Every Stage of Someone’s Time With You Is a Leadership Moment

My name is Jennie Reis, I’m one of the new executive coaches here at CoCreate Work. However, I’ve been in the executive coaching space for years. Today, I want to touch on personal development and what it means to lead through every moment at work.

Think about someone who’s worked with you for a couple of years- colleague or a mentor. The version of your organization they met on day one isn’t the same version they know now. How they were onboarded, how their first weeks went, and how often their progress was measured cumulates over time. .

Most leaders treat those moments as separate: hiring and onboarding is a recruiting conversation and a checklist. Development is something that happens once a year in a review. But team members don’t experience your organization that way. They experience one continuous relationship with your organization, and continuity is what actually builds trust.

There’s a version of this conversation that happens in almost every company. Retention is suffering, so the instinct is to simply fix retention. Engagement is low, so leaders go look for an engagement strategy. New hires are having trouble adapting, so onboarding just gets a simple refresh.

What I see over and over in my work with organizations is that these stages aren’t separate, they’re connected. What happens in hiring shapes what’s possible in onboarding. What happens in onboarding shapes whether development ever truly takes hold. What happens in development, or doesn’t, is what’s quietly driving people out the door. And this quickly becomes a cycle when leaders only look at the outcomes instead of reevaluating the causes and the disconnect that exists between them.

You can’t solve retention at the retention stage. By the time someone is thinking about leaving, the real work was almost always left undone somewhere earlier on.

So, where do those gaps actually show up?

I want you to think back to the last person who left your team. Or, think about the last new hire who just couldn’t seem to find their footing. If you really trace it back, there’s going to be a thread that runs through more than one stage. Maybe they were hired into a role that was described one way and experienced another way. That may have led them to feel disconnected from their sense of purpose and what the organization was actually building. Maybe onboarding gave them the logistics but not the context on how things really get done. Maybe the first real conversation about their growth happened in an impromptu performance review not in a structured, every few months, timeline.

Every stage leaves a residue. It shapes what someone believes about the organization, about their leaders, and about whether the investment they’re making into the organization will actually be returned.

One report found that 94% of employees say they’d stay longer at a company that invests in their development. You can’t invest meaningfully into someone’s development without onboarding that gives them a foundation to build on or a workplace culture to believe in. Replacing someone is estimated to cost six to nine months of their salary, a number that’s rarely just a retention problem.

Now, what does this mean for you as a leader?

HR can build a structure and help design the onboarding, but leaders are the ones who make it real. Showing up for the onboarding conversations, making development feel like a priority, setting the day-to-day expectations that tell someone whether this is a place they can grow.

When you as a leader treat these moments as separate, it sends a message that leaves people feeling frustrated and fragmented. As a leader, you might feel angry and confused as to why someone left, but the person who considered leaving likely felt the same way. When leaders treat their organization as a connected entity, people experience continuity. And that is one of the biggest drivers of trust.

Your Weekly Practice

1. Look at the story you’re actually telling

Reflect on the last three people who joined your team and the last three who left. Write down what you know about their experience in each stage: how they were hired, what onboarding looked like, what development conversations happened, what their last year felt like. Look for where things consistently break down. Pay attention to whether people are moving through the same organization, or through different versions of it depending on who they are or what role they hold. You’re not looking to assign blame. You’re looking for the throughline you might not have seen while you were in the middle of it.

2. Build the bridge between hiring and onboarding on purpose

Someone’s experience of your organization starts the moment they read the job description, not on-site day one. Sit down with the last role you hired for and ask honestly: is what we described what someone would actually experience? Is the culture we discussed in interviews the one that shows up on a random day of the week? Does a new hire leave their first month with a clear sense of how their work connects to something that matters like their personal growth or the team? If there’s a gap, it might not solely be a recruiting problem. That’s worth naming.

3. Make development an ongoing conversation, not an annual one

The leaders who keep people long-term don’t wait for the annual review to ask what someone wants to grow into. They ask it during onboarding and revisit it in one-on-ones. They think about development not just as training or promotion, but as giving people more ownership over meaningful work. This week, pick one person on your team and ask: What do you want to be better at a year from now?

Then, ask yourself what you’d need to build to help them get there. Staying close to that question is how leaders stay genuinely connected to where their team is and where they want to be. This is a map of the experience you’re creating for every person who chooses to work for you. Treating each stage as connected to the next allows you to see where the gaps you’ve been trying to fill are and what has already been built to close them.