5 Conversations to Have with Your Boss



“No man goes before his time – unless the boss leaves early.” — Groucho Marx

Have you ever got off on the wrong foot with a new boss?

What if you could avoid friction and conflict with a new manager, by having the right conversations?

What are the right conversations to have with your boss to set expectations and start off on the right foot?

In The First 90 Days: Critical Success Strategies for New Leaders at All Levels, Michael Watkins writes about the five conversations to have with your boss.

5 Conversations with Your Boss

Early conversations focus on situational diagnosis, expectations and style.

  1. The situational diagnosis conversations.
  2. The expectations conversations.
  3. The style conversation.
  4. The resources conversation.
  5. The personal development conversation.

1. The Situational Diagnosis Conversation

You need to establish a shared understanding of the situation of the organization in terms of people, process, and product.  This shared understanding is the foundation for everything you will do. If you and your boss do not define your new situation in the same way, you will not receive the support you need to achieve your objectives.

Watkins writes:

“In this conversation, you will seek to understand how your new boss sees the business situation. Is it a turnaround, a start-up, a realignment, or a sustaining-process situation? How did the organization reach this point? What factors – both soft and hard – make the situation a challenge? What resources within the organization can you draw on? Your view may differ from your boss’s but it is essential to grasp how he or she sees the situation.”

Matching support to your situation:

  • Start-up. In a Start-up situation, typical roles for your boss include: help getting needed resources quickly; clear, measurable goals; guidance at strategic break points, help staying focused.
  • Turnaround. In a Turnaround situation, it’s the same as start-up, plus: support for making and implementing tough personnel calls; support for changing or correcting the extreme image of that organization and its people.
  • Realignment. Same as start-up, plus: help making the case for change, especially if you are coming in from outside the organization.
  • Sustaining success. Constant reality testing: Is this a sustaining-success situation or is it a realignment?; support for playing good defense and avoiding mistakes that damage the business; help finding ways to take the business to a new level.

For more information on these four STAR situations, see STARS Situational Diagnosis (Start-ups, Turnaround, Realignments and Sustaining-Success).

2. The Expectations Conversation

You need to have a conversation with your boss about expectations.  Specifically, you want to create clarity around what success looks like and how your performance will be measured.

Watkins writes:

“Your agenda in this conversation will be to seek to understand and negotiate expectations. What does your new boss need you to do in the short term? What will constitute success? How will your performance be measured? When? You might conclude that your boss’s expectations are unrealistic and that you need to work to reset them. Also, as part of your broader campaign to secure early wins, keep in mind that it is better to under promise and over deliver.”

Keys to success:

  • Match expectations to the situation.
  • Aim for early wins in an area important for your boss.
  • Identify the “untouchables.” Figure out what your boss is sensitive about.
  • Educate your boss. Shape your boss’s perception of what you can and should achieve.
  • Under promise and over deliver.
  • Clarify, clarify, clarify. Some bosses know what they want, but aren’t good at expressing it; you could reach clarity only after you have headed down the wrong road.
  • If you work with multiple bosses, balance perceived wins and losses among them carefully. If you can’t get agreement by working with your bosses one-on-one, then force them to the table to thrash things out.
  • If you work at a distance, then exert even more discipline over communication, scheduling calls, and meetings to be sure that you stay aligned.

3. The Style Conversation

You need to have a conversation with your boss around communication and interaction styles.  By having this conversation early, you can improve your effectiveness with your boss.

Watkins writes:

“This conversation is about how you and your new boss can best interact on an ongoing basis. What form of communication does he or she prefer? Face-to-face? In writing? By voicemail or e-mail? How often? What kinds of decisions do they want to be consulted on and when can you make the call on your own? How do your styles differ and what are the implications of your differences for how you should interact?”

Keys to Success:

  • Diagnose your boss’s style. Pinpoint the specific ways in which your styles differ and what those differences imply about how you will interact.
  • Scope out the dimensions of your box. What sort of decisions does your boss want you to make on your own, but tell them about? When do they want to be consulted before you decide? When do they want to make the decision themselves?
  • Adapt to your boss’s style.
  • Address the difficult issues. When serious style differences arise, it is best to address them directly. Otherwise, you run the risk that your boss will interpret a style difference as disrespect or even incompetence on your part.

4. The Resources Conversation

You need to have a conversation with your boss about resources.  This forces you to create clarity around what you need to be successful.  It also helps your boss support you more effectively by creating clarity around critical resources that you need to be successful.

Watkins writes:

“This conversation is essentially a negotiation for critical resources. What is it that you will need to be successful? What do you need your boss to do? The resources in question need not be limited to funding or personnel. In a realignment, for example, you may need help from your boss to persuade the organization to confront the need for change.”

Matching resource needs to your situation:

  • Startup. In a startup situation, your most urgent needs are likely to be adequate financial resources, technical support, and people with the right expertise.
  • Turnaround. In a turnaround situation, you need authority, backed by political support, to make the tough decisions and secure scarce financial and human resources.
  • Realignment. In a realignment situation, you need consistent, public backing to get the organization to confront the need for change. Ideally, your boss will stand shoulder to shoulder with you, helping you pierce through denial and complacency.
  • Sustaning-Success. In a sustaining-success situation, you require financial and technical resources to sustain the core business and exploit promising new opportunities. You also need periodic pushes to set stretch goals that will keep you from drifting into complacency.

Keys to Success

  • Focus on underlying interests. Probe as deeply as possible to understand the agendas of your boss and any others from whom you need to secure resources. What is in it for them?
  • Look for mutually beneficial exchanges. Seek resources that both support your boss’s agenda and advance your own. Look for ways to help peers advance their agendas in return for help with yours.
  • Link resources to results. Highlight the performance benefits that will result if more resources are dedicated to your unit. Create a “menu” laying out what you can achieve (and not achieve) with current resources and what different-sized increments would allow you to do.

5. The Personal Development Conversation

You need to have the personal development conversation with your boss.  Identity your desired future state in terms of skills, capabilities, and experiences, and ask your boss for support.

Watkins writes:

“Finally, discuss how your tenure in this job will contribute to your personal development. In what areas do you need improvement? Are there projects or special assignments you could undertake (without sacrificing focus)? Are there courses or programs that would strengthen your capabilities? Don’t restrict your focus to hard skills. The higher you rise, the more important the key soft skills of cultural and political diagnosis, negotiation, coalition building, and conflict management will become. Formal training can help, but developmental assignments – in project teams, in new parts of the organization, in different locations – are indispensible in honing these key managerial skills.”

Key Take Aways

Here are my key take aways:

  • First and foremost, get on the same page in terms of diagnosing the situation.
  • Use the five conversations to set a firm foundation and focus on what’s important.
  • Keep the focus on situational diagnosis, expectations and style.
  • Manage expectations, or they will manage you.

As you can see, a few core conversations up front with your boss, can help you avoid unnecessary friction and conflict, as well as set the stage for accelerating your success.

You Might Also Like

STARS Model for Situational Diagnosis

STARS Model of Business Evolution