How to make impact in your first 100 days in design leadership

In my work with CEO’s hiring design executives, there is a big emphasis on the first 100 days to determine the person hired's success. A successful first 100 days starts with hiring the right person at the right time with the right remit.

If you’ve hired the wrong person (which many do!) this will be made obvious.

Whether you’re taking over an existing leadership role, or a new one, it presents challenges and opportunities. It’s likely you’ll be going into something that already exists, or wider business stakeholders will have conceived ideas of what you do and why you’re even there. You will bring fresh perspective, and that comes disruption to the status quo.

My hope is the 15 design leaders that have shared how they would approach a new design leadership role will give you some clarity.

And if you’re reading this looking to hire a design leader, this will help to set them up for success. Your hiring process should shorten the time to identify the right leader and onboard them as well as giving the appropriate clarity to set up for success in the first 100 days.

Worth noting in this article the initial drafts had similarities so I’ve shortened some answers as to not repeat for the user.

1. Resist the urge to make immediate changes

Understand the Product/Service: Use the product. Not just clicking around, actually sign up and buy the product as a user would for the first time or get pitched on it by the sales team. Listen to how they sell the product to prospects.

Understand your customers: Review customer feedback, talk to customers, go visit them in their own environment.

Know Your Team: Schedule one-on-ones, observe team dynamics in group meetings, assess skills. Look for strengths and weaknesses of not only individuals, but the team as a whole.

Capture Insights: Take detailed notes during every meeting and document existing processes. You can’t have too much data at this stage!

Create a Knowledge Repository: Centralise all gathered information, tag it as if it was user research. I’ve actually used Dovetail in the past for this purpose.

Engage with people as people: Let them in to you and your life. Learn about them authentically, learn what makes them tick.

Foster collaboration: Create partnerships. Encourage cross-functional collaboration with your peers.

Identify Quick Wins: Look for opportunities to make small but impactful improvements.

Develop a Strategic Plan: Start developing a long-term vision and create a high-level roadmap.

Share what you’ve observed and learnt. Talk about the why behind your plans, bring people along for the journey of change. Don’t just create change for them.

Somewhat counterintuitively, to have the most impact, don’t do anything in your first 100 days. Focus on listening, observing, and understanding. Resist the urge to make immediate changes. This foundation will set the stage for meaningful and lasting impact. - Thomas Rimmer, Senior Design Director at Intercom

2. Assess your team + plan hiring

When one of your responsibilities is to enhance our design abilities across strategy, product, service, and visual design you need to assess your current team's skills and identify any gaps that needed to be filled. After determining the necessary roles, start collaborating with the HR department to develop a hiring strategy and initiate the process. Hiring top talent can be lengthy, often lasting between 3 and 6 months. - Esther Duran, CXO at Cognizant

3. Establish responsibilities

Often what your designers crave is empowerment and space to do their best work. A leader can come aboard and build trust that their words are heard and actioned (no lip service), and instil best practices that enable higher impact.

Establish an understanding of responsibilities, curtail sprawling context switching, so they have a focus they’re motivated by. Automate or systemise the most mundane, predictable design tasks away, and give your people the time back to explore and test the unknown. - Glenn Hitchcock - Designer at Poolside, ex-Vercel.

4. Remember, Design is a business function.

I don’t believe in the idea that you should race out of the gate and prove your value with fast wins in the first 100 days of any new design leadership role. It’s true there are instances of a team or product line in crisis. Focus on relationships and learning the business. Without these foundations, your impact as a leader is likely to be superficial. Spend quality time getting to know your team, your peers, and your superiors in the organization. Demonstrate curiosity and humility— do not mistake your new job for a repetition of your previous one. Find out what they know rather than demonstrating what you know. There’s time for that to become evident later.

Design is a business function, so understanding what really makes the business work— despite what you may have imagined on the way in to the new role— is paramount. Where is the real money made— not just revenue, but profit? What’s growing, what’s dying, and why? What’s the SWOT? What are customers and users saying? Where are the pain points and unmet needs, and what really motivates the buying decision and a long-term relationship? Look at data as much as you possibly can. Your fresh perspective may identify phenomena that the veterans miss. Look for trends, success rate of meeting targeted goals, and see if the reality of processes and outputs match the initial plans. You can find valuable clues about the organization in that last one.

There is one change I believe you can and should do quickly. If you find a sequestered design team and process— a locked-door studio, a lack of visibility of the design process until each design is frozen— I strongly doubt you will ever regret opening it up to more conversation and visibility with your partners in the organization. It says to the rest of the org that you recognize design is a business function and that your motivations match theirs— to build the business. - Gavin Ivester, VP of Design at Cisco

5. Set the scene for long-lasting impact

As a new CDO, consider your first 100 days as critical for building the foundation for your success. Understand the psychology and expectations of others, listen and learn in the early days, and build momentum. Choose some smart strategic initiatives, and set the stage for further long-term impact. Your quick wins are important, but your work on the design organization and on design culture are equally so: they drive sustained business value and you cannot start soon enough preparing for that. It is an art to balance the immediate need to demonstrate value with the longer-term goal of embedding design as a core driver of the company’s success. - Rogier Van der Heide ex-CDO at Philips Lighting.

