Grow as a Design Manager

Understand the real problem a design is solving

Designing for designers is a common mistake. Make sure your design is actually making an impact.

Be confident the design is making an impact

After you've established the problem, evaluate the design is solving the problem. Use data to back up your original assumptions for the solution.

Demo the design in "show and tell" formats, with context and data that prove it made an impact

Always preface your design with the problem before the design was introduced and how it addressed the problem.

Make a case to management for how many problems need to be solved and how few design resources exist.

Once management sees design is generating value for the company, it becomes easier to present a strong argument for growing a design team.

Provide clear problems they can help solve.

Experienced designers are seeking problems that are interesting to them, either building on deep experience/insight or allowing them to grow in some new way. Know what interesting problems they can help you solve. If you can match the right types of problems to the right designer at the right time, bingo!... See more

Know what it means to be a senior IC at your company.

If a senior designer has no interest in becoming a manager, you better have a clear answer to the potential growth path for a maker/individual contributor. What does success look like? What skills are they expected to grow?

Craft your narrative.

Most folks fail to tell a compelling narrative about their product and team that differentiates them from the next company (or the 100 recruiting emails in any senior designers' inbox). Like any important communication, know your audience and the key message. Ping pong tables, VC rounds, and the latest launches aren't going to cut it. Where are you headed? What change are you creating? What's the role of design in all of it? And, be sure the answer the next two sections:... See more

Invest in your relationships. Always.

The most successful recruiting tactic (for senior talent) is building authentic relationships. It's about getting to know what works for them, letting them get to know you... and the big secret: being around when they're ready to take the next step. You'd be surprised how those relationships follow you throughout your career. It's a long-term investment for anyone on the management track.... See more

Search like a talent scout

Senior design talent is one of the most in-demand roles in the entire tech industry and as such, you're going to have to invest a LOT of time and resources into finding and recruiting them. To start, you're going to have to think like a talent scout on the hunt for the next great music act, actress, comic, quarterback, or pitcher. That requires you to scour the Web, app stores, and elsewhere looking for products that you love and then mining sites like LinkedIn and Dribbble to figure out who designed them and how to contact them. In some cases you're going to have to track talent for years as you cultivate the relationship. It takes patience, persistence, and operational organization but it's also your best chance to find top talent.... See more

Sell like a sports manager

Once you've identified someone you want to go after, you need to figure out how to pitch them on joining your team. You'll need to craft a credible story about how their unique talents are a perfect fit for the problem space, corporate culture, and existing team. You need to not only have a clearly articulated job description but also convince them that THIS role at THIS company at THIS moment is tailor-made for them and is THE natural step forward in their career. In addition, you need to paint a picture so they can see themselves being challenged by the work and inspired by the team. They need to believe that the opportunity you're offering is the best possible opportunity for them to do their best work. And while not everybody needs to believe they're going to be the MVP, everyone still wants to be part of a team that is serious about winning a championship.... See more

Communicate like a concierge

Once you've identified someone and gotten them interested in joining your company, it's time to lead them through the interview process. Obviously you'll need to be sure you have a well-designed candidate experience since the interview process itself is far and away the best approximation of what it's like to work at your company. If the hiring process is disorganized, interviewers are unprepared, or the follow-up communication is sloppy, candidates are going to leave the interview thinking your company is a mess and by extension unable to make decisions in a timely or disciplined manner -- all signs that the organization is fundamentally incapable of producing great products. By contrast, if the interview experience is thoughtful, punctual, and has clearly communicated timelines and follow-ups, the candidate will walk away thinking your company is an environment where great design is at least possible.... See more

Advocate like an agent

Finally, if you're the hiring manager and you've found some someone you really want on your team, then it's up to you to internally advocate for them and to shepherd them through the process. The candidate needs to know you are excited about their unique skills and talents and the other interviewers need to understand why you think they'd be a great addition. Senior designers have so many options in the current market that if you don't believe in them from the start, they're not going to care all that much about you or the opportunity. Recruiting senior designers is probably the single biggest challenge you'll face as a hiring manage but you'll greatly increase your chances of success by clearly communicating how they're a great fit with the existing team, what you see them contributing, the impact they'll have, and what they stand to learn.... See more

Pair them up with another designer

The new designer gains a dependable point of contact, building confidence and competence more quickly. Additionally, the more tenured designer has the opportunity to develop mentorship skills.

Document and collect important information in one place.

Design research, customer interviews, process outlines — all this should be collected in Google Docs, Dropbox Paper, or something similarly accessible. If your team is very small, a lot of this information may not be documented consistently. Get it all down in writing, so new team members can catch up quickly.... See more

Walk the new designer through your team's process.

