Breaking Barriers: Strategies for Conquering Digital Business Challenges

Results by Design: UX Insights for Business Leaders

Description: In the latest episode of our series, Breaking Barriers: Strategies for Conquering Digital Business Challenges, join us as we unpack the top 5 hurdles organizations often encounter on their digital journey and unveil practical solutions to conquer them.

Topics Covered:

  • Leadership and Vision
  • The Problem with Departmental Silos
  • How to Choose the Best Team Members
  • The Importance of Having Good Processes in Place
  • Is Your Company Operations-Minded or Innovations-Minded?

Interview Participants:

  • Craig Nishizaki, Head of Business @ UpTop
  • Michael Woo, Director of UX @ UpTop


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:
Hello everyone. I’m Craig.

Michael Woo:
And I’m Michael. And we’re your hosts for the Results by Design podcast. Happy New Year. Craig, how was your holiday break?

Craig Nishizaki:
Yeah, it was great. It was refreshing. It was nice. It took the time during that week to really disconnect and came back feeling fresh and ready for the new year. How about yourself?

Michael Woo:
Yeah, I think I mentioned last time around that I went down to Portland. I don’t even know if I mentioned it, but I went down to Portland for the first time. So the first Christmas away from home, stayed at my sister-in-Law’s and it was great. It was great. She was gracious and a little shout out to my niece letting us stay in her room and crash that. So thanks Ken, appreciate it putting up with us.

Craig Nishizaki:
Oh, that’s awesome.

Michael Woo:
What are we going to be talking about today?

Craig Nishizaki:
We’ve been thinking about this and over the last 15 years working in the consultancy and agency space, we’ve seen a lot and we’ve done a lot. So we thought it’d be, or I thought it’d be, and you agreed with me, thought it’d be interesting to peel back the onion on the five most common problems that we’ve seen organizations face when trying to build a successful digital business, digital product or digital project. How’s that sound?

Michael Woo:
I think it sounds great, man. I think the audience will enjoy this one. Seriously.

Craig Nishizaki:
I hope so. Well, working with hundreds of companies on well over a thousand projects, we found the five most common problems that hold companies back from being successful in building their digital business, digital product or digital project fall into these categories. Leadership and vision, silos, people, processes and culture. And whether you’re an internal team or a consultant brought in from the outside, identifying these problems early and working through or in some cases working around them is as critical as working on the digital product itself.

Michael Woo:
Yeah, you know what? I’m weird like that, but I’ve said this before that I personally love working through what I call the challenges within the challenge the most. I think they’re super interesting to navigate because oftentimes they involve people and psychology. Those are two things that I really, really love.

Craig Nishizaki:
Yeah, I’m with you on that. Challenges within the challenges, that’s a great way to put it. In addition to being the experts brought in to improve the user experience in many ways would function as digital therapists, if you will, uncovering the issues and obstacles within the organization. And that digital therapy that we provide often is the highest value activity that help the client, the customer or the company achieve a breakthrough. So let’s jump in and talk about the observations on each problem. I’ll start with leadership and vision. So an organization’s culture is set from the top, and the same thing is true of that team or that team’s preparedness for a digital initiative. If your leadership team isn’t engaged or aligned around a shared vision for the business effort, digital business effort, that initiative’s already set up for failure and for mid-level leaders and team leaders especially, this can be very challenging.

And really for people that are wired as change agents, this can be really challenging. You’re the people that once you see a problem, you can’t unsee it. The problem may not fall under your direct responsibility, but it impacts your ability to achieve your objectives and you want to fix it. And I feel like I’m one of those people a lot of times, I don’t know Mike, I think you are as well, and you’re just wired in that way. But some symptoms that you might recognize regarding leadership and vision issues might be lack of executive engagement. After the sponsorship, they sponsor the project. In my mind, every project or every digital initiative needs an executive sponsor, a champion, and a compelling reason why. Now, what happens if we do nothing and who loses their job if it fails? And if those things aren’t in place, oftentimes that’s a signal that leadership isn’t really behind the initiative.

