3 Conversations every Leader needs to have with their employees

3 Conversations: The first time I led I team I made a lot of mistakes. I didn’t prioritize my team. I felt like by delegating power to them, and giving them space I was empowering them. The truth was I was ignoring them. The problem wasn’t the daily tasks, because they were fine with my hands off approach. The issue came with the perception that I was not investing in them. I said I supported their development, but the reality was I wasn’t putting in the effort to support them.

If I am honest with myself, this was one of my biggest failures as a leader. Not being a micro manager is a good thing, but I wasn’t fully investing in my people. On the surface level I cared for all my direct reports, but I don’t think I truly knew them. I didn’t know their core values or their dreams. Even though we were having developmental discussions, I wasn’t truly invested in their future.

Luckily / Unluckily for me I had a difficult conversation with my boss. He basically sat me down and explained that I was getting passed over for a promotion because of how I managed my team. It was difficult feedback to hear, but he had the courage to walk me through it, and create a plan on how to improve. And as part of my development I came across an interesting book: Radical Candor by Kim Scott (which I have written about in a pervious blog).

While the book covers a lot of different aspects of being a great leader, there was one process that really stuck in my mind. A leader in Google had developed a simple process for conducting truly beneficial developmental discussions, which was something I knew I wasn’t good at. This technique is built around 3 conversations, each about 45 minutes in length.

Now it might not sound like a lot, 3 x 45 minute conversations, but this technique has not only shown results in my life, but also in the engagement results in Google. In an internal survey in Google, employees whose leaders followed this three-conversation methodology were significantly more optimistic about their future at Google and their positive feelings towards their managers. Google HR believes this was one of the biggest shifts they have recorded in employee engagement.


Conversation 1 – Learn their life story

The first conversation you need to conduct with your direct reports is focused on their life stories. If you have been managing your team for a while, you might think this conversation is pointless because you already know your employees. I know I thought I did. But while I knew some cursory facts about my people, I didn’t know much below the surface.

In reality, most of us just have a surface level understanding of our colleagues. We might know their spouse’s name or what college they went to, but we don’t always know the key moments in their life. For this conversation, we really want to dig into the history of the person, because it gives us the best chance to understand their motivations.

Instead of starting at college (where a job interview might start), its better to start with their childhood. Now some of you might be wondering what your childhood has to do with having developmental discussion. And in many ways, you are right to wonder. But keep in mind, you’re not wanting to know their favorite color or nap time story. What you want to be listening for are moments of change in their lives, and how they reacted to those moments. Moments of change will highlight a person’s values and underlying motivations.

For example, imagine your person says “after two years of studying to be an engineer, I realized I wanted to get into finance. I didn’t want to spend years working on some small component of one project. I wanted to help oversee the whole project.” Or imagine they say “I grew up seeing my parents struggle to make ends mean. I got into finance, because I saw that’s where the money was being made and I didn’t want to struggle like my parents.” Both of these are answers give you an indication of what the person values. The first person might value ownership and being a part of the bigger picture, while the second person might value financial stability.

This conversation isn’t just to have a feel-good conversation about their life story. By understanding their past, you will better equipped to understand their future.


Conversation 2 – Discover their dreams

The second conversation moves from the past into the future. The goal of this conversation is to understand their dreams for their future, but the key is not to limit the conversation to just professional goals. If all you are asking about is the person’s job, then the conversation will end up being focused on promotions or specific job roles. Instead, you should broaden the conversation so you can understand their overall dreams.

I often made this mistake. I only focused on the professional side of my direct reports, and so I missed key dreams they were having in other areas of their lives. For example, I thought Ted had significant potential and so I kept pressing him for his career vision. But the truth was he wasn’t driven that way. He had dreams about his family, and what his kids would be doing in the upcoming years. I kept trying to force him going down a path he didn’t really want, and because of it we never really worked well together.

In order to avoid biasing your conversation, have the employee come up with 3 to 5 different dreams for their future. Get them to reflect on themselves and their future. What does the pinnacle of their career look like? What is their situation, personally and professionally? What are they super excited about when they get out of the bed 5-10 years from now? These are the types of questions you should be asking, and digging deeper into?

Once they have identified their dreams, ask them to create a document with 3-5 columns (matching their identified dreams). Title each column as one of the dreams, and then begin identifying the different skills needed to achieve each dream. Once they have identified what skills are needed per dream, then you should go through and have an honest conversation about their current competency level on each skill. This part of the conversation will help you both identify which skills are critical, and where the person should focus first.

Finally, throughout the conversation, you should always be reflecting on how their dreams match up with their values and motivations. If they are dreaming about retiring early, but they are motivated to achieve elite status in their field, then there is probably some disconnect. Act as a mirror for the person, and if needed highlight the mismatch. And then have a conversation about the mismatch. Because in the end, if their dreams aren’t aligned to their motivations, then you supporting those dreams won’t necessarily lead to a more engaged employee.

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Conversation 3 – Create an 18-month plan

The final 45-minute conversation is all about helping people translate their values and dreams into a tangible plan. Google’s managers were taught to get people to reflect on the following questions. “What do I need to learn in order to move in the direction of my dreams? How should I prioritize the things I need to learn? Whom can I learn it from? How can I change my current role to learn it?”

The conversation stemming from these questions helps the employee and the manager identify opportunities at work that will help the employee develop skills in the next eighteen months that will help them achieve one of their dreams. As a leader you need to spot opportunities that your person hasn’t thought of, and you need to be willing to invest the time and resources into the person to build those skills. It’s all great to create a plan. But if you aren’t going to give the person the time or space to build these new skills, then it really isn’t worth much.

Finally, your role is to play the supportive leader. Some people find it scary to work towards their dreams. In their mind, it’s better to keep dreams as a faraway concept, instead of working towards the dream but failing. With these people, you need to support them in taking their first steps, and remind them that working towards their dreams is a lot more fun than just working for works sake.

Being a Leader means you need to Care about your people

Being a leader is about caring deeply for your team, and that requires you go beyond your surface level of caring. To truly care about your people, you need to understand their values and their dreams. Only by understanding those things can you help them grow and develop. And it doesn’t require a huge investment from your side. All it takes is 3 x 45-minute conversations.

If you have already read Radical Candor, here are some more of my best books for Leaders

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