Explain each step of your process, detailing both the *what* and the *why*. Describe which parts are set in stone and which are flexible, and ideally have your new teammate shadow an existing designer as they go through the process on a real task.... See more

Give your new teammate some quick wins.

Give your teammate the tools to start contributing quickly, so they feel like a valuable member of the team and not just "dead weight" until they're fully onboarded. Give them some smaller design tasks that they can help with right away, and help walk them through the team's design process if they get stuck.... See more

Ensure the new designer has contact with the rest of the organization.

Introduce them to all the stakeholders and points-of-contact they'll be working with throughout the organization. This ensures that (a) they'll be familiar with the people they'll be talking to, and (b) makes them more approachable to sales, engineering, customer success, and other teams throughout the company.... See more

Write a Career Track

Everyone on your team needs the same context in order to properly evaluate folks. If you don't have one, it can be as simple as just a set of bullet points for each role's responsibilities at different skill levels. Regardless, make sure that it's actually representative of the work people do day-to-day, and that the people you assign to interviews have read over those bullets.... See more

Be Targeted With Your Interviews

Every interview should have a purpose behind it! Every interviewer should be attempting to gather data that's different than what's being gathered by other interviewers. Have people focus on different areas, rather than performing general-purpose interviews in order to allow people to go deep on specific topics and get a clear picture. Additionally, help interviewers come up with questions that get you, the hiring manager, the information you need to make a good decision.... See more

Don't Let Individual Interviewers Evaluate Candidates!

If you think about it, each interviewer only has a sliver of the information you need to make a decision about whether to hire a candidate or not. If you have 5 different interviewers, each only has 20% of the overall picture from the interview, so having people "evaluate" a candidate based on their one interview is at best misleading as an indicator. Instead, ask interviewers to document where candidates are clearly strong, and where they may need professional development. Take all that data and compare it to the shape of the role you're hiring for. Do the strengths and growth-areas make sense for that role, level, team, part of the org, etc.? Do they make sense in another role you have open? You as the hiring manager are the one with the holistic perspective and understanding of what the role entails and what strengths and growth areas are dealbreakers.... See more

Make a list of each design practice your team is responsible for, and each practice you’d like your team to be responsible for.

Understanding what you want your team to be accomplishing is the first step in determining what roles you will need to hire for.

Clearly understand the weakest points of your design process.

Under each design practice falls a set of processes. For instance, UX design requires understanding the problem space, wire framing, and designing.

Identify and hire to stengthen your team’s weaknesses.

Each designer on your team brings skills to the table. By understanding your weakest points of the design process, you will have a better understanding of your team’s weaknesses. Hiring for the areas you are weakest is often a good strategy for building our your team’s spectrum. (I.e. Your team may be strong in UX but weak in research. Hiring a Design Researcher may help your team improve its research capabilities.)... See more

Coordinate. Assign one POC per candidate.

When candidates receive reach-outs from multiple people across a company, it can come across as disorganized and less personal. To avoid this, assign a single person to reach out and follow up with a specific candidate. It's not only a better experience, but also leads to better long-term relationships and thus greater potential for converting candidates to employees. Recruiting is often a long game!... See more

Make space

Quiet pauses in a conversation are great times to think. Avoid filling the silence immediately.

Be on time

Know your schedule. End your previous meeting 5-minutes early so you can be fully present when the 1:1 begins.

Do your action items

Try to take the first step of your action items within 24-hours and share an update afterwards. If you can't follow through or will be delayed, set that expectation.

Define and agree upon the purpose up-front

First-and-foremost, you'll want to set a clear agenda or purpose for the meeting. The agenda can be high-level (e.g. "Catch up on everything that happened over the last week in our lives.") or more focused (e.g. "Discuss a decision I need to make tomorrow around Project X.") The key thing is to have a clear purpose or agenda both parties understand before meeting. What do you each want to get out of the time? What would a successful sync look like? What is most valuable to the relationship? Even if the time is spent just catching each other up, that's immensely important time for teammates to have.... See more

Be clear about the time and recurrence

It's not enough to agree on the purpose of the one-on-one, both people should know in-advance just how much time will be dedicated to the meeting and how often they will occur. Some people use 1:1s as a way of getting updated on work, others use it as a chance to just chat and get to know the other person, in either case the amount of time required will play a key part. Discuss and agree on how much time you'll need to fulfill the purpose of the sync, and how often you should be meeting. Consider how close your relationship is to the person: if you work very closely, weekly is a good cadence. If more casually, as far out as once a month can suffice. It will vary for every person you meet with.... See more

Use the time for things you can't do elsewhere

Email, group posts, chats in Stride or Slack, these are all good ways to stay in-sync with your peers about ongoing work. What you may not have the ability to do through these mediums is sync on more personal or pressing matters; things you can't say in the other formats or things which may not be suited for those channels. Focusing on the individual, the working relationship, or things which may impact others but need to be figured-out in advance. Consider the value of any one-on-one is being able to discuss these important subjects on a micro level, without interference or the ears of a larger audience.... See more

Keep it casual and human

This is my personal preference, but I think it's worth noting: one of the best parts of a one-on-one is that they're done in real-time, usually face-to-face, with the other person. Meaning: you can see the person, you can better understand what they're saying or how they're listening, and you can interject the conversation with questions or ideas on-the-fly. Keeping the conversation casual and friendly builds the working relationship and enables you (as a team) to better tackle work subjects.... See more

Focus

Don't bring your laptop, put your phone on do not disturb, and try to listen actively.

