Messy Middle #25: The best journeys aren’t always the smoothest
“82% of managers feel overwhelmed by their responsibilities, and 60% report struggling to balance the demands of leadership with the needs of their teams. ”
Middle management in design is one of the most complex leadership roles—sandwiched between high-level strategy and on-the-ground execution, responsible for translating vision into reality while keeping teams engaged and productive. It’s a role defined by constant ambiguity, shifting priorities, and the weight of competing demands. No matter how well you plan, things will break, deadlines will slip, and difficult trade-offs will need to be made.
As leadership expert Brené Brown aptly puts it in Rising Strong, “Vulnerability is not winning or losing; it’s having the courage to show up when you can’t control the outcome.” This mindset is crucial for middle managers, who must model adaptability and emotional intelligence for their teams.
So, how do you thrive in an environment where uncertainty is the norm? The key isn’t about avoiding failure—it’s about developing resilience, setting boundaries, and coaching your team through challenges without burning out.
This article explores three essential shifts for middle managers:
Reframing Your Relationship with Uncertainty – How to pivot from perfectionism to adaptability, shifting your mindset from “I have to fix this alone” to “Who can I bring in to help?”
Putting the Load Down – How to let go of unnecessary burdens, set boundaries, and focus on what truly matters instead of getting caught up in reactive problem-solving.
Coaching Your Team Through Challenges – Why middle management isn’t just about execution, but about developing the next generation of leaders by fostering resilience, ownership, and confidence.
By embracing these strategies, you’ll navigate the complexities of leadership more effectively and build a culture of growth and trust within your team.
Step 1: Reframe Your Relationship with Uncertainty
Perfection is an illusion, and the most successful leaders understand this deeply. Research from Stanford University reveals that leaders who embrace uncertainty and adaptability are 1.5 times more likely to outperform their peers in high-pressure environments. Instead of viewing challenges as insurmountable roadblocks, the key is to shift your mindset:
From “This shouldn’t be happening” → “This is happening, so what’s next?”
At Target, when I led the transformation of the loyalty ecosystem, there were multiple moments when unexpected challenges surfaced—whether it was tech constraints, shifting priorities, or resistance from stakeholders. Instead of dwelling on why things weren’t going according to plan, I learned to reframe the situation. One instance was when we realized our product infrastructure wouldn’t support a key feature we had envisioned. Rather than seeing it as a dead end, I pivoted the conversation: Given the constraints, what’s the best path forward? This shift reduced frustration and helped us find a creative workaround that was even more scalable in the long run.From “I have to fix this alone” → “Who can I pull in to help?”
When I was leading the redesign of Venmo’s credit card experience, there was a critical moment when the project hit a roadblock due to legal and compliance concerns. My instinct was to dig in and problem-solve solo, but I quickly realized that wasn’t the most thoughtful approach. Instead, I pulled in a cross-functional team—engineers, legal advisors, and product managers—and we held a rapid working session to break down the issue. By distributing the challenge and leveraging different perspectives, we resolved the compliance concerns and uncovered an opportunity to improve the user experience in a way we hadn’t considered initially.From “I failed” → “What did I learn?” Early in my career, I led a feature launch that didn’t land well with users—engagement was much lower than expected, and we had to sunset the feature within months. At the time, it felt like a failure. But instead of letting it define my capabilities, I leaned into it as a learning experience. I conducted post-mortems with the team, identified where we had made incorrect assumptions about user behavior, and refined our approach to validation before launch. That experience fundamentally changed how I approach product strategy, making me more rigorous about testing ideas early and often. Today, I bring that same mindset to teams I lead—normalizing reflection and iteration instead of fearing missteps.
Try this: At your next team meeting, normalize uncertainty by sharing a recent example of when something didn’t go as planned and what you learned from it. This practice builds trust and encourages your team to view setbacks as part of growth.
Step 2: Put the Load Down—And Let Others Do the Same
Middle managers often bear the weight of competing demands: leadership expectations, team challenges, and their drive to excel. However, research shows that 60% of managers feel overwhelmed by their workload, leading to burnout and decreased effectiveness (Forbes, 2021). To sustain your impact, you must release what you can’t control and focus on what truly matters.
