Name: Matthew Holloway

Title: Vice President, Global Head of Design

Organisation: SnapLogic

I have spent my career transforming companies into human-centric businesses. I have held executive roles in both consumer and enterprise companies, including Apple, Shutterfly, WebMD, and SAP, building high-performance product design teams. I have also co-founded a number of start-up companies leveraging ML & AI to create agentic solutions for improving collaborative business processes.

I am currently a board advisor to two start-ups, including the Design Executive Council, an executive leadership community for design. And I serve on The Ohio State University, Department of Design’s Advisory Board.

Thank you to the 2,000 leaders who’ve generously done the 7 Questions on Leadership!

We’ve gone through the interviews and asked the best of the best to come back and answer 7 MORE Questions on Leadership.

I hope Matthew's answers will encourage you in your leadership journey. Enjoy!

Cheers,

Jonno White

1. As a leader, how do you build trust with employees, customers and other stakeholders?

Listen to them. Respect both the people and their ideas. And demonstrate lived integrity. That means do what you commit to doing, and for those things you choose not to act on, provide clear explanations of your position. And again listen. It's about making sure the values you talk about are the same values that you demonstrate in your daily actions.

Too often, people frame trust as being 1:1, but in reality, it’s a community, a network, it’s your reputation. You are more likely to trust someone you just met if they come with a recommendation from someone you already know and trust. Likewise, if you burn a bridge with a colleague or customer, the people who trust them will be less likely to trust you.

2. What do 'VISION' and 'MISSION' mean to you? And what does it actually look like to use them in real-world business?

Vision and Mission are probably two of the most overly subscribed words in business. Most often, I view them as what you are going to achieve—the vision. The future state of the organization, or for many start-ups it's the future state of the world (every start-up expects to at least change the world, right?) And the mission focuses on how you are going to achieve it. The day-to-day business activities you need to focus on to be successful.

However, to be honest, in my experience, too often companies conflate the two and spend far too much time debating what goes into the vision vs the mission. Which is why I prefer to replace the mission statement with OKRs; they are more tangible, immediate, and actionable. By their very nature, they achieve the day-to-day part of the “mission" but with greater clarity while allowing for the people who are doing the work to respond to changes in the market.

3. How can a leader empower the people they're leading?

It depends on the people. You start by listening to them—this goes back to building trust. You want to make sure you’re on the same page about what everyone is expecting. Some people only need to be pointed in the right direction, others don’t even need that; they just know what needs to be done. While still other people may need more mentoring and encouragement, they might even need guardrails.

The one thing all these people have in common is the need for them to share a set of clear and commonly understood expectations with their leaders. Again, going back to trust and integrity. Empowerment really relies on everyone having a well-aligned set of expectations.

4. Who are some of the coaches or mentors in your life who have had a positive influence on your leadership? Can you please tell a meaningful story about one of them?

I have been very lucky to have been able to work with a great set of mentors over my career. My first mentor, Liz Sanders, encouraged me to go to grad school to study cognitive systems engineering, which not only changed my career but literally changed my life. Every place I have worked, I have benefited from mentors: Don Norman at Apple, Lori Neumann and Mike McCue at Netscape. Mike Tschudy and Ishantha Lokuge at WebMD…

All of these people have shifted my perspective and expanded my understanding of what it means to design and to lead design. While I was at SAP, I was fortunate to be in a leadership development program that included executive coaches, presentation training, etc. I was fortunate to work with David Gerard as my executive coach. It was a great experience.

Given my role at SAP, one insight that had a profound impact was working with David to develop a different point of view regarding politics; I had always seen them as bad, but David helped me understand that politics are just the reality of people working together. He provided me with frameworks to model the politics and change zero-sum scenarios into win-win scenarios. That shift opened so many doors for my team, allowing us to really deliver on our charter.

5. Leadership is often more about what you DON'T do. How do you maintain focus in your role?

Well, if you have built trust within the team, set out a clear vision that everyone is aligned with, and have empowered your teams to develop both their OKRs and the solutions to achieve them, then it's easy to maintain focus. If you design your team and your organization well, then you should have no problem focusing on what matters: mentoring the people on your team as needed, working with your customers, and partners. Laying the groundwork for the growth of the business.

6. If you fail to plan, you plan to fail. Everyone plans differently. How do you plan for the week, month and years ahead in your role?

It starts by delegating effectively: I am a strong believer in delegating so I can focus on the high-impact activities that I am best suited to deliver.

For the week, I spend an hour on Friday afternoon identifying 3–5 priorities based on long-term goals to focus on for the following week. I also maintain time blocks on my calendar to ensure I have time to work on those 3-5 priorities. I also make time for strategic thinking/writing, team meetings, 1:1s with my team, peers, manager, skip levels, etc. It’s also important to make time for some self-reflection at the end of the week; did you get done what you wanted to get done? etc.

For the month, I look at the long-term projects and break them into monthly milestones, so the team has clear expectations, measurable targets. Along with that, I assess the team performance, both for my directs and the teams they are on. (I view management as a collective actively regardless of disciplines—it takes a village to ship.) This helps streamline any requests for increasing headcount and capacity planning in advance of the annual company-wide planning. I also plan out time with key stakeholders (i.e., customers, partners, or industry peers. I will also identify one area for my personal development and continued education. I sponsor our company book club to ensure everyone is also growing. And of course, working with peers from Product, Marketing, Sales, and Engineering, we will do regular reassessments of our strategies, metrics, etc,. relative to the market and competitors.

For the annual: I start by analyzing my team's OKRs from the previous year, what worked and what didn’t. This helps me prepare for the larger cross-functional planning and corporate objectives. Once we have the updated company-wide plan, I circle back with my team to focus on roadmaps, priorities, capacity needs, development, etc. Of course, throughout the year, you will need to work on contingency plans as things shift. Again, this all requires a strong focus on building and maintaining trust, respect, empowerment, etc. throughout the year.

7. What advice would you give to a young leader who is struggling to delegate effectively?

This is a much larger conversation than a single question. I would encourage them to reflect on a time when they have felt the most empowered. It was likely when someone delegated a critical project to them and they were asked to run with it. I would ask them what they had done to gain that trust. To have someone believe in them enough to be given responsibility for a critical project? And I would ask them about how the project went. Did they and their manager have check-ins? Were there Milestones? Feedback and mentoring? Then I would flip it around and ask them what are they doing to recreate that same situation for the people on their team? How are they helping their people get ready to take on those types of responsibilities? And to ensure their success when they do.

If the leader I am working with does not feel that they can trust the people on their team to do the work, they are doing something wrong as a manager, and we explore that. They likely need to focus on developing their people, setting better expectations, or hiring more competent staff. There is clearly work to be done to build that trust. However, if it turns out that the leader simply wants to do the work themselves (rather than doing the work they need to do—leading their team), that begs the question: why are you a manager? And we explore if they are really happy leading teams, or if they feel that is simply what is expected to move forward in their career.