Keep it short

Long 1-on-1s can get into the weeds, and cover too much ground to be actionable. I like to keep mine around 15 minutes.

Don't skip them!

Regular cadence is important. Don't let the other person skip, either — reschedule if needed.

Take care of your body.

You hear it all of the time, but it's true. Eat right, and exercise weekly. It's good for managing stress.

Learn something new.

If you haven't learned anything new in awhile, that will burn you out. Take a year and focus on a new soft skill, or meet some interesting people.

Research the signs of depression and anxiety

Not only are the symptoms similar in burnout, but you may also be experiencing legitimate imbalance in your mental health and should try to figure out if the source of your burnout is bigger than just your job.

Prioritize your health and well-being.

Without your health, you have nothing. Identify the source of toxicity and then explore the various options, including reexamining if you are in the right environment to begin with. Freelancing in particular can lead to an unhealthy lifestyle where all structure and safety nets are out the window.... See more

Give yourself a break, take some time away from the source of toxicity

If possible, see what kind of time off you can arrange as soon as possible. This could mean a mental health day, spending a long weekend camping without access to the internet, or A Real Vacation.

Go back to your roots

Remind yourself why you went down the path of XYZ in the first place. Look at your old drawings from high school (Yes, your DeviantArt account is still out there on the internet, I promise), revisit a record you haven't heard in 10 years and let it transport you back to a time when all you had was the drive and a dream to get to where you are now. Volunteer or mentor young people who are just starting out, and let their infectious passion and curiosity override your cynicism.... See more

Meditate, daily.

Use apps like Headspace or Calm to get started

Say "No" to 90% of things.

Write down your work, and life, priorities. Refer to this daily or weekly to ensure what you're doing is aligned with those priorities.

Talk to people.

Don't Assume anything.

Your teammate might not want help, or help from you. What you appreciate when you’re upset isn’t necessarily what they would, either. If you come across a colleague who's visibly upset but they seem to be avoiding attention, perhaps it's not the best time to offer support. One thing you could do is send a message later (if your coworker doesn’t want to discuss the issue, they don't have to respond). Depending on your established relationship, your message could be as simple as “Hey! Want to grab a coffee and catch up?” Then you can feel things out in person, make it known that you’re available to listen. The choice would be up to your coworker on what and how much to share, if they want to share at all. Sometimes they may appreciate company but not want to talk about what is upsetting them.... See more

Listen, don’t talk.

When we see someone experiencing hardship we’re often eager to offer solutions. This can be well-meant but unsolicited advice isn’t always welcome. It can even come across as pushy, patronizing, or presumptuous. I myself have resented the “helpful” barrage of suggestions when I’m upset. Sometimes the person just wants to vent and already knows what they need to do to address the issue. Sometimes the issue can’t be “addressed” except with time (e.g., a death in the family). The safest thing is to listen. If your presence is welcome but the coworker isn’t saying much, be patient and get comfortable with silence. And when they finally begin to share, please don’t interrupt or offer advice unless they ask.... See more

Open the door and keep it ajar.

If you feel your colleague wants to share but doesn’t know how to begin, you can say things like “Want to tell me about it? It’s OK if you don’t. I’m happy to just be here.” Or "Take as much time as you need.” If they express appreciation for your support, and you’re so inclined, check in with them again at a later time too.... See more

Alleviate load.

If there’s something concrete you can do, such as pick up the slack on a project (transparency and communication are super important here, obviously), do so.

Oxygen mask on yourself first.

If you’re also overwhelmed or having a tough time, it’s OK if you can’t put someone else first right then. Do what you can without adding more stress to your life (a kind word, a hug, a cookie!) as appropriate in the context of your relationship and circumstance. In extreme cases, you may need to involve someone more appropriate to handle the situation (this can be sensitive, tread carefully).... See more

Encourage self care

Life and loss happen. And they doesn't care about your launch date. Some people need extra encouragement to take time off. Help your teammate put themselves first and work second.