Another symptom that we’ve seen or and experienced over the years is a squishy decision-making. Everything is discussed like a committee with no clear commitment, direction and urgency comes and fits and starts. But over time it feels like commitment waivers and there’s really no bias for action. And again, that’s a sign that leadership may not be fully aligned and onboard. Another one is you have the initiative set, you’re already in process, you’re getting things going, and the leader comes to the table with ideas and experience without a hypothesis to test it’s shiny object syndrome where they’re chasing after ideas. And these ideas and experiments often create churn and delays unless you can get buy-in for performing research early in the project. Big yellow flag that we’ve seen or that we notice is a lack of discussion or healthy debate in meetings or reviews that could be coupled with passive or passive aggressive behavior deferring to others.

Or even worse, the meeting goes silent or the tone changes when a particular person joins the meeting. And that to me is a big red flag that often signals a closed mindset where that person or that team is not open to ideas and they may see themselves as the smartest person in the room. And I would guess that most people that have been working in a company have run into this situation before. And you know what it looks like, what it smells like and what it feels like to be in that place.

And finally, the really big one, I think this one really underlies everything, is misaligned objectives or misaligned incentives. Excuse me. What are the quarterly midyear and annual objectives of the individual, the team leader and upper management? Are they aligned cross-functionally or do they conflict with what you need done for this initiative to be successful? Bottom line, at a personal level, how are you measured to receive your bonus? How is your manager measured to receive their bonus and how is their leadership measured to receive their bonus? Those things, you can put all the training, the frameworks, the workshops, the process in place, but if those things are misaligned, people’s human behavior and their job is really on the line to meet their objectives. So those are just some of the symptoms that we’ve seen. Anything you’d like to add, Mike?

Michael Woo:
Yeah. Gosh, man. When you were going to do that symptoms list, I was agreeing the shiny object syndrome was and is definitely a thing that I saw at almost every single company that I’ve worked for. And truly it was, I recall very demoralizing for the team when it happened because there was a lot of hard work put into doing something, some sort of initiative that was super important at the time only to get deprioritized for what we call pet projects or whatnot. So yeah, that definitely brings back some bad memories there. But the second barrier that I wanted to talk about is our age old enemy silos. It’s ironic, we were just on a call and it felt like we were just talking about silos. I don’t know why, but when I think of silos, I also think of the whole that whack-a-mole game at the, and it’s like no matter how hard you try to prevent them or when you do eliminate them, they just keep popping up everywhere.

So it’s just something that comes in my mind when I think about that. But here are five reasons though, why departmental silos are problematic. They create duplicative work, misalignment across teams, loss of company vision, communication problems, and collectively, when you look at all of those things, a loss of revenue, but there are symptoms that you can look out for and here are some of those top ones. There’s inter departmental conflict. Everyone has done it said some negative comments about how difficult another department is to work with, usually behind closed doors after the meeting or something like that. Then there’s negative customer experience. I think this is often a good measure of silos within our organization because if you think about the customer experience, it is a byproduct of the work of each contributing department. So when you see a fragmented customer experience, it is likely a representation of how things are internally structured.

So that’s a good one. Another is inconsistent marketing. I’ll be the first to admit that it’s very difficult for organizations of any size, but especially larger ones to maintain consistent marketing. But when it comes to a company’s brand, a disconnected look and feel or disconnected messaging across channels, for example, it could be a website, a mobile app, social media can be a telltale sign that silos exist. And lastly, unfamiliar employees. This one is an easy one and also can be an awkward one for those employees who have been around for a while, not knowing basic information about other employees on the same team or teams that you regularly work with, for example, what’s their name or what are their roles can contribute to a lot of problems that were stated earlier.

Craig Nishizaki:
Yeah, that’s a great list of symptoms. It’s interesting too because with silos, just like with any relationship, there’s water under the bridge, there’s resentments that happen, there’s things that have been done. And really, like you said, psychology and human behavior and relationship building is a big piece of that. The third problem we’re going to talk about is people. We love Patrick Lencioni’s model of humble, hungry, and smart as characteristics of great team players for digital businesses. In addition to the character of the individuals, the digital dexterity of each individual directly impacts the team’s effectiveness. Gartner defines digital dexterity as a set of beliefs, mindsets, and behaviors that equip individuals to successfully build and run digital businesses. And Gartner created a four quadrant matrix called the Profile of digital Dexterity based on the CEB 2018 digital dexterity survey of 3,481 employees. And the quadrants cover ambition to build digital business, ambition to work digitally, ability to build digital business and ability to work digitally.

