Critical Conversations For Every New Manager

Ever seen The Bourne Legacy?

The movie starts out with Aaron Cross (Jeremy Renner) in the middle of a cold, snowy wilderness. You’ve no idea who he is, where he’s going or why he’s there.

That’s exactly how most new leaders feel when they take on a new role.

As a new leader, you’ve entered a whole new world of possibilities, challenges and obstacles. While there is a way to get through it all successfully, you won’t stumble upon it by accident.

Say you don’t just want to scrape by. Your aim is effective leadership. Transformation in the lives of people you lead, your company and the broader world.

If that’s your goal, you’ve got to get your bearings quickly and know you’re moving in the right direction.

Anything else might derail you.

This article will help you get your bearings by laying out six critical conversations that every new manager needs to have.

In a perfect world I’d recommend completing these within the first 30-60 days of taking on a new leadership role, but if you’re already past that point it’s not too late to go back and make up for lost time.

Critical Conversation #1: With Yourself

Leadership starts with you.

If you want to be a world-changing leader, you’ve got to start by having a conversation with yourself.

Find clarity on who you are and what you stand for.

Work out your values and priorities.

“Leadership comes more from who you are inside than from what you do on the outside.”  – Brian Tracy

Consider the great leaders that you admire.

One thing all great leaders have in common is that they drew a line in the sand somewhere. They said, “This is what matters most. If I must, this is the hill I’m willing to die on.”

  • Abraham Lincoln: “I expect to maintain this contest until successful, or till I die, or am conquered, or my term expires, or Congress or the country forsakes me…” (on preserving the union, in a letter to William Seward dated June 28, 1862)
  • Dr. Martin Luther King, Jr.: “Darkness cannot drive out darkness, only light can do that. Hate cannot drive out hate, only love can do that.”  (from  Strength to Love, 1963)

Commitment like this can make leaders out of people who aren’t even trying to be leaders. Consider Mother Teresa:

“Let us touch the dying, the poor, the lonely and the unwanted according to the graces we have received and let us not be ashamed or slow to do the humble work.”  – Mother Teresa

Her commitment to love and serve those in need in Calcutta changed the world. She didn’t serve because she was seeking fame and fortune. She believed that loving the destitute was worth of her life, and she acted on that belief.

The effect? Not only did she transform the lives of those she served, but she inspired thousands around the world to care for those in need. Her personal values and commitment – inspired by her faith – had a ripple effect across the globe.

As a new leader, start by looking inwards. Ask questions like these:

  • Who do I want to be?
  • What do I want to be known for?
  • If I knew I could do anything and not fail, what would it be? 
  • What leaders do I admire? Why?

The goal of questions like this is to drill down to your personal values. Take them seriously and these questions will help set the trajectory for your entire life, not just your leadership.

Critical Conversations #2-4: With Your Boss

If you’re an entrepreneur, you may not have a boss. That’s alright. It can be trickier to find the answers, but this section applies to you as well.

In most organizations, goals and priorities are top-down.

Senior leadership says, “Here’s where we’re headed.” Managers and leaders throughout the organization are then tasked to translate this info for their teams and figure out how to make those things happen.

To succeed at that (and to avoid a number of other problems) there are three critical conversations every new leader should have with their boss.

If possible, I’d recommend aiming to complete these within the first 30-60 days of your leadership. They’ll help you start out on the right foot.

The Diagnostic Conversation

When you’re new to leadership, your boss can be a great source of information on your new team’s current state. Chances are they’ve seen the team grow and evolve over time. They know the team’s strengths and weaknesses.

Even if you’re leading a team that you used to be a part of, your boss has had a different vantage point. Use that to your advantage.

Your goal in this conversation is to answer one big question:

Where are we at?

This big question includes a million little questions. Things like:

  • What resources are at my disposal?
  • What’s been tried so far?
  • What’s worked and what hasn’t?
  • What are my team’s strengths, weaknesses, opportunities and threats (SWOT analysis)?
  • Is everyone on the same page?
  • Are particular employees “problem children”? If so, how did my predecessor try to coach them?
  • How open are you to new approaches?

A successful diagnostic conversation requires honesty and objectivity. Your approach to a team that’s functioning well will be vastly different from how you’d approach a startup team or a team that’s struggling to get things done, which is why this conversation is so important.

When done well, you should walk away with a much clearer picture of your team’s situation and the larger context that you are leading within.

The Expectations Conversation

Everyone has expectations, even when they don’t share them. Unvoiced and unmet expectations can derail an entire team. 

(Note: If you’re married, you’ve probably already learned this lesson. Marriage is a great teacher…)

Effective leadership requires a clear understanding of your boss’s expectations. To that end, the outcome of a successful expectations conversation is clarity.

It’s an attempt to sync with your boss and to make sure you are on the same page regarding priorities and goals.

To that end, ask questions like these:

  • What are the critical things you need me to accomplish in the short-term? Mid-term?
  • What does success look like?
  • What timeline am I on to achieve that success?
  • How is my success measured as a leader? What about my team’s success?
  • How much liberty do I have to improvise?
  • Do you have any other expectations of me?
  • What were the strengths of the person who led this team before me? What were their weaknesses?

