Flip the Script: What’s Your Five-Year Plan for Me?

We’ve all heard the classic career question: “What’s your five-year plan?” 

But in this episode of Relationships at Work, host Russel Lolacher flips it on its head—asking leaders to consider their five-year plan for their employees. Why? Because true leadership isn’t reactive—it’s intentional, strategic, and supportive. Russel explores how leaders can align employee growth with organizational goals, share industry insights, and build flexible development roadmaps. It’s time to turn career conversations into shared journeys, not solo missions.

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Transcript

Welcome back to Relationships At Work – your leadership guide to building workplace connections and avoiding those pesky blind spots. I’m your host, Russel Lolacher.

I’m a communications and leadership nerd with a couple of decades of experience and a heap of curiosity about how we can make the workplace better—for ourselves, our teams, and our organizations.

If you’re a leader trying to understand and improve your impact on work culture and the employee experience, you’re in the right place.

This mini-episode is a quick mindset shift for the week ahead. Something short, useful, and thought-provoking—straight from our R@W Note newsletter.

Today’s insight?
 Flipping the Five-Year Vision

 You’ve probably been asked this at some point in your career:
 “What’s your five-year plan?”
 It might’ve been during a check-in, a job interview, or a casual one-on-one. It’s kind of the grown-up version of “What do you want to be when you grow up?”

And you know what? It’s not a bad question.
 It encourages reflection. It invites us to think about where we want to go, beyond the day-to-day. It can give us purpose, direction, even motivation.

But here’s the problem...
 The conversation usually stops there.

So next time someone asks you that question, try flipping it:
 Ask your leader, “What’s your five-year plan for me?”

[Pause for effect]

Now, this is where it gets... awkward.
 You’ll likely see a pause. Maybe some squirming. Possibly a furrowed brow or that classic “Oh no, I wasn’t expecting that” look.

Because let’s face it—many leaders aren’t prepared for that question. And that says a lot.

We expect employees to chart their own course—and yes, they absolutely should take ownership of their careers. But here’s the thing:
 They don’t know what they don’t know.

Leaders have access to a bigger picture:
 – What roles might be needed down the road
 – Where the organization is headed
 – How an employee’s skills and interests align with future gaps
 – And how industry trends might reshape those needs entirely

So, why wouldn’t we ask leadership to share their plan for us?

Great leaders don’t just react.
 They support, guide, and grow their people with intention and preparation. And that takes having an actual plan.

So let’s turn this into something actionable.

Here’s how we can better prepare to answer that flipped five-year question—on behalf of our teams:

1. Connect Employee Development to Organizational Strategy

Your team wants to know how they fit into the big picture.
 Understand the long-term goals of your organization, then actively look for ways your employees’ skills and goals align with those ambitions. Talk to them about it. Make that alignment visible—it adds purpose to the work.

2. Understand Industry Trends and Share Them

The future of work changes fast.
 Remember when learning to code was the skill to future-proof your career? Now we’ve got AI doing a lot of that.
Stay up to date—attend conferences, read industry reports, and talk about what you’re learning. Help your team navigate the evolving landscape so they can grow in the right direction.

3. Build a Flexible Framework for Talent Growth

Rigid five-year plans break under pressure.
 Instead, build flexible roadmaps that account for multiple scenarios. Focus on growth mindsets, adaptability, and curiosity.
 And most importantly—check in often. Make career planning a living conversation, not a one-time document.

Career development shouldn’t be a solo mission.
 It should be a partnership—a collaboration between the employee and their leadership. That’s how we ensure the growth is realistic, aligned, and meaningful.

And hey, this isn’t just about employees. Leaders need this too.
 I can’t tell you how often leadership development gets ignored the higher up you go—as if responsibility is the reward, not something to be supported.

So let me say this as clearly as I can:
 If you’re in a leadership role, helping your team envision and work toward their future is part of your job.
 Shrugging it off isn’t leadership.

We can do better.
 They deserve better.
 And if we want stronger, more engaged, and more connected teams—we have to make career conversations an ongoing priority.

As leaders we have to welcome this question. Encourage it. 

When our employees ask us what our five year plan is for them, we have to be prepared. And join them on their journey. 

Thanks for joining me for this quick episode of Relationships at Work. If it sparked something in you, pass it along to someone who might need to hear it too.

Take care, and I’ll talk to you soon.