The Art of Managing Up

Fostering a Positive Relationship with Your Boss

The Art of Managing Up
The Art of Managing Up

Fostering a Positive Relationship with Your Boss

We all know the agony of working for a boss we don't connect with—the kind who makes you count down the minutes to 5 o'clock every evening. Unfortunately, having a disagreeable or disconnected supervisor is an all-too-common experience. But here’s the good news: you have more power than you think to transform the relationship. With some insight into your manager's style and priorities, plus a little strategizing on clear communication and mutual understanding, you can cultivate a supportive partnership that benefits you both.

The Power of an Effective Working Relationship 

Managing up is about recognizing that the relationship with your boss goes two ways. It's not about manipulation or fakery. Instead, it means learning how to adapt your communication style to align better with your manager while understanding their needs, hot buttons, and goals. The payoff can be immense: employees who self-report having a solid relationship with their supervisor tend to have much higher job satisfaction, productivity, and commitment to the organization. They also typically receive more career-boosting mentoring and advocacy. 

Take Brian, for instance. He was a diligent employee, but he always felt overlooked by his boss, Ana, despite his good work performance. When I coached him, Brian realized that while Ana responded better to detail-focused updates with concrete metrics in writing, he preferred quick, informal chats at her desk. By sending Ana succinct yet informative weekly reports, her affirmation of his work rose dramatically—as did his visibility to higher-ups with whom Ana shared them. Instead of wishing she would adapt to his style, he stepped up to her style. This example illustrates how understanding your boss's communication preferences can significantly improve your relationship with them. 

The ABCs: Understanding Your Boss's Communication Preferences

We experience the most friction when someone (like a manager) communicates differently than we do naturally. Learning your boss’s preferences is crucial to tailor your approach accordingly. 

Start by paying close attention to determine if your boss skews toward any of these tendencies:

  • Direct versus indirect: Is their communication blunt or subtle? Do they prefer unambiguous requests or hints toward their needs?
  • Task-oriented versus people-oriented: Are they all about efficiency or more focused on team relationships?
  • Big picture versus detail-focus: Would they want the 30,000-foot view or to delve into the nitty-gritty? 
  • Formal versus informal: How do they expect to be addressed in conversation and writing? 

Once you identify any leanings, adapt your communication style to align. This isn't about changing who you are but about understanding and respecting your boss's preferences. For instance, detail-driven bosses appreciate comprehensive status updates, while big-picture thinkers want high-level recaps. People-focused leaders respond better to polite check-ins at their office door before diving into dequeuing their endless email backlog. By adapting, you're not just accommodating; you're taking control of the situation and fostering a more productive relationship. 

The key is being flexible, based not on your preferences but on understanding them. After all, Dale Carnegie was right that people want to be understood even more than they want to be loved, agreed with or admired.

Pro Tip: Pay attention to what your boss says and how often and through which medium. The frequency of communication you need to satisfy them can differ significantly from person to person.

Positioning Yourself as an MVP Through Smart Showcasing 

Managers have a lot on their plates. As much as they may want to, most barely scratch the surface in fully recognizing their direct reports' accomplishments. Therefore, the onus falls mostly on you to showcase your wins in a compelling yet professional way. Doing so will lead to you getting your due credit and reveal you as leadership material for handling bigger projects or promotions. 

First, timing is vital. While some managers may check in frequently, once a quarter is pretty standard for a full progress and results review. That said, there's no need to list everything you've done since your last conversation. Be strategic. Call special attention to milestones achieved and provide evidence for the fruits of projects that concluded under your ownership. 

Second, quantification is your friend. Numbers, metrics, percentages—anything that demonstrates tangible impact in a metric way makes accomplishments all the more stark and vivid for evaluators. CEOs love key performance indicators (KPIs); managers do, too. 

Let’s say you created an improved onboarding system. Don’t just say you implemented it; spotlight how it reduces turnover due to faster ramp-up time. Or perhaps you identified a broken business workflow and devised a solution that is now saving 100 employee hours per month. Highlight extraordinary outcomes like this. By showcasing your wins in a strategic way, you're not just listing achievements; you're demonstrating your value and contributing to your own recognition and career advancement.

Lastly, consider the medium. Written reports may best suit detail-driven managers, while big-picture thinkers appreciate high-level presentations they can easily digest. Know when a quick shout-out email update hits the spot or when it's worth booking time on your boss's calendar for an in-person meeting, complete with slides to walk through your wins.

Pro Tip: Avoid info overload. However, they prefer to receive communication; bosses tune out anything overly cumbersome, complex or lengthy. Craft-focused, sharp updates instead.

Even in the best manager-employee relationships, differences of opinion crop up. Disagreements need not be viewed as conflicts so long as they don’t veer into personal attacks. By keeping cool-headed, focusing on solutions and employing active listening techniques, you can express disagreement diplomatically. Remember, disagreements are opportunities for growth and understanding, not threats to your professional relationship. By approaching them with professionalism and respect, you can navigate them successfully and maintain a positive working environment. 

First, set your ego aside. This isn’t about winning or losing an argument. Approach the situation from the stance of wanting to reach a greater mutual understanding as well as an outcome aligned with shared goals. You hired your boss just as much as they hired you; you’re both there to advance the organization’s interests.

Second, reframe the disagreement as a problem to be solved, not a person to blame or condemn. Detach it from emotion by sticking to facts. What viable solutions could you both live with to move past the impasse? Who needs to participate in making that solution happen?

Third, painstakingly practice patience and open-mindedness. Listen without immediate judgment or bursting in with a counterargument. Paraphrase what you’re hearing to demonstrate absorption of your manager’s position. Thoughtfully consider their reasoning and how it makes sense from their perspective. Once convinced, you understand where they are coming from, explain your standalone point of view.

Lastly, if talks grow circular without amenable compromise, it may be beneficial to ask HR or a neutral colleague respected by both parties to mediate. This should be done in a professional manner, with the goal of finding a solution that benefits both parties and the organization. Having worked through my fair share of disagreements with my bosses, I’ve found that calm, solution-focused language keeps tensions from escalating into resentment. Plus, it builds your reputation as cool under pressure. Remember, the goal is not to 'win' the argument but to find a solution that aligns with shared goals and advances the organization's interests. 

The Takeaway

Few things impact job satisfaction and workplace advancement potential more than the manager-employee alliance. Investing in consciously managing upward bears tremendous fruit now and in your career trajectory. Prioritize understanding your boss's communication preferences, strategically tout your value by showcasing quantifiable impact, and diffuse disagreements gracefully. Doing so boosts your sense of purpose and empowerment and forges a dream team with leadership cheering you on.

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