Year One is a long slow curve.

But I can’t see where I’m going. Design Leadership — Year One

Getting started in your design leadership career? Here’s the first of a 3 part series that breaks down how to navigate your first few years.


The role: What am I doing here?

Setup the new laptop. Get to know the product. Meet all the department heads. Check, check, check. Now you need to make sure you know your role. Find your job description and/or contract and take a good hard look. Often the role posted for recruiting efforts differs from what you are doing day-to-day. The differences may be dated reporting structures or small nuances regarding responsibilities. Copy the job description into a Google Doc, make edits and review the description with your manager. Once you agree on the changes communicate out to your team and your CFX partners. This exercise is less about CYA than ensuring the wind is at your back before you set sail.

Inquire about who came before you and what became of them? If possible, reach out to folks who previously held your position. If it’s a new role, what organizational or market shifts made the role important? In the event you weren’t hired, who would perform the work? How long has the organization been working to fill the role? Without making waves, dig into the natural order of decision-making systems and try to understand how the organization determines what is important vs. what is urgent.

In your first 90 days talk to as many customers as you can. Work with PM’s or DesignOps to map their concerns and suggestions against stories in the pipeline. Now that you have a good sense of how you got here, and what might lie ahead, dig into what success looks like? Often your success is linked to someone else’s — find out who they are and what they need to deliver. In short, make sure you understand why you were hired and ensure you are set up for success. Bear in mind, it will take a few months to get your sea legs before you’ll be able to make a full assessment.

The team: So how’s the team?

Early in your design leadership career, your goal should be team success with CFX (cross-functional) touchpoints. Assess each of the individual’s soft and hard skills based on this vantage point. How do they perform their work? How do they work with others? In order to answer these questions, you need to understand the people as people. How long is their commute? What motivates them — money, freedom, power, camaraderie? What are their career aspirations? How do they solve problems — in a group, solo, talking out loud or guided? These aren’t questions you send out in a Google Form. These insights require patience, care and a commitment to understanding without judging.

Heads up, gaining employee trust may take time. The team you inherited may have had three or four managers before you. There may be an — “I’ve heard it all before” vapor lingering across your tenure. While you are figuring out how to navigate your career through collecting these insights, in the eyes of the team you are their gatekeeper. Once you have a general understanding of the individuals, focus on placing them in a position to be successful. Sometimes this will mean rewriting (and communicating) new job descriptions. Often it requires a kind, but hard, talk about ways to improve. Sometimes it will require a move to a different department or a supportive conversation about moving on to greener pastures. Clarity and kindness are your friends here.

Team dynamics is the next assessment. Watch how the team works and socializes during both simple and complex interactions. Situational inclusion has a tendency to uncover true power dynamics. Take a look at how teams with differing seniority levels interact during heads-down work, pre-meeting and post-meeting? How do they critique one another? Is their communication open, honest and clear?

The essence of being a good leader centers around the ability to craft a healthy and effective team. This starts with you being healthy and honest with yourself. So, can you be a good leader to everyone on your team? Are there personality types that you struggle with? Are you aware of your frustration triggers? Use these explorations as an opportunity for everyone to grow.

The business: Align and refine

Map out the next 4 quarters of business initiatives and map how your team will contribute to each initiative, quarter-by-quarter. Try not to slow down or kill any in-flight projects during your first 3–6 months. Manage these projects and use them as ‘tours around the organization’. Examine how, and how quickly, information moves from the executive level to the IC level. Ask your manager what numbers he/she looks at each week or month.

The politics: Signs, signs. Everywhere there’s signs.

Determine who the key influencers, connectors, decision-makers, and cynics are. Rank the design maturity of the organization. Attend varying levels of meetings and functionally map attendees across departments (IC to IC, manager to manager, director to director, etc). Walk around the office (and the online tools) and look for department declarations: signs on the wall, mission statements, etc. These signals highlight validation and trust-building that you may need to interpret, mirror and support in order to be successful. Understanding the lay of the land, the players and the rules are imperative in year one — don’t try to save the world. Play nice and commit to delivering one medium-sized win.

Year one is one of those long on-ramps with a curve that never seems to straighten out. Stay the course.

Next up: YEAR 2



Strategic design leader — focused on people, culture, and users. Ex. Mailchimp, IBM, Razorfish and EatMedia.

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Ian Alexander

Strategic design leader — focused on people, culture, and users. Ex. Mailchimp, IBM, Razorfish and EatMedia.