Design Leadership Years 3 through 5

Year 1 there was something new around every corner. It was exciting. Year 2 we had to make a career choice. Years 3–5 is when we begin to fly solo.

Just to set the table; the average tenure of an employee in the US is 5 years. The average tenure of a tech employee in Silicon Valley’s top 15 companies averages 3.3 years. The average tenure of a design leader lasts about 3 years.* Year 3 is a big fork in the design leadership road. You’re either all-in or looking for the next thing.

YEARS 3–5:

The role: Ambiguity and prioritization

Your success in choosing the appropriate career topology and marching ahead tactfully has brought you this far. If you played the safe (but still difficult) road, you picked the right battles and made the right allies. You likely have a cross-functional peer-group rising up in the ranks together. If you limited your scope it proved to be a good gamble. Perhaps you were able to build out a new department or your work was folded into another department with you leading or co-leading. If you decided to be an agent of change — you carved a new path and likely have a rabidly loyal team. Successful change management tends to open new doors and provides an opportunity to tackle hairy, unclear problems. In all cases trust was established and your design leadership career is on the upswing.

You’re a veteran now and walking towards the bridge that brings you from Director to VP land. Pro tip — don’t_look_down. The valley below is littered with resumes full of good, talented folks who stumbled navigating this path. Some took a look in the mirror, turned around and got back closer to the work. Others made it all the way across to take on a new set of challenges. Many are struggling to get their bearings in the middle. If getting across the bridge is your goal then your success rides on your ability to discard most of the tactical tools that got you here. A design leader once told me — “The closer you get to the P & L, the higher you climb. But the gear you're dragging around now will slow you down up when you get up here.”

At this next level, the players are similar but the number of moves that need to be calculated is much more complex. Decisions that you used to make very deliberately after digesting many data points are now made quickly, based on less information. Decisions you used to be at the tail end of you‘ll now be spending months discussing with other leaders. Your vantage point has forever changed. Your new friends are ambiguity and maniacal/objective prioritization.

Directors are successful when they can build a great team within their department. VP’s are successful when they can create business value across multiple departments. Directors say yes a lot (often too much). VP’s say no a lot.

The team: Your team is a painting that is never done.

At this juncture (if the company is healthy) you should be spending +30% of your time recruiting and 20% of your time skill-building and promoting. This means lots of interviewing and networking for new employees. It also requires a continual investment laddering up your current employees' skills through 1-on-1’s, group work and increasing their responsibility. The org chart is going to feel like a 5-in-1 tool that you are constantly pulling out of your back pocket. Who should present given the cross-functional breadth of this meeting ?— org chart. Strategic direction planning for next year? — org chart. Need to let a senior designer go? — org chart. Depending on the size of your organization you may be tempted to hand this responsibility over to someone else, don’t.

The business: You’re in a bigger boat now.

In your first two years, you may have contributed to cost-savings initiatives, managed marketing enhancements (rebrands/redesigns) or shipped features. In the coming year, you’ll need to trade in the microscope for binoculars. Your ability to look 12–18 months out will usurp weekly sprint schedules.

At some point during this new phase, you’ll encounter a fork in the road. Focus on the shiny new thing (feature/product line, acquisition, etc) or continue with the iterative improvement of the core product/service. Before you take on the new shiny thing take a look at who is sponsoring it, what the projected headcount is for launch and support, and finally dig into the why. Why the change, why now, why is it being led by first, last name. This focus on the “why” and the “who” is important because it allows you to tailor your message, help your team steer clear of landmines, and be a good partner.

You’ll have access to new numbers that represent the true health of the company. A shared focus on these numbers with your rising CFX peer group will make your transition from Director to VP easier.

The politics: Oh, that’s why.

While you may have sussed out the rules of your department, senior leadership sits across the organization. How things are run in design most likely don’t 100% align with the way things are run in engineering or marketing. Your ability to communicate clearly and effectively about design got you this far. But your domain expertise may take a back seat to a more objective POV. Shared goal communication will take the lead in all conversations. In previous years there was a 60% your department + 40% core business lens. You’ll need to flip the department and core business lens this year. (McKinsey uses a: business, culture, team, self framework that is worth reviewing.)

The ease of politics for you starting in year 3 is highly dependent on the health of the business, the amount of trust you have established and your ability to delegate. Think back to the last — ”why are we even doing this” conversation you had as a designer — for better or worse, this is where many of those decisions originate. What may or may not make sense for an isolated department may make sense for the business. It’s a tender balancing act to defend your department and operationalize an “our” vision. In my experience, most design leaders fail not because of their design skills, or people management or business acumen but rather their inability to understand and support another department leader's POV.

Years 3–5 are the Spartan Race you trained for. Pace yourself.


Risus nulla sapien, tempor donec. Et nullam aliquam ornare velit dignissim. Laoreet elit at quis suspendisse. Eget egestas sodales ut massa praesent id tristique enim quis. Auctor turpis quam leo, at pharetra elementum scelerisque pellentesque proin. Tortor purus vestibulum sit eget adipiscing libero vitae. Arcu rhoncus volutpat, vel massa dolor iaculis.

Adipiscing feugiat pretium sed sit pellentesque quam penatibus turpis. Cras tristique scelerisque molestie viverra sociis. Pellentesque purus habitant pretium ante aliquet sit sed quisque nullam.

“Here is an interesting quote to highlight from the main body of the story.”

Felis nibh aliquet et leo magna. Faucibus nibh feugiat semper mattis condimentum amet tortor egestas congue. Risus sed pretium diam sagittis nunc diam, id. Neque at eros et proin scelerisque viverra ac. Fermentum bibendum arcu nulla sit nibh phasellus nisl vitae duis.

Morbi tellus tortor sed id vestibulum ipsum. Massa nibh augue nec urna. Faucibus dolor sem bibendum duis amet, in. Maecenas amet aliquet sed est. Faucibus enim, in facilisis eu fames dictum. Blandit diam vestibulum curabitur amet magna nisi. Mi vivamus nulla feugiat lacus suscipit lobortis neque. Lacus quisque sodales nunc, viverra nisl, dolor odio nibh. Habitant in in morbi adipiscing habitant pharetra amet. Varius bibendum.

Here’s a bulleted list:

  • Faucibus enim, in facilisis eu fames dictum. Blandit diam vestibulum curabitur amet magna nisi.
  • Mi vivamus nulla feugiat lacus suscipit lobortis neque.
  • Fermentum bibendum arcu nulla sit nibh phasellus nisl vitae duis.