Trouble connecting with the boss?

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BossWhile many folks complain about them, bosses are also something all workers have in common. Perhaps that’s why pop culture is filled with so many who intrigue, inspire and infuriate us — because we’ve all worked for versions of them.

Think about it. Some of the entertainment industry’s most popular characters are bosses. There’s Michael Scott from “The Office,” Miranda Priestly from “The Devil Wears Prada,” Jack Donaghy from “30 Rock,” Ari Gold from “Entourage and Mr. Burns from “The Simpsons.” The list goes on. The reason we love (or love to hate) these characters is because we can see traits of our own bosses in them. Watching them lets us know we are not alone in some of our everyday battles.

Love her or hate her, she’s still your boss, and she still signs off on the paychecks, gives you your review and recommends you for new projects or a promotion. While you don’t need to be best friends with your boss, the two of you still need to have a civil working relationship.

Today, we have  a guest post from behavior strategist and performance management coach Joe Takash, the author of the newly released “Results Through Relationships: Building Trust, Performance and Profit Through People.”  Takash tells us the key to a great boss/employee relationship takes just simple steps. Here’s how:

The 5 Steps to Connecting With Your Boss

By Joe Takash

Managing Up
1. The rare act of transparent communication with one’s professional superior or superiors to get needs met, thoughts heard and contribute to the success of boss, team and organization.
2. Courageous upward leadership with the intent to establish trusting partnerships and own one’s results.

Interns and entry-level employees, even employees at high levels, don’t apply the tips for effectively connecting because they’re never provided a blueprint early on in their career. Practicing these diligently can expedite career opportunities and differentiate you in an economy that is in need of high-flyers more than ever.

1.  Choose Good Timing
Discover the best times in which to approach your boss by simply asking, “when are the best times to meet with you if I have questions?” This simply inquiry can build credibility because of the awareness and consideration of their busy schedule. An added benefit is that when you meet with them, you’re likely to have a more focused, less distracted listener.

2.  Prepare and Plan
Practice your approach vs. just winging it so you can succinctly explain up front why you’re there and what you need from them. WARNING: Be solution-focused! Bosses want to know what you have thought of or would suggest about the inquiries you have. This is a crucial component for demonstrating leadership and initiative.

3.  Align Understanding
If your boss does not state his or her expectations or ask about yours, don’t waste energy griping to others about it. Instead, rise above and them to be clear about what they need from you. Requesting the primary duties you should be focusing on or discovering the qualities that make up the ideal professional in your position not only impresses them, but provides you with a roadmap for success.

4.  Follow-up/Follow-through
One of the biggest barriers for positive change is lack of accountability. In managing upward, you can hold yourself and boss accountable by agreeing on times/dates to follow-up at the conclusion of each meeting or communication exchange. Your boss may think, “These behaviors would be great in a client services or sales position” which may be a promotion you earn twice as fast as you may have.

5.  Own Your Results
A young lady named Karen once approached me after a keynote presentation I delivered to her company. With a pleasant, apprehensive smile, she said: “Joe, I really believe I’m equipped to be our marketing manager. I have experience, passion and knowledge, but I don’t know what to say to my boss. I was wondering if you have advice.” I said, “Karen, I have for you a magic formula and it can be described with one word: ASK!” I politely explained to her that the biggest success stopper is that cynical voice within each of us. Owning your results doesn’t mean you won’t experience fear as you navigate your career, it’s the commitment to courageously ask for what you want and be prepared to state why and how all will benefit. 

Tell us what you think below! (No registration required.)

  • Who is your favorite boss from pop culture and why?
  • How you were able to get through to your boss in a difficult situation?
  • If you’re the boss, what advice would you give employees?
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  5. That is total bull – ask? How about an article about a boss who learns how to spot a great, loyal and skilled employee so that we don’t have to ask and our potentials are seen and recognized. I don’t think I should be telling my boss how great I am and what skills I posess, he or she should recognize them on their own. Isn’t that what makes a great boss?

    • Most bosses are either too busy or too LAZY to notice the great jobs we do. On the other hand, there are bosses who worked their way up from the bottom and are on the look out for great performers. I was lucky enough to have had a boss who saw and believed in me.