Check in

In Sheryl Sandburg’s book Option B, she shares the story about the sudden death of her husband. She share “how are you” feels like a ridiculous, unanswerable question. But “how are you today?” or “how are you feeling right now?” is a much easier question to answer. Find a quiet, private space for a one-on-one conversation.... See more

Ask for permission before sharing

Hardship is personal. Find out if your teammate wishes their news to be kept private or shared. It's possible you can also help your teammate by taking on the burden of making the hard news known to the team (especially if they'll be out of the office) or if they needed a confidant at work they can trust. Either way, get consent.... See more

Pair on manager tasks

Not necessarily the one-on-ones, but pair activities like hiring, thought leading, facilitating, running critiques, etc. Start by doing tasks together and eventually delegate the tasks fully. That will make a promotion easy.

Ask for help, offer trust

New managers can bring a fresh perspective to old problems. Share some team challenges you have that need solving and give your individual contributor the time, space, and trust to explore a creative solution.

Create opportunities for mentorship

Partner your managers-to-be with other individual contributors hungry for mentorship. Both will grow exponentially.

Are you already “managing” or influencing others without the title?

Some of the strongest IC’s who have developed in-depth knowledge of the company they work at or the practice they work within often become the strongest influencers on others. In these cases, transitioning from IC to manager is very natural because in many ways, they are “managing” already.... See more

Is the company or product growing?

As a product scales so will the team. In this instance, transitioning from IC to manager might be needed to help the company continue to grow.

Tell a good story

It's best to get your thoughts laid out ahead of time. This is a poor time to try and wing it. Make sure you cover: what happened, how the news impacts your team and how it impacts the employee directly. (details are key here). Framing and verbiage are huge! "Julie is no longer with us. Julie couldn't hack it. Julie realized she wasn't passionate about her role anymore" All the same outcome, completely different perception.... See more

Be quick, Be direct

When news happens, don't allow others to twist the truth or create rumors. Address it head on as soon as possible. Yes, these are hard conversation but, the longer you let it fester the more false expectations you have to address.

Go for a walk

Find a location outside of your typical flow. You'd be surprised how honest people are outside of the "company walls". Other ideas are grabbing a coffee, lunch, or finding a room in your office that's warm and friendly to discuss the news.

Timing is key

Put yourself in their shoes - when's the best time to talk about this? Set them up to digest the information accordingly. Example: Dumping bad news on someone before a client pitch, a weekend or a big deadline they're under is not ideal. If it has to happen under this scenario, let them know you're there to help with their workload if they need time to deal with the situation.... See more

Follow-Up

Not everyone deals with change or bad news the same. Following-up after your initial conversation allows you to see how they're dealing with the situation. Key in on changes in behavior from their normal traits and see if they need some time away from the office if they're handling it very poorly.... See more

Treat the recipient like an adult.

When you're giving bad news, be as direct as you can. Don't put so much lipstick on whatever your pig is that the recipient struggles to understand what you're telling them. Think about how you'd want to hear negative news and give others that same respect.... See more

It shouldn't be a total surprise.

By the time you are delivering bad news to someone, the topic shouldn't be completely fresh. If it is, start by apologizing for that, and make sure you do better next time. But then go ahead and deliver the news clearly and directly.

Contextualize the news and identify positives.

Most clouds have some silver lining. You don't want to tell something other than the truth, but look for legitimate positive side effects from the news and help explain those as well. Let's say you're letting a direct report know that their budget will be lower this year than last; contextualize the fact that this happens and (see point above) it was a risk we knew was possible, but that with the tighter budget we'll have a chance to focus the team and exercise more creativity than before.... See more

Explain how things can get better.

If appropriate, articulate the steps that this person can do to improve things in the future. For example, if you're delivering the news that you've decided not to promote someone, help them understand what they could change to be eligible for the promotion in the future.... See more

DEFCON 1

Ooof, these are the moments that tear people up. "DEFCON 1" bad news tends to be deeply personal, painful, many times it catches people off guard, and people get the most defensive about this kind of news. You have two things you need to pay attention to here. First, make sure you've done everything possible to help this person before delivering this news. Second, remember that in this moment they aren't your direct report, they are human. Tread softly, listen intently, and speak deliberately. Any hesitation in tone or delivery will yield a "do they know what they are doing?" in the other person's mind and that's a really bad place to end up after delivering the news. No one wants a plane to go down with an amateur pilot at the helm. Sully!! Finish by finding ways to be helpful and keep only the other person's best intentions at heart. No matter if you don't like them, in business karma bites back twice as hard. Do not burn any bridges.... See more

