The highs and lows of making yourself obsolete, and why so few managers do it.

I’ve been a people manager for over 10 years, but it’s only in the more recent roles I’ve held that I’ve approached team management with the explicit goal of making myself obsolete. If I’m honest, prior to that my focus was largely about earning more scope and responsibility personally. As a person who has recently joined a new company, and gone through the journey of making myself obsolete in my prior role, I thought I would share my experiences: the joys, the sorrows, and why I feel the process is so fulfilling.

What is the process of making yourself obsolete?

Building the product

As a design leader, the process of making myself obsolete starts with ensuring that the product we are working on is compelling enough that the best designers will want to work on it. At Intuit I worked with the small business design team to redesign QuickBooks. At Asana I spent the first year of my time there working on a product redesign and rebrand. In both cases the goal was to create a better experience for customers and results for the business, but I was also looking to create a design language that the best designers would want to work in. It’s hard to build a high performing team if the product you are working on doesn’t draw the best talent.

Building the team

At Asana there were times when I spent up to 50% of my time in recruiting based activities. I love the process of finding designers in the world who have the skills I’m looking for. I searched dribbble for designers with the skills I admired and reached out to them personally, telling them specifically what I saw in them. I spent time connecting with the design community at speaking events & conferences. I made a point to have coffee meetings at least once a week (and often much more) with people in my network who might be a fit, or lead me to someone who was. I approached every meeting with the mindset that I had just as much to learn from them as they from me, which helped me learn a lot about what designers are looking for in a company, team, and manager.

In the months following the redesign, we tripled the size of the design team but we were very thoughtful and careful about who we hired. I wanted to make sure that we had a diversity of perspectives and range of skills, but that each member of our team had a shared sense of egolessness & camaraderie. We hired generalist designers to partner with PM and marketing partners. We also hired specialists like illustrators, motion graphics designers, and UI engineers. They work across the product to make things consistent end-to-end.

As a manager, when you find these talented people you really come to love them. I don’t use that word lightly. These are people who have the exact same purpose and passion in life as you do. They understand you in a way that your friends, family, even spouse can’t because they do the exact same work you choose to do out of all the jobs on the planet. Together you debate the minutia of various design decisions and care about every detail. As a manager you are responsible for their effectiveness and happiness, so you get very close. In most cases you are hiring people whose level of craft exceeds your own, so your level of respect and appreciation is very high.

How do you mentor toward obsolescence?

Eventually as the team grows it becomes important to add more managers to the team. When some of the designers took on manager responsibilities at Asana, we went through an in-depth process of defining our roles and responsibilities. It was a challenging time in some ways, with some difficult discussions, but it was important to clarify roles for ourselves and the extended team. My goal was to give each manager enough scope to be challenged, and to keep adding more responsibilities as they built confidence in existing ones.

I look for managers who are thinking more in terms of team happiness than personal happiness. These are people who don’t hesitate to give away the best design projects and take on the tasks that no one else really wants to do. I look for effectiveness in simplifying processes and fostering a sense of teamwork. I look for people who can motivate and make people feel secure during times of ambiguity.

Throughout my last year at Asana, I kept giving away responsibility to the point where I was more of a whitespace leader, available for questions as needed. Each thing I gave away was hard for two reasons: first, I’m giving away responsibilities that bring me joy personally, and second, it feels really uncomfortable to me to be less busy. I struggle with internal doubts around whether I’m truly adding value, but as a manager, is there anything more important than empowering the leaders you are mentoring?

I was open with my directs about my desire to make myself obsolete and invited them to tell me when I had succeeded in doing that, though they never did. :) I made a point to talk through difficult management situations that have no right answer, so they could start to see where I operate from certainty, and how much of the time I operate from a best guess with the information I have. I talked openly about mistakes and what I learned, and how I approach decision making.

Why do so few managers work to make themselves obsolete?

For many people, especially those working in larger companies, making yourself obsolete in one role means that you prepare yourself for moving into a similar role in another department. As a department head though, it’s often the case that there isn’t another function lead role at your company. Most startups have only one “Head of Design”. Therefore, making yourself obsolete means facing the idea of leaving the company to find another role externally.

Even if that’s the case, making yourself obsolete opens you up to the possibility of new responsibilities. Unless you are able to mentor, delegate and scale, you can’t create space to grow yourself. It’s only by creating this space for yourself that you are able to tackle bigger/harder problems, identify new opportunities, learn new skills , etc.

Deciding to make a change was an emotional one for me on a lot of levels. Asana is a fantastic company and culture. I felt attached and connected to my team and knew I would miss seeing them each day. I worried that I would be seen by some as disloyal for leaving, and that the next place I worked might not make me as happy as my prior role did.

At the same time, when you observe that your team is ready to operate effectively without you, it feels really good to acknowledge that and celebrate it. The positive sentiment from helping others grow lasts longer than the accomplishments you earn for yourself. There is nothing that makes me prouder than seeing a team I’ve helped shape succeed independently; to watch them build new ideas I wouldn’t have imagined. As I embark on my next chapter at Facebook, I know I’ll go through the same rewarding journey.