How To Build A Winning Relationship With Your Boss

You never truly know someone until you’ve walked a mile in their shoes” – American Adage, Source Unknown”

Far too often when we are meeting someone for the first time, we tend to focus more on ourselves than we do the other person.

Unfortunately, and in our effort to make a good first impression, we inadvertently miss an important opportunity to learn about them, and the possible points of interest we both might share.


Taking A Page from Big Brother Winner Derrick

For those of you who watched the Big Brother finale, you know that this year’s $500,000 winner, Derrick Levasseur, became the undisputed master of the game. In talking about his win, Derrick revealed that his job as an undercover police officer provided him with the skillsets to get close to people, learn what was important to them and how to connect on both a personal as well as a game level. What was most impressive was the fact that he accomplished this while still maintaining a high degree of integrity. In other words, and by expressing a true interest in what made the other person tick, he positioned himself to win without being insincere or manipulative.

Refocus Your Lens

Whether meeting a new boss for the first time, or trying to connect with your current boss, now that you have refocused your lens on getting to know them, there are a number of important connecting points for building a long and mutually beneficial relationship.

1. Treat Your Boss Like Your Number One Customer

  • Use your authenticity and sincerity by seeking out their thoughts on how you can serve them. Seek to understand what keeps them up at night so that you can carve out your value proposition in their eyes.
  • Learn what success looks like to them. Being on the same page will cement your relationship and create a harmonious and trusting bond. Pay attention to your boss’ priorities and make them yours.

2. Identify Your Boss’ Communication Preferences

Boss Chart

Click to zoom in on chart

3. Become An Information Broker

In many instances, especially when being appointed to the position from outside of the company, new bosses go through an adjustment period in which they have to orient themselves to the lay of the land in terms of people and politics.

Because of this, you can establish yourself as a valued asset and a key “team” player during the transition period by doing the following:

  • Encourage your boss to depend on you by providing access to information and tools in addition to your network.
  • Help them to capitalize on opportunities they may not know about as well as challenges that might be brewing.
  • Lighten their load by volunteering to attend meetings on their behalf for gathering important information.

4. Position Yourself As A Confidante

We are all familiar with the saying that “it is lonely at the top”. Even the most confident boss can experience feelings of isolation and uncertainty. While many employees may assume that because they are the boss they have it all together, the fact is that while different, their pressures and challenges are no less daunting than a frontline worker trying to meet a deadline.

  • Use your emotional intelligence and observe your boss’ moods to identify the triggers and pressures that impact their behavior.
  • Always be aware of their priorities, and if they are shifting direction due to changes in the company.
  • Share your wisdom, experience and observations with colleagues, while reinforcing your boss’s vision of the business. This will be a testimonial to your boss that you are an important connecting point with your co-workers and someone who can reinforce their big picture view.


5. Communicate On A Regular Basis

Even if your boss gives you carte blanche to do your job, make it your top priority to always keep them in the loop through regular updates on what you are doing and how it aligns with their stated goals.

  • Meet on a regular basis, including getting your boss out to the occasional lunch away from the office.
  • Have frequent, unstructured conversations to inquire if they are satisfied with your performance and to confirm that they see the value that you are bringing.
  • Last but not least, create a special relationship with their admin, so that you can get priority access.

6. Be Vocal in Meetings

Become a regular contributor in your boss’ meetings. Before each meeting, decide how many times you want to speak so you’ll have a target that motivates you to participate. If you delay speaking up, it becomes harder to break into the discussion.

  • Know the agenda and ask your boss how you can be relevant to the discussion topics.
  • Speak up within the first ten minutes of a meeting to show that you’re engaged.
  • Ask thought provoking questions with genuine curiosity.

7. Be Low Maintenance

Let your self-motivation guide you to accomplishing your targets without having to be managed.

  • Sign up for significant assignments that can be accomplished without your boss’ involvement.
  • Proactively solve their problems before your boss reaches out to ask you to.

8. Honor your Commitments

At the end of the day, you are there to do a job, so make sure that you do it to the best of your abilities!

This means:

  • Building trust and dependability by not only meeting but also exceeding expectations and deadlines.
  • Demonstrate your organizational skills by being overly prepared and proactive.
  • Stand out by volunteering for roles that showcase your commitment to your boss. Do what no one else wants to do.

By following the above guidelines, your boss will see you as an important asset, include you in key projects and become a sponsor for your next promotion.




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