And the most impactful individuals score well in all four areas. The second most impactful individuals make high marks in ambition to work digitally and ambition to build digital businesses. The third most impactful individuals score well in ambition to build digital businesses and ability to build digital businesses. And so as a leader, if you’re assessing individuals on the team or across the organization, there’s five competencies that Gartner references as drivers of digital dexterity. There’s business acumen, adaptability, political savvy fusion collaboration and systems thinking. And for each of ’em, there’s a way to evaluate that individual’s digital dexterity. So for business acumen, the question would be how well does this person demonstrate an awareness of the broader internal and external business context For adaptability, the question would be, how well does this person demonstrate an openness to new and iterative ways of working regarding political savvy? The question would be, how effective is this person in building and influencing stakeholders networks internally and externally? And for fusion collaboration, does this person collaborate effectively with employees with diverse perspectives and experiences? And finally, for systems thinking, the question would be, how well does this person understand the internal and external relationships between technologies and processes? And you can create a simple Likert scale of one to five and rank each person’s aptitude in each of the criteria to evaluate their strengths and weaknesses. And this will really help you understand where the gaps are in your team’s digital dexterity. Mike, any thoughts on this?

Michael Woo:
That was a lot of great information you just drilled off with regards to Patrick Lencioni’s hungry, humble, and smart model, being able to see people through that lens truly has made the hiring process at our agency a whole lot easier. Next up, I want to talk about processes. It’s been said that organizations that have good processes in place save time and increase overall efficiency, and in turn, this can dramatically improve your business by allowing you to make quicker and smarter decisions. That’s pretty obvious, but what if good processes only show up in parts of your organization? So for example, there are a lot of organizations who have development teams that use agile processes, which is great and all, but what if other parts of the organization like product design, marketing are not operating under those same principles? Or conversely, what if your internal UX design team is all in on, say, design thinking and design thinking methodology where the goal is to fail fast by leveraging user insights and it’s your dev team that’s operating at a snail space.

It’s cliché, but everyone needs to be rowing in the same direction, so you can see where the friction is there. Here are some top symptoms that I want to share that we’ve observed when working with other companies. For example, there’s the website team butting heads with the development team constantly about how much effort and time changes or new features take. Remember the reference I said earlier about people saying unsavory things behind closed doors? Yeah, we’ve witnessed those on calls. Another is when project managers assigned to your digital initiatives are absolutely not empowered or given the autonomy across organization to define success for their projects.

That’s basically setting them up for failure. Then there are delays, delays and delays. So for example, delays in getting answers or resources during the early stage of your project. There’s ghosting. After you sent five emails on the same topic over the course of two or three weeks without a response, you start to think all sorts of crazy thoughts like, did something terrible happen? Did the person go on vacation? It just didn’t tell me. Or, Hey, does that person still work? There? All sorts of crazy thoughts like I said. And then there’s the serial rescheduling of meetings, even though, and they should know that with every passing day is another day delayed in the schedule. Then lastly, how often do you experience this? One, you’re about to start an important digital initiative, but there are no business requirements documented in site. If you haven’t experienced this one, good for you, but unfortunately, not everyone is so lucky. So here’s a true story. Craig knows this very well, but I recall a client in the healthcare industry years ago that highlights this very fact. We were brought in to redesign and build an entire member portal, and there wasn’t one aspect of that portal documented, but our team s slowed through it all. Though it wasn’t easy and most definitely wasn’t efficient. The project took so much longer than it should have, and there was a lot of churn, but boy was there a lot literature, something

Michael Woo:
Thank you, sir. By the time the project was in development, I remember that’s when the business or the organization actually brought in a business analyst to start documentation on the whole system. I just think about that and those were just good times. But no, honestly, to summarize, processes that have been created for digital innovation are only effective if they are organization-wide, and if you allow your organization to properly frame the problem, extract requirements, define the product and vision and UX strategy, identify and prioritize features, and ultimately develop a product roadmap.

Craig Nishizaki:
That’s great stuff. Mike. I think the last part, the summary that you gave really is a roadmap for, or a checklist for any product team, business team, et cetera, to think about their process. The process doesn’t have to be rigid, doesn’t have to be overbearing, but you have to have some fundamentals. Framing the problem, extracting or eliciting the requirements, knowing that you may not have all the requirements sussed out a hundred percent, and you need to go through a design process to do that. Defining the product vision and the UX strategy, which then brings leadership into alignment, identifying and prioritizing the features, which allows you to scope and budget and put a timeline to it and then have a roadmap. I mean those, it seems fundamental, but it’s amazing how many times that something in there is missed and it really does slow down the entire project, so that’s great stuff.

