The Redesign: Questions To Ask Before You Start

You start a new job at a new company. They talk about infusing design thinking, and the VC’s get all excited. Images of awards go dancing through the CEO’s head and the company is heralded as the next Apple.

A year later the design team is fired, nothing gets launched, and the legacy product design keeps plodding along. It’s status quo, but the company slowly moves towards profitability and a sale.

Hundred of thousands of dollars are down the drain because of political miscalculations, and a culture of design never was adopted. What went wrong?

Doing a redesign right means putting pieces in place to make sure you can change culture. Doing it wrong can get you fired or kill a company. You aren’t just redesigning an application; you’re hopefully redesigning a culture that has higher expectations. Change like this is tremendous, and affects every department in the company.

Here are lessons learned from observations and personal experience. You should ask yourself these questions before starting the process.

What’s the weather forecast?

Do they have the capability understand design?  Does someone at the executive level call you a “Userability Expert” or have they worked with Interaction Designers before? Do they even follow some kind of established process?

Before you can start a redesign you have to understand your environment. Take the first few months doing a “design 360” of the business. Judge the capabilities of the team. Determine if they can allocate the right resources to a redesign. Learn if your users want a redesign.

Determine up front if you want to play the long game — slowly putting the pieces in place so design is part of the culture.

It might take months. It might take years. It might never happen. Whatever the amount of time you think it’s going to take, double it. And then think about if you want to stick around and see it through.

Should you ask for permission?

Your roadmap has to be the same as your boss’ because his job is on the line, too.

Ask the VP of Something Something, “What’s your vision for my job?”  This conversation is a good indication of whether your boss is someone you can work with and if design thinking is something that’s important to both of you. For this to work, you have to have advocates, starting with your boss, because they are also putting their job on the line.

When the redesign on the roadmap and the resources can be put in place to make it happen, present a plan to get there. The ROI has to be there: what seems to be a simple redesign can cost hundreds of thousands of dollars and has to generate that much revenue to make sense. If the company is willing to take that kind of risk, present your case with data, case studies, and competitive analysis documents to show that design thinking can help the company leapfrog their competitors.

Sometime, asking for forgiveness instead of permission doesn’t just put you in a bad spot, it puts everyone above you in a similar situation. If you do go that route, you better hit it out of the park because it might be the only way to save your job.

Who’s driving the bus?

What’s the company’s dominant culture? Is it engineering? Is it sales? Is it marketing? Is it product?

It’s like playing a chess game — you have to get your pieces in place before you make the next move.

Put together a company structure in your head. Learn who else you have to educate about design thinking before you embark on that redesign. Not only do you have to get your boss on your side, there might be a few other people within the company that will be useful advocates. This will take time.

It’s like playing a chess game — you have to get your pieces in place before you make the next move. You may have to sit down with a lot of people to understand how your desire to do a redesign will impact their ability to do their job.

Are the resources capable, competent, and plentiful?

Can your engineering team cash the checks you’re going to write? Do you have enough resources to do it well? Is the product team committed? Can customer service handle the transition gracefully?

It’s one thing to sit in the corner and prototype beautifully. It’s another thing to get that prototype implemented in a production environment. Sometimes making that transition will mean having the right pieces in place to complete that redesign.

Sometimes I realized early during a redesign on that the engineering team couldn’t deliver, so I had to recruit resources myself to put the right team in place. Be prepared to do that in your situation.

Can designer be integrated with the teams?

To build the right product design culture, you have to involve everyone in the process.

Can you sit with the product managers? Will you be equal partners in the three-legged stool of design, product and engineering? Will you be able to teach design, every day, or are you in a separate group?

Designers may think they want to be an agency in a company — but that is what isolates us most. We should be part of product development, not a service component, where the designers act only at the request of product managers. This fails to deliver great products.

To build the right product design culture, you have to involve everyone in the process. You have to educate people one day at a time. The best way to infuse design thinking in a company is to build teams where designers collaborate with other  team members. Sketch ideas, post screens on the wall, and involve everyone in the process. If they see the design and want to contribute, they’ll get involved. It’s collaborative and requires everyone to be on board.

A non-collaborative environment creates silos and gatekeepers. This never leads to a design culture.

Is a redesign really needed?

Are you losing users? Is revenue still growing? Is there other reason your losing to your competition, like product direction?

The first instinct of any designer it to redesign, because they want to make it their own.

A couple years ago I designed a website for a friend’s business. It’s a bit dated, it’s not responsive, the content should probably be rewritten, and a design refresh would be nice. But does it really need a redesign? No.

His site,, converts at a 15 percent clip, and has done so for years. His customers love him. The general consensus is “Let it be” because it works.

The first instinct of any designer it to redesign, because they want to make it their own. This is obvious after watching the uproar about iOS7: Every designer is turning their dribble account into their own personal iOS7, as if they’ll be hired tomorrow to assist Jony Ive.

A redesign may be a poor business decision. If you watch many of the major web properties, they go for years before doing a redesign. Some sites don’t redesign at all because there’s no reason to. While that may increase the risk that users will use other better designed services, a redesign done poorly can kill a company.

Redesigns place stress on other parts of the business that may not be capable of handling it.

Designers should respect the business decisions that are made. Design is only one part of the business, and has to be balanced against the rest.


Being successful with a redesign isn’t just putting a fresh coat of paint on the application, it’s about changing the thought processes of a company. It requires the right game plan and asking the right questions.

Remember, it’s not about padding your portfolio, it’s about making a positive impact on the company. If it’s the right approach, your impact will be huge.