Get Your Boss On Your Side

This approach must be based on a shift from a judgmental mindset to a learner mindset

I have to admit that in my career, I always had an authority issue. I maintained criteria and expectations for anyone I reported to. My criterion was that I had to respect the person, be able to learn from him/her, trust she/he will give me valuable feedback, and support me. Although it helped me in choosing whether to accept an offer, this attitude is also a set up for the boss. Why? I had an internal set of criteria as conditions for our relationship. When my boss didn’t meet them, I reacted with disappointment, anger, and sometimes resentment. This isn’t a recipe for trust and respect, since I rarely shared these criteria with my managers. I was coming from a pretty judgmental mindset. To successfully manage up, I had to confront my biases and expectations – not make them “wrong”, but shift them from expectations to wishes and become willing to share these in a conversation for mutuality.

But first, I had to become willing to get to know my boss – and express a true interest in what makes this person tick. This “learner” mindset positions me to connect and build a relationship based on focused curiosity, without being insincere or manipulative. If you find yourself identifying with my original mindset, then consider shifting to an attitude that will allow you to truly connect with your boss.

My colleague, Roz Usheroff – a leadership, image and branding specialist, suggests ways to win over a boss. This approach must be based on a shift from a judgmental mindset to a learner mindset:

1. Treat your boss like your number one customer. Do this by using your authenticity and sincerity to seek out their thoughts on how you can serve him/her. Seek to understand what keeps them up at night so that you can carve out your value proposition in their eyes. Also, 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’s communications preferences. Does he/she prefer face-to -face, email, phone/voicemail, text, Skype, lots of detail/lists, bottom line, pictures/diagrams? How about timing? What are the best and worst times to communicate? Does she prefer start or end of day, weekends, on the fly, last minute or scheduled meetings? If your styles are different, it serves you to adjust to your boss’s style.


3. Communicate regularly. Operate within the guidelines you both set for optimal communication to meet frequently face to face informally and formally. Keep your boss informed on updates on goals. This builds reliability, your value in his eyes, and builds trust.


4. 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 by meeting and exceeding expectations, being prepared for your meetings, and showing your commitment by volunteering for things that others don’t want to do.


A mutually satisfying relationship with your boss brings short-term gains in the form of coaching, developmental assignments, meaningful performance reviews, and salary increases. The long-term benefits bring sponsorships for career opportunities, strong referrals, and introductions to other helpful people in your network – just to name a few. My best champion today is one of my former bosses. How about you?

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