From Misalignment to Momentum: A Leader’s Guide to Breaking Down Silos and Driving Collaboration

Results by Design: UX Insights for Business Leaders

Description: In our latest episode, Craig Nishizaki chats with Deborah Roberts, Senior UX designer at UpTop, about the challenges and solutions for bridging silos in companies. Deborah shares her experiences working with major brands like Amazon and B2B companies like F5 and Everbridge, discussing the impact of organizational structure, communication, and cultural dynamics on team alignment. Together, they explore actionable steps to foster collaboration, including structured workshops, user journey mapping, and regular check-ins that build trust and empathy across departments.

What You’ll Learn:

  • Why silos form and their impact on user experience
  • Practical strategies to promote cross-functional teamwork
  • The role of leadership in sustaining alignment
  • Tools like user journey maps and North Star prototypes to visualize collaboration goals

Interview Participants:

  • Craig Nishizaki, Head of Business @ UpTop
  • Deborah Roberts, Senior UX Designer @ UpTop

Transcript

Intro:
Welcome to Results by Design UX Insights for business leaders, the podcast that dives deep into the world of UX design, strategy and insights. Tune in, take action, and design your way to success.

Craig Nishizaki:
Hi, I’m Craig, your host for the Results by Design podcast. Today I’m excited to be joined by Deborah Roberts, senior UX designer at Up Top. Hi Deborah. How are you doing?

Deborah Roberts:
I’m good. I’m happy to be here. We had a nice weekend going to the pumpkin patch and now I’m excited to jump in and share on the podcast today.

Craig Nishizaki:
That’s great. It’s that time of year, isn’t it?

Deborah Roberts:
Exactly,

Craig Nishizaki:
Yeah. And you at the pumpkin patch, did you all dress up or did you just go as civilians?

Deborah Roberts:
We went as civilians. It was a bit of a rainy day in Seattle and we went to a farm incarnation and my daughter’s two and a half years old, and so we just geared her up in full rain suit so she could chomp through the puddles and we all got pretty muddy, but it was a lot of fun.

Craig Nishizaki:
Oh, that’s great. That’s great. Well, just for introduction’s sake, Deborah, let’s get people familiarized with who you are and your background. You’ve worked with many organizations as a senior UX designer. Can you tell the audience a little bit about your background and the types of companies that you’ve worked with?

Deborah Roberts:
So I’ve had the opportunity to collaborate with large retailers, including Amazon on multiple projects that have range from research and design updates to enhance the customer return experience to serving as an embedded designer on their operations team, working to optimize the driver and delivery experience. I’ve also had the opportunity to work with a number of B2B companies like F5 and Everbridge to help them develop a deeper understanding of their customers and create more engaging online experiences.

Craig Nishizaki:
Well, that’s great. Well, today we’re going to talk about how to bridge silos and gain alignment. So your background I think is perfect. You’re the perfect guest to have this conversation with because of the variety of companies and projects that you’ve worked on and also how effective you are in both of these areas. So why don’t we go ahead and just dive right in. Let’s talk about silos. Why do you think silos exist in most companies?

Deborah Roberts:
Yeah, I think in my experience, company size, UX maturity and then also competing departmental priorities can all contribute to silos. So in larger organizations, just the sheer scale can segment teams well in companies where UX is less established or may be limited trust and prioritization of UX efforts for things like customer research and cross-functional workshops. And then even in mature organizations, differing agendas and competition for limited resources can lead to barriers in communication and collaboration. This ultimately undermines agility in results or can result in a disjointed user experience.

Craig Nishizaki:
And from your experience, what are the most common contributing factors to this?

Deborah Roberts:
I would say organizational structure, inconsistent communication and resource competition. So in larger companies with specialized departments, teams often operate independently, which creates natural divides. And then when there’s competition for budget, this can shift focus away from collaborative efforts and fosters a mindset that prioritizes individual success over unified outcomes. And even concerns can arise over how initiatives from other departments may impact personal performance metrics, which can further entrench silos and it can become really personal for people.

Craig Nishizaki:
Yeah, it’s all about relationships in a lot of ways. So you talked about the organizational structure being part of it, but do you think also organizational structure and culture can be a cause of these silos?

Deborah Roberts:
Yeah, I think it’s a little bit of both. I think that silos often will stem from the organizational structure, but then they can be reinforced by company culture. So the structural divides keep teams focused on their specialized goals while the culture can determine if teams work together or stay isolated. So when a culture encourages collaboration and alignment, I think silos are less likely to form.

