From 0 to 365: My First Year as a Design Executive

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As I think about my career in User Experience and Design, much of it has unfolded in an organic way rather than following a detailed career plan. I have always kept my eyes open for the next engaging and interesting career opportunity that would offer a challenge and something new, but never had a prescribed notion of what each step would be. As I sat in my last role as a director of user experience, I did not have focused ambitions of joining the executive ranks. I never ruled it out, but it was not by mission—then opportunity came knocking.

Approached by an executive recruiter regarding a vice president position at a well established and growing company with interesting technology I suddenly found myself asking…is this something I am interested in pursuing? How would it differ from my current role? What are the upsides? What are the risks? Would it nurture me? Overwhelm me? Take my career down a different path?

Assessing the Opportunity

Assessing my job opportunity was a two-way process. Of course, the company wanted to evaluate me, but was this the right opportunity for me? I tend not to be someone who hops from job to job. I don’t jump in and then determine if it is the right place. I wanted to learn as much as I could up front. So that is how I approached the opportunity.

Before the Interview

I asked myself, “Is this a company that is of interest to me?” Different things drive different people. Sure a VP job would bring a salary increase and a fancy title with nice perks, but is this a company that I want to work for? I looked at the company performance financially and examined its products. Are these products that I believe in? Will they keep me engaged? The corporate site and related websites piqued my interest. I spoke with the recruiter to get a sense of why they were hiring for this role. In this case it was a new role and a new initiative within the company. It was an opportunity to build a centralized team from the ground up. I was curious, but not sold.

During the Interview

My research having proved promising, I was ready to move forward—this is where the dance began. The interview process gave me my first insight into the true importance of the role within the company. I expected a lengthy interview process with people with a variety of roles and different levels within the company, and this proved to be the case. If there was not such a gauntlet, that would be a red flag. I was vetting the company very closely and I expected them to do the same.

Who I Met

Who you interview with is very telling. Because this was an executive position I expected to interview with other executives. Getting a sense for what the leaders within the company think of design was essential. I wanted to understand: Do they understand the need for the role I would be in? What is their current understanding of design? Will they support and champion my initiatives to incorporate design into the process if I join the team? Will they just pay lip service to design or really work with me to integrate it into the process?

Meeting with the executive I would report to was the most important meeting. I knew that research says that the most significant factor that keeps people in their jobs is their boss. Is this someone I would want to work for? In this case it was apparent that he was a great champion of design and understood the critical role it plays within the organization. If he could not articulate this, I would have been nervous. The success of this new design organization’s success would hinge on this person’s commitment to design. He clearly understood that it was not an easy role and was dedicated to fighting the fight with me as needed. At this stage, my thoughts on the job moved from curiosity to an actual interest in the position. Maybe this is a job I am interested in.

Conveying My Value

Obviously, the interview process was not solely designed for my benefit. The majority of the questions came my way. My plan was to focus on specific examples around

  • proven results and design innovation (I gave examples showing the before and after effects),
  • design as a key factor in the business (customers choose us over the competitors for our ease of use),
  • leadership style and philosophies (my strong belief in hiring A+ players and fostering transparency and open communication), and
  • organization leadership and process transformation (I highlighted my involvement in my company’s rollout of Agile and 508 compliance).

I focused on the business and strategy with supporting examples as much as possible. I knew the people I interviewed with were not likely interested in the minutia of user centered design. I specifically stayed out of the details as this was not what was expected in an executive. I tried to present myself as what I thought a VP was—interested in the business and the big picture.

Making the Decision

I survived the interview process and emerged as a candidate for the job. Believe it or not, when I received the call I was thrilled and horrified all at the same time. These discussions were all hypothetical until now, but now I had to make a decision. Did I want this job? I loved my current job, but did I really want to leave it behind? Did I want the responsibility of a VP role?

It was incredibly helpful to chat with others in executive user experience roles to understand the reality of their worlds. In doing this I got beyond the job description and gained new perspective into the day-to-day. I knew this role would be more strategic…but what does that really mean? Hearing other people’s experiences was invaluable. I also spoke to people who held executive positions in past lives, but decided it was not for them and those who had consciously avoided that career path. In most cases it was because they preferred to be closer to the work or because the increased stress and commitment was something they did not want to commit to. The clear message was that as an executive of design (or any other area) you are accountable and you have to be ready for the good and bad that can come with that. I would likely be working more hours a week, and I might be traveling more than I had in the past.

