5 Conversations You Need to Have With Your Boss

Whether you’ve just been promoted or newly hired, it’s difficult to adjust and find clarity in new circumstances. Face the challenge and talk things out with your boss with these five conversations, guaranteed to bring you peace of mind and clear expectations.

Kevin Kruse, NY Times bestselling author, Inc 500 entrepreneur, and keynote speaker on Wholehearted Leadership and Extreme Productivity, recently interviewed Michael Watkins on the LEADx podcast about the kinds of conversations that are missing in the employer/employee relationship. Below is an excerpt from that interview with a link to the full article and podcast provided at the bottom of the post.

KK: You say that when you get promoted, you need to start by preparing yourself. What do you mean?

MW: Every major move you make… Let’s give you two really quick examples: Joining a new company — coming in from the outside, joining a new company, a new culture, a new political system. The second classic example: Being promoted to a new level. You have to stop and ask yourself not just what you need to learn, but what you need to unlearn and what is really going to take you to the place you need to go in this new organization.

For example, if you don’t have a lot of experience working with different organizational cultures, you can get into a lot of trouble if you think that the culture of your new organization is going to be something like the culture of your old organization. You need to prepare yourself, in that sense, to join a very different political and social system.

The same story with promotion transitions. “What got you here,” in Marshall Goldsmith’s words, “Won’t necessarily get you there.” What is it that’s going to take for you to be effective at that new level? What do you have to do more of? But critically, what do you have to do less of? That’s the sort of thing I mean by preparing yourself.

KK: What are the five conversations with your new boss to make sure you get to negotiate a success.

MW: Sure. The big issue here is really making sure that you’re as aligned as possible with your boss and potentially with other key stakeholders. It could be peers; it could be other power parties in your organization. One of the most common reasons why people fail going into new roles is the expectations they build up during the recruiting or promotion process turn out not to really hold up when they get into the role. I have a structure of conversations you go through to make sure that doesn’t happen to you.

1. Situational Conversation

It starts really with the situational conversation, which is, “Is my view of what I’m here to do the same as the boss? Am I here to turn something around? Am I here to sustain success? Am I here to accelerate growth?” If I think I’m doing one of those, and she thinks I’m doing another, that’s a big problem.

2. Expectations Conversation

Are we clear about what success looks like? Over what timeframe? If important, what kinds of approaches and methods do I need to use? Who do I need to bring along with me? Being as crystal clear about expectations as you possibly can is the second big conversation. That’s, to some degree, a negotiation as you get to more senior levels. At junior levels it’s “Do this, hand it in by next Tuesday”. When you get to the level of running complete businesses, there is a negotiation over what’s you’re going to deliver and in what timeframe.

3. Resources Conversation

What are the resources you have available to you to get done what you need to get done? That can include headcount; it can include funding. It can also include how much commitment of your boss’ time are you going to have to really make the case for a change, for example.

4. Conversation Style Conversation

How are we going to communicate and interact in a way that’s going to make sure that we are effective together? You look―for example―at influence style or the way that someone prefers to be communicated with. Are they more face to face? I need to talk it through with you kind of person or drop me a message of some form. Do you like more detail? Less detail? When can I wake you up in the middle of the night? Clarity about that side of things can really help shape the early interactions, because otherwise, differences in communication style can be sources of irritation, if you’re not careful. The onus is really on the person reporting to the leader to adjust their approach to match the leader. You shouldn’t expect your boss is going to alter his communication style to fit you.

5. Feedback Conversation

It’s not one that happens necessarily right away in a transition, it’s something I typically like to see people get into around a 90-day mark, which is personal development conversation, in the sense of, “What am I doing well? What am I not doing so well?” Getting that early, often informal feedback. Because what the research shows consistently is people taking new roles often don’t get feedback early enough, and therefore get themselves into much more trouble than really needs to be the case, because people tend to be a little bit hands-off, “Let’s give Kevin time to find his feet.” Going out and having that personal development conversation, pushing to get some feedback, make sure you can make course corrections before you end up in really deep trouble.

Read the full LeadX Show Interview or listen to the Lead X Show podcast.