DEFCON 2

Great managers deliver this kind of news early and often. When done well it helps grow the other person. Bad managers let this kind of news linger, they take no action, and they surprise the other person when this situation reaches "DEFCON 1." In many ways you were put in charge to manage these situations out of the team. No one needs to be "managed" when things are easy and breezy. You're going to get better at this type of news with experience, don't expect to be great out the gate. The best you can do early on is identify that there is a problem, synthesize it to a point where you can make the problem clear, think about how to deliver it so that it sticks (no yelling, use simple words, to the point, use examples), deliver it candidly, and offer guidance on how to fix this going forward.... See more

DEFCON 3

Again, immediacy is the key. This is the type of bad news that is non-threatening and team members will want this news early. I think the best thing you can do is show the person that you're willing to communicate with them clearly and honestly, that you have their back, that you're there to help them navigate the issue, and that as a strong member of the team they're expected to pull out of a nosedive. DEFCON 3 is normal, it happens on every job, most people tend to make a big deal out of it because misery loves company but in the grand scheme of things, it's just another Wednesday.... See more

My role is...

Defining your own roles from your perspective can help shed light on why a team member may be behaving in a certain way. This may be a good time to agree on the key characteristics of your respective roles.

Expectations of me by others are...

What burdens are you carrying? Are they realistic?

Expectations for myself are...

Learn about the internal standards you have for yourself and how that changes your behavior.

Needs/wants from the team/partner are...

What support are you expecting? What kind of communication style do you prefer?

Professional needs/wants...

Do you have the tools/environment/time/space that you need to be successful? You may not be able to change all of these. Calling them out will help build empathy with others.

Personal success is...

Knowing what is important to you/others will give you awareness about how to navigate tricky ownership situations. Learn when to give and seek praise at the appropriate times.

What I want to learn is...

This is your opportunity to connect with someone who has something to teach you or has the ability to support your learning. Commend each other on your drive to improve. Also good to be aware of too many/unrealistic learning goals. It is not wrong to be hungry, but you can ask yourself/each other questions about priority.... See more

Worst thing that could happen...

Call out your fears. Be aware of how fear motivates you/others to act.

What risks exist?

Personal, professional, problem space risks? What can you do to mitigate those risks together?

A lot of teams confuse creativity for design.

Creativity is problem solving. Design is the visual expression of that problem solving.

Creativity has much more value to a company and will greatly elevate the perception of your team.

If you just focus on design then the company will many see you as a commodity opposed to if you focus on creativity then that is something they will see as a critical asset.

If you want more...

I did a whole episode of my podcast dedicated to this subject that might also help. Check out episode 30 - https://itunes.apple.com/us/podcast/the-crazy-one/id1128248295?mt=2

Spend a lot of time with partners and peers in different departments

This one gets overlooked a lot. Get away from your desk and talk to people in marketing, sales, support, data, engineers, HR etc. Get to know people personally and professionally, make it about more than work. This simple act will gain you quite a few allies. Allies are important if you are trying to be a change agent. People are more likely to change or try experiments with people they know, like and respect.... See more

Be strategic when you pitch ideas

I teach my design teams to pitch ideas with this simple template- What problem does your idea solve? How do you know? Why should we solve this now? What is the user benefit? What is the business benefit?

Make your design process transparent

Non-designers need to understand how you work, this understanding builds a lot of up-front trust and buy in. Take a slide deck, draw a step by step process on it that's easy to understand and socialize it to people in the business. Teach non-designers what your process is so the next time you say a flow will take a week, the process isn't a mystery box.... See more

Make your design process inclusive

Include business people and engineers in design decisions. Other than the obvious \togetherness\ factor, they're very helpful in offering diverse sets of insights that will enable you to be more informed with your design decisions.

Teach your design team the \business\ and business vernacular

Designers tend to focus on craft whenever they're cornered into explaining design decisions. They're better at responding with \here's why the design looks this way\ but business people really just want to hear \here's how we expect this design to convert\ and \here's how we know.\ The other side to this is designers need to make a strong effort in understanding how the business works, how many lines of business there are and how their work impacts each line of business.... See more

Overshare your work

Simple steps you can take here are to use a products like Invision and Wake to make your work available for business leaders and engineers to review on their own time in a comment-able format. I'd also recommend buying large foam-core boards and pin your work up on there for people walking by to see. Leave post-it notes next to the board so they can leave comments for you asynchronously.... See more

Do great work

Put out work that you're proud of, that's thought through, that's rooted in a clear problem that the business agrees is a problem, that's build-able, that's considerate of the user, and that included insights from stakeholders (aka not you designing alone like a rockstar designer).... See more

Make the data team your best friend

Our \data friends,\ as Rochelle King from Spotify puts it, are powerful allies to designers. If they can help you make informed product decisions, you're always going to walk into a room with anyone and make a defensible, logical and thorough case for your design work.... See more

Lead the way.

Designers may feel uncomfortable with transparency because there's no precedent and lots of unknowns. Find a safe opportunity to demonstrate the value of transparency by volunteering to open up your own work, process, plan, or experiences.