At the end of the day, I collected as much data as I could, but then I had to ask myself two important questions:

  • Is this company ready for the role of VP of user experience, and do they understand what it takes to make the VP successful? Hiring an all-star user experience executive is not a quick solution to product success. It is a journey that requires support from the organization (top down and bottom up)
  • Do I want to work there? Am I inspired by the people and products? If my answer was no, but I was still considering the job, I knew I should take a closer look at my motivations.

In my situation, the answer to both questions was yes. I was being hired for a brand new role. The company recognized that they were not giving design the attention it required and decided to start by hiring someone to build a centralized team and integrate design into the development process. They intentionally made it an executive role, because they believed that design needed a high level of visibility within the company. After interviewing with numerous executives and the CEO, I believed that they were committed to the initiative and they recognized that the road to great products would be a journey that requires long-term commitment, as opposed to something that would happen overnight. I also sensed that they were excited by the initiative and potential for change. I felt a connection with the person who would be my boss. He was someone that I could learn from and that is something that I valued. I thought about where I was in my current role and company (a job and team which I loved) and realized that this opportunity provided me with something that my current position would not provide—a more complex suite of products, a global development team, and increased executive visibility for design. I acknowledged that for at least the first year I would be handing my life over to this job, but the combination of great products, organizational support, a set of new challenges, and career advancement made the opportunity too good to refuse.

I Took the Job!

Congratulations…I think. I am now a user experience executive! What now? A new job is always overwhelming. For me it was important to create a distinction between the first 90-days and the longer term. This is the duration of a quarter so it felt reasonable to propose that I would spend the first quarter listening and learning. It is impossible to be effective on day one without having any understanding of the company, people, and process.

The First 90-Days

As I started to think about my first day, my mind overflowed with great ideas of how I would add value and the changes I would make. I had to resist the temptation to jump in and drive change. Each organization is unique and although I may have had great success in past user experience leadership roles by using a particular strategy, there is no one size fits all. That is why I knew it would be critical for me to spend the first 90-days focusing on other things such as

  • defining the mission and success criteria for my role,
  • absorbing and learning,
  • meeting and greeting, and
  • planning for hiring.

Define the Mission and Success Criteria

My mission and success criteria were relatively high-level on day one as I had much to learn. But having a discussion with my boss about what I envisioned and what he envisioned was very helpful. It was important to get alignment before I dove into initiatives. For example, we discussed the overall goal of creating an exceptional user experience of products. Short-term that would mean getting up-to-speed in 90 days, starting to hire top talent, beginning to educate teams about user experience and design, etc. Because I did my due diligence before taking the job, there were no big surprises on either side. I also discussed the specifics of my 90-day plan, asked for input, and arranged to check in as my discoveries unfolded. I wanted to establish a good open working relationship and raise both great discoveries and concerns early on. This was a role with high visibility so I knew that setting expectations with my boss was of great importance.

Absorb and Learn

I had entered a new product space. I needed to invest time in understanding and using these products. I needed to find out who the users were. Are there target industries? What is the product strategy moving forward? Many companies offer intensive product classes. I regret that I did not take one. As I had the luxury of time in the first weeks, I attended endless product and customer meetings. I made sure to introduce myself and let people know that I was new and participating in the meeting to absorb and learn. I wanted to make this statement so people would not think, “Wow, she is quiet.” My role was to be an active listener. I was often tempted to jump in with my opinions, but did my best to refrain. It was often hard to be silent.

I was lucky that my company has an executive briefing center. This was a great opportunity to hear the company pitch, see demos and hear customer questions. Definitely a treasure I often took advantage of. I was not going to be doing design work in my role, but at the end of the day I was the one on the line for creating great product experiences. I knew I could not do this without first understanding the products themselves.

Meet and Greet

I spent as much time as I could meeting people throughout the company, because I knew I could not expect people to find me. There was a small team of user experience resources for a specific product line (not initially reporting to me), so I started with them. I wanted their assessment of the current situation…people, products, process, and politics. I asked them to be candid and tell me what was working and areas that needed improvement.

