Cultivating Career Confidence

Cultivating Career Confidence

     Cultivating Career Confidence

Adding a bit of wit and wisdom to your day!

Secrets to Navigating Your Boss!

It’s June,  so you know what that means, right? Mid- Year reviews are upon us!

This means that we will all likely be having conversations with our managers about how we’ve been doing -  both the good feedback and the feedback on where we can improve. But this got me thinking…sometimes this feedback comes from managers who are genuinely interested in building up their teams and making their associates better. Other times, managers are difficult, unfocused or can take power to their heads.  I want to talk about THOSE leaders! Let’s talk about something we have all experienced (or will!) but rarely have the courage to address. Let’s talk about horrible bosses (and how to deal with them!)

I’ll start by saying that I am an advocate for the adage that what you do is just as important as who you work with. However, you cannot control the latter. The amazing leader that you work for might take a new role and be replaced by the devil. You may love your job but not quite connect with the person who signs your paycheck. A lot of people run for the hills when they are faced with a difficult management situation, but I think  there’s a lot to learn about yourself in navigating a manager who…is the worst.

(Note: this does not apply to toxic environments, corporate bullies, or situations where HR should be on speed dial. I am not supporting the notion of becoming a corporate martyr)

I have had some great bosses, some decent bosses, and some awful bosses. In each of these scenarios, I have had to learn to work with them: the good, the bad and the ugly.  On the positive side, the best boss I had kind of spoiled me into thinking that all leaders would be as amazing as her. She knew my strengths and weaknesses as much as she knew her own. She pushed me when she knew I could do better and taught me to delegate when it just wasn’t going to happen. I knew her expectations and she was consistent with them. She trusted my judgement and I trusted her enough to rely on hers. She knew my personality so well that she knew not to drop bad news on me without starting and ending with buffers that often consisted of conversations about comedic current events, song lyric guessing games, or any food related topic. She was a leader who cared about my work and my non-work and taught me be a better leader myself.

But I've had bosses that weren't so great too! On the exact opposite end of the spectrum, I've had bosses that made me feel as if I'd joined The Hunger Games of the corporate world and volunteered my sanity as tribute. I’ll blog about that one once I get out of therapy. I had the toughest time figuring out how this leader without a standard work style worked and it was like learning how to manage a toddler who’s mood changes with the wind.  While an approach may have worked one day, the next day he doesn't know why we chose it. One day,  he may have asked me to send out a communication to the team, but the next day he said I should have waited to let him do it.  One day the presentation looked great (insert high fives and exclamation points), but the next day, at 5am the whole thing was deemed garbage and needed to be redone. Learning a new leader’s work style is exhausting! It’s one thing to get past the interview, but  a whole other animal to learn to meet and manage a new leader’s expectations.

Which brings me to my first point. Working with a tough boss requires managing their expectations. And to manage their expectations, you have to KNOW their expectations. You might think you knew what you got yourself into, but I assure you…you do not! You don’t know how he or she works and you can’t apply past learnings to new people (unless you’re dating. Then apply, apply, apply!). The most difficult boss I've had was actually really good at what he does. He was ridiculously smart, had worked his way up the ranks in a very short amount of time and seemed to have a handle on the pulse of an industry that changes constantly. He was someone you'd want to be connected to. However, he did not sugar coat his views, bend for others’ comfort, or slow his pace to make sure his team was traveling in a pack.  While my leadership style is quite different, I had to learn how to manage how he worked, what he expected, and how to run the marathon of learning this without burning out.

So here are some tips on working with your “difficult” boss:

  • Become like a parrot and repeat everything for clarity. Repeat what you heard and restate what you thought it meant. This ensures you are on the same page AND have the same interpretation. Do not leave the discussion without having the confidence that comes with clarity.
  • Write it down. I cannot stress how important documentation is. Our brains can only handle so much and this is no different than your boss’ brain. To err is human, but to remember is technology. Use it!

            For example:

   In a follow up email:

        “Hi [insert boss’ name here],

        Great meeting today… Just wanted to recap our discussion….

            -  Review strategy with Lisa, Bill and Sue for sign off

            -  Present strategy in VP meeting on xx/xx/xxxx

        Let me know if there’s anything I missed.


        [insert name of a suited and savvy woman]

    In a follow up instant message or phone call:

    “Hi [boss' name] , I just sent you an email about the budget report. Let me know your thoughts. Please also     let me know if there’s anything I missed."


    [insert name of a suited and savvy woman]

  •  Learn to manage up. There are times my difficult leader wouldn't remember what he said he was going to do and sometimes that directly impacts my work. I learned the hard way that I was waiting on him to do things first and that resulted in my timeline getting behind. I wanted to play the blame game and let him know that x, y, and z would have been done if he wasn’t being the biggest B (B = bottleneck), but I also value relationships and blah blah blah… Instead, I had to learn how to manager him. This means you must learn to remind, nudge, and gently prod even the people you report to if it means success for the whole team.

    For example:

    In an email:

    “Hi boss,

    I’m ready to push project X along and am just waiting for your budget update. If you’re able to provide your     deliverable by [insert realistic date] then I can submit this by the end of the week and strike it off the list.


    [Insert name of a suited and savvy woman]"

    In a follow up instant message or phone call:

    “Hi boss, I just sent you an email about the budget report. Let me know your thoughts.

  • Leverage your peers and coworkers. They may have inside information that you don’t know. My teammates told me what to do and what not to do which has saved me so many times! Tips like “don’t go to him with a problem without recommending a solution” or “have an opinion even if it’s different from his." This tips help me prepare for interactions with my difficult boss.

  • Take your personal hat off. I’ve had mentee tell me that her manager didn’t like her because she was pretty. I gave her the most audible eye-roll I have ever given a non-relative. Toss your biases and emotions (and in this case your craziness) aside and put the work front and center. You succeed as a team, so you have to learn to behave as one. On a team, there are many different personalities, preferences, work styles, temperaments, but when you believe in what you do, then you also have to believe that the work is more important than all of the personal things that cloud our work environments.

  • Emotional intelligence is your friend. Go high, girl! Take a breath, choose the high road, and manage your emotions to help guide difficult situations.

  • Keep a list of wins and fails. As you figure out your leader, keep a list of things that work and things that don’t work. I noticed once that a boss I had was really nice to me when I was sick so I faked a cough before I give bad news. I’m kidding! But in all seriousness, I learned that one particular boss appreciated status updates because he felt it gave him a better grasp on his team's movement. That was a win. I learned another boss didn't like to look at presentations that weren't polished or were considered to be “drafts”. That went on the “do not do” list. Keeping a list of things that resonates will help you start understanding patterns and govern yourself accordingly.

  • Finally, remember that your leader is a person. Managers are people too. We have good days. We have bad days. I lead my team the way I want to be led, but I fall short more times than I’d care to admit. We are human and we all need a level of grace and reprieve.

Check out The National Best Seller  "Working With You is Killing Me"  and "Working For You Isn't Working For Me" for more tips and tricks to keeping cool on the job.

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