Thank you to the 1646 leaders who’ve generously done the 7 questions! I hope reading 7 Questions with
helps you in your leadership.
Name: Matthew Holloway
Title: Global Head of Design
With a career spanning more than 30 years, Matthew has co-founded six start-ups and has held leadership and executive roles at Apple, WebMD, Shutterfly, and SAP. Collaborating across the organization, Matthew helps executive teams fully engage design as a key differentiator, successfully using design to shift the strategic direction and deliver increased market share, improved customer satisfaction, and competitive advantages.
Matthew has also helped design leaders make the shift from creative thinkers to business executives. Many of the designers he has managed and mentored have moved on to executive roles at companies such as SAP, GE, Oracle, Google, Meta, Amazon, Apple, JPMorgan Chase, Nike, etc. In his current role as Global Head of Design for SnapLogic Matthew is responsible for designing integration products and services, including bringing generative AI into the user experience enabling SnapLogic’s customers to unlock the hidden value in their data and application integrations.
Matthew is also a Board Advisor to the Design Executive Council, the world’s first network supporting peer-to-peer learning and professional development for design executives.
1. What have you found most challenging as a leader?
In 1966 Thomas Watson, the legendary CEO of IBM, wrote a memo that opened with the sentence: “Good design is good business”. Fortune 1000 companies represent nearly 60% of the US economy, and $2 trillion in profit, and yet only 5% of those companies have a senior design executive. Even though McKinsey, Forrester, Harvard, and others have shown repeatedly over the last 10-12 years that companies who place design on par with technology and marketing outperform their competition by 200-224% depending on the study.
That means higher ROIs, greater market share, increased competitive advantage, and stronger brand recognition & loyalty—proving Thomas Watson was right. Yet the majority of companies still discount the value design brings to their business. And it’s not like these companies are skeptical about investing in areas they don’t understand. A great example is generative AI–whose long-term value is still very much speculative at this point, but it has caused a massive shift in every one of those F1000’s strategies.
Yet I would venture to guess none of the executives fully understand how it works, or what exactly it will bring to the table. So how is design any different? Design historically was a core differentiation for companies, the shift to digital products shifted the focus to technology, but companies like Apple have shown technology is the most effective when it's incorporated into a design that exceeds the customers expectations, indeed even their imagination for what is possible.
2. How did you become a leader? Can you please briefly tell the story?
I got on a plane.
I was working at a B2B2C start-up during the dot.com boom, we were in the process of acquiring three companies, when we decided to merge with another start-up that was in the process of acquiring a couple companies of their own. There was a big summit meeting planned for the consumer leads from all these companies to define an integration plan. My company's consumer product was in its early stages, there were only two of us leading the effort, but we were not invited. When we learned about this summit, we realized that if no one from our company was going, we’d be shut out moving forward. So we bought a couple plane tickets and flew to Portland (where the meeting was being held).
During the meeting people were talking past each other, focusing on their respective solution but no one was trying to come up with a plan to bring them all together, so I grabbed the white board markers. After capturing all the various business models, the assets, engagement, revenues, etc., on the second day we started turning that into a vision. Brainstorming different portals, products and services we could provide we added potential revenue streams, B2B transactions, etc. By the end of the second day, I had taken over facilitating the meeting and collectively the group created a strawman of a consumer business strategy. The person who had been tapped to be the group’s GM post merger, came up to me at the end of the summit and asked me who I was again? Why was I there? Then she told me she and the CEO had spoken the night before, and I was now the Vice President of Consumer Products and that I would be reporting to her.
I spent the next two years making that whiteboard into reality, working across the organization to build out WebMD’s consumer health portal. Based on our success I went on to take on leadership roles at a range of other companies.
3. How do you structure your work days from waking up to going to sleep?
Given the nature of design, I don’t have a routine schedule. But I prioritize my time based on Customers, Company, Team, and Individuals. It should not come as a surprise that customers come first.
I spent 60% of my time focused on delivering improvements in our products, services, etc. My second priority is the company, helping to deliver new customers, retaining existing customers, gaining market share, etc. My third priority is the team. As any leader will tell you there, your first team are the cross-functional leaders you align with to deliver customer value. Your second team is your own organization, in my case that is the Global Design Team at SnapLogic.
Here I am focused on how it’s set up for success, how it delivers value, and the skills, processes, and tools needed to ensure consistent quality in our execution. Finally there are the individuals. This includes the people I am responsible for developing and managing, as well as myself. Throughout the week there are 1:1 coaching sessions with colleagues and of course my team members. I try to be very supportive of the people on my team and help them grow, develop and reach their goals, professionally and personally.
I apply the same concern to myself, I make sure I give myself time to grow, to learn and develop. Throughout the week I try to make time to connect with other design executives, mentors, peers, etc., outside the company to help keep current on the latest trends. In the evening I enjoy cooking dinner with my husband, entertaining friends, etc. And I wind down trying to do something creative whether it’s writing or painting.