I also met with leaders of product management to understand their concerns and how they would like to work with user experience. How could the design team support them in their efforts? I asked lots of questions with the goal of learning as much as I could about their world and how user experience can support or partner with them. The overwhelming response was enthusiasm. I repeatedly heard, “We are so glad you are here.” But the follow-on statement was often, “You have a tough job ahead of you.” I actually thought this was a good thing. This meant that they realized that great design does not just happen by putting someone in my role.

As an executive, it was also important to meet executives from other divisions. I spent time with executives in sales, HR, finance, support, and other areas. It was essential for them to know that the company was investing in user experience. I knew in the near future I would be making requests for items like budget and headcount. I wanted other parts of the organization to be aware of why the company and I were investing in this effort as, ultimately, I would be asking for funds that could be going to other parts of the business. These leaders were also responsible for teams that I knew I needed as allies for usage data, customer access, dollars, recruiting support, etc. The earlier I gained allies the better. People were curious about my role. Many had never worked with an executive in charge of design and wanted to learn about my mission. With this audience I made sure to avoid jargon and the details of user-centered design. I tried to bring everything back to the value to the business and not just the value design would add to the products.

I took the extra time to meet everyone in person. I felt it was important to demonstrate the importance of these meetings by taking the time to travel. I believed it would make for a much better and more memorable discussion if done in person. Lastly, by visiting offices in other locations I was able to get a better sense of the culture and how it varied from location to location. This was a surprise to me and an important insight I would not have gained if I only met people over the phone.

Plan for Hiring

I had the luxury of a budget for hiring, and I knew that I needed to start thinking about it immediately. We all know that hiring user experience talent takes time in the best of situations. It was an incredibly competitive market and the talent pool was small. I was entering an organization where they had limited experience hiring this kind of talent. I needed to work with recruiters to write job descriptions and educate them on the kind of people I was seeking, their skills and where to find them. I met with recruiting in my first two weeks and then held weekly meetings. Even with this level of investment it took 4 months before my first hire. This was a combination of the newness of this type of hire for recruiting and the competitive landscape. My first hire had to be very experienced and those individuals were in high demand.


I made sure to write up my 90-day findings. Who I met with and what I learned from them. I shared my findings broadly. I made sure to send a copy of my findings to all those I met and my boss. I believed that it demonstrated that I took the discussions seriously. In the first 90-days of a new job you have the luxury to question everything and I did. In an executive role, you are considered leadership within the company and as a result it is important to provide feedback on all aspects of the business that you encounter. It was particularly important to highlight challenges that I foresaw. For example, there was great interest in the new user experience initiative and it was going to be a challenge to handle the demand. Understanding the business priorities would be key as we hired and assigned resources. It was important to relay this finding to my boss and others. At the end of the 90-days I was feeling both tired and exhilarated. I had traveled the globe, met literally hundreds of people, and had received great enthusiasm and support for the new user experience effort.

No Longer a Newbie

My 90-day newbie time rapidly expired, and it was now time to dig in and start to do what I was hired for. By this time I was able to develop some relationships and establish trust and credibility with key players. The following sections discuss some things that I primarily focused on in my post-90-day world.

Focus and Prioritize

I knew I could not attempt to boil the ocean, by doing so I would accomplish little. I had to focus on a subset of key initiatives where I saw momentum and align myself with those. It was important to chat with key product stakeholders and my boss to prioritize. I could not do this in a vacuum. Factors that contributed to my decision included products that were strategic, new initiatives, and teams that wanted to engage. I had to get some wins sooner rather than later. I focused on the areas where I was confident I could have an impact. In particular, there were two high-profile projects being lead by general managers who were seeking design support. Seemed like a good place to start. I would not be doing myself any favors by choosing a subset of high-risk complex problems early on.

Hire the Best and Brightest Talent

As I mentioned this was something that I started within the first 90-days, but I believe it must be a top priority always. Whether you are building a new user experience team or expanding an existing one, your hires are critical. As an executive or manager, I strongly believe that hiring is one of your most important roles. It was tempting to just fill open requisitions, but that was a strategy I knew I would regret. I did not anticipate how much of my time this would take. I was an individual contributor for my first several months. As a team of one, the majority of the hiring and interviewing burden was on me. I had hours dedicated to this each week.

