When a New Hire Has Impossibly Big Shoes to Fill

5 tips to help teams adjust when a new hire replaces a well-liked teammate

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There’s a special kind of awkwardness that can sometimes settle over a team when someone new arrives to replace someone everyone loved.

The new person feels it – that invisible presence of the person who came before, the inside jokes they don’t understand, the subtle ways they don’t quite measure up to a memory that’s grown more golden with each passing day.

And existing team members feel it too. They’re trying to be welcoming, but there’s grief mixed in with the hellos, and it’s hard to give someone a fair shot when you’re still missing someone else.

If you’re leading through this transition – or living through it as a team member or perhaps that new person – here are five tips to help you improve the situation.

P.S. Thank you Becky for sharing this wonderful topic request in a comment!

1. Name the Elephant in the Room

When someone new replaces a beloved team member, you might catch the team (or even yourself) talking about that past person in hushed, reverent tones when the new hire isn’t around.

But this isn’t the best approach.

Instead, acknowledge the situation directly – ideally before the new person even starts. Tell your team: “Jamie was wonderful, and we all miss them. And that’s exactly why we need to be intentional about giving Alex room to be Alex, not Jamie 2.0.”

With the new person, you might say something like: “I want you to know that the person before you was really loved here. That might make your first few months harder than they should be, and I’m sorry about that. But it also means you’re joining a team that’s capable of deep loyalty and connection – they just need time to extend it to you too.”

Does this feel vulnerable and a little uncomfortable? Yes.

Is it better than months of unspoken tension? Also yes.

2. Stop Saying “That’s How [Previous Person] Did It”

Every single time you say this phrase, it’s like you’re telling the new person they’ll never measure up. (Not intentionally, but that’s likely how they’ll take it.)

Here’s a better approach that both leaders and team members can adopt: “In the past, we did X. I’m curious what your take would be.”

Or even: “We used to do X, and honestly, I’m not sure it was the best approach. What do you think?”

This shift is subtle but powerful. You’re sharing institutional knowledge without weaponizing nostalgia, and you’re giving the new person permission to bring their own strengths to the role instead of trying to mimic someone else.

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3. Give the New Person a Safe Space to Be Imperfect

New team members who are replacing beloved predecessors might feel like they need to be perfect immediately. They’re hyperaware of every mistake, every moment they don’t know something, every way they’re different from the person everyone misses.

Leaders and team members can counter this by deliberately normalizing the learning curve.

Share your own early mistakes. Laugh about the time you completely misunderstood how a process worked. Ask genuine questions about the new person’s previous experiences instead of just throwing information at them.

And critically: defend them when they make reasonable mistakes.

If someone on the team sighs heavily because the new person did something differently than their predecessor, that’s your moment to step in. “Hey, Alex is learning our systems, and this approach actually makes sense given her background. Let’s give her room to find her footing.”

4. Help the Team Grieve Properly (So They Can Move On)

Sometimes teams get stuck because they never actually processed losing someone they cared about. Maybe the person left suddenly, or the team felt like they couldn’t be sad because “it’s just work,” or they went straight from one person to another without any breathing room.

If you’re a leader and you sense this is happening, it’s worth creating space for it. This doesn’t have to be dramatic – a simple team conversation about what made the previous person special, what you’ll all miss, and what you want to carry forward from their influence can work wonders.

Once people feel heard in their loss, they’re much more capable of opening up to something new. Unprocessed grief tends to come out as judgment, comparison, and resistance to whoever’s new.

This approach tends to work much better for Feeling personalities, by the way. It likely won’t be a good fit if your team is primarily made up of Thinking types.

5. Celebrate the New Person’s Unique Contributions (Loudly)

This is where you actively shape the narrative. When the new person brings a fresh perspective, solves a problem in an innovative way, or uses their particular skills to help the team – make a big deal out of it.

“Alex, that approach you took with the client presentation was brilliant. That’s a real strength you’re bringing to this team.”

“I love how you reorganized the workflow – it’s so much clearer now.”

“Great job handling that difficult conversation today.”

You’re not making comparisons. You’re simply noticing, naming, and appreciating what this specific person contributes. The more you do this – and the more you encourage the team to do it too – the faster everyone starts seeing the new person as a whole individual with their own valuable skills and approach.

Over time, this helps the team build new positive associations with the role, rather than constantly measuring against a memory.

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The honest truth?

Some of these transitions are just going to be hard, no matter how thoughtfully everyone handles them. The new person might struggle a bit before finding their groove. The team might take longer than you’d like to fully welcome them in. There might be moments of tension and hurt feelings.

But if everyone involved can extend a little grace – to the new person finding their way, to the team processing their feelings, to the leader trying to navigate all of it – these situations can become growth opportunities.

People will learn to hold complexity, make room for change, and build something new without erasing something that mattered.

And sometimes, a year later, everyone looks around and realizes: this person wasn’t meant to fill anyone’s shoes. They were meant to walk their own path, and the team is better for it.

Measure Your Team’s Effectiveness

If you’d like to measure how effectively your team currently operates, consider taking our free Team Dynamics Quiz.

It only takes a couple of minutes to complete.

It evaluates the key aspects of team dynamics that contribute to your team’s overall performance. And if you find that your team may benefit from boosting effectiveness, we’ll share tips and advice on how to do so.