Hold Fast: Managing Design Teams When Projects Go Sideways

Aaron "Ron" Irizarry
Beyond The Screen
Published in
8 min readJun 14, 2016

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Our experiences during projects good or bad, successful or not, have a large impact on our growth as team members and leaders. If you work in our field long enough you are bound to experience hurdles, frustrations, chaos and shit hitting the fan and going everywhere during projects. I think the key to surviving these experiences is a combination of perspective and how we choose to manage through them.

More often than not our view of how projects should go is often very rose colored, [insert mental image of designers celebrating while being praised by clients and business partners here].

We may have some reasonable expectations, but we often end up glorifying what is ideal over what is real and find ourselves lost in a dark forest of project chaos unsure of how to get back on the right path.

That being said, it is ok when projects hit hard times, it happens, we work on complex projects for complex clients and companies.

“Technology companies are expected to move at an incredible pace, and building software is complex”~ Alex Schleifer — VP of Design at Airbnb

The clients and companies we work with are complex for a variety of reasons… Departmental make up, internal politics, global team distribution and varying understanding of design’s role. Once we start to understand these contexts better we can start to get an idea of what warning signs to look for before during and after projects.

I know this approach sounds a lot like project management, and it is, I am a firm believer that project management is a part of design management, whether we like it or not. As design managers we are responsible for the output of our team, both from a quality and a timeliness standpoint.

When a project go sideways we can help direct priorities, weigh in on tough decisions in light of the current situation, help with communication, eliminate distractions so they can focus on meeting deadlines, and back up our team members when they have to push back on something. As design managers we should put equal amount of effort into “contingency plans” for when things go sideways as we do our design/project plans.

We often focus so much on having a plan(project plan) in place to get software out the door that we rarely have a plan in place for what comes after we ship. Shipping is is just the beginning, our design process should also account for what happens and how we want to respond once our product is in the market.

Even if we feel as though we have a good plan in place we need to be prepared for what could go wrong. Having a plan doesn’t ensure that everything will go smoothly.

Almost every problem we run into with projects can be traced back to communication issues with our cross functional teams about the projects and process that surround them.

When it comes to managing through frustrating situations before, during, and after projects there are three areas that I think the design manager has to focus on… Business partners, design team members, and the design process. Understanding how to manage each of these areas is crucial to weathering the storm and righting the ship.

Start by Striving for Transparency

Transparent communication with your business partners, the team you manage, and about your process goes a long way. By being willing to have candid conversations about the good, the bad and the ugly you set the precedent for more transparent communication that isn’t focused on personal agendas, finger pointing, or departmental politics. You can foster transparency within your cross functional teams by:

Taking responsibility for areas where you or your team may have missed the mark. It is not uncommon for teams to shy away from accountability and point fingers at others when they make a mistake, this only puts hurdles in the communication process.

Avoiding un-necessary conflict with teams and team members, you can call things as you see them while still moving towards a positive resolution. Conflict isn’t always avoidable, but it doesn’t have to be negative. Frame tough conversations in the context of how things look from your point of view and ask the other teams members to validate whether your view is correct. A great tool to use here is The Ladder of Inference, it allows you to explain how you are seeing things in a structured format and verify if your assumptions are in line with what is really happening in a given situation.

The Ladder of Inference helps you draw better conclusions, or challenge other people’s conclusions based on true facts and reality. It can be used to help you analyze hard data, such as a set of sales figures, or to test assertions, such as “the project will go live in April”. You can also use it to help validate or challenge other people’s conclusions. — Mind Tools

This helps reduce defensiveness and shows a willingness to work through the issue together. This allows for transparency about how you are feeling about the project without putting walls between cross functional teams.

Admitting when you don’t have an answer. When projects go sideways we will encounter situations where we don’t know have answers or know what the next steps should be. Be honest, let the team know you don’t know, but are willing to give it some thought and find out. If you don’t have an answer or solution you can also ask other team members to work with you on finding them.

Managing Stakeholders and Business Partners

As our roles change from designers to design managers our deliverables change. We are no longer faced with just designing for complex systems, and managing the teams that build them, we now face new complex relationships as we manage up to our stakeholders and executives.

