Courageous Coaching for Designers

“So, who do you think you’re going to fire?”

The question caught me off guard. It came from a leader at a company I’d joined a few months prior. I’d inherited a team of designers who had been without a manager for some time. While they varied in years of experience, they all shared some level of demotivation and were struggling to be taken seriously by their engineers and product managers. As the leader’s question shows, many people at the company didn’t respect them and felt they were already a lost cause.

After a pause, I responded, “I’m hoping I won’t have to fire anyone. Let me work on encouraging a growth mindset and giving my designers the tools they need to improve, and check back in a few months” (ok I’m paraphrasing, but it was something like that). As I left, I knew the clock was ticking.

My strategy to help the design team grow and improve had two parts: first, focus on establishing a culture of feedback. Next, start coaching the designers. I’ve written about giving feedback in a prior post. In this article, I’ll share my personal approach to coaching designers. If you’re new to coaching, my hope is that this mini-guide will give you the courage to start having coaching conversations with your team. 

Coaching versus Feedback

I’ve laid out the differences between feedback and coaching in another post, but as a reminder, here’s the main characteristics of coaching:

  • Coaching focuses on the future (unlike feedback on a particular past incident or piece of work)

  • It focuses on the learner’s goals

  • Rather than instructing or making statements, people in coach-mode spend the majority of their time asking open-ended questions

  • Coaching is done in an established relationship, for example where a more junior designer is learning from a senior designer

  • A coaching conversation is usually scheduled ahead of time

When I say “coaching conversation”, I mean a specific meeting where you and your direct report set aside time to just focus on their skills and career goals. For this type of conversation, both you and your designer need time to prepare beforehand as well as time during the chat to understand the designer’s goals and creatively brainstorm ways to reach them.

However there are also times in which you might do ad-hoc coaching during a regular one-on-one. It might happen after you give feedback, or it might be in response to a skill your designer is working on. For example, if you know that your designer wants to improve their public speaking skills, you might follow up on a recent presentation they gave:

“How do you feel your presentation went yesterday? How could you improve it for the next time?”

We often think of coaching as happening rarely, perhaps during our annual performance review. Some of us unfortunately have never even experienced coaching. But in the best manager/direct report relationships, it happens regularly. During the rest of this article, I’ll share with you my tips for how to prepare for and conduct a scheduled coaching conversation.

Step 1: Preparing for a Coaching Conversation 

When I first started managing designers, I would try out questions in my one-on-ones that I’d read about in articles on leadership. “What skills are you trying to improve?” I’d ask, or “What are your career goals?” This often resulted in the designer quickly racking their brain to come up with an answer, or simply giving me a deer-in-the-headlights look. 

It wasn’t fair to expect the designer to answer such broad questions without any context or warning. I soon realized I needed to give designers a heads-up if I wanted to get into this deep water. They needed time to consider their career goals and how they wanted to grow. 

In addition, I realized that it was hard to choose what to improve unless you have a sense of where you are already. For this reason, in my second manager role I started giving my designers and user researchers a list of skills and competencies. It contained role-specific skills such as “information architecture and flows” as well as more general skills everyone needs, such as “follow through”. 

A screenshot from the design growth framework by Jenny Shirey

Part of my Designer Growth Framework that I created and for coaching

I put these skills together with a rating scale that designers and user researchers could use to evaluate themselves and called it the “Design Team Growth Framework.” Team members filled out the Growth Framework before our coaching conversation so that we could look at it together, talk about their strengths and weaknesses, and choose specific areas for them to improve (I won’t going into more detail on the Growth Framework here, but I do use it during my one-on-one career coaching sessions).  

At your company, you might already have a list of skills you expect from your designers, or a career framework that lists out skills and competencies for each level. If so, use that! Give your designer a week or two to go through and evaluate themself against each competency and ask them to bring their notes to your coaching one-on-one. An hour is usually necessary for an initial coaching conversation—put it in the calendar and show your designer that you value their career growth.

Step 2: Having the Conversation

Coaching conversations are all about helping the learner uncover their goals and decide how to reach them. Of course as a coach you can still give your opinion and advice, but for the most part you’ll want to hold back from talking too much, especially in the beginning. 

Let’s say you’re looking at a list of skills and your designer is telling you she thinks she needs to improve her low-fidelity design skills. Rather than stating that you agree right away, you might ask questions, such as:

“Tell me more—why do you think that you need to work on this skill?”

or

“How do you think you might improve your low-fidelity designs?”

In addition to going through a list of skills and talking about how the designer sees themselves, I also ask where they want to go with their career. This helps us focus the conversation on areas that the designer will use most in the future. For example, if a senior designer’s goal is to become a design manager, you might want to steer them toward improving their leadership and design strategy competencies. If you have a visual designer who wants to move into a UX position, choose a few UX-specific skills and focus on improving those. Remember, while it’s totally ok for you to give your opinion, ultimately the skills that your direct report chooses to work on should be up to them.*

*Obviously, I’m assuming your designer is performing well in their role already and also is self-aware enough to know what their weaknesses are. If they are under-performing or have no clue that their skill level is less “guru” and more “newbie”, you may have to step in and point them toward specific areas for improvement. This will mean you’ll have to flex your constructive feedback muscles.

At the end of the conversation, make sure to leave at least 10 minutes to talk practicalities. Ask your designer to choose at least one skill to work on, and together brainstorm ways they can improve in that area. You can get creative—books and trainings are always an option, but maybe there’s a side project that they can take on or someone else on the team they can learn from.

Step 3: After the Conversation

Following up is easy to forget, but also crucial to success. If your workplace utilizes a goal setting tool, you can have your designer use that to track the skills they want to improve. I’ve also gone the old-fashioned route and had people write down their goals on a piece of paper that they kept in sight on their desk (science shows that writing down a goal makes it more likely that you’ll achieve it). 

The “commitment form” I created for one company

Although I struggle with remembering to do this, it’s a good idea to review the progress on these individual goals on a regular basis, the same as you would with company or team-level objectives and key results (for more details on OKRs, I’d recommend reading Christina Wodtke’s book Radical Focus or reading this article). A review doesn’t have to formal, it can be just a few minutes you spend in each one-on-one asking what they did over the past week to work on, say, low-fidelity design skills. 

At the end of the quarter (or whatever time period you used), it’s time to evaluate how things went and set up another coaching conversation! While it’s difficult sometimes to see progress, especially with skills such as “curiosity” or “driving results”, try and come up with specific behaviors and results that you noticed that showed growth. We designers are problem-focused by nature; being able to look back and see how much they’ve improved will boost your design team’s energy levels and motivation.

Back to the story…

Are you wondering how things went with the team that I inherited? 

I’m happy to report that a few months later, that same leader told me they’d noticed a big change overall in the team. While none of us were perfect, we were all learning and improving together. Being able to see designers grow in their careers is one of the best parts of being a manager. I hope you’ll get to experience it too.


If you’re interested in how individual coaching can help you grow in your career, you can find out more here.

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Product Discovery Fundamentals

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Constructive Feedback for Designers