developing, presenting and communicating skills are embedded in those.

Can you talk more about how change management awareness factors into tech project success?

We need to reach out to the communities and become active to help create a bigger [tech talent] bench.

Caldas: We need to train everybody around the table to be able to recognize where the team is at collectively and what they need to do to keep the progress going. You have to sometimes accelerate because market conditions demand that, and your customers need something new. But you have to understand how ready people are and decide how will you bring them along from point A to point B.

If you miss the [readiness] signals, you might fail even if you have the right tech.

Given the IT talent shortage, how can leaders develop more talent?

Caldas: Even when I started my career 20 years ago, there wasn't enough tech talent. It's only become worse.

We're not graduating enough tech talent. So start there: How do you continue to work with universities and communities to create the bench [of the next generation of tech talent] and motivate groups that are not traditionally perhaps attracted to technology? We need to reach out to the communities and become active to help create a bigger bench in technology -- not just diverse talent, but also more broadly.

There's also internal talent development. For example, we have an incredible group of people already in our organization in technology at Liberty, and we talk often about creating the space and time for them to train on new technologies. Having leaders help employees and empower them to go and engage in upskilling and training is another piece of IT talent development.

The third method of developing tech talent is looking to new avenues of tech upskilling that weren't there before. Use data science as an example: In insurance, it's always been important, but it wasn't important in other industries like it is today. So, if you are very good at coding, you might now have another avenue to grow your career than what you might have originally envisioned when you started down the career of being in technology.

So [IT leaders should] talk to people about different paths of how employees can grow and how they can add value. Then you've got to connect all the dots to what is important for that person, meeting them where they're at and where they want to go, rather than just having a traditional model. It's really personalizing that learning and development experience, always intersecting with what the business needs and what our customers need.