4. What's a recent leadership lesson you've learned for the first time or been reminded of?
The power of humor. Watch Ted Lasso and you can see how a little humor can be a very effective addition to a leader’s toolkit. Oftentimes given our responsibilities, and the expectations placed on us as leaders by everyone from shareholders and investors, to team members and the organization at large, we tend to take ourselves far too seriously. I have found that a little well placed humor, mixed with compassion and active listening, is one of the strongest forms of motivation and team building.
Not to mention it's a great way to reduce stress. Humor is also a great way to convey optimism, and it helps people let down their guard and open themselves up to exploring new perspectives. Nothing reassures people that you really do treat failures as opportunities than finding a way to laugh about it together. Let’s face it, we are meant to enjoy life, so have a little fun.
5. What's one book that has had a profound impact on your leadership so far? Can you please briefly tell the story of how that book impacted your leadership?
Would it be wrong to say Machiavelli? I know it’s got a bad wrap, but if you apply it for good and not for evil he has some great insights. (see humor above). My copies of “Crucial Conversations”, by Grenny, Patterson, and McMillan, and “Five dysfunctions of a team”, by Lencioni are ear-marked and worn. But if I had to pick one book that had the biggest influence on me, I think it could be “Design for the real world”, by Victor Papanek. Papanek’s vision was far ahead of his time.
He championed things like sustainability, accessibility, and even open-source decades before any of those things became mainstream. He also championed socially and morally focused design principles–making ethics a part of the discussion for every product. He also introduced his idea of telesis, which is recognizing there is a relationship between a thing and the time and place it was created. Which on the surface seems self-evident, but Papanek doesn’t limit the definition of “things” to products, he also includes economic and organizational models, manufacturing processes, even labor practices and business policies.
And when you consider that we tend to hold on to things that are familiar and predictable even after they are shown to be out of sync with the current time and place, it puts a new perspective on our need to iterate and make commitments to improving. And that we should be obligated to put our greatest effort into planning things that have the longest telesic life span. The book provides a great framework for giving ourselves permission to evolve. One other book I will give a shout out to is “Stolen Focus'', by Johann Hari. It’s a deep dive in the impact that social media and mobile devices have had on our ability to focus, to get into a flow state. He interviewed dozens of neurologists, psychologists and data engineers, etc. It is frankly a wake-up call. I deleted my Facebook account half-way through the book.
6. If you could only give one piece of advice to a young leader, what would you say to them?
Learning to let go, to empower the people on your team is one of the hardest things for new leaders. But you need to give people space to do their jobs, you have to trust them to deliver. Yes, they will do it differently than you would have done it, and that’s OK. The secret to letting go, is to first believe in yourself.
Which includes believing you hired the best people you could; that they are smarter than you, more creative than you, and that they can do the work you used to do better than you did it. And second, that requires you to support them, listen to them, and turn their failures into learning opportunities, not take it over, or re-do it. Letting go is the critical first step in allowing yourself to focus on what you should be paying attention to: the big picture, strategy, value inception, organizational alignment, etc.
7. What is one meaningful story that comes to mind from your time as a leader, so far?
When I was at SAP my team was called a “design” team, but our role wasn’t to design things like UI’s, rather we were tasked with re-designing how SAP conceptualized and built solutions. I reported to Hasso Plattner, SAP’s Chairman and co-founder. He was friends with David Kelley from IDEO and while David had not yet talked Hasso into funding Stanford’s d-school, Hasso was already a huge believer in design thinking. He established my team to embed design thinking throughout SAP in order to adopt a customer-centric, design-led approach to innovation. However, the other executives at SAP had their doubts, among them Henning Kagermann, then CEO of SAP.
So our first challenge was to prove design thinking worked. We selected two initial projects that were priorities for Henning. The first one focused on our internal HR Performance and Compensation, and the second one on the integration of 3rd party analytics in our business suite. When I was asked to give Henning an update on our progress, I started by presenting the HR project. He was initially confused that the team had not redesigned a new user experience for our HR tools. I explained that while we could redesign the UX, the more pressing issue was to get alignment between the different global divisions’ methods of assessing performance and various regional compensation models. So we worked with HR leadership to redesign their policies.
He was still confused but impressed with the results–especially that we got the global HR leadership to collaborate on the new policies. Our work on 3rd party analytics had a similar story arc: it started out exploring how we could better utilize the services provided by the vendors but it quickly became apparent there was a bottleneck in how the contracts were structured. So my team worked with our legal team to redesign the contracts, resulting in an immediate cost savings of $6 million per quarter. That really got Henning’s attention. After I finished, Henning sat back and looked at the artifacts I had brought–the HR policies and the new contracts.
And then he looked at me, and said, you designed a policy, and you designed a contract? But you are a designer not a lawyer. I explained that everything is designed–whether its contracts and policies, or products and interfaces, even organizations and financial models. And that design is simply the intentional arrangement of elements to create the desired outcome. I pointed out the real question he should be asking is how we designed them. That led to a long discussion about the nature of design, design thinking, and how SAP could benefit from making it part of the company’s DNA. From that moment on Henning was our biggest supporter. By showing him the artifacts, demonstrating the value, and explaining how he could make it predictable, he understood that the potential of design was far more than fonts and colors.