Craig Nishizaki:
That makes a lot of sense. And from your experience working with multiple different types of companies as well as different company sizes, different cultures and organizational structures, I’m sure you’ve probably put together a process. So when you start working with a client, what types of things do you do to quickly ramp up on the problem space and get the lay of the land?

Deborah Roberts:
So I typically start by reviewing any existing research requirements, business goals to understand the foundation of the project and align with the overall objectives. And this helps to give me context and also highlights initial opportunities or gaps if we need to conduct more research on the space as well. Next, I’ll often conduct stakeholder interviews across departments such as product marketing, sales to tech, whoever is touched by the specific project that we’re working on. And these conversations are really essential for gathering insights on the initials, potential impact on different roles and departments, understanding what success looks like from various perspectives, and then identifying concerns or blockers early on. And I found that involving stakeholders from the start, it doesn’t just help me get oriented, but it also brings people from different areas of the business along on the journey. I think it makes them feel heard and like we’re prioritizing or listening to what they think is important. So it helps create alignment and ensures that we’re all moving in the same direction. And I found it to be really crucial in spotting opportunities that might otherwise be missed and ensures that solutions are also well-rounded and impactful for the user and business.

Craig Nishizaki:
I love that involving the stakeholders from cross-functional parts of the organization early on. I think the key is early on in your process. And so as you’re doing that, are there specific indicators or patterns or symptoms that you look for when identifying silos within teams?

Deborah Roberts:
I’d say one of the biggest signs is a lack of communication or competing priorities. So right from the start, you might notice that certain team members aren’t talking to each other, and it’s often evident when individuals want specific people excluded from meetings or certain aspects of a project. And this exclusion really only creates and reinforces those silos when key people or departments are left out early on, they can become blockers later in the process. And this can lead to delays in the project. You might find yourself waiting days or even weeks for input or resources from others who aren’t the primary project owners. They might not feel that same sense of urgency and without the right representation of the room, the ideas end up being less rich and diverse. So ultimately this can lead to watered down solutions or worse missing the mark entirely on the problem that we’re trying to solve.

Craig Nishizaki:
As you’re talking, I can just remember various projects and engagements that had those elements and all those patterns. Are you able to share a story about a project where you quickly identified silos and helped address them? What did you notice and how did you approach it?

Deborah Roberts:
Yeah, the one that stands out, I was working on a project for a B2B company and we were engaged to conduct research to develop better understanding of the prospective customer in order to improve the user journey and ultimately the performance of the website. And I began by conducting stakeholder interviews. And through that it became clear that many of their teams across marketing tech product were not well aligned on data sharing practices or on go-to-market strategies. And that led to limited collaboration and efficiencies and particularly with their lead processing. And then a lot of them also shared that they had challenges in creating a streamlined customer journey because they had this complex product mix of over 40 products and new acquisitions with differing terminology that was used across departments and that just really complicated consistent messaging both internally and also to their customers. And we had intended to engage prospective buyers for interviews, but the organization lacked an established research program.

And the BDR team who engaged with the prospects were really protective of customer communications. And the stakeholder that was responsible for recruitment was not directly involved in the project, and so was just not responsive to our timeline. And this led to delays. So to tackle this, we had weekly check-ins with our main stakeholders, and I suggested pivoting to existing customers for insights, our main project owner to over recruitment efforts, and that yielded much better results. And all of it at the end of the project is this culminated in an alignment workshop that brought together a cross functional team of stakeholders, including all the people I had interviewed in the beginning to review our findings and recommendations across content design technology strategy. And this provided our client with clear actionable steps to build a roadmap for website improvements that would improve their customer experience, drive revenue growth, and also try and increase collaboration between their different departments.

Craig Nishizaki:
That’s great. The one thing that you said here about initiating the weekly check-ins. I’d love to dig a little deeper with you on that. It sounds like you did that to help foster faster turnarounds, but it also must have done some other things in terms of building trust. I’d love to dig a little bit deeper with you on what the outcomes of those weekly check-ins were.

Deborah Roberts:
Yeah, I found I led those meetings and I came to each meeting with a checklist of items of firstly where were we, the current state of affairs in our process and anything that was holding us up any blockers and just coming prepared to those meetings really helped to build trust with our main stakeholders, and I think it helped them to trust our process. And so I just helped to build alignment with them and that ultimately helped us to continue moving the project forward. Even when we hit roadblocks, I was proactive to come to the meetings with proposed solutions, other avenues we could take, especially for recruitment because their research was just not, they didn’t have a history of research at the company with customers. And so we ran into a lot of recruitment efforts at almost every stage. And so just coming with other ideas of how to get that data and to proceed forward really helped to move things along.

