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Want to hold onto your highest performers? Help them pursue their big dreams



As an executive, one of your greatest concerns is retaining high performing talent. If you have excellent team members and are worried that they’re thinking of leaving, spark a dialogue with them to identify what skills and experiences they want to have in the near future in order to achieve their long-term career dreams. A recent McKinsey study demonstrated that employees are highly motivated by growth prospects and feeling valued by their managers, so talking to them about their plans will kill two birds with one stone.


Many years ago, this worked on me. I started a job that I would be a good fit for about 2 years. In my interview, they asked about my long-term ambitions. Then we'd periodically evaluate what else I still wanted to learn or experience within the organization to pursue my bigger dreams. With time, my responsibilities grew and evolved - and I ended up staying for just shy of 5 years. It's a classic win-win that any executive can pursue with enough creativity and emotional intelligence.


In Radical Candor, Kim Scott recommends a three-conversation series that managers can conduct with high performing direct reports to assist them in setting their growth trajectories (whether they’re steadily-growing rockstars or quickly-growing superstars). Here’s how to apply this method within your company.


Step 1: Beginning the Process

To get you started, here’s some suggested language for introducing the topic:

“We really value your work within the company and, as your supervisor, I want to make sure you’re set up to grow as much as possible during your time here. If it’s okay with you, I’d like to schedule three 45-minute conversations in the next six weeks or so to think big together. This model comes from the book Radical Candor and has been used by countless managers across North America and internationally.


In the first conversation, I’d love to learn more about your life before you joined us, to learn more about your personal values and motivations; in the second, we’ll talk about your big dreams for your career; and in the third, we’ll make a plan for what skills and experiences you can gain here to set you up for making those dreams a reality.”


Step 2: Questions to ask in the three conversations

1. Life Story – “Starting from kindergarten, tell me about your life.” As they describe pivotal moments, ask why they made certain decisions, what motivated them to pursue those paths, what they’ve been most proud of, and what’s been most important.

  • Keep a running list and point out the values you’re hearing tucked away within their answer – for example, excellence, hard work, integrity, professionalism, honesty, justice, community, problem-solving, etc.

2. Dreams – “What do you want to achieve at the pinnacle of your career?” Ask how they imagine life feels at its best and then ask them to elaborate. Just be curious. Ask for more detail. Ask “what else?” Part II of this conversation is asking what skills they need to achieve each dream. Make a list. What aligns with their current role and what doesn’t? Among the skills that don’t, where else can they gain them within our organization?

  • Double check: are the values they mentioned in the first conversation here? If not, ask about them, or about others that have emerged instead.

3. 18-Month Plan – start with the skills list you made in the last conversation. What do they want to prioritize in the next year and a half to get on track for achieving their big dreams? The outcome should be concrete action items with timeframes.


Step 3: Nail the follow up

Once you’ve had these conversations with each of your high-performing direct reports, make sure to follow up on the action items.

  • Do you have homework? If there are resources that need to be freed up or secured, make sure it’s clear who’s responsibility it is to do so and the associated timeframe.

  • If some of their work needs to be shifted to someone else on the team, be as transparent as possible about the process.

  • Finally, set yourselves reminders in both your calendars to check in on their progress.

Skeptical? Here are answers to potential concerns

This seems like a lot of work. My leadership team and I don’t have time for all these chats.

While it may seem like a lot of time, it’s a long-term investment in your company’s stability. If you want your highest performers to stay, they need to feel valued, and nothing is more valuable than time, especially undivided attention from their boss.

I’ve worked with some of these people forever – can I skip to the second conversation?

You’d be surprised what can come up when you ask someone to tell you their life story. It may even be more powerful to hear from people with whom you’ve worked for many years. Unless you’ve already asked them, it’s never too late to express interest.

What if the conversations lead to the fact that they’re ready to move on?

If that’s the case, they’d leave whether you ask them these questions or not. These conversations may extend their time with you or it may give them extra motivation to work hard while they’re still around.

What if they ask to pursue steps we can’t accommodate?

Be realistic, but more importantly, be creative. Maybe you can’t give them certain responsibility now, but it may be possible in the future. There may be milestones that they need to hit before the step they want to take. Maybe other resources can be shifted around to help make room for the experiences they want to have.


What if they’re too exhausted to dream big?

If they push back due, acknowledge the low energy level. They may simply want to schedule for later this year (if so, pick a date for revisiting the conversation). If the dreams conversation turns into venting about burnout, listen, validate, and encourage them to try dreaming big anyway. If in the workplan conversation they express a desire to do less, not more, then you can ask, “If you were doing less of what you’re doing now, what would you do with the time you’d get back?”



In short, take heart. These conversations require courage from you too, as don’t know where they’ll lead. Being present with your most valued team members and partnering with them on developing a growth plan that aligns with their values and dreams is perhaps the biggest gift you can give them in these uncertain times.