Get Over Yourself: Being Open to Challenge

To be a good design leader, encourage your team to challenge your decisions

Alex Jones
Aug 9, 2019 · 8 min read
Photo: suedhang/Getty Images

OOver the last couple of years, I’ve had the privilege to lead a design team at a well-established SaaS company as we’ve built a whole new suite of products. During that time, our team more than tripled in size, with a combination of full-time employees and contractors spread across the U.S. and engineering teams located overseas. It’s been an exhilarating ride, to say the least.

At our peak, we had a well-balanced cadence of reviews and meetings, which helped us feed a large number of development teams while holding a high bar for usability and a cohesive experience.

Simply put, we had the right formula to meet high expectations amid furious growth.

As we wrapped up the initial push, the team shrank to about half of its peak size, yet we kept the same cadence of reviews and meetings. A problem emerged: What had helped smooth our way as a larger team was now a subtle source of friction.

And I’ll admit, I didn’t see it. The change was a gradual one, easily lost amid the day-to-day. Lucky for us, one of our more recent hires, frustrated with the status quo, challenged how we were working.

My initial reaction was a defensive one. I explained why we did what we did, feeling fully justified that our past decisions were right and there was no need to change.

Thankfully, he didn’t let it go, and the next time we talked about the same issues, the situation clicked into place for me: We were following practices that we had established for a different team in a different era of our product cycle.

Sure, that setup still basically worked, but only because we were putting in more effort than we realized to keep things moving forward. Once that sunk in, it was easy to let go of this familiar system and, as a team, lay out how we should work going forward.

This was a mixture of “aha!” and “duh!” moments. It taught me a critical lesson that I thought I already knew: True leadership requires that we encourage others to challenge us, that we be truly open to changing past decisions that no longer serve the team.

Effective decisions come from being open to challenges

A good leader knows that being open to different perspectives — embracing situations where past decisions and outlooks are openly challenged, often by people with less or different experience — opens new possibilities, which leads to more informed decisions.

That’s not always easy to handle in the moment. We humans can get attached to our ideas, and our emotions can outweigh logical explanations, especially if the recommended change affects something we’ve built.

But a good leader understands that a challenge from someone on her team is more likely highlighting an environmental or process issue than it is a direct challenge to her personally. (Handling personal challenges is a topic for another post…)

Plus, once we’ve hit a routine, it’s easier to keep going than it is to pause and reassess. Then, slowly, frustrations build, which can go unaddressed or be dismissed because, you know, “That’s how we’ve always done it.”

Ugh… There’s no excuse for that.

Build a positive, challenging environment

It is the job of a good leader to craft teams of people who care deeply about shared success and to provide an environment where those people not only feel comfortable challenging the status quo but are expected to do so. The sense of personal investment within each person on the team grows as they become involved in and partially responsible for the shared environment.

It isn’t easy to pull this off, especially in the midst of the daily chaos of running a team in an active business, but we must if we’re going to attract and retain the best people possible.

It taught me a critical lesson that I thought I already knew: True leadership requires that we encourage others to challenge us.

“Bring me solutions, not problems” is a great way to be blindsided by an issue down the road. A good leader should actively encourage people to raise friction points, even if they don’t know how to improve them. A huge benefit of having a team is that we can bring the combined brainpower and experience of a group to bear on an issue.

An environment where positive challenges are encouraged ensures we achieve ever-higher goals and avoid going stale.

Our teams deserve better than that. So do our customers. And so do we.

Crafting the right environment

Here are a few ways that you can start to build this environment:

Listen to your team. Seriously, listen to each idea and every complaint. Do not prepare a response or an explanation as they’re talking. That’s a sign that you aren’t listening.

Provide context. Once they’re done voicing an idea or opinion, talk through how the team/situation got to this current point. What was the path for adopting this tool or requiring a specific sign-off? That discussion will give them a better understanding of why things are the way they are, which levels the playing field for your discussion and possibly provides insight as to whether something should change and how.

Ask them how they think it could improve. Again, listen as they speak. It doesn’t matter if their idea was previously tried and scrapped. Situations change, so revisiting old ideas may pay off.