Lastly, what we’re going to cover is culture and most of what we’ve talked about already makes up your company’s culture, but what we’re going to focus on here is whether your company or organization is operations minded or innovation minded and operationally minded businesses focus on maximizing productivity and efficiency. They refine rather than revolutionize in general, and innovation businesses zero in on new opportunities in uncharted territory. Big difference is that innovation is inherently wasteful. Innovation demands new processes, collaboration and technology, and for operationally minded individuals and teams that take pride in the way we’ve always done things. You hear that every so often, these changes can seem nonsensical and even threatening, but being operational minded or innovations minded culturally, it’s neither right or wrong. It’s more about knowing if your company is one or the other operations minded or innovations minded to help provide perspective to decisions, investments and initiatives that the company might focus on, and in some cases, a company can be both operations minded and innovations minded.

A great example is one of our clients is a 65-year-old applied architectural products distributor, and they saw an opportunity to grow their value in the supply chain by building a new e-commerce line of business and digitizing their distribution business. They’re excellent operationally. They operate multiple distribution centers and traditionally sell and fulfill wholesale orders to hundreds of retailers in their space. But 10 years ago, they saw that e-commerce was forever changing the supply chain and they made an investment. It was an experiment to build an e-commerce line of business or e-commerce site and the associated business with it, and then they began digitizing their business and they’ve really positioned themselves for the future as a business overarching. They pride themselves in their operational excellence, but the key is that their leaders have a growth mindset and they see technology as an opportunity to grow and change and differentiate. They’re not technologists, so they partnered with outside experts to help them with the technology, the strategy and the build, design and build of it, but they drove the internal strategy and discussion around how does this impact our core business and is it something we need to do now or can we wait?

I would hold them in high regard. In terms of an organization that’s really had to wrestle with the operational mindset and the innovation mindset, and they’ve done just a great job of it. We’re going to close with five steps towards becoming a better digital partner or being more digital ready, and these are pretty fundamental. We would say start at the top. Your organization’s ability to create a successful digital business, digital product or digital project starts with an aligned leadership team. So you need to ensure that your C-suite, the mid-level leaders and the team leaders are aligned on a shared vision for your business’s digital future. You want to assess your organization’s digital readiness, reflect honestly on your team’s strengths and weaknesses to identify gaps in your organization’s digital dexterity. Then set the cultural tone. Communicate an inspirational vision of your business’s digital future, help your employees understand why it matters, what needs to change in order to get there and what you expect from them.

Then walk the walk. Carve out a digital innovation budget that lets your team know that you expect them to pitch digital innovation ideas, but make sure that they frame the ideas with a hypothesis to test solving a problem for our customers or end users, and how to measure the success and failure. That way they’re not just throwing ideas out there that are a waste of money, adopt design thinking or some other method of getting cross-functional teams problem solving together. Then break down silos. Break down the institutional silos that you have. Encourage cross-functional collaboration with an eye to increasing your team’s digital dexterity. Give your IT staff the opportunity to teach their business counterparts about emerging technologies, agile software development processes and requirement solicitation processes, and then have your business team educate your IT team about systems thinking and business objectives. By regularly sharing their insights as individuals and their experiences as individuals, your team will start to develop deeper empathy for one another and learn to collaborate more effectively. And finally, be willing to let your external digital partners take the lead. If you’re working with external digital partners, find opportunities to allow them to take the lead and expect your team to follow the recommendations, requirements and deadlines. The experience of working with seasoned digital experts can push organizations to improve their digital capabilities more quickly than they can do on their own. Any additional thoughts from you, Mike?

Michael Woo:
I think those are great recommendations that you just went through. I think a lot of what we discussed today starts with having the right people in your organization that’s reflective of the culture that you’re trying to achieve or trying to build. Once you get that part right, and yes, it’s not easy, but if you get it right, the systems and the structure part of it will flow from there.

Craig Nishizaki:
Yeah, those are great points, Mike. Great way to wrap up the conversation. Well, that’s it for today’s episode. Thanks for joining us. Join us again 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.

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