Top 6 Critical Conversations You Should Have With Your Boss

This post was originally seen on Career Rocketeer and was written by .

Communication seems to be the most under-rated, yet most critical thing we do as humans.  There are all too many things we should be discussing and communicating about, yet for some reason, we don’t.  Call it lazy, busy or reluctant; we don’t communicate enough about the right things in the most effective way.  Think of just how much better all your undertakings would be if all you did were improve this one critical capability.

In the workplace, almost all of us have a boss or someone we must be responsible to.  That means the place to focus your communication as your highest priority is the boss.  When you work well with the person in charge, chances are exceptionally high that you will like your job.  As a place to start, use this as a checklist for your communication plan with your boss:

Work or project.  You should be finding a variety of ways to keep your boss in the loop on what you are working on.  Don’t just go silent and hunker down in your office.  If you do that, you will force them to come extract information from you.  Consider sending short emails, hallway conversations or sound bites in staff meetings.  You can also consider preparing a monthly report that covers highlights, status and challenges–all the things the boss really wants to know.

Discuss problems you encounter.  Some people are reluctant to let anyone know they are encountering a problem.  Problems are why we were hired.  Consider discussing Situation-Action-Response or S-A-R.  Don’t just take a problem to the boss without offering at least one possible solution.  When you do the S-A-R approach you first outline the situation, and then outline what action you either did take or propose to take, followed by what result you expect.  This way the boss isn’t solving your problems, but is being given a “heads-up” on an issue and the opportunity to validate your approach.

Clarity.  If ever the boss gives you direction or communicates something you don’t understand or think you agree with, it’s time to seek clarity.  It only takes a few minutes to catch the boss to ask a few questions.  Keep in mind, their only ability to get their job done well is if you do; so don’t think of your questions as an interruption.

Your career goals.  Every boss wants to think they have hired real go-getters.  You can show that you are in a number of ways, and central to that is to engage your boss with your career goals.  If you discuss your goals and create development plans that mesh with both of you, you have a built-in advocate.  Your boss can’t guess what you want next; you have to let them know.

Your performance.  You need to start every new job by gaining an understanding of exactly what their expectations of you will be and how they will go about assessing you.  Once you know those details, take it upon yourself to seek ongoing feedback about how you are doing.  If you do this, you will avoid running your job off into the ditch.  If you need skill building, make your request when you have your performance discussion.

When it’s time to go.  Hopefully, you work for a boss and company where you can have open, honest discussions about things like leaving.  Many of us don’t.  If you do work in an environment where you can, let the boss know when you have reached your professional “expiration date.”  Keeping them in the loop and being a transparent professional will help their planning tremendously.  They will also respect you for doing so.

It’s not possible to over communicate with the boss or most people you work closely with.  Look for opportunities to share what’s going on with you every time you can.  You will find you work better with others when you do and you will be sought out as someone great to work with.

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Managing Your Relationship with Your Boss

This is a guest post, originally seen on the Wall Street Journal.


Do you have a boss who lacks the skills for managing others? Or one who is not interested in becoming a better boss?

Don’t be disheartened. Instead, take the lead in managing your relationship with your boss.

This is not as difficult to do as it may sound.

You have been hired to be productive. Your productivity–which benefits you, your boss and your organization—depends upon a high-quality relationship between you and your manager. To develop this, you need to understand what is expected of you, your boss’s needs and preferences, and your own needs and preferences.

Here’s how you can master these three worlds:

World of Work: To do your job effectively and efficiently, you need to be clear about what is expected from you. But if your boss is always rushing from one meeting to another, or is poor at communicating, you may be working without proper direction.

In that case, it’s up to you to get the answers to three key questions:
– When is the assignment due?
– Is the work a top, middle, or low priority?
– Whom can you ask for help, if necessary?

For example, perhaps your boss needs a report or slideshow, a convention or exhibition to be organized, a follow-up with a client, a vacancy to be filled, or a product design. As soon as you get the assignment, ask for a deadline and get a sense of how much priority the boss gives it. This will help you decide how much time, energy and skills to devote to that assignment versus your other projects.

Also, find out who you should turn to if you run into problems. Some bosses may prefer that you check back with them. Others may not have the bandwidth to help you with problem-solving – he or she will want you to talk with co-workers or someone with more experience.

World of Your Boss: Like it or not, subordinates have to adjust to their manager. To do this, you need to understand your boss’s needs and preferences. Look for clues about your boss’s approach to processing information, making decisions, working with others, and communicating. In these four broad areas of managerial action, every boss has a distinct style.

Management guru Peter Drucker said that managers with an auditory orientation have to be talked through information, while managers with a visual orientation prefer a written summary of main points. Decision-making preferences also vary. Some consult broadly with many co-workers, others with a trusted group of associates, and still others fly solo. When working with subordinates, some are hands-on, issuing a continual stream of instructions so that the job is done exactly as they would have done it. Others give subordinates the autonomy to implement an assignment in their own way.

Communication styles vary even more. Some bosses are formal and have occasional interactions, while others prefer continual camaraderie. Some start with the big picture, others with details.

Chances are that your personal style will not be totally compatible with that of your boss. Regardless, your wisest course of action is to aim at being an honest, dependable, and loyal employee who willingly makes many adjustments to your boss’s work habits and style.

By adjusting, you will connect better with your boss.Note that if your boss is abusive or patently unfair, then adjusting is not the solution.

Your World: In order to establish a good relationship with your boss, you also need to learn how to better manage yourself. Each assignment that you complete gives you a snapshot of your abilities and limitations.

In some of your conversations with your boss, you can familiarize him or her with a few achievements of which you are particularly proud. At the same time, you can ask for guidance and feedback about what you do well and how you need to improve.

Simply observing your boss can stimulate self-development–you may feel inspired enough to emulate him or her, or disenchanted enough to do the opposite when it is your turn to manage others.

Get rid of unrealistic expectations. A boss is not a parent. A workplace cannot satisfy all one’s personal needs such as desire for affection, attention, inclusion by others, adventure, or total control over circumstances or other people. A realistic assessment of how one’s personality is wired is very helpful for managing relationships with any boss (and others) with greater finesse.

By arming yourself with self-knowledge and the willingness to continually learn and improve, you prepare yourself for making your way in today’s ever-evolving world of work.

Meena Wilson is Jamshedpur-based senior associate at the global leadership development firm Center for Creative Leadership and author of “Developing Tomorrow’s Leaders Today: Insights from Corporate India.”