Involve everyone in the process.

Ask questions and get feedback from everyone, not just the other designers. By keeping outside stakeholders involved, your team will build a reputation for openness and transparency.

Provide a venue for sharing.

Make sure there's a consistent time and place to share your work — maybe it's a weekly design review open to everyone, or maybe it's a tool like Wake that lets anyone peek into a stream of work that designers are uploading.

Share your work before it's ready.

Don't be afraid to showcase works-in-progress, wireframes, and even napkin sketches. Just make sure you make it clear whether you're looking for feedback yet, or just showing your work.

Run short sprints or adopt hacknights

Shorter timeframes require people to think smaller and get more comfortable iterating and experimenting towards a longer-term objective. Long timeframes allow for the nursing of perfection, resulting in the guarding of ideas and concepts.

Break designs down into groups of common parts.

Where possible, consolidate similar elements to make them identical.

Create a centralised repository for all the common elements, so new layouts can reuse those elements. This means designers can work faster, but it also helps maintain consistency.

When researching this topic, searching for “design system”, “sticker sheet”, and “style guide” might provide some good answers.

If things seem like they are getting out of hand, try to step back and take a more systematic approach.

The centralised repository should have a process for updating, maintaining and expanding.

Foster a culture of sharing

Create a culture of sharing so people get quality feedback early and often. In sharing and discussing work, the team will start to unify around common patterns.

Give the team a venue to share and critique

Whether you use Slack, Wake, Hipchat or Hangouts, look to to create a space for design and lead your team to start sharing their work before formal reviews or in-person critique sessions. It is important to call out new design patterns or changes to existing patterns so that the team can address inconsistencies.... See more

Ensure clear approvals/rejections

There must be clear approvals and rejections in your workflow, whether this is a single person, a team lead or a creative director. With clear approvals, your team will be able to prioritize critical feedback against peer reviews. Feedback loops are essential but so are clear instructions on whether a design is solving the problem effectively.... See more

Create a style guide

Once you have a team that is working well together, you'll need to create a pattern library or style guide. Style Guides should be used as a reference for design and interaction patterns, as well as a source of truth for production-ready options.... See more

Align on what types of ideas matter

Not every good idea is important right now. Leaders could drive self sufficiency and autonomy by building the team's confidence in pursuing ideas that matter. I've found that this often comes down to understanding what business problems are the most burning and how that coincides with specific parts of the user journey. As an example, at Candid we've found that one of the most important things the team could be working on is getting people to return their diagnostic records in order to get them to the next step in the funnel. With this knowledge, designers and engineers are free to work on new ideas within the constraints of that problem area. Anything else will be backlogged for later.... See more

Show progress to see progress

Confidence is built brick by brick. I personally have the most fun when I see designers push the needle in the right direction, no matter how big or small the move is. Nothing get's me happier at work than to sit down with them and show them how well their solution is working. Doing this every week builds their intuition, ownership and makes them want to contribute more, more often, and with a learning mindset in place. Ideas that don't move the needle suddenly become learning moments and science projects to take apart and do better the next time they try.... See more

Use data tooling to build confidence in solutions

An often overlooked piece of the puzzle is showing designers how to use data instrumentation to help form hypotheses' and to bring that thinking to meetings or into their decision process in their workflow. Data trumps opinions and a designer armed with data is more confident in their solutions. As an example, in a recent design sprint to build a checkout flow for Candid, a designer was prompted to design a single-page checkout. He looked through artifacts the company uses in sales calls and coincided that artifact with data on success rates for the sales calls; he was then able to use that as a data point to suggest a multi-step, higher friction and educational checkout process is actually better at qualifying the customer. He confidently proceeded to change the design without any instruction from the product or sales team and the flow was better for it (data on success rate here is still pending and is being tested.)... See more

Investigate your teams gifts, talents, learning styles and outside interest.

A great tool for this is Strength Finders 2.0

Assign "Owners" to each step of your design process.

After you review the Strength Finders results, schedule a 1-on-1 meeting with each critical member of your team. For large team, assign roles to managers and/or directors. If you don't have a design process and/or design ethos then creating those should be step #1.... See more

Schedule "Design Days" with process step owners.

Design Days are where you allow the process step owners to lead and go deep in their respective owners. At Jordan/Nike, I called this "The 5 areas of Distinction". Each of these areas were intended to create a distinct product offering vs. a differentiated product offering. DD's allow each process owner to have a sense of agency and autonomy in how they work. Your role as a leader is to provide support and advise, not to dictate. Once again, if you have a solid design process, you won't have to be in the weeds. Empower your team and watch them grow.... See more

Prototype, constantly.

