February 21, 2022 Leadership

Transitioning Well

Transitioning to a new team is hard, doubly so as a leader.

Transitioning teams is hard. Transitioning teams as a leader has a whole swath of extra challenges. Whether it be a new job or a new role within your current company, there’s plenty to figure out each time…

My most recent transition

I moved to a new area in Shopify about 6 months ago to form a new organization. I didn’t have a clear mandate. I didn’t know which teams I could pull in. I didn’t know who I’d even be working with to pull this off.

No matter how many times I’ve made a change, each time a swarm of emotions floods my senses:

Imposter syndrome always finds its way to the forefront. Why does this always surface? I don’t know. Not a psychologist. Just another human. Trying to figure out a little bit each time. But reflection, intentionality, and naming things makes each change easier.

We face this discomfort with a plan centered on one idea: trust.

Context gathering

Do you know the domain? Do you know the organization? Do you know the history? Do you know the people? Figure it out, fast. Context is necessary to succeed. Context is necessary to ensure each challenge faced can be learnt from.

Start by reading: documentation, tech designs, blog posts, product briefs, a little code. Everything you can get your hands on. You need to put in the work. You need to show that you care.

Now that you’ve read, it’s time to connect with your new humans. Be upfront that you don’t know much yet. This’ll go a long way to building trust and getting you good answers. Ask your team, ask past leaders, and ask skip-levels. Seek their perspective. Ask every question you can think of. Ask them what they think you should know. Be a sponge.

Clear and authentic communication

While gathering context, you’ll get ample time with your new team. Be honest, authentic, and clear. Another opportunity to build trust.

You came to this org/team/company for a reason. What is it? Share that. You may not have a lot of context yet, but you’ve (hopefully) got passion. Share your ambition and excitement. Share your goals and where you’ll focus. Share the opportunities you see ahead and the challenges you’ll learn from. Share tidbits of your background that are relevant and show you’re capable. Share who you are, as a human, and who you are in this company.

And while you’re sharing, be brutally honest on what you don’t know. Start asking for feedback feverishly. Set the stage for how you’ll be showing up.

And even more important than sharing: listening. Ask your new team what they expect from you. What they need from you.

Deep care and trust

And that open curiosity will provide the chance to care deeply.

Don’t discount how important care and trust is at this stage. While you’re nervous about this transition, your new team is doubly-so. Focus on building deep and caring relationships. Focus on being human with your humans. Once again, more opportunity to build trust.

Setup 1:1’s with everyone in your new team. Everyone. Spend time sharing history. Spend time sharing ambition. Spend time sharing concern. Spend time being human, together. But also, dig a little. Ask what can be better. Ask what should stay the same. Ask what challenges they’re facing. And begin helping.

I also love setting up intentional time to go deep. Think playing The Ungame or 36 Questions That Lead to Love (which I know sounds strange, but these are excellent). Focused time to move past small-talk will accelerate trust and empathy on a whole other level.

All together

These three approaches lean on and compliment each other. And importantly, they all drive trust with your new team. While you gather context to understand what you’ve walked into, you can be vulnerable. While sharing clearly why you joined, you can listen. In all these conversations, you can focus on deep human connection. Building deep deep care and trust for each human in your new team.

There’ll be new challenges (and old ones). There’ll be surprises. There’ll be ample mistakes. But, with this foundation of trust, you (and the team!) will be ready to weather them with grace and anti-fragility.