Leadership and Management for Designers: 7 Action Items from Jen Dary

Jen Dary is the founder of Plucky, a company that specializes in creating healthy dynamics at work through coaching, consulting, workshops, and education. A few weeks ago, our Head of Design sat down with her for Episode 72 of the Hustle Podcast, and we pulled together together a few highlights from the conversation.

Get a 3rd party perspective

Leaders can get a lot of value from bringing in someone who isn’t on the org chart to objectively look at the challenges facing their company. A consultant with a proven track record can allow leaders to see their business from a different perspective, eliminate blind spots, and find new areas for growth.

Events can help with this, too (as long as it’s the right event). Surrounding yourself with other leaders in similar positions allows you to see that other people are facing challenges like yours. Being able to look at their issues from an outside perspective can give you a better understanding of your own problems and provides a sense of comfort and community knowing you’re not alone.

Understand ‘creator grief’

“Creator grief” is a common curse in the design industry. Team leaders, managers and executives typically started out as makers. When their responsibilities change, all that making stops. This can kick off what Jen calls an “identity quest” where leaders struggle to justify their role in the company on a daily basis.

Jen works with her clients to help them understand that even though their role is different, they’re still designers. The only difference is: rather than designing a product, they’re now designing design teams, culture, and strategy. That simple shift in perspective gives them a new way to address challenges and can help leaders find that sense of fulfillment again (I know it did for me).

However, Jen does understand that there’s something about that need to physically make things that might never go away for some people — and that’s okay. She guides many of her clients toward extracurricular activities outside the office so they don’t leave that feeling of creation behind.

Don’t view management as the only path

Many have a hard time knowing whether management is right for them. Jen helps people navigate this decision by encouraging individuals to look back at previous situations — outside of work — to determine whether they enjoyed leading people. Sometimes, there is an internal motivation to take on leadership roles that could translate well to the office. If someone enjoyed those experiences in the past, it’s not a huge leap to think they might be fulfilled by a management role.

But what about those who know management isn’t for them? In the past, it was generally understood that the only way to advance your career and earning potential was through management. But Jen says the old model is busted. There are other, equally viable paths that have emerged in recent years. For instance, there’s now the “deep-level expert” path, in which people can become sought-after specialists in their field and help others through writing, video, speaking engagements and other avenues.

Jen believes companies that accept and foster multiple paths will be better off in the long run as they’ll be able to attract and retain great people with different career aspirations.

Foster trust with your team

Ideally, leaders should be able to come to their team for help when making decisions. However, there will always be times when that leader has to ultimately make the call themselves. To be as effective as possible, leaders must be able to make that decision without fear of losing the support of their team. You need to know someone isn’t gonna flip a table when you make the call. If you don’t know that, decisions will inevitably become more stressful, difficult and time-consuming.

Jen takes teams through trust building exercises and micro movements in order to prepare leaders and teams for the moments when tough decisions must be made. Getting those decision-making reps in early can really help when it matters most.

Experiment without judgement

Funsize has never been averse to experimentation. We’re currently playing with a downstream mentorship structure from director to lead to designer to apprentice — something we think will help everyone hone their leadership skills.

Jen supports experimentation and encourages teams to try things and figure out what works. The key is to do so without judgement. Teams have to be able to have a sense of humor about things. If an idea flops, who cares? You now know one more idea that does not work (insert Thomas Edison metaphor here). That certainly doesn’t mean you stop innovating.

Remember that teams reflect leadership

Jen frequently conducts employee experience audits with companies. In these conversations, she looks for patterns. Are the same strengths and weaknesses being mentioned across interviews?

As it turns out, a lot of the time, the characteristics of the company are reflections of the person in charge. Although this isn’t necessarily a huge shocker, understanding this phenomenon is useful for leaders. Because if the leader is nervous about trying new things, it’ll be more difficult for that company to innovate and adapt. If management is too lax, laid back, and disorganized, employees might not take their job seriously enough.

It’s also important to realize that if relationships between executives are strained, that tension at the top will have ripple effects. Team members will be more nervous about communicating roadblocks, asking questions, or offering alternative points of view. Because of this, Jen says it’s vital that leaders make sure they’re taking care of themselves outside of the office so that they can be the best version of themselves for the team.

Don’t forget what it’s like to follow

To be a good leader, you have to remember what it’s like to be led. Many of the executives Jen works with have been in leadership roles for years. It can be difficult to remember what it was like to be under someone else’s direction, and that hurts leaders’ ability to empathize with their team.

Jen counsels her clients to throw themselves into situations where they’re not in charge. Whether that’s a yoga or coding class, strengthening that direction-taking muscle allows leaders to understand and accommodate for their own leadership flaws when they’re back on the job.

Funsize is digital service and product design agency that works with inspiring teams to uncover opportunities, evolve popular products, bring new businesses to market, and prepare for the future. Worked at by friends.

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