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

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

Read time: 4 minutes


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):
  • Their role and diagnosis of the situation (The diagnosis conversation)
  • What you expect from them (The expectations conversation)
  • How you will both communicate with each other (The communication conversation)
  • What they need to do a good job (The resources conversation)
  • What they need to grow (The personal growth conversation)
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:
  • What is working well and not so well in the team?
  • What are challenges this team is facing?
  • What are you and the team missing to do a good job?
  • If you were in my position, what would be the first thing you would address?
  • If all went well, what is the value this team could deliver?
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:
  • Do you know what is expected of you in your role?
  • What do you expect or do you need from me?
  • Discuss what will constitute success for your direct report.
  • Explain how their performance will be assessed.
  • Discuss any untouchable you have.
  • Clarify any quick win that can be leveraged.
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:
  • Communication style: Should you use emails, face-to-face, phone?
  • How often should you interact with each other?
  • What kind of decisions you want to be involved in?
  • What kind of decisions you let full responsibily to your direct report but need to be informed about?
  • What kind of decisions you let at complete discretion?
  • Discuss about your different communication style and how each of you have to make some step forward to come to middle ground.
  • Discuss how you want to give and receive feedback (in public, in personal conversations, etc.)
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:
  • What do you need to do your job well?
  • What are you and the team missing to do a good job?
  • What do you need me to do to help you in your job?
  • Do you understand what alternatives you have to do your job when resources are limited?
  • How would your performance and that of the team change if you had these resources?
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:
  • Clarify how performance of the direct report in the role will contribute to personal development and growth.
  • Discuss what projects or activities you could delegate over time to support your direct report’s growth.
  • Are there courses or trainings your direct report is interested in?
  • What is their career plan? In the next 18-24 months? Long term?
  • Clarify what your direct report needs in order to be a strong leader for their team.
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!
I wish you a great read. I’ll see you next Saturday!
TL; DR (Too Long, Did not Read)
5 + 1 critical conversations to have with your direct reports
  1. The diagnosis conversation.
  2. The expectations conversation.
  3. The communication conversation.
  4. The resources conversation.
  5. The personal growth conversation.
  6. +1: The human conversation.

Whenever you’re ready, there are 3 ways I can help you:

1️⃣ Work 1-1 with me to step up as the authentic leader you aspire to be.

2️⃣ Hire me to help you build a high-performing team.

3️⃣ Start with my affordable digital courses on Mastering Difficult Conversations for Leaders and Goal Setting