Four years ago, I wrote about my first bitter lessons as a design manager. A year later came the second part, and now it’s time to share some more hard-earned lessons that shaped my journey to becoming a more seasoned and confident design leader.
What’s inside this article:
1. Wait for higher-ups to decide or tread on their toes?
When I stepped into design leadership, I had a simple expectation: I would set the pace. I thought I’d set the vision, clear the path, and watch my team execute. The frustrating reality hit fast: in large organizations, your speed is rarely your own; you move only as fast as the network around you allows. You can either blend into the average pace — dragging your feet through endless syncs and dependencies — or you can surge ahead and risk being seen as a rogue. Besides, it’s no longer just about your personal progress; the success of your entire team hinges on how smoothly you navigate this friction.
The hardest part comes when the slowdown is caused by people higher up the hierarchy than you. That’s where things get especially delicate. You can’t move forward, but at the same time:
- you can’t give them tasks;
- you can’t set deadlines for them;
- and you certainly can’t escalate every single blockage — because those are the very people you need as allies tomorrow.
Here are some common scenarios that freeze a design team’s progress:
1. The lead solution architect hasn’t confirmed the technical constraints for next year’s initiatives, leaving your team unable to finalize design directions with confidence. Your designers are sketching on sand.
2. The business strategy director is still debating the target market for the coming years, making it impossible to kick off the foundational customer journey mapping that must inform new solutions. You have a map, but no one has told you the destination.
3. The company is undergoing a reorganization, and top management hasn’t yet assigned product and engineering leadership for a vital transversal topic. Separate teams are building discrete features without an integrated vision, leaving your design team paralyzed in its mission to drive consistent, unified customer solutions.
4. The customer success lead hasn’t shared prioritized pain points from top enterprise clients. Your team is left guessing which high-impact improvements to focus on, risking a massive investment of effort in a minor feature.
Your team is ready to go, but the senior leaders holding the keys are often zoomed out on big-picture strategy. They just don’t see the headaches their indecision is creating for you right down the line.
However — and this sounds almost like blasphemy — higher-ups aren’t all-knowing gods: they often cannot decide because we, middle managers, haven’t fed them the essential intelligence from the design frontline. The solution isn’t brute-force escalation; instead, try reframing the conversation from one of demand to one of shared urgency and risk mitigation.
A high-impact design leader doesn’t wait for permission; they offer a better path forward. This requires a shift in tactics:
- Stop asking for an answer, start presenting a choice. Instead of emailing the strategy director asking for the target market decision, you present 2–3 high-level solution options, each tailored to a different potential market. Frame the email not as a plea, but as a risk assessment: “Delaying this choice pushes our timeline back by X weeks. To keep the project on schedule, we need to commit to Scenario A or B, as they have different design and architectural implications. Which risk profile is the business most comfortable with?”
- Move from dependency to co-creation. When the solution architect is slow to confirm constraints, don’t wait for a formal sign-off. Schedule a working session — a 1-hour “design constraint workshop” — where you walk them through your proposed direction. Critically, you present your work as a strawman for critique rather than a beloved idea seeking approval. As a result, you lower the cognitive load and drastically increase the likelihood of a rapid decision.
I call this strategy acting with radical transparency, or being constructively audacious.
You don’t ask, “What should we do?” or “When will you decide?”
You state, “We are facing options A, B, and C. These are their pros and cons, and here are the likely scenarios of how things will unfold. The design team is leaning towards option C because of X, Y, and Z, but we need to make a holistic decision, taking into account business goals and technical vision. Let’s use this canvas to prioritize and decide.”
2. Your “Schrödinger’s promises”
You’ve probably heard of Schrödinger’s famous thought experiment: a cat in a sealed box has a 50% chance of being poisoned. Until the box is opened, quantum theory suggests the cat is simultaneously alive and dead. It’s a good metaphor for design managers who often find themselves in a kind of quantum superposition, too.