New Role and New Responsibilities

Many of these long-term initiatives just discussed are relevant regardless of level. The following sections discuss some aspects of my current position that distinctly stand out as I compare my past role as a Director to my current role as a VP.


Suddenly when you have VP in front of your title your level of accountability increases. The buck stops with you and if your mission fails you have to step up and take accountability. As a result, this was why when interviewing I strongly focused on making sure the business was really ready for a VP of Product Design. If they were not, I knew that I may end up being a scapegoat. In this case, I had the needed organizational support and was committed to the effort, so the position had proved to be incredibly rewarding. I have been granted a level of empowerment to make the right decisions, and I am expected to dive in and go as opposed to wait to receive orders. As someone who loves crafting a vision and bringing it to reality while maneuvering the realities of politics and pressure, I have derived great satisfaction from my role.

CEO Engagement

I am very fortunate to have direct communication with the CEO of our organization. This is a very powerful asset. He recognizes the importance of the design initiative and contributes top-down support. For example, he has taken the time to create personal videos about the importance of design that I have shared with the development organizations. He discusses design at executive management and board meetings. Truly, he is an evangelist for user experience. Having him sell the importance of the mission is invaluable. He has created massive awareness. I also have regular meetings and reviews with our CEO. I use my time with him to focus on results and impact. Timing is always key. I do not want to highlight projects and declare victory too early, and I also do not want to inundate him with the details of design work, because he is concerned with the big picture, not details.

Justify Existence

In a world where everyone is competing for resources and dollars, I needed to show my value and impact. I had to create awareness around design successes, not just to the product team executives, but to the other areas of the business. The people who spent time with me in my first 90-days are the people that I have frequent touch-points with. I can’t expect people to proactively find out what is happening in the design world; I have to push the message. This means my life is meetings. All those projects that I loved being hands-on with…forget it. I quickly learned that I did not have time in my calendar and that I would be a bottleneck for the teams. There is no doubt that this is a clear distinction in the role. I spend much of my time selling, educating, reviewing, but for the most part, I am not involved with the details. I do wish I had more available time in my day, even just to read email, but that is not going to happen. Even though I sometimes miss being on a team and delivering a product, I get greater satisfaction from seeing the design team succeed as a whole. The key take away is that if you love both, I am afraid you cannot have your cake and eat it too.

I have had to find ways to make it easy for individuals, executives, and anyone within the organization to understand what the design team is working on and our progress. Our team created a user experience vision statement with strategic goals and I have shared it broadly. Design is visual. It is important to show the advancements the team is making. We show how the products are improving. I hold a weekly design showcase meeting to highlight work and progress and have quarterly one-on-ones with key executives. I also travel a lot. Again, face time is very important. I find myself on the road about once a month. I actually, just committed to increasing my travel to this level because of the importance of the personal connection.

Executive Education

This is beyond just sharing the roadmap and successes. I have to get executives to understand why the business is investing in this initiative. I share articles on design with our executive distribution list. More and more of these kinds of design articles are targeted at executives in publications like Harvard Business Review, Business Week, and The New York Times. These kinds of articles bring credibility to the design story. Also there have been a surge of books in the past several years focused on design and business. A couple of my current favorites are Do You Matter and The Design of Business. When I find one I like, I buy it and distribute copies. Also there are specific design classes targeted towards executives. For example, Stanford offers a class specifically targeted for executives on Customer Innovation. This month two general managers and I will be attending such a class. A full week of their time dedicated to design—a significant commitment on their part.

In Summary…

As I reflect on my transition to the role of VP of Product Design, I know that for me, personally, it was an excellent decision. I definitely felt at the time that taking the job was somewhat of a risk as I was leaving behind a world I knew and found very rewarding, but I was ready for the next challenge in my career. I was very fortunate that I landed in an organization that fully supports the initiatives of the design team from the individual engineer to the CEO. I am rewarded by the increased responsibility and challenges that I face on a daily basis. I enjoy the increased accountability and visibility. I have learned a tremendous amount from the insight I have gained into a variety of aspects of the business that the position affords. The hours are long and there is always a fire drill or two, but I have learned to take it in stride. Seeing the growing impact that the design organization is having on the business makes all the hard work worthwhile. This is very fulfilling for me both professionally and personally.