Three offer letters. Three exits.

What three trial-period exits taught me about what ”lead” really means.

I have worked in UX, brand and strategy since 2008. I have designed platforms, systems and products, evaluated teams, led projects and initiatives, and mentored designers. I have set up design from scratch as Head of Design and led design across mobile, web and enterprise products for startups, scaleups and corporations.

I consider my career a good one. But careers are built on discipline, effort, setbacks and the ability to recover from them. Over the years, I joined three companies as their design lead and left all three during the trial period.

This is what happened.

The audit no one asked for

The first company was launching several products at once. There was no design system, and teams were working in silos. On paper, I was hired as a lead. In practice, the design team was small and what ”lead” meant was never really defined.

I did what I thought leads do. I ran an audit, mapped the gaps, and proposed a design system, starting with the information architecture and a component library. I expected pushback on timeline or resourcing. What I got was silence.

No one disagreed openly, but in retros and stand-ups the message became clear: the team wanted me embedded in one squad, helping developers ship screens. Not shaping foundations. Not asking why.

I delivered the audit and the design system foundation anyway. Soon after, I was told I wasn’t the right fit.

Looking back, they needed a hands-on UI designer, not a lead. But I also never asked the question that would have revealed that early. I read the silence as space to lead, when it was a signal to check in. In my first week, my manager set out what success in ninety days would look like, but the team saw it differently. I should have brought those two views together before building anything.

The comparison I couldn’t win

At the second company, I joined a small design team as their lead. One of the designers had applied for the same role and was disappointed not to get it. That’s a completely human reaction.

From the start, I could feel the tension. Questions landed as challenges. Decisions were revisited in conversations I wasn’t part of. A quiet narrative formed: someone on the inside knew the product better, and the new lead was the outsider.

Being measured against someone threw me off balance. I don’t naturally compete, and instead of naming the tension, I tried to work around it. As delivery slipped and friction grew, more of it landed with me, and some of it rightly so. My managers were supportive, but the situation didn’t settle, and in the end they decided to end my contract.

I’ve asked myself whether anything could have changed the outcome. I think one thing might have: I had a direct, honest conversation with that designer in my first weeks, acknowledging the situation and asking what they wanted from their own role. I focused too much on that conversation neglecting the rest of the team and the other stakeholders. I wouldn’t now.

Too much access, not enough alignment

My third role was at a large company that spent over four months recruiting me. References, case studies, multiple rounds. When I started, most people were on holiday. The calendar was empty. The inbox, quiet.

I used that time the way I had been encouraged to: exploring the organization, connecting with teams, and understanding how design and AI tools were being used across it. When people came back, the tone shifted. What I saw as initiative, my manager saw as reaching beyond the role. I was let go for not meeting expectations.

What I missed seems simple in hindsight. Encouragement to explore is not the same as agreed scope. I should have checked in with my manager before going wide, so that my curiosity was visible and sanctioned rather than a surprise on their return.

You start to wonder: is it me, or is it the pattern? Honestly, it’s both.

The pattern

Looking at all three together, I see a pattern of mismatch. Each company hired a lead but needed something different day to day: a hands-on UI designer embedded in one team, someone who could step in without unsettling an existing team dynamic, and someone who would work within a narrower scope than the title suggested.

I did lead work in organizations that weren’t ready for it, and it looked like overreach. But mismatch only explains part of what happened. The other part is that I didn’t surface those differences early enough, and neither did anyone else.

Are there things I would do differently? Of course.

First, I would agree on expectations in writing before signing the contract, not after I start.

Second, I would earn trust through quick, visible delivery before pushing strategic work, and be honest with myself early about whether the role could ever become what I was hired for.

Third, I would bring the people with informal power onside earlier. In every role, someone’s trust mattered more than the org chart suggested: the colleagues who had been there longest, the person who had hoped for the role, a manager whose expectations I never asked about directly. I treated them as people to align with later. They needed to come first.

Could I have succeeded in these roles? In some of them, honestly, yes. I missed signals I can see clearly now. I pushed for foundations before I had earned the standing to ask for them. I assumed good work would speak for itself, when leading also means making sure the right people understand it and want to support it. Those are leadership skills too, and at those moments I didn’t use them well enough.

I don’t believe I failed because I don’t know my craft. The gap was in how I read the room, not in what I brought into it. That difference matters to me, because reading a room is something I can practise, and I am.

What these three failures taught me

These trial-period exits have clarified a few things for me.

Role clarity matters more than title. “Head of Design” or “Design Lead” can mean very different things in different organizations. The same title can be a strategist in one place and a pair of hands in another.

Politics are part of the job. Informal power structures, internal candidates, and unspoken expectations will shape your success as much as your output. You can’t ignore them and call it integrity.

Trust is earned in layers. Strategy only lands after you’ve proven you can deliver tactically and work well with the people already there. Foundations matter, but they come later.

Hard conversations are cheaper early. Every situation I’ve described got harder because an important conversation happened late, or not at all.

I’m still a design leader. I still believe in design teams, systems, strategy and design quality. I’m just more careful now about the environments I step into, and more explicit about what ”lead” means before I start.

If you’re hiring a design lead, ask yourself: do you actually want one? If you’re a senior designer moving into leadership, protect your footing and ask the uncomfortable questions early. And if you’ve had your own trial-period exits, know that mismatch is not the same as failure, as long as you’re willing to look honestly at your part in it.

Sometimes the market is telling you something. Not always that you’re wrong, but often that you’re in the wrong room. And sometimes, that you walked in without asking the right questions at the door.

Hi, I’m Cristina, a Digital Design Lead and Product Designer based in Copenhagen. I write about creative leadership, design culture, and the quiet moments that shape how we grow as professionals. My work connects UX, brand, and strategy to help teams turn complexity into clear, meaningful digital experiences. I lead the design community in Denmark through IxDF, and through fractional design leadership I help ambitious teams build stronger products, sharper practices, and more confident design cultures. I’ve worked across technology, healthcare, fintech, and public-sector products helping teams move from early ideas to focused, production-ready experiences. Forever learning, mentoring, and helping designers find their voice in rooms built for noise.

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