Design managers stand at the intersection of their team’s aspirations and the company’s priorities. While this is what makes managers valuable, it’s also the source of their largest challenges. In many cases, you cannot be sure about the fate of an initiative you are pushing forward until it clears all approvals and becomes a reality. But if you wait until the last minute to share anything, the team will be left in the dark, missing transparency and a vision of a better future to work toward.
- If you don’t make any promises to your team, you avoid creating false expectations, especially in a larger organization where many factors are beyond your control. But this also means fully submitting to decisions from above and not taking an active role in driving bottom-up change. Yes, you are “safe,” but will your people respect you and just go along with whatever happens?
- If you promise something to your team, you earn respect and motivate people through the vision of a better future. However, in a complex organization, success is never guaranteed. When things don’t go as planned, especially in the last stages, disappointment can hit the team’s morale even harder than if you had said nothing at all.
As you can see, design managers must pay attention to what they tell the entire team and team members individually. Here is an example of such a “Schrödinger’s promise”:
You hired Andrew for a mid-level role, but in just a few months, he has shown performance comparable to senior designers on your team. It’s clear to both him and you that Andrew deserves a promotion. However, the promotion cycle has already passed, and you’ll need to fight for an exception.
If you tell Andrew you’re working on it, he’ll naturally ask about the timeline and salary increase amount. Your reassurances will create expectations. Can you guarantee your initial estimates are accurate and that the outcome won’t be disappointing? Or should you stay quiet until there’s a final decision — risking that Andrew starts job hunting because he sees no clear growth path in your company this year?
Here is one more case:
Your team is stretched thin, so you push for reinforcements. After weeks of discussions, leadership finally gives a verbal green light to hire two additional designers. Relieved, you promise Sophia and Lucas — both overwhelmed and on the brink of quitting — that help is on the way. One new hire will support Sophia, the other will support Lucas.
You couldn’t have stayed silent about it because you might’ve lost two best-performing colleagues. But then, budget constraints hit in, and top management reconsiders priorities. Eventually, you get an approval for only one additional designer. Now, instead of feeling supported, either Sophia or Lucas will feel misled. You raised their expectations, and the one left without help will be even more frustrated than before.
Situations like these happen all the time. You need to set expectations while also being responsible for their accuracy. Even the best-intentioned commitments can backfire if things don’t go as planned. But avoiding promises isn’t an option either: your team needs clarity and direction, which is the most vital part of the design manager’s job. So, what can you do about it? Recognizing the challenge is the first step; you can make better choices when such a situation arises.
3. Pet projects: more harm or value?
Working as a designer in almost any company sometimes feels like a lottery. Some designers are lucky to get exciting projects with decision-making freedom and responsibility — consequently boosting their careers, while others have to work on monotonous, restricted projects — and lack opportunities to grow.
When I moved into management, I wanted to make sure everyone had solid growth opportunities regardless of their current assignments and areas of specialization. And kicking off an exciting pet project seemed like a great way to make that happen.
So, what can go wrong?
Well, at first, you may notice a terrific improvement: team members will complain less and will try new methods and tools outside of their dull main projects. It’s a win-win: designers feel like they’re growing again, and the business benefits from a more skilled team.
However, problems are just around the corner.
Human energy and motivation are limited, and it’s hard to go the extra mile (main project + pet project) long enough. There are two main risks:
- Drop in work quality. People may fall in love with the pet project and perform their primary tasks worse. The contrast between a desirable pet project and obnoxious primary tasks will only deepen their demotivation.
- Burnout. Highly responsible team members will try to get involved equally in the main project and the pet project, which might lead to their quick burnout.
I’ve been in this position from both sides — as a guy who had a pet project and a manager who organized a pet project for the team. Let me get this straight: people rarely engage in pet projects just because everything is fantastic. In most cases, they aren’t challenged enough by their main work, so of course, they start seeking “added value” on the side, including freelancing after work hours.
So, what can be a better alternative?