If we are not aligned with our business partners, the day to day of our projects can be very difficult, not to mention when we find ourselves in a scenario when the project has gone sideways. We can reduce the possibility for additional strife if we establish some guidelines for our teams. These guidelines should contain alignment and a shared understanding of what the product team as a whole is trying to achieve, what our roles are in the process, and communication standards to help guide how we treat and communicate with each other.

We Need to Build Trust

You can build trust with your cross functional teams by approaching situations (especially the shitty ones) with a sense of collaboration. Finger pointing does no good, accountability can be dealt with in a retro after the team has weathered the storm.

Focusing on other people instead of solution to the problem at hand, only leads to additional conflict and away from a problem’s resolution.

Frame questions, statements, and conversations within the effort to do what is best for the customer and/or product. The more the focus is on the product the easier it is for the team to feel a sense of shared ownership and collaborate to resolve issues.

Managing Your Team

Just as with managing up to stake holders our role has changed within out teams. Instead of designing specific interactions per se, we are designing how our teams design, we set up processes, team structures, feedback loops and mentorship. All of these shape our teams, the work they produce, and hopefully prepare them for those unfortunate times when the shit hits the fan.

Every experience, good or bad, our teams face will change them. No team comes out of any experience, good or bad, the same. Some team members will rise to the occasion, others will back away, and some will leave. All of these are ok. As managers we need to be able to see those affects on our teams and allow that information to inform the decisions we make.

Observation is such an important part of our design process, but it can often be overlooked as an important part of how we manage and support our teams.

As we learn about how our teams respond to difficult situations during projects, we should be noting reactions and making adjustments to our teams structure and process. Doing this will show our teams that we are aware of their needs and want to put them in positions to be challenged in their roles without being set up for failure.

It is not enough to just manage our teams during challenging project situations, if we want to be successful and more importantly help our teams be successful we need to lead.

Making these adjustments requires a flexible team structure, setting up teams so that they can be more resilient can allow for roles to change based on what the needs of a specific project are or a specific scenario dictates.

Managing the Process

One thing that can help us as we work through difficult moments during projects is to have a shared understanding of the product design process that our teams are following. Having an agreed upon process in place will provide a starting point for trouble shooting when caused a project to go off the rails. If the team has strayed from the process then the team can use the process as a guide to getting back on track.

All this considered there are going to be times when to work through a situation or fire drill you will need to ditch your normal process. This can come in the form of how your sprint works, the type of deliverables you provide, or even team members roles. This is ok. It can be hard to break away from what feels comfortable, heck we probably even want to cling to our process even tighter when things get messy.

Remaining flexible is the key to weathering the storm. It is great to have process in place that allows teams to work collaboratively and efficiently, but when things go sideways you will need to make adjustments.

Just like with our process, we should also look to remain flexible in our approaches to solving the issues our teams and projects are facing. Regardless of how tried and tested some of our problem solving techniques may be, or how aligned they are with best practices, there is always a chance that they will not work for the situations we are facing.

“Everyone has a plan until they get punched in the face” — Mike Tyson

Have a plan B, even a Plan C that helps the team work through the situation for the needed solution.

Notice that in the last paragraph that I said the “needed” solution. Sometimes the needed solution isn’t the best solution. Sometimes the correct solution will require compromise and trade offs. We can’t let our pride get in the way of executing, we should be striving to find the the balance between execution and maintaining principles.

No two projects are alike, sometimes a projects you think is going to be a disaster turns out ok, and other projects that look like a walk in the park will become a nightmare. The key is to do everything you can to be aware of what might be coming… Have foresight and do your best to avoid blind spots. Use project kick offs, sprint planning, team retros, and any other opportunity that comes up to ensure that you are looking back at projects past and using that info to inform your strategy for projects moving forward.

In the end we can’t control everything that comes our way. We can choose to focus on what we can control and try to influence the rest. Stay the course, remain flexible, and most importantly remember that leading nets more results than just managing situations and people.

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Aaron "Ron" Irizarry
Beyond The Screen

Sr. Director — Head of Servicing Platforms Design at Capital One. Co-author of Discussing Design http://amzn.com/149190240X