Answering these questions will help you to focus your efforts, increasing your likelihood of success and decreasing the likelihood of an unwanted surprise at your next performance review.

In most companies, expectations also exist on a broader scale. Yale University provides a good example of a high-level set of expectations for a leader. Every leader in their organization is expected to embody these key attributes.

Does your organization have something similar that applies across the board? If so, start by familiarizing yourself with those expectations, then dive deeper with your boss into his/her specific expectations.

The Style Conversation

Every boss is different (can I get an “Amen”?).

The Style Conversation is closely related to the Expectations Conversation, but it has a slightly different focus.

With this conversation your goal is to figure out how you and your boss can work well together.

“Style” doesn’t mean your preferred way to dress or your favorite music – it means your preferred style of communication.

My last boss was incredibly informal. He preferred walk-up conversations, rarely responded to emails quickly, and trusted me to take care of things and update during our regular one-on-ones. My current boss is the opposite – she hates surprises, wants to know all the details, and wants to be informed about everything.

This isn’t meant as a critique or me passing judgment on their styles. They’re both good leaders, and in both cases we’ve been able to build a healthy working partnership.

Rather than a critique, it’s an illustration of an important principle:

What works well with one boss may not work well with another.

If you’d like to make sure you understand your boss’s style, I’d recommend asking questions like these:

  • What is your preferred method of communication? How often?
  • What types of decisions do you want to be involved in?
  • When should I feel comfortable making the call on my own?
  • How do you learn and process information? Visually? Talking things out? Doing?
  • How “hands on” do you like to be?
  • Do you have any hot-button issues that you simply won’t tolerate?

These questions will give you a ton of valuable data on how your boss prefers to work with his/her team.

Once you’ve got the data, identify any gaps. Where are your preferences different? Where do you need to make accommodations or adjust they way you do things?

As the subordinate, it’s probably best to consider it your responsibility to “mind the gap” between your style and your boss’s style and to make any adjustments needed.

Critical Conversations

Photo Credit: Marcin Wichary (Flickr.com)

Critical Conversations #5 & 6: With Your Team

The Individual Expectations Meeting

I turned the wrong way onto a one-way street in downtown Chicago once.

Momentary panic set in when I saw a bus barreling towards me. I think I may have had a minor heart attack, but I never got it checked out by a doctor.

Expectations are kind of like that.

When all the other drivers think they should head one way and you’re going the other, you’re in trouble.

You’ve already clarified expectations with your boss (see conversation #3 above). Now it’s time to turn around and do the same thing with your team. Without clear expectations, your team won’t know what they are supposed to be doing and you’re guaranteed to get frustrated with them.


After talking with your boss, you hopefully have a much better feel for the state of your team and where you’re headed. Use this wider context to help shape the expectations you deliver to your team.

I find that it’s helpful to think of expectations in two separate categories: performance and behaviors.

While these two aren’t mutually exclusive, it’s a useful way to make sure that you’re helping your team understand their performance goals (“Sell X widgets per month”) and your behavioral expectations (“Don’t be late”).

Below are some questions that will help you get clear on these things (in addition to the conversation you’ve already had with your boss):

  • Performance
    • What is the minimum acceptable level of performance? 
    • What type of output do I expect from each team member?
    • Are there any assumption people may be making that I need to clarify?
    • Do our goals and metrics make sense?
    • Am I changing any goals?
  • Behaviors
    • How do I want my people to behave?
    • What behaviors are completely unacceptable? 
    • What behaviors am I willing to allow?
    • Have I already heard complaints or concerns from any team members about their peers?

I’d also encourage you to check out your company’s policy and employee handbook. While these resources often tend to have much broader guidelines around expectations (dress codes, maintaining a safe workplace, etc.), it’s important to ensure that your personal expectations as a leader don’t conflict with them in any way.

The Inspirational Conversation (“The State of the Union”)

While I’d recommend you have the previous conversation in one-on-one meetings, this conversation is best held as a team.

This is the fun part of leadership – rallying your troops towards a common goal.

Anytime a leadership change occurs, it’s a good idea to bring the team together and remind them about what you’re trying to accomplish together.

Not doing so risks confusion and disengagement.

In this conversation, your goal should be to get everyone on the same page and to motivate.

Pro tip: While I’m often not a fan of PowerPoint decks and presentations, I often find it helpful to create a deck (whether I use it or not) to clarify my line of thought and make sure everything makes sense and is presented in a logical order.

One other thing: Be honest. 

Your team already knows the good, bad and ugly. They know where things need to improve and where goals are going to be a real stretch. Acknowledge these challenges, and then verbalize your belief in their ability to band together and overcome any obstacles set before them.


Gear Up

Having this info is great, but if you don’t have a way to put it into practice then it won’t help.

That’s why we created a Critical Conversations Guide. It’s a free, downloadable PDF that you can print off and use to prepare for each of these conversations (click here to download). It’s got more questions to spur your thinking and create more clarity around your goals.

Get the tools you need to succeed. Have for these critical conversations soon to set your leadership off on a good trajectory!


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