- Co-pilot approach. Instead of assigning a valuable, complex project to a single senior designer, pair them with a less experienced teammate. For example, if someone is preparing a UX strategy workshop, ask them to involve another designer as an assistant — to actively participate, not just watch from the sidelines. With guidance from a seasoned colleague, the learner gains hands-on experience in new design activities within real business constraints.
- Designer rotations. As a manager, you have a broad view of all projects, making you well-positioned to facilitate rotations. When a designer’s current work no longer challenges them or fails to fully utilize their skills, consider moving them to a different team or product area where they can grow. Rotations encourage cross-pollination of knowledge — designers bring fresh perspectives that lead to better problem-solving. However, for this approach to be effective, rotations should be intentional and planned in advance, balancing individual career growth with business needs.
- In-house hackathons and design sprints. Organize designers to brainstorm and prototype solutions for real but non-urgent problems. Such events provide a safe environment to experiment with new methods and tools while delivering value to the business. Unlike pet projects, these initiatives stay aligned with the company’s goals and don’t compete with designers’ core responsibilities.
That said, pet projects aren’t a solution — they’re a symptom of suboptimal work distribution. Fortunately, there are many ways to address the root cause without relying on pet projects.
4. “Ask me anything” is not an onboarding
When managing a team, you’ll inevitably handle onboarding — whether it’s welcoming a new hire or, let’s say, introducing a designer to a new project. A usual approach is to assign a buddy who knows the subject well and can guide the newcomer through it.
For some reason, free-form onboarding is a common practice in many companies. A buddy might say, “I’m here to help, just ask me anything!” — and then return to work. While this openness is well-intentioned, it’s no substitute for a structured program.
The problem with this “I’m here to help” can be explained using the Rumsfeld Matrix, derived from a statement by former U.S. Secretary of Defense Donald Rumsfeld in 2002. While he was discussing evidence linking the Iraqi government to weapons of mass destruction, he actually outlined four universal types of knowledge:
- Known knowns — things you are consciously aware of and understand.
- Known unknowns — gaps in knowledge that you recognize.
- Unknown knowns — implicit knowledge that is your second nature as an expert in the topic, but not consciously articulated.
- Unknown unknowns — areas you don’t even realize you’re missing.
If you’ve ever played a real-time strategy game, you’ll immediately recognize this concept. It’s just like the “fog of war,” where parts of the map stay hidden until your units explore them.
So, free-form onboarding often fails because newbies tend to focus only on their known unknowns. There is little chance they’ll ask about unknown unknowns — things they don’t even realize exist.
For instance, a newly hired designer might ask where to find the design system or which tool the team uses for prototyping — these are their known unknowns. But they probably won’t ask why a particular UX pattern was designed a certain way, which past experiments failed, or how decisions get influenced by stakeholders outside the design team.
Now that I’ve explained why free-form onboarding isn’t effective, what’s a better alternative? Hopefully, it is not an exhaustively documented process — keeping everything up to date would require an enormous effort! Just thinking about the amount of information to write, record, and constantly maintain is overwhelming. And the reality is, you don’t need a perfect write-up. It’s completely fine if knowledge is spread across different formats or exists only in certain people’s heads. The real secret to effective onboarding isn’t centralizing everything — it’s having a clear plan for what needs to be covered.
Continuing the example above, your plan may include the following points:
— Company’s business model and key differentiators.
— Market landscape and competitors.
— User and customer personas and their journeys.
— Product demo: key workflows, versions, and plans for the future.
— Stakeholder environment and decision-making processes.
— Organization structure with the newcomer’s place in it.
— Design processes, methods, and tools.
— Design assets: design system, guidelines, etc.
— Mission and vision. Strategy: for this year and long-term.
— Design roadmap for the current year.
— Design team’s rituals, conventions, and processes.
— …
To sum up, start by creating a solid checklist. No documentation? No problem. Simply list the key people to talk to for each topic. Break down large subjects into sections and suggest specific questions to ask. Encourage the newcomer to document their findings visually — using a digital canvas with sticky notes and arrows — and share it with everyone they’ve spoken to. It will help to map out complex concepts and ensure their correct understanding.
