TSLH #059: 5 + 1 Critical Conversations To Have With Your Direct Reports

Any leader taking on a new role and a new team is facing an almost immediate task: Connecting with their direct reports in ways that create trust, mutual respect, and engagement.

In some of my previous newsletters, I have described how you should introduce yourself first to your team, or how to go about assessing your team and structuring it for best performance.

Today, I want to tell you about specific conversations you should have with your direct reports to create the engagement you need.

Typically, there are 5 things you want to discuss with your direct reports when you start as the new leader of the team (in fact there’s a sixth one, I’ll tell you about it at the bottom of this newsletter):

Of course, I am not implying you need to have 5 distinct conversations with your direct reports. For instance, the first 3 points above can be one discussion, likely the first one you have, the discussion about what they need to do a good job should happen pretty quickly after the first one, and the discussion about what they need to grow could happen a few weeks or a couple of months after the initial discussion.

The diagnosis conversation. In this conversation, you want to align with your direct reports on what the situation of the team and the business is, what people see as challenges, what they think is going well, what they think needs to change, what resources people on the team have to do their work.

Here are a few questions you can use to dig deeper into that conversation:

The expectations conversation. Here, you want to create clarity and alignment on what people are doing in the team, what is expected of them and how the performance will be assessed.

Here are a few points you can use to dig deeper into that conversation:

The communication conversation. In that conversation, you want to clarify what method you and your direct report should use to allow the most effective communication between you. It’s also about when you want to be involved vs. when you want your direct report to show leadership of their own.

Key points you want to touch on during this discussion include:

The resources conversation. Once you have worked for a few weeks with the team, you can have the resources conversation, which can build on the previous three discussions. However, it should really be focused on what is needed by the direct report to work effectively.

Here are a few questions to help you with this discussion:

The personal growth conversation. This should be the last conversation you have in that series of early conversations with your direct reports. The reason for this is that you want to be able to assess the situation and the performance of your direct reports and their teams before committing to anything they need for their growth. Likewise, if you see your direct report stay accountable for what has been discussed and agreed in all previous conversations and you see tangible results out of these discussions, then, your motivation to help and support their personal growth will be there.

Here are a few things you can touch on in this conversation:

And that’s it really. If you nail these 5 conversations, you will establish a strong relationship with your direct reports and have clarified what you need from them and how they can tap into you for support. With these conversations, you will also have clarified what the measures of success will be, so there is no surprise when annual performance reviews come. The sixth conversation I was hinting at early on should actually happen before the other 5, and ideally even before your official day 1 in your new leadership role. I call it the human conversation. This conversation is much more informal and aims at knowing who your direct people are (in life, after work, etc.) as well as letting them see that you, the leader, are also a human being. It is your strongest opportunity to share more personal things to establish a first strong connection. Last but not least, these conversations should also happen between you and your own boss. Remember that as a leader, you need not only to manage your team, but also to manage up!