Craig Nishizaki:
Yeah, I remember sitting in on a few of those weekly check-ins, and what I thought was really impressive and helpful from our side was to help them help themselves in a way, because if I recall correctly, there was a little bit of pushback from the person that was supposed to be doing recruiting to the team that needed the participants recruited and there was some distrust or mistrust, if you will. And so you being the mediator and the facilitator of that really helped get things moving along and created some velocity.

Deborah Roberts:
And I think honestly, being an outside party, being an agency that’s not tied to the company can sometimes be helpful because you’re not tied to the politics. And so you can come in as this neutral party and help to facilitate that alignment to move things forward and to keep the focus on what are our key objectives here? It’s to improve the user experience to meet our business metrics that have been identified. And so I found that that coming in as this third party has been really helpful to our clients to move forward and not get kind of entrenched in the silos that happen.

Craig Nishizaki:
Yeah, I think you’re right. That’s a great observation. So when working cross-functionally, how do you balance the differing priorities between teams like marketing, product and engineering?

Deborah Roberts:
Kind of building on what we were talking, just talking about, starting with clear communication and alignment around shared objectives, having the regular check-ins and then cross-functional activities like workshops are so helpful and addressing conflicts early, and then they help to foster collaborative culture that encourages open sharing of ideas and challenges, really embracing that no idea is a bad idea. I’ve also found that conducting and referencing user research is a great tool for aligning stakeholders across team. Just having a better understanding of user needs and pain points helps to foster empathy, which then drives a consensus priorities.

Craig Nishizaki:
Yeah, that’s great. I mean, I feel like in a lot of ways, because you’re more senior in your role that you’re obviously expert at the process and the methods and how to tease out the answers to the questions or the problem that you’re trying to solve, but also really just moving them along from a project management almost or a consultative manner where you’re helping them see things more clearly along the way. And you referenced user research, and I think that your use of that has been really effective throughout these projects. Well, once you identified that there are silos or there’s some friction there, what tips do you have to help get people organized and moving in the same direction?

Deborah Roberts:
Yeah, so I mentioned, we’ve talked about this a little bit, but I think cross-functional workshops are just an extremely effective way to get everyone in the same room and on the same page. So in our workshops, we often start by reviewing research, and then we’ll take stakeholders through structured activities to allow all voices to be heard. Oftentimes in a meeting format, sometimes loud, its voice will dominate. And that’s something I love about the structured nature of the workshops is it gives everyone a space to allow their ideas to be heard from across departments, doesn’t matter your seniority. And it just gives us a better understanding of the problem space and more opportunities to discover really interesting solutions and build alignment.

Craig Nishizaki:
And so how do you foster collaboration between teams, those teams that have competing priorities?

Deborah Roberts:
I think it’s helpful to bring everyone back to the shared user and business goals. I found user journey maps to be a great tool for building alignment and facilitating discussions. And for those who aren’t familiar, it’s essentially a visual map of the user engagement with your organization at every step of the process. So in our workshops, we often start by presenting a draft of the user journey that we’ve built out based on research. And this is a visual tool and it serves as kind of a focal point for conversation, and it allows participants in the workshop to jump in, provide additional insights on key areas of the journey that they might have more specialty or information on. And as we go through this process, we’ve often experienced aha moments where different team members or even people in senior positions get a deeper understanding of the user’s experience and each other’s perspectives, particularly around critical pain points and opportunities for improvement.

And when you’re looking at the map, once it’s all built out, it often becomes very obvious visually what parts of the journey have the most pain points, and then it’s easier to kind of align around that. And then another effective tool is creating a roadmap for improvement. So at the end of the project, we’ll often provide recommendations that assess both the impact on users and the business alongside the technical effort required. And so this approach helps team to prioritize based on potential value and feasibility. And by visualizing these priorities, teams can then align their efforts and make more informed decisions about where to focus their resources.