5. Management has its “pixel work”
Last year, I wrote an article called “How to bring value as a design leader without getting hands-on.” Now, I’m going to contradict myself a little bit because leaders do get hands-on.
But first things first.
There’s a widespread belief that great leaders should delegate everything, stay ultra-strategic, and step away from details. While there’s some truth to that, it creates a dangerous illusion that leadership means zero hands-on work. In reality, you’re not eliminating hands-on work; you’re just swapping one kind for another.
As a leader, you won’t spend time fine-tuning interface prototypes, adding colors to the design system, or personally scheduling user tests. However, leadership comes with its own kind of repetitive and tedious work. Here are three examples of such situations:
- Running an on-site team workshop. Sounds exciting, right? Until you’re deep in budget estimates, juggling travel schedules, securing approvals, and handling all the logistics to make it happen.
- Firing a team member for underperformance. It’s not just a one-time decision — it’s months of coaching, creating improvement plans, making and justifying the decision, and navigating the final settlement.
- Requesting additional design capacity. You don’t just ask the execs and get an instant yes. You must see the gap before it becomes a crisis, list the strategic projects that can’t move forward, estimate hiring costs, and prove the impact of missing resources.
These tasks come with a fair share of what some might call “dumb” work — filling out forms and spreadsheets, scheduling meetings, taking notes, and chasing approvals. It’s not glamorous, but it’s the reality. And some days, it eats up an alarming amount of your time.
The key is making sure all this “dumb” work actually leads to something meaningful. If you’ve moved from hands-on design to design management, as I have, you’ve probably trained yourself to see the UX impact behind every pixel shift. But spotting the strategic value in management’s nitty-gritty tasks? That takes time.
Let’s get back to the examples above:
- Running an on-site team workshop. Budget estimates, logistics, approvals — it’s tedious and far from strategic. And for what? A bit of team bonding? I bet you don’t need design expertise to book laser tag for two hours for a bunch of people. But what if this workshop is the key to closing a major gap in strategic alignment? What if it shapes the entire 2025 roadmap and priorities? Then, suddenly, all that hands-on work isn’t just worth it — it’s essential.
- Firing a team member for underperformance. On the surface, it’s just a bureaucratic nightmare: endless check-ins, justification documents, and legal hoops to jump through. Wouldn’t it be easier to just stick the guy on a low-impact project and focus on more valuable tasks? Maybe in the short term. But that move sets a dangerous precedent. It tells the team that mediocrity is tolerated and that going the extra mile doesn’t matter. If you want a team that stays motivated, you have to show that performance and accountability actually count.
- Requesting additional design capacity. So, you’re crunching numbers and juggling spreadsheets and slides. But why not just wait for product management to notice the gap and push for more resources? That way, you can focus on something more meaningful, right? Wrong. If you don’t take the lead, designers risk being seen as just a resource — something to be shuffled between projects. Before you know it, your team’s cohesion is gone, its maturity level drops to the bare minimum, and you’re stuck trying to fix the mess. So yes, taking capacity under your control is very strategic.
Leadership isn’t escaping hands-on work altogether — it’s swapping the pixel-pushing part for spreadsheets, forms, approvals, and logistics. The key is to see the strategy within the grind — or better yet, ensure that as much of your routine as possible drives real, tangible results and is not just for the sake of it.
In a nutshell
- Stop waiting for decisions from above. Assume senior leaders lack the full picture and then use your team’s “frontline intelligence” to propose options and mandate the next step.
- To motivate your team, you must make promises, but those promises risk backfiring spectacularly if they fail. Therefore, the only viable path is to replace vague assurance with structured, conditional transparency.
- While pet projects can temporarily boost engagement, they often indicate deeper problems and can become a refuge from the main work rather than an inspiration for it.
- Free-form onboarding isn’t welcoming — it’s chaotic, but that doesn’t mean you need a manual for everything.
- A leader’s hands-on work shifts from pixels to bureaucracy. Don’t eliminate the grind — uncover the hidden strategic goal behind every spreadsheet and approval form.