Every idea, sketch, insight should be brought to life on the spot. Keep maker material in easy accessible and well organized areas. This creates a central hub where Designer's can grab creative materials and bring their ideas to life.

Show + Tell

By constantly inviting your audience or consumer into your process you are encouraging visual communication over verbal communication. Who doesn't like show and tell?

Assess What Works + Discard What Doesn't

This is not the only way to do things. This is a fluid process that can and should constantly evolve based on the composition and needs of your team. If you stay in motion, you encourage growth, discourse and discovery.

Make It Fun!

The team that plays together, stays together.

Be direct & concise when providing feedback

Be sure to encourage the team to provide feedback that's clear, direct, and hopefully even actionable. A good way to get valuable feedback is to ask for 2-3 things that went really well and 2-3 things that can be improved on if the team were to work on the same project all over again. Make sure someone in the room (preferably the project owner) is taking notes. Also, try to draw themes from all the feedback that you’re hearing. This will be helpful when you’re summarizing relevant points at the end.... See more

Focus on learnings instead of regrets

Hindsight is 20/20. When looking back at a project, it's easy to get negative and defensive, which leads to finger-pointing. Make it clear in the beginning of the meeting that the post-mortem isn't about bringing up regrets or playing the blame game, it's about learning and growing together as a team. It's not worth the team's time discussing what the project could have been if only... It is, however, worth it to talk about how a certain situation can be handled differently in the future to ship a more successful project.... See more

Talk about the project & its attributes as opposed to individuals

One of the most important things to do in the beginning of the meeting is to clearly state that this post-mortem isn’t about accusing each other, it’s about learning and growing as a team. In other words, let’s not get personal. It’s a good idea to discuss goals related to the project as opposed to who did what and why. Shift the conversation from something like ‘who was responsible for the final decision and why wasn’t the email sent in time?’ to ‘how can we get ahead of this problem in the future?’ Make the discussion about the process instead of about individuals.... See more

Consider the timing.

It’s helpful to wait a few days after the project, maybe a week or two, to provide people with some space and time to gather perspective. It shouldn’t be too long (no more than two weeks), or you’ll start to lose important information.

Share learnings.

Summarize your key learnings into a single page or less, and share these with the larger organization. When you share your learnings, you model what a healthy debrief looks like, while also multiplying the value you’ve created.

Get a facilitator, preferably external to the team.

By asking someone from the outside to run the process, the whole team can focus on the debriefing while the facilitator drives the structure, asks unbiased questions, and helps navigate tough conversations.

Set the tone.

A debrief should be framed as an opportunity for learning. If the goal of the session is focused on finding areas for improvement, it shifts the conversation from finding problems and faults to identifying opportunities and successes. This does not mean ignoring things that went wrong along the way, but it does mean not blaming any single person for the outcome. To keep focus on the opportunities, you can structure the conversation into three parts: (1) identify what happened (fact), (2) consider areas for improvement and potential solutions, (3) extract key learnings and future actions.... See more

Consider regular check-ins.

Beyond the debrief, consider scheduling more frequent check-ins throughout the duration of the project. This creates a moment for the team to make changes along the way, improving the chances of success. Furthermore, the debrief can shift from identifying faults that were long ignored to learnings from different approaches along the way.... See more

Align your team with business metrics and goals

Unless you're doing strictly philanthropic work, your company likely exists to grow and make money. Great design can make a huge impact on growth and revenue. Being able to speak in terms of business goals will get your team more buy-in from the rest of the organization. Find the link between the business needs and the impacts that your team can have on them. How will investing in a design system impact product velocity? How will a meticulously crafted icon set impact subscriber numbers?... See more

Align your team around the people whose problems they solve

Make the time for research to happen, even if it's really scrappy. Get designers to sit with Sales or Support or other user-facing functions. Invite people from those functions into crits or brainstorming sessions. Encourage your team to speak in terms of user narratives and goals.... See more

Align on values and principles

Have your team collectively write and agree upon a set of principles. Orient your crits around these principles. Make sure to revisit them occasionally as new members join or new insights come to light.

Align on a shared design language and process

Find the common patterns and document them. If you don't have a design system, a good place to start is creating a shared definition of the language used to describe your product. Make a visual map of what a typical project looks like, and have your team help you find ways to streamline it.... See more

Align other teams with design

Great design execution cannot happen without PM's, Engineers, QA, Support, Leadership, and other functions in your company. Make the experience of working with designers a delightful one. Invite other functions into the creative process. Encourage your team to seek feedback early and often. Teach the format of critique so that feedback is constructive from all angles.... See more

Choose the right tools.

The tools you use will set the cadence for communication and help determine your company's culture. A company using Slack is different than a company using Basecamp, etc. Intentionally choose the tools you use for communication, project management, sharing, and more.... See more

Purposefully build routines and traditions.