  6. All this is true–if you are not working with a paranoid schizophrenic…Too many employees think that if they only did “this or that”–they would better be able to “work with” -aka- “connect with the boss.” Where there are major mental issues with any individual whom you work with in an organization, sometimes “dis-connecting” is more helpful. That “dis-connect’ does not necessarily mean one should physically leave his job (the economy is not supporting that concept for many people). Sometimes the “disconnect” must be in “mentally” separating your feelings and thought processes from a “Boss” that “lost it” a long time ago; yet, is tolerated by the company. Usually, such a “boss” is the brunt of the jokes of his own colleagues/peers; yet, they are powerless in getting the “odd” ball out of company. My advice: Take frequent “mini- vacations.” That makes it easier to survive another week/month at work. Few people need advice on connecting with a “boss” who is reasonably happy on the job and happy with himself as a person.

  7. While this article had valuable information, the writing was poor. See #3 above. “Instead, rise above and them to be clear about what they need from you.”

  8. Ask your training and development dept to purchase an Everything DiSC Management Assessment for your boss and a Everything DiSC Workplace for you….. have the DiSC provider create the free Comparison Report for you. This is one of the best assessments used throughout the corporate world to reduce the communication learning curve and minimize communication misunderstandings. It also creates a language for discussion of any workplace topic. See sample reports at or just call us to discuss the use of assessments in your career. A top defense contractor First Line Leader said, “This is like Gold to me” when referencing her DiSC project with her direct reports.

  9. I work for the county government so all bets are off on having some type of strategy to impress your boss for future advancement. As a matter of fact, you are better off not showing any exceptional skill, you will just get more to do. Stupid people are given little responsibility and no difficult tasks. They cannot be fired from the government for being stupid.

    I have noticed a trend in the workplace that will be the downfall of employment as we know (knew) it. You can read about it in my blog post:

  10. In an ideal environment, the five steps to connecting with your boss could be successful. However, the workplace isn’t a perfect environment. The steps do not consider other intangibles. Some employees can’t articulate their grievance no matter how organized they may be. Other employees are poor performers so no matter what they request, it will be taken with a grain of salt and dismissed. And, there are always other employees who want you to fail or will be jealous of your intiative. So if you achieve your goal, there will always be someone who will try to undermine you.

  11. Nice story – thanks! So many problems arise out of fundamental communication problems – problems that have easy solutions.

    You can’t really go wrong with being solution-focused and being able to back-up your claims.

    One thing I’ve noticed is when a group lead seems to be berating me with questions, it’s actually an experience where I am witness a very intelligent person gathering and processing information to produce a solution – I just needed a change of perspective to understand where he was coming from. Ride that “solution-focused” wave and a bunch of trust will grow from it.


  12. Nice advice assuming an ideal situation. However, the matter is more complicated when one must navigate office politics, personal agendas, desires of others to “one up” each other–especially the often prankish attitudes of targetting the newbies to swamp them with work and blame them for all the problems–especially those that don’t quite fit in or who are a little . . .too nerdy in their brown-nosing. Sometimes no matter what you do, there is always someone who will sabotage your efforts to make you look bad to the boss. Although the advice was great and sure to work in the ideal situation, it is way too idealistic for the usual workplace.

  13. My favorite boss is Mike Fhaherty on Spin City

    Tell him/her to get out of my way or do it themselves

    If you are stuck in your job, start fresh someplace else with your experience and skill. Start someplace new and don’t give family & friends your work #, if you screwed up but learned, go someplace new and don’t screw up.

    If you are permanently stuck and can’t change jobs, compartmentalize your work hours, be as productive as possible. Go to your personal life and revel in it, make it worth the hard hours you need to spend at work.

  14. Love this. They are harder skills to learn then you would think because it all seems so logical. Yes, it would be great if your boss recognized you at a fabulous employee (and in a good company that will happen), but how can anyone give you something they don’t know you want? Asking or, rather, SUGGESTING what you want is something you have to do if you want to move up in business. You just have to make sure you can layout how it will be beneficial not only to you, but the company, too.

    Bosses have a lot to think about so they may simply not have noticed the way you keep the company running like clockwork while they’re away…but they will appreciate your suggestion if by giving you a promotion the company would be better off.

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  18. Very nice article.
    one must not forget that the boss of ones boss is the client! The customer is the boss of all bosses. So in the long run we all work for someone.

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