How to Build a Good Relationship With Your Boss

This article is an excerpt from the Shortform book guide to "The First 90 Days" by Michael Watkins. Shortform has the world's best summaries and analyses of books you should be reading.

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Has your company appointed a new manager? Why is it important to make sure you and your new boss start off the right foot from the get-go?

The relationship you have with your boss can make or break both your performance and job satisfaction. That’s why it’s important to negotiate success in your role by understanding his/her needs, priorities, and communication style from the get-go.

We’ll discuss some tips on how to build a good relationship with your boss

Navigating Relationship With Your Boss

You may find yourself working with a difficult boss or a boss with a fundamentally different style from your own and thus need to take initiative in setting up the framework for your role.

Take, for example, Michael, who accepted a new job as Chief Information Officer in his unit but was told by coworkers that his new boss, Vaughan, would be impossible to please—especially because she was intensely action-oriented, whereas Michael was more of a planner. Still, Michael proactively approached his boss with a concrete plan of action for the first 90 days in his new role. Even when Vaughan tried to accelerate his plan, Michael pushed back with a clear rationale for his plan. Eventually, Michael gained Vaughan’s confidence and trust because he was able to deliver results, even though his process and style were different from Vaughan’s preferred approach.

Below are several tips on how to build a good relationship with your boss just like Michael did. For example, consider the following “Dos and Don’ts”:  

Do:

  • Clarify expectations on a regular basis. 
  • Take responsibility for developing and growing the relationship. 
  • Be patient and take time to accurately diagnose what action is needed.
  • Prioritize early wins in areas that matter to your boss. 
  • Remember that your boss will be evaluating your performance not just from direct interactions but from information shared through other conduits. Keep this in mind as you navigate relationships with peers, heads of other groups, and so on. 

By contrast, don’t:

  • Avoid your boss. If she is not proactive about establishing a relationship, don’t lean into the temptation of flying under the radar. Get on her calendar early and stay actively in touch about expectations.
  • Shy away from giving bad news. Communicate concerns early on so that your boss is on notice and not surprised if or when things escalate. 
  • Use your boss as a dumping ground for problems. Be prepared to problem solve by having initial information or insights into options for moving forward.
  • Use meetings as an opportunity to tick off your to-do list in front of your boss. Focus on sharing three key issues that would benefit from her input. 
  • Try and change your boss. As the subordinate, it’s your job to identify her style and to adapt accordingly. 

Keeping these considerations in mind, start planning to formally engage your boss. There are five key conversations that you’ll want to deliberately approach and that will help to inform your 90 day plan: the STARS conversation, the expectations conversation, the resources conversation, the style conversation, and the personal development conversation. 

The STARS Conversation

How would your boss diagnose which STARS phases are applicable to your new role? How does that impact resourcing your role? Getting on the same page for this question will fundamentally inform the kind of support that you’ll need from your boss moving forward. For example, 

  • If you are in the start-up phase, you’ll need support accessing resources quickly, establishing clear goals, and focusing energies on key tasks.
  • For a turnaround, your boss’s support for hard calls will be essential as you prepare to make deep and quick changes.
  • In an accelerated growth stage, you’ll likely need similar resources as the start-up phase but you’ll also need financial investments to propel growth as well as support in communicating and implementing new systems and structures.
  • Realignments may also rely on similar resourcing as start-ups but will most importantly require support from your boss in communicating the case for needed change within the company.
  • If you are entering a sustaining success situation, your boss will be an important resource for brainstorming ways to grow the company and anticipating possible challenges that might be coming down the pike.

The Expectations Conversation 

What are the expectations (short and long term) for your role and how will you define success? Additionally, what processes or metrics will be used to evaluate your performance? Consider these key principles as you engage your boss:

  • Ground your conversation about expectations in the previous dialogue you had about the STARS stages that are pertinent to your work (e.g., maybe you are in a turnaround situation and there is a clear expectation that you’ll help avoid a particular threat or failure).
  • Identify possible early wins that your boss would be excited about and invested in.
  • Gain a better understanding about which work falls into your boss’s territory. You don’t want to step on his toes or undercut his own goals.
  • Educate your boss about what is realistic so as to proactively inform expectations.
  • Underpromise/overdeliver—this helps with credibility.
  • Keep open lines of communication for regular check-ins to ensure that expectations haven’t shifted. Keep reapproaching issues from different perspectives and angles, particularly from your boss’s vantage point, to ensure clarity about where you are and where you should be going.