6. The first 100 days starts in the interview process

In the first month I spend most of my time listening and taking notes, acting as my personal discovery process.

In the first 60 days I plan with a list of identified issues and suggested actions. I talk with stakeholders and my manager to understand together if the plan makes sense.

At 90 days mark it’s time to execute by looking at what are the low hanging fruits I can start tackling to have some quick wins.

What is more important, especially for leadership and executive positions?is to really do a good job interviewing the company before you start. That's when you try to identify:

1) What are the expectations for your position and your team;

2) What they value and see potentially value from your team's job;

3) How far or close they believe your team and product is from being ideal.

I ask a lot of questions about how they want to approach their product and change: is this an established product that won't need a lot of change? Or is this a change business? You should compare that with your profile: are you a person who likes change and ambiguity? Or do you prefer to be on the operational side optimizing things? - Koji Pereira - VP of Design at Sigma Computing, ex-Lyft, Twitter

7. Find your allies in the organisation

If you are taking over an existing role, don’t assume your peers, stakeholders or uplines know exactly why you have been hired or what your responsibilities are/should be. Build a stakeholder map, evangelize and establish your charter.

Resist the urge to fix org issues immediately or restructure without understanding the company and team culture. Every company has its own DNA and centers of power. Spot the dynamics and don’t assume your role or title will ensure automatic buy in. Observe, reflect and find the right sponsor to support large changes. - Arin Bhowmick, CDO at SAP

8. Understand the culture and what matters

The most important thing you can do is understand the culture of the company you joined and what matters most to them.? I’ve joined some companies that value really learning about them and taking it slow in your first 60 days to acclimate to their culture.? I’ve joined other companies where the most important things to do was to have a major transformational win demonstrating speed to action.? And the options for what matter are as varied as any culture/industry combo that you can imagine.?

Being able to get a clear understanding of the culture sign posts, validating all that you learned during the interview processes as to what’s important and then using those to inform your action plan is what matters most for your success.

A key thing to then validate is the design maturity of your team and the company at large and if there is an opportunity to further drive that maturity further or advance design’s seat at the table. From there you can set things like key relationships to nurture, org structure, career paths/ladders, ways of working, put forth your hiring approach and process, if applicable, and set up larger operations like communications, team development, your leadership and coaching model and ultimately the culture and rituals that will drive engagement and retention of your team and help them have the greatest impact on the business. - Christina Goldschmidt, VP Product Design at Warner Music Group

9. Identify the true believers

Get a sense for how your partners talk about the role of user needs, identify people who truly do put people first, and ask them questions about their experience instilling user centricity throughout the organization. Identify opportunities together and co-create plans to propose new ideas to other stakeholders.

Spend time with the team (at all levels) to understand their perspectives, challenges, and successes. This helps you gain insight into the team’s dynamics, strengths, and areas needing improvement. You’ll quickly “see” the patterns, themes, and trends by simply listening. You’ll also hear what is NOT being said too. Listening is a lost art, yet can be very effective learning tool.

10. Listen + build

Spend time with the team (at all levels) to understand their perspectives, challenges, and successes. This helps you gain insight into the team’s dynamics, strengths, and areas needing improvement. You’ll quickly “see” the patterns, themes, and trends by simply listening. You’ll also hear what is NOT being said too. Listening is a lost art, yet can be very effective learning tool.

Build your (virtual + physical) network: As you know, I joined 3M during the pandemic which posed some ‘new’ challenges on how one might typically on-board, meet people or build relationships. Those serendipitous face to face encounters, hallway or coffee line chats didn’t exist during my first year or so. I had to be very deliberate in asking new colleagues I met in my early months and ask, “who else should I meet?” As a CDO, you’ll need to work closely with other functions like R&D, marketing, and engineering – so it becomes important to understand the business dynamics and how the organization “works” both formally and informally without the benefit of an office drive by or the ability to ask an impromptu question. - Brian Rice - Chief Design and Brand Experience Officer, 3M

Tactical Wins

While the specific asks of you will vary from role-to-role and company-to-company, as a design leader, I typically find the most impactful revolve around the following: Depending on what company you join, you will be expected to create some tangible impact on the product or service. “Low hanging fruit” as we call it.

11. Develop a foundational knowledge of the product & problem-space

It Goes without saying, but if you don't develop empathy for the people you design solutions for, then you can't meaningfully serve them.

Select the method that will onboard you most efficiently - be it deep dives with teams, joining user research/sales calls, auditing the experience, reading documentation - but never avoid doing it.

Always prioritise these needs and get a win under your belt - it's a great way to demonstrate impact and build momentum. - Gregor Matheson, Senior Design Manager at Remote.com

12. Define a plan

In the first 100 days of a leadership role, it's crucial to bring a structured approach focusing on people, product, and process, while also adding your personal touch to the business. You were hired for a reason, so confidently own your domain and use your influence to shape and direct your area effectively. Digital transformation is a significant undertaking and will present challenging days. Your ability to inform, communicate, and articulate your thinking is key. Your team looks to you for direction; they want to understand your vision for the function, where you aim to take it, and the objectives, metrics, and impact you foresee.

