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Managing Digital Transformation — an Insider’s View

In increasingly online & connected environments, digital structures and experiences matter more than ever.

Leading efforts to break free from the status quo to better deliver services to the public is always a worthy mission. But it’s not for the faint of heart. The work of modernizing outdated systems, processes and ways of thinking in any organization, especially government, is a long-term undertaking.

As part of a technology focused team (Team Skylight) supporting organizations in this effort, I was curious about the experience of our partners — changemakers managing digital transformation projects on the inside. Are they seeing progress in making the changes they set out to make? What wisdom would they offer other leaders embarking on larger projects like this?

To answer these questions and more, I spoke to Rachel Leventhal-Weiner, Chief Research and Planning Officer for Connecticut’s Office of Early Childhood (OEC). Though new to public service, Rachel has a deep background in working to build data capacity and literacy through her previous work with the Connecticut Data Collaborative, a public-private partnership advocating for public data that is open and accessible. At OEC, Rachel is engaged in a multi-year effort with our team to upgrade the way the agency uses data and technology to serve children and families in the region. Halfway through this work, managing projects ranging from an overhaul of the agency website, to piloting a new data collection tool, Rachel shares a window around moving the needle internally.

Rachel Leventhal-Weiner

What’s been the most challenging part of this work?

In a marathon, you need to start small. It’s like here’s the one hill. Don’t worry about what’s at the top of the hill because it could be more hill, and it typically is. It can be a challenge to get people over the hump to see that the whole system is really fractured. We’re a newer agency that has its roots in other agencies and because of that, we still have ties, and are still hooked into other agency systems. Just building that understanding and infrastructure internally to make sure we have what we need is really an important thing we are still working through. That’s going to remain a challenge.

Long-term change and transformation in any form is more of a marathon. What progress do you think has been made?

The biggest progress I’ve seen is that people are paying attention to information and there is a growing enthusiasm for evaluation. They are paying attention to the information they generate as a matter of doing the work. The fact that folks from a number of different OEC programs are bubbling up with data and evaluation requests is exciting for me. It signals that my colleagues not only care about the information, the quality of it, and its existence, but they care about knowing whether or not they’re having an impact on people.

What have you learned about your agency and harnessing the power of technology to advance your work so far?

I’ve learned a lot about the way we do our work, and the opportunity to work and think differently using data and technology. If we trust the place we put data and information, and if we trust the tools we use to manipulate it, or the reporting that we offer out, then we have to trust all the little granular pieces. I’ve learned that sometimes we either put too much trust in what technology can do for us, or we assume the limits of technology are really broad when they should be more constrained, or we don’t dream big enough.

With more time to go, what keeps you motivated?

All the data and information. I’m coming into this opportunity at the absolute most perfect time. I have a very supportive leader who cares about information. So that’s number one the most amazing thing, and I get to sit at multiple tables every single week with other agency leaders who also care about good information and partnering. Having done this work out in the social sector with health and human service organizations who struggle to have partnership with their funders or their supporters, just knowing that you have partnership and support is great. Data problems are people problems. To have all these really supportive people who care about getting it right so we can redirect investments and support services for kids and families, it’s the best job.

What advice would you offer leaders managing a huge digital transformation effort on state and local levels?

Having support and buy-in from your executive or your leader is the most important part of the work. That can come before or after you start. It’s better if you walk into a situation with support. It’s also important to find ways to convince people early on about the value of both digital systems and technology and the way it can facilitate all kinds of data collection and information gathering.

If you could go back in time to the beginning, would you have done anything differently?

If I could go back in time, I might have told myself to pace myself, and manage my expectations a little differently. I thought I had a lot of knowledge about the internal workings and how hard it can be. If you think you know, just dial that back ten-fold. Then maybe walk it back another ten steps. Only then will you have a chance of feeling prepared for all the challenges you’re going to face. The work is really a long game. It’s knowing the context, being willing and aware to move the chairs because sometimes there’s just not enough capacity to do the things you want to do. And just being really patient and kind to yourself, that you are changing people’s minds every day about the value of the work. But it’s not an overnight process.

What do you think is required for digital transformation efforts like this to be successful?

Capacity is really important. Even if people are excited to do something, and when working with an external team especially, the external team has more capacity than you do at all times. You still have all of your regular things. Maybe you’re working on something so specialized that nobody really sees the value of it yet. Keeping this in mind is very important and having that leader who really cares and gets this matters.

Also, making space for creativity matters. But I honestly don’t know if that’s something we will have in full force in government in the near term. If you think about the kind of digital transformation that has happened in the world, in the universe, there has been so much that’s happened and specialty knowledge that’s developed and creativity around processes that we can adopt. None of that infiltrates now because of gatekeepers who might still be holding on to old processes and old methods.

It’s also important to have a willingness from everyone in the organization to see themselves as part of the effort and as working with data. I recently gave a talk called, ‘I’m a data person and you are too’.

It’s important to convince others that this digital transformation work is actually going to make our work better, smoother, more efficient, and more helpful to other people internally and externally. We won’t get there unless we all see ourselves as part of it.

Malini Sekhar is a storyteller and engagement strategist with Bloom Works who loves helping others identify and express their own superpowers. She’s worked on various projects that promote social innovation including work with Ashoka and the innovation lab within the U.S. Department of Health and Human Services (HHS IDEA Lab).

Pollinator is an open space for sharing lessons learned and insights curated by Bloom Works. Have practical wisdom to share with other changemakers in this space? We’d love to learn more. Drop us a line at — pollinator@bloomworks.digital



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Malini Sekhar

Malini Sekhar

I heart #socialinnovation, #creativity, laughter & ninja unicorns. Fellow traveler on this silly, sacred road trip of ours.