Implement quick improvements. When you hear an idea for a small change that makes sense, make the change quickly, communicate what it is and why it happened, and ensure everyone knows which team member made the recommendation.

Widen the discussion for large changes. If something will have a big impact, pull in the rest of the team to discuss, following the same patterns above, while encouraging everyone else to be open and provide ideas to solve the issue. Again, make sure to credit and thank the person who challenged the norm.

Acknowledge that not all change makes sense. Not every idea for change is feasible, and not every challenge can be solved. When something can’t or shouldn’t change, ensure everyone understands the larger context and what eventual changes may allow you to effectively address it.

Make it easy for people to bring new ideas to the table. Hold a Start, Stop, Continue retrospective with your team(s). You’ll see a bunch of those small ideas roll in, as well as some big ones. Odds are good that you’ll learn that some of your processes may not be as effective or meaningful as you think. You may also discover that you need to do a better job explaining why your team does or doesn’t do certain things, so everyone is on the same page.

Rinse, repeat.

Work with all of the people on your team

A lot of folks aren’t comfortable openly, or even privately, pushing back on their manager, which is understandable. There’s a strong power imbalance that we need to be aware of and actively work to counteract.

Some people will grow into the concept after they’ve witnessed us consistently walking the walk. Others may not get there, but we need to keep trying, as their voices are important. In every case, we need to demonstrate our openness to these challenges and encourage the team to participate.

One strategy that I’ve used to encourage quieter folks to speak up is to privately ask the bolder (typically senior) members of the team to visibly challenge my ideas or past decisions in a positive way in front of the others on the team. It’s not staged — I don’t know what that challenge will look like — but having their help as an ally to demonstrate that challenge is welcome and valuable shows that not only is it safe, it’s a part of our culture.

It’s also possible that you have someone on the team who challenges everything. Having everything questioned can be very draining. But, so long as that person has good intentions and gives feedback in a constructive and positive manner (“Hey, I think this could be better,” not “This sucks.”), you may well have found a catalyst that ensures the team constantly improves.

“Bring me solutions, not problems” is a great way to be blindsided by an issue down the road.

An environment that welcomes challenge also makes you a better manager, as you won’t be able to make off-the-cuff mandates that aren’t really justified. We do that far more often than we recognize, often with the best of intentions or a belief that a decision doesn’t need deeper insight. Knowing that a decision may well be challenged by those it affects can give you just enough pause to make sure you’re making the right call, or better yet, delegating it to someone closer to the issue.

Getting personal — being challenged is uncomfortable

It’s hard to step away from our egos in these situations. I’ve definitely had a hard time accepting feedback when the practices and structures I put in place are questioned, especially by someone new to the team. My brain immediately reminds me of how much time and energy I invested in establishing the practice, particularly when it has served us well.

So, this is where I battle hypocrisy: I absolutely hate hearing someone say, “Well, that’s how we’ve always done it,” but avoiding change is often the easiest path. I have to actively remind myself that these challenges are opportunities to improve and learn.

The hardest lessons are often the most valuable, so it’s worth it.

A quick note of thanks

While I won’t name names here, I want to thank everyone throughout the years who has pushed back on me, sharing different angles and, often, better solutions than mine to drive our team forward.

I’m trying, and I am certainly better for it.

And thanks to the leaders who’ve been open not only to being challenged, but also to acting upon the ideas I’ve raised throughout my career. I know it hasn’t always been easy.

Photos have been modified by me. Originals by Headway, Charles, Randy Fath, Alex Kalinin, You X Ventures, and Ross Findon.


Helping designers thrive.

Alex Jones

Written by

Leading at the intersection of strategy & design. Autodidact. Barbecue acolyte. I start fires (the good kind).


Helping designers thrive. A Medium publication about UX/UI design.

Alex Jones

Written by

Leading at the intersection of strategy & design. Autodidact. Barbecue acolyte. I start fires (the good kind).


Helping designers thrive. A Medium publication about UX/UI design.

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