Additionally, driving the value of design within the organisation is essential, in most organisations including mine, maturity is still low. This is a message I often ask my team when we’re trying to influence. Clear and consistent communication, transparency, and collaboration are vital to building a cohesive and motivated team. Managing relationships at all levels - up, down, and across is crucial for influencing various stakeholders. Establishing these connections will help you drive your initiatives forward. Finally, being an expert in your craft and effectively communicating your goals and plans will solidify your leadership and pave the way for impactful change. - Helen Arvanitopoulos, Senior UX Manager at Decathalon

13. Find your quick wins

Find your 'T' in the first 100 days. Dive deep into the organization, get those 1:1s going, join as many ceremonies as possible, and really get the lay of the land. Then, pick one to three things you can seriously turn around. Quick wins are crucial—they not only show what you're all about but also build momentum. Maybe there’s a project that’s been on the backburner that you can spark back to life given business impact is real, or perhaps there’s a noticeable gap in how things are done that you can streamline (look at variables like speed, quality, cost). These immediate impacts make a big splash and set the tone for your leadership.

With that said, while you're soaking up the nuances of your new environment, don’t lose sight of your own principles and philosophies — remember that that’s why they chose you in the first place. Trust your gut from the start. Staying true to yourself isn’t just authentic, it’s an effective way to ensure that the changes you implement resonate deeply and lastingly across the organization. - Tiago Caba?o - VP of Design at Delivery Hero

14. Get into the shoes of the customer and business

“As a design leader entering a new organization, we need to act as designers in our first hundred days—by this I mean, observe and learn with an open mind. Take the time to observe and learn openly without preconceived notions or judgments of what you think you might already know. Start with the people on the front line first, (e.g. for example, if it's a retail company, hang out on the store floor, by the registers, in the backroom etc...) to learn and observe what the business looks and feels like to the customers. If it's a B2B organization, shadow sales phone calls or hang out with the developers. Then, work your way up to the top so that the last input you receive is the executive view, not because it's not valid but it won't make as much sense unless you have seen the way the organization operates day to day. Try to have as many conversations as you can to learn how things operate, how they make products, how they earn money and so on. By taking the time to do this, it will accomplish many different things:

1. You will learn all of the nuts and bolts of the operation making you fluent in conversation and decision-making

2. It will help you demonstrate how design works to people who might not be familiar with it (long term payoff)

3. It will earn the respect of people across the org who might not ever have met you otherwise

4. You just might make some great friends along the way” - Wayne Suiter

15. Get a win under your belt

Take time to understand the culture of the business and the design culture, review existing process, systems and tools to identify improvements.

Link your Design vision and strategy to the corporate, category and brand vision, so it ladders back to results, performance and corporate strategy.

Find the ‘coalition of the willing’ who want to help lead the change you want to make and work with them first, don’t do everything and try and boil the ocean.

Find projects that get early runs on the board quickly to show progress and intent, and find these projects that appeal to different stakeholders, cost savings, consumer centricity, HR, finance, supply.

Lastly communicate like your life depends on it, engage, sell, coach, show through doing, live action learning, celebrate early wins, keep the vision front and centre.” - Andrew Barraclough, Global Head of Brand & Experience Design at Imperial Brands

Conclusion

Your first 100* days serve as a litmus test to understand if it's a mutual fit for you and the company.

You are accessing the culture, the ways of working, the team, and the product while you are being evaluated against the expectations for the role and the overall compatibility.

To give any tactical advice, we need to agree on the goal. Let's say, your goal is (A) to understand weather you can be successful in this role in this company long-term or not. And if yes, (B) to inform the positive decision from the team (read: “your manager”*) on the outcome of your probation, by evidencing the ability to transfer, gain and apply necessary skills towards the specific business challenges in the organizational context.

— Here’s a TL;DR list of things you might want to consider to successfully hit the goal:

1. Proactively form and manage expectations.
2. Build relationships beyond transactional.
3. Learn in’s and out’s of the business model.
4. Observe the existing processes, obtain historical context and identify gaps.
5. Interview your team on what’s working, what are the problems and what they’d like to change
6. (Over)communicate to ensure clarity.
7. Choose quick wins, while defining long-term strategies.
8. Deliver against the immediate priorities.
9. Understand your customers, their needs, pains and motivation.
10. Drive (informed*) change - Vlad Zely, VP of Design at Zoe

My key takeaways from speaking to 16 leaders:

• 100 day plans depend on what company you’re joining.
• The 100 day plan often starts within the interview process.
• Don’t be quick to rush in and change. Seek to understand.
• People is a big part, without a team, you don’t have anything.
• Find your allies, who will enable design for you to be successful.
• Your first 100 days is you building the foundation to be successful.
• Design is a business function, it must be immersed in the business.

Thank you for reading, I hope you found this useful. Until next time!