The Resources Conversation

Beyond your boss’s support, you’ll also need access to other resources. What do you already have access to and what will require your boss’s buy-in? This should be evaluated not just in terms of money or personnel but in time and energy. It’s important that this conversation occurs after you have already identified your STARS situation because each phase will demand different kinds of resources. For example: 

  • Start-up: You may need technical assistance, competent personnel, and financial resources.
  • Turnaround: You may need authority and political support to make tough calls and tap into limited resources. 
  • Accelerated growth: You may need financial investments for growth and buy-in for creating new structures and processes will likely be important. 
  • Realignment: You may need vocalized and/or public support to affect perspectives about what kind of change is needed. 
  • Sustaining success: You may need technical and financial resources to continue building growth and momentum together with regular check-ins to avoid stagnation and complacency. 

Some resource requests may be simple and fit into the current structure and political climate. Other times, more substantial requests will need to be made, requiring you to put your neck out but also to secure allies and insights to build support. In order to gain that support consider (1) helping your boss understand how your resource requests will also benefit their priorities and interests or those of your peers, and (2) making your “ask” by laying the issues out in a menu form of “if you want this, I will need this” so that a clear link is established between expectations, your request, and what you’ll ultimately be able to deliver. 

The Style Conversation

What is your boss’s style of communication and management? How often and through what medium will you check-in? When should he be consulted and when can you independently make a call?

First, diagnose your boss’s working style and begin to evaluate how it might interact with your own. For example, your boss’s tendency might be to micromanage while you flourish with some semblance of independence. Below are some tips to evaluate your boss’s style and then successfully navigate it: 

  • Speak with individuals who have worked with him in the past. But be thoughtful about how you approach the conversations so that you are not perceived as soliciting criticism.
  • Evaluate where your boss wants to be incorporated into decision-making and where you have leeway. Initially, he may give you a small box of autonomy to make key decisions. But, with time, it may grow. Stay observant about what most interests and concerns him so that you can build-out his confidence and your capacities around those spaces. 
  • Adapt to your boss’s style and preferred communication methods. For example, if he never responds to texts, don’t use them. If you are uncertain about those preferences, consider asking directly. 
  • Confront stylistic differences head-on so that they don’t simmer and explode. Focus on shared expectations and on results. Acknowledge that you might have different ways of getting to those results but that you are both committed to doing so. As your working relationship grows, you’ll have more opportunities to observe nuanced stylistic considerations. 

The Personal Development Conversation 

What will your personal development at the company look like? Checking in after a few months provides some context to think through your role moving forward and how you can continue growing and improving. Where can you still improve? What has been successful thus far? Your boss will respect your proactive approach to gaining constructive feedback. Don’t forget to ask for feedback about soft skills too (political, interpersonal, and so on)—those can be just as important as technical abilities in new leadership roles. 

Additional Considerations for Negotiating Success

These five conversations will set you up well to negotiate success in your new role. However, some additional factors might impact your approach, including:

1. Having multiple bosses. The same principles discussed above still apply, but you may need to prioritize one of the relationships over others depending on who has influence and power. 

2. Working at a distance from your boss, which presents unique challenges such as a higher risk that you will miscommunicate or fall out of step without realizing it. If possible, try and schedule at least one face-to-face meeting early on. 

Incorporate your strategy for negotiating success with your boss into your formal 90 day plan. Try creating three blocks of 30 days and schedule a check-in with your boss after each. After the first 30 days, you should have clarified a diagnosis of the STARS situation and identified key expectations and priorities. Use the next 30 days to continue evaluating and planning. The 60 day check-in might be a good time to have your conversation about resources or perhaps to discuss your initial team evaluation (as was discussed in Chapter 2). 

Finally, consider applying all of these same principles to your relationship with your subordinates and direct reports. Transition others as you would want to be transitioned by scheduling the five conversations with your team and giving them time to prepare. 

Implementing each of these steps for negotiating success can feel overwhelming. Create more structure and accountability by identifying explicit goals for a 30 and 60 day check in with yourself.

30 day check-in 

  • What STARS situations have I diagnosed that are pertinent to my role?
  • What did I learn from my expectations conversation that will fundamentally inform my next steps? Which expectations will be most important to follow-up on at the 60 and 90 day check ins?
  • What are my key priorities for the next 30 days?

60 day check-in

  • What have I learned so far about my boss’s style and how we communicate? Are there any possible tensions I should confront?
  • What resources do I still need access to in order to meet the expectations articulated for me?  
  • What are my key priorities for the next 30 days?

90 day check-in

  • What has gone well and what could be improved from my first 90 days? 
  • How will my boss continue to evaluate my role and provide feedback moving forward? 
How to Build a Good Relationship With Your Boss

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Darya Sinusoid

Darya’s love for reading started with fantasy novels (The LOTR trilogy is still her all-time-favorite). Growing up, however, she found herself transitioning to non-fiction, psychological, and self-help books. She has a degree in Psychology and a deep passion for the subject. She likes reading research-informed books that distill the workings of the human brain/mind/consciousness and thinking of ways to apply the insights to her own life. Some of her favorites include Thinking, Fast and Slow, How We Decide, and The Wisdom of the Enneagram.

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