Craig Nishizaki:
Yeah, that’s great. I love the workshops, the journey mapping, the roadmap. I think those are all just so foundational because the business leaders can review those things and understand where the opportunities lie and where the gaps are. Exactly. So that’s great. In situations where teams are resistant to change, how do you build trust, I should say, and encourage open communication

Deborah Roberts:
First, fostering a safe environment, so creating a culture and opportunities for team members to feel safe to express their ideas and concerns. I think that’s so important. We’ve talked about this previously, but engaging early involve team members in the change process from the start. This approach I think helps to reduce fears and builds ownership in the process so that people are more invested. And then lastly, just having more transparent communication. So just clearly explaining the reasons behind changes and how they benefit the team users and business goals.

Craig Nishizaki:
Yeah, I think just my reflection of some projects that I’ve worked on with you is you do a great job of making the environment feel safe, allowing people to share and feel like it’s okay to share openly. And I think that that is really effective in of us teasing out the root cause of issues and things like that.

Deborah Roberts:
Yeah, I think it helps to really listen and to take notes, to listen, to refer back to what people said and to build that going back to the stakeholder interviews that we do, and then we refer back to that even in the workshops. And so throughout that process, people do they feel heard, and then I think it makes them feel more comfortable to join in.

Craig Nishizaki:
Yeah, absolutely. I just feel like that’s like 101. Listen, actively write down notes, follow up. It seems like everyone wants to be the one that throws an answer in instead of being the one that’s asking the question and listening. Well, in terms of engaging leadership, how do you get leadership engaged and invested in a cross-functional alignment, especially when silos exist?

Deborah Roberts:
Yeah, I think highlighting the tangible business value of bringing different teams into the design process. So when you involve diverse perspectives early on from product, from engineering, marketing, customer support, it leads to solutions that are more holistic and aligned with user needs. And this alignment helps to avoid costly missteps later in development as teams are already on the same page about goals, timelines, challenges. Additionally, I think cross-functional alignment drives agility. So if tech and UX are aligned from the start, there’s a shared understanding of technical limitations or user pain points which help as to prioritize effectively. And again, I think tying any design changes directly to key business KPIs, how cohesive design improves metrics like customer satisfaction, revenue growth, efficiency. I think when leaders see how integrated processes positively impact user experience and the bottom line, they’re more likely to champion and support collaborative efforts across departments.

Craig Nishizaki:
Yeah, I think that’s key in making sure that you’re aligning what you’re doing to what their objectives are, helping them learn more about the customer, helping them identify ways to be more effective and things like that, not just designing the screens I think is really important. So that’s great. What advice do you have for business leaders who are trying to create more collaboration within their teams

Deborah Roberts:
To help move past silos? It’s really great to take a structured approach to collaboration like the cross-functional workshops and make that just a part of the regular process. These workshops bring together teams from across departments like product engineering, marketing to discuss key insights, user your needs and project goals. And I think when leaders encourage this type of structural alignment, it just becomes more a part of the company’s DNA and bridges gaps between teams that might have competing priorities and then again, conducting department goals to the overall company objectives. It reinforces where everyone is working together. One technique that we’ve used is creating a service blueprint, which actually it maps out the customer journey alongside the internal processes and systems that support that journey. And I found that that really helps to foster empathy and allows everyone to better understand how each other’s work impacts the end user and the broader business goals.

Craig Nishizaki:
And one thing that you and the team, I think does a really good job of in terms of the alignment workshops and having structured collaboration is all the prep work that you do prior so that you come into the workshop with lots of information: the research, the data, existing state, things like that, the journey map that may not be all the way fleshed out, but it is where it’s at so that you can ask questions to dig deeper and it makes that time so useful and valuable, I feel.

Deborah Roberts:
Absolutely. For sure. And then we always will follow up after with a report kind of summarizing the findings as well, so that it can be a lot of information at once, so then people can take it back. And then we have recommendations upon how to connect with those teams and have follow-up meetings to discuss further. It’s such a great initial first step to level setting, getting everyone on the same page to move

Craig Nishizaki:
Forward. Yeah, I agree. I agree. So what role does leadership play in sustaining this alignment over time?

Deborah Roberts:
I think that communication style has a large impact on team dynamics. A positive collaborative approach can foster cooperation while an US versus them mentality can lead to silos. I think having also regular check-ins and open forums for feedback can enable leaders to proactively address challenges and ensure that everyone remains aligned with common goals, and then really clearly communicating the company’s vision and objectives and how each team’s contributions align to the broader goals. I think that goals, I think that all helps to foster commitment and accountability.

Craig Nishizaki:
Yeah, makes a lot of sense. Communication’s key. Could you share an example where leadership played a key role in breaking down silos or alternatively where a lack of leadership support led to challenges?