Some examples: Each week, call out coworkers who are doing great work; have a set time to discuss "wins for the week"; have a themed GIF competition each day; give kudos to achievements; have occasional workshops via video chat in which a teammate presents about something they're passionate about.... See more

Make time for off-topic communication.

Create space for non-work-related, "watercooler" communication. At my company, we have a video chat every Friday where anyone who's available stops in for 15-30 minutes to talk about anything except work. This helps build an understanding beyond just our professional relationships.... See more

Meet up in-person occasionally.

Meeting your coworkers in-person can create a foundation to support your remote culture. Schedule company off-site meetups, or even just informal gatherings, on a predictable schedule. Make sure everyone knows when they'll next be seeing each other face-to-face. There's no better way to build company culture (and inside jokes!) than this.... See more

What is your budget? Will the cost of your tool bundle pay off?

Can you afford to buy licenses or subscriptions for your entire design team? What about the developers? On the other hand, if you put together an ideal list of tools your team wants to use, are you wasting money on duplicative feature sets? If there's an expensive piece of software that only one person will use for advanced prototyping, such as a lead designer, will anyone else need to access that file on a regular basis? In my mind it is worth just springing for the license if it means that the work will come out faster and free up your lead designer to move on to the next project.... See more

Windows vs Mac, Android vs iOS, etc.

Some design tools aren't cross-platform compatible. (Looking at you, Sketch!) Beyond the scope of your own design team or company, keep in mind that most of the world still uses Windows. I had a series of international clients last year who requested the working files as part of the deliverables. Their internal design team all used Windows and assumed we were working in Photoshop. It took a lot of time and energy at the very end to convert all of the files from Sketch to PSD for the handoff session.... See more

Not exactly a design tool, but let's talk about file storage, organization and naming standards.

Whatever your preferred product, you should absolutely have a system that is outlined very specifically when it comes to where your files and assets are living. If your team uses dropbox, there should be a strict expectation that everyone is putting their files in the team dropbox every single day. It is no fun trying to guess where something might be when you need it urgently, and it's even less fun to have to call every number on file to try and contact your junior designer who is out sick just to ask where her files are. Getting people to adhere to organizing their files and follow a coherent naming standard is a challenge, but well worth it. Think of your project folders as you would a shared house. Clean up your mess, fold your laundry and use actual version numbers instead of "Final1, Website V2, FinalDraft_3.0", you filthy animals.... See more

Asset cross-compatibility

Currently in-market we have a variety of tools available at our fingertips, but they don't all play nicely together, even during an export process. You can pull vector elements into Sketch from Illustrator, but your Sketch symbols can't be exported and plugged into Illustrator (functionally, that is). If I have a VSCO mobile preset I apply to our product photos, the DNG files being processed in Lightroom can't use those same presets. Should you keep all of your branding assets in Lingo, a folder on dropbox, or in a Creative Cloud library? These are all things to consider. Choose wisely.... See more

Show your work early and often.

Don't be afraid that you're the only one doing it. You may have to do this for a while before it catches on.

Get excited. Share the excitement.

Right at that moment where you're pumped on the thing you're working on, share it. Pull people in and show them. This starts to get excitement going on the team and it eventually becomes contagious. And don't worry, if you end up not using your idea, it will only show how good you are at editing.... See more

Gradually start to ask to see some of their work.

When you're walking by and see something on their screen, don't be shy to say "That's super cool. What's that for?" It get's the conversation going.

3 Compliments for every 1 critique.

Especially when you're starting to look at the work of other people, you kind of have to stroke their ego a bit. But this is a good rule always. We tend to look at what can be better but forget what's already working. Start with what's working. That's maybe most helpful early in the process anyway. It starts to build confidence—not only in the project, but in being able to show work early.... See more

It’s natural to have a gut reaction.

Maybe it’s “I don’t get it,” maybe it’s “This is so cool!” Hold on to that reaction. Take time to ask yourself: “why am I having this reaction?”

Make sure the recipient is ready for critique.

Even feedback with the best intentions can be unhelpful if it’s given at the wrong time. If the designer hasn’t asked for critique, but you still want to share your thoughts, reach out and suggest that you discuss when it’s the right time.

Understand the goals, audience, and constraints of the design.

If you can’t find this information, ask questions.

Make it actionable, not personal.

Divorce your ego & preferences from the work, and focus on the user’s needs.

Create a shared repository, ideally accessible to the entire company (or public, for openly sharing learnings with the community)

Give people a template. Templates are so much easier to fill in than starting off with a blank page

Make it a crucial part of the process. Consider a project unfinished until one of those notes is written.

Consider learning notes impactful and celebrate them. Share them widely, and make them part of people’s contribution when comes performance reviews, etc.