Secrets to Winning Over Stakeholders and Navigating Leadership Challenges

Slava Shestopalov is a design leader with over a decade of diverse design experience. He describes himself as someone who thrives on forging connections between different fields of knowledge rather than confining himself to one specialty. His key areas of interest revolve around user experience, design workshops, enterprise and B2B solutions, and accessibility. Slava works at Wolters Kluwer, where he leads the design team of Enablon, an enterprise platform dedicated to fostering sustainability and ensuring workplace safety. 

We had a fascinating conversation with Slava, where he shared valuable insights on communicating the value of design to non-design stakeholders, essential skills for a design manager to develop, and addressing significant challenges faced as a leader in product design.

How do you communicate the value of design to non-design stakeholders within an organization?

As a subscriber of Andy Budd (Product Advisor and Venture Partner at Seedcamp), I recall a short essay named “Why executives don't want you involved” by him. The main idea is that, in order to make business decisions, it’s essential to keep the group involved as compact as possible. Adding new voices, no matter how insightful, can often lead to delays. Thus, if designers are perceived as merely another voice in the mix, their contributions may not be fully recognized. So, how can designers transcend this perception and showcase their value in a way that resonates with stakeholders?

The most effective way to communicate value is through incremental delivery instead of promising it or asking for permission to act. Demonstrating tangible results provides proof of concept, paving the way for greater value in the future. In leadership roles, it’s crucial to empower every member of the design team to communicate the value they contribute. While some may feel uneasy about speaking up, it’s an integral aspect of the job. Investing a bit of discomfort for the sake of enhancing collaboration and achieving better results is well worth it in the long run.

Establishing a platform where designers can regularly showcase their work is crucial. Rather than sharing finished projects internally, in the designer team, designers will benefit more from critique sessions about their work-in-progress. On the contrary, showcasing finished case studies with tangible results and metrics to a broader, non-design audience is essential to highlight the outcomes of design efforts.

Furthermore, design workshops serve as a powerful avenue for both contribution and facilitation. They go beyond merely expressing opinions; workshops enable individuals to collaborate, align perspectives, and collectively develop ideas or concepts that are stronger than any single contribution. By engaging in such activities, teams effectively communicate the value of design while fostering collaboration and growth.

What are the most important skills for a design leader to develop?

You’ve hit on a crucial point! Many of us in design leadership roles, like myself, started out as hands-on designers. While we are good at the design stuff, becoming great leaders doesn’t come to us naturally. We need structured training to develop those skills, rather than learning from our mistakes the hard way.

This issue is especially tough in fast-growing companies, for example, those that boomed during the COVID-19 pandemic. They were so focused on growing quickly in the favorable market conditions that they didn’t have time to properly train their middle management. Now they’re facing a “leadership debt” because of it.

What’s really important is strategic and people skills. It’s all about working well with business (design quality, UX impact on the final outcome, team performance, etc.) and other designers (giving guidance and support, seeing things from their perspective, enabling their professional growth, etc.). It’s not just about the design itself; it’s about the people daily doing the design. And getting good at it takes a lot of effort.

Can you share a success story where design thinking significantly impacted a business decision or strategy?

That’s a great question, but before I dive into an example, let’s clarify what design thinking is. It’s basically one of those frameworks that put the user in the center, in other words, focusing on the real pain points and needs of real people. But it’s also about getting everyone involved, like having workshops with different folks who have a stake in the game. Now, since we’re talking about design leadership here, I’ll share a story about how we applied this approach not to a digital product, but to managing the team.

Let’s talk about performance management, which is a big deal in any large company. How do you ensure that your designers are really adding value to the business? How do you prove to yourself and others that your team is doing a solid job and contributing to the company's success?

When performance management is not set up correctly, it’s essential to put team members in the center because they are the “users” in this case and explore what's going on with designers: what projects they participate in, what they think the value they deliver is. Besides, we involved product and engineering leadership.

Instead of coming up with a perfect concept of something in the silo and then presenting it to others and facing criticism, it’s important not to forget about design fundamentals, i.e., conduct research and involve people from the start to figure out contradictions in their opinions and together with them co-create a proper solution, test it, have checkpoints and see if it works.

In my situation, it was about building a new performance management system, setting goals, and measuring the value designers bring to the table, and communicating that value to others.

What are some of the most significant challenges you face as a leader in product design, and how do you address them?

One of the toughest challenges I face as a design leader is the constant feeling of falling short or underperforming. The nature of the job is volatile, with things shifting and changing rapidly. For example, yesterday, you were thinking about retaining a valuable employee and discussing different plans for how to make it work, and today, something rapidly changed, and all your work was in vain because this person just talked with someone from the team and was involved in another project, and it was interesting enough for them to stay.

There are lots of other things. You can spend half a week discussing how to find capacity in your team for an urgent ad hoc project, and then after half of the week or two weeks of discussions, it turns out that it was not urgent at all.

What I find the most challenging and can’t be easily solved is the constant feeling of underperforming or falling short of stable ground. A manager’s work depends on other people, and nothing is less predictable and complex than that. This challenge makes work attractive and interesting because you discover something new daily. Still, at the same time, it’s a lot of responsibility and unclarity that doesn’t disappear over time.

What do you do about that?

There are different ways to verify your position.

In UX research, there is an approach called triangulation. When you want to ensure that a specific UX insight is accurate enough and is not biased or false positive, apply three different UX research methods to the same topic. For example, if the survey shows you something, user interviews confirm it, and usability testing demonstrates precisely the same thing, so you can ensure this is what really happens. Then, you can act more confidently that you’re solving the right user problem.

The same thing applies to managerial performance: if I need clarity on where I stand and if that is good enough, I can check it with different stakeholders in various ways.

Slava will be on the stage at the Refresh Conference on April 11 at 10:05 AM. Buy a ticket to hear more about his thoughts!