Deborah Roberts:
Yeah. I actually have a good example of how leadership played a role in breaking down silos effectively. So we had a B2B client who had a lot of acquisitions and their current web experience was pretty disjointed, and they were working to get internal buy-in to get funding for a website redesign. And so we led them through an envisioning workshop where we reviewed research and we included stakeholders in a structured design activities to quickly explore new ideas and solutions. And with this company, there were a lot of opinions on what this design should be.

Our team took all of that into design exploration, and the output was a video of a clickable prototype that they could share internally to get buy-in. And the great thing was they already had buy-in because we had involved a lot of these key stakeholders in the process, and it ended up being a really successful approach, and it led them to getting budget approved for the redesign, which we then collaborated with on the following year.

Craig Nishizaki:
Yeah, that’s great. It’s tangible.

Deborah Roberts:
Yeah,

Craig Nishizaki:
Exactly. When people hear that they’ve been heard and they see it in the prototype, I feel like that’s super powerful to them. Exactly. Yeah. That’s awesome. Okay, so what are two to three practical actions that a business leader can start taking today to break down silos and foster a more collaborative environment?

Deborah Roberts:
I’d say one thing is to start small to demonstrate impact. So we’ve found that an incremental approach works really well. Rather than trying to overall the entire organization focus on a smaller initiative that involves cross-functional teams and make that a success and showcase the benefits of collaboration, which will help to create buying and set the stage for expanding these collaborative efforts across more significant projects. Next, I think established more structured, cross-functional collaboration, create regular touchpoints like workshops or collaborative check-ins that we’ve talked about previously and just make that a part of your normal process. Again, we found these structured meetings really allow everyone to share insights, build alignment, and contribute meaningfully from their area of expertise, and it really can help to address silos by integrating insights and ownership across functions. I think that ownership is key. And then highlight the quick wins in customer and business impact. So showcase the success metrics from collaborative projects, whether it’s user satisfaction improvements, faster feature delivery, or customer retention boosts. I think leaders who tie these resolve back to KPIs help to reinforce the value of collaboration and it makes a compelling case for continued investment in cross-functional efforts.

Craig Nishizaki:
Yeah, I think those are spot on. I mean, quick wins are huge because otherwise people get fatigue. That’s the one reason why digital transformational projects fail because they don’t see any quick wins. They just see that we’re doing all this work to change. And I love this establishing that structured cross-functional collaboration because it takes work to build these relationships and start working together. So I love that. To wrap things up, I mean, Deborah, if you had one final piece of advice for a business leader on creating alignment, what would that golden nugget be?

Deborah Roberts:
I would encourage business leaders to leverage to communicate the value and vision of UX and collaboration. So start with user journey maps based on real user research. This just makes it so much easier to visually highlight key pain points and opportunities in a way that resonates across departments. These maps can help teams understand exactly where users struggle and see where improvements can make the most impact. So what we’ve found that to just be so helpful for unifying teams, another effective approach is creating highlight reels or decks with direct quotes or user insights from interviews. I think hearing users’ own words, help teams build empathy and connect more deeply with the needs of customers. And then lastly, develop North Star prototypes that bring future experiences to life. Like that example I gave, I think it helps leaders and teams to experience the vision firsthand and make it much easier to rally around the vision and long-term goals.

Craig Nishizaki:
And what I think I took away from this that’s interesting because it aligns with my thought process, is business leaders oftentimes think, oh, I need to go find a UX team to help me. I have a project, but wind it back to these things. We have silos that we need to break down, or we have a problem that we need to solve, or we have customer insights that we need to tease out, or we do need a journey map these things that are foundational to actually have success in the broader project or opportunities to pull in your internal UX team or an external UX team to help move things along. Right,

Deborah Roberts:
Absolutely.

Craig Nishizaki:
Well, this has been great. So where can listeners learn more about your work and find out more about you?

Deborah Roberts:
Yeah, you can see some of my work in our case studies@uptopcorp.com, and then you can also find me on LinkedIn at Debra Roberts design.

Craig Nishizaki:
Oh, man. Well, Debra, this has been great. I really appreciate your time and sharing your knowledge, and I hope the audience got a chance to really see how your experience and the insights that you have from working across all these different types of companies and projects really lends to your T-shaped expertise. So that’s it for today’s show. Join us next time as we explore innovative approaches to enhance your products and services, optimize customer interactions, and ultimately drive success for your organization. Tune in, take action and design your way to success. We’ll see you next time.

Outro:
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