5 Things To Talk To Your Boss About Today

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What are the 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.

Michael Watkins is the author of the international bestseller The First 90 Days: Proven Strategies for Getting Up to Speed Faster and Smarter, and the co-founder of Genesis Advisers, a leadership onboarding and transition acceleration company. I recently interview Michael on the LEADx podcast about the kinds of conversations that are missing in the employer/employee relationship. (The interview below has been lightly edited for space and clarity)

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

Michael Watkins: 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: be 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.

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

Watkins: 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.

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.

Second one: expectations. 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.

Third: conversation, resources. 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.

Then there's two conversations that have a slightly different kind of slant to them. I call it the ‘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.

Then, the final one, and 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.

Kruse: Let’s say you've taken on a new position, and you've got people you haven't with worked with before. How can you evaluate the team members? 

Watkins: You're at the heart of something I'm very interested in these days, which is the problem of leading the team you inherit. The reality―as you've said, Kevin, exactly―is most leaders don't get to build their teams, they get to inherit somebody else's team. That team may have been shaped by their predecessor, their predecessor's predecessor, by their boss. There may have been a variety of influences. There's basic questions about, “Are these people the people I need to take me where I want to go?” That's a basic question that you go through as you assess.

Then, beyond that, “How am I going to align these people powerfully in the direction that I think we should be going? Am I going to shift the roles and responsibilities? Important ways to better match the capabilities to what we need to do or to the new strategy that we're going to be going after?” Think of it as an operating system for the team that's going to make us run as efficiently and as effectively as possible. “How do we shape the right team culture to make sure, for example, we can have those difficult conversations where there is disagreement, but we could have transparency? How do we build trust in the team?” There's a lot of work you need to do when you're inheriting a team and reshaping it that is not the same at all if you're building a team from scratch.

Kruse: How long might it take to conclude that someone can stay or needs to go?

Watkins: I'm an academic, originally. My answer to every question like that, Kevin, is it depends. Then the question is what does it depend on? What it depends on a lot is what kind of situation you're in.

For example, if you're in a turnaround situation and it's pretty clear the team has failed, you may be moving extremely quickly to replace a good portion of that team. You're coming into a situation, where the name of the game is realignment or sustaining success. You may be spending six months before you really reach conclusions about reshaping the team. The degree to which you reshape it may be quite different than if it was a more serious kind of circumstance.

I'm working with a CEO right now, a healthcare company, and he's now been in position for a little over a year and I've been coaching him through his transition into his new role. It's only now after a year, that he's got the full team in place that he needs to go for. Now, it wasn't a “burning platform,” it was something is in need of transformation and realignment, but it wasn't a crisis. Had it been a crisis, he would have been moving much more quickly and I would have been counseling him to move much more quickly.

Kruse: I like to challenge our listeners to become 1% better every single day. What's a specific thing that you can challenge our listeners to try to do at work today?

Watkins: Sure. One idea I've been working a lot with lately is the degree to which leaders are really able to connect themselves at an emotional level to the people that they're leading. For some people, that comes incredibly naturally. For others, it really is a struggle. The struggle, to my mind, really revolves around the degree to which you are comfortable with revealing things about yourself.

The challenge I give to leaders these days is how do you increase the amount of safe― I want to underline the word safe―self-revelation, as a way of increasing your connection to the people you're leading and, in fact, the people you're following?

Kruse: Safe, so not anything that will make people uncomfortable.

Watkins: No, no. You're not going to say, “Hey, I was partying last weekend, actually you know what? It happened again. I blacked out and I can't remember most of the weekend.” Whereas, it could be maybe it's some activities you're engaged in. Maybe it's a little bit about what you're doing for your holidays. For some leaders, there's a real reluctance to bring anything personal into the workplace. For those leaders, they miss an opportunity to connect themselves more deeply.

Sometimes it's because they feel like they're faking it till they make it, and so revealing too much about themselves may reveal insecurity. Obviously, you don't want to say, “Hey, I think I feel like I'm faking it until I make it and frankly, I'm faking it mostly these days.” That's unsafe self-revelation. There are, even still, things that people like that can do to bias themselves in the direction of more connection with people. If you're one of those people that tend to be pretty reticent about what you reveal about yourself, I really challenge you to think about upping the amount of safe self-revelation that you engage in.

Kevin Kruse is a New York Times bestselling author, host of the popular LEADx Leadership Podcast, and the CEO/Founder of LEADx.org, which provides free world-class leadership training, professional development and career advice for anyone, anywhere.

CEO of LEADx, and NY Times bestselling author, of Great Leaders Have No Rules and Employee Engagement 2.0. Get a FREE trial of the LEADx platform at https://leadx.org/preview.