From “Why is this happening?” → “What can I control?”Early in my career, I spent much time frustrated by decisions outside my control—whether it was leadership shifting priorities or a project getting blocked due to organizational constraints. Over time, I realized that my energy was better spent focusing on what I could influence. A pivotal moment was during the loyalty redesign at Target when conflicting stakeholder needs created delays. Instead of dwelling on the misalignment, I focused on what I could do—facilitating workshops, clarifying priorities, having more minor conversations to get us unblocked and reframing the problem in a way that got different groups on board. That shift reduced my stress and allowed me to drive meaningful progress despite the challenges.
From “I have to say yes” → “I can push back and prioritize”: At Venmo, I once had an engineering leader push for an accelerated timeline on a redesign that would have compromised the user experience. The proposed path forward had usability issues; if we had launched prematurely, we would have only introduced new ones. I had to push back—not by saying “No,” but by reframing the conversation: What problem are we solving, and what trade-offs are we making by rushing? I reset expectations by showing the risks and offering an alternative roadmap that met business goals. We didn’t build the best experience forward, but both sides made compromises, and we launched in the timeline the leader wanted. That experience reinforced that advocating for the right priorities isn’t about resistance but ensuring quality outcomes.
From “I need to be available all the time” → “I can set boundaries and empower others” I used to pride myself on being the go-to person, always available for questions and last-minute requests. But over time, I realized that constant accessibility wasn’t helping anyone—it was just creating a cycle where my team relied on me instead of developing their problem-solving skills. When I started leading teams, I intentionally set boundaries—blocking focus time, delegating decision-making, and modeling a culture where people could troubleshoot before escalating. One of the most rewarding moments was when a team member told me, “I used to come to you for every roadblock, but now I feel empowered to figure things out first.” That’s when I knew setting boundaries wasn’t about being less available but helping others grow.
Try this: Identify one responsibility you’re holding onto that someone else on your team could take on. Delegating isn’t just about reducing your workload—it’s about creating opportunities for others to grow.
Step 3: Coach Your Team Through It
Middle management isn’t just about execution—it’s about developing people. Once you’ve learned to let go of what you can’t control, your next step is to help your team build the same resilience. According to a 2023 LinkedIn Workplace Learning Report, 94% of employees say they would stay at a company longer if it invested in their development. Coaching your team through challenges is a powerful way to demonstrate that investment.
From “Here’s what you should do” → “What do you think is the best next step?”Early in my career, I thought being a good leader meant having all the answers. If someone on my team were stuck, I’d devise a solution. But over time, I realized that wasn’t helping anyone grow. When a team member comes to me with a problem, I ask questions instead: What have you tried so far? What do you think would work best? Nine times out of ten, they already have a great idea—they need the confidence to act on it. And when they do, they build the skills to tackle the next challenge without waiting for my approval.
From “We have so much left to do” → “Let’s celebrate the small wins” I’ve worked on projects where the scope felt overwhelming—so enormous that progress seemed impossible. One that stands out is the rethinking of loyalty at Target. The vision was massive, but we broke it down into smaller wins instead of trying to solve everything simultaneously. First, we got alignment on the core problem. Then, we ran quick pilots. Each step forward gave the team energy and confidence to tackle the next one. Celebrating those small wins, even a simple “That was a great insight” or “We just cleared a major roadblock” made a huge difference in keeping the momentum going.
From “React immediately” → “Pause, assess, and respond calmly” I used to work with a leader who completely unraveled anytime things didn’t go as planned. It created a ripple effect—everyone on the team would mirror that stress, making even minor problems feel like disasters. I’ve learned that staying steady is one of the most important things I can do as a leader. That doesn’t mean pretending everything is fine when it’s not, but it does mean taking a breath before reacting, asking better questions, and focusing on solutions instead of panic. When I stay calm, my team follows suit, and we can tackle problems with a clearer head.
Try this: The next time a team member asks for your help, resist the urge to give them a solution. Instead, ask: What do you think we should do? This slight shift builds autonomy and decision-making skills.
Final Thought: Be OK with the Mess
Leadership isn’t about perfection—it’s about resilience. Being a middle manager means existing in the messy middle, where uncertainty is part of the job. The key is not to fight it but to embrace it, reframe challenges as learning opportunities, and coach your team to do the same.
As leadership expert Simon Sinek reminds us: “Leadership is not about being in charge. It’s about taking care of those in your charge.”
So, as you step into another day of balancing leadership and execution, ask yourself:
What’s one thing you can put down today?
