Happy Handshake with the Boss

Managing Your Manager

Ok, this is my last post of 2015.  For those keeping track: yes, I fell off the wagon in November and most of December.  Something about taking a new position that requires a rather high level of output and time-on-task.  But I digress.

I’ve written previously about the perils of focusing on technical skills at the expense of other skills.  This topic is one of those “other skills” that can make a tremendous difference in the evolution of your career.  In my view, there are times when this particular skill can be more important than your technical chops.

I invite you to ponder this question:

Are you aligned with your manager?

Do you actually know how your manager sees your contributions?  Does he or she know what you do in a day?  Do you know what your manager’s pain points are?  How do you know if you are really adding value to your organization?  Should you be more transparent than you currently are?  Should you pay attention to activities that you aren’t even aware exist?

In the context of a small startup in which you physically sit close enough to your boss that you can hear his or her Pandora station, these questions might seem unimportant and the answers might seem obvious.  But if you are in a larger company, your manager might have fifty other people to oversee.  Perhaps your manager isn’t even in the same country.  In extreme cases, you may never meet your manager in person.  This might be hard to imagine, until you experience it.

In reality, it is very easy to fall out of sync with your organization’s management, while being totally unaware that it is happening.

What is Managing My Manager?

Managing your manager does not mean you become your manager’s boss for a day.  It involves spending some time and energy understanding things from your manager’s viewpoint, then adjusting your own behavior to ensure that you both have a productive working relationship.

The ability to manage one’s manager is a very important skill in any company.  It becomes especially crucial in companies where your direct manager can make or break your career trajectory.

Done right, managing your manager makes working life a bit easier on both of you.  The side benefit is that you will start to understand that there is a different way to interpret and measure the value of your work.  This in turn can open doors that you were previously unaware of.

How To Start Managing Your Manager

In my experience, one of the best ways to align your own day-to-day habits with your boss is to ask how he or she would like to work together.

It’s that simple.  Just ask.

For example, when I start a new role at a company (assuming I didn’t already ask during the interview process), I will ask my new manager something like this:

“I’m coming here from other companies, each with their own ways of doing work, so I would like to understand how we should work together, from your perspective.”

Normally the reaction to this question is something like “wow, nobody has ever asked me that before.”

Once that novelty passes, this question usually leads into a conversation that covers some very important  elements from the manager’s point of view.  Things such as the manager’s pain points, and whether my work can have an impact on those pain points.  I will probably learn about the manager’s need for transparency – including how often, and in what form, project status is gathered.  I might also learn about how the manager relates to the rest of the organization’s power structure.  In the best cases, I leave the conversation with a better understanding of what it means to be “successful” in the context of the organization in which I work.

If you have not guessed it, this information is gold!  And it can be yours for the asking!  Let’s look at some examples where your alignment with your manager can be very useful.

Out-Micro-ing the Microboss

A common example is the case of the infamous micro-manager.  You know, the one that stands in your cubicle at 4:30PM every day asking you for a status, even though you had a standup at 9:00AM that same day, and there is another one tomorrow.

If you had the previous discussion with your manager, you might already know that this manager needs to report status to his manager at the end of the day.   So, if you agree with him that you will send a status report by 4:25PM, then he may have no reason to visit you in your cubicle.  Just fulfill your end of the bargain, so that he can fulfill his.

Like magic, you have just taken a step into the world of managing your manager.

Solve Organizational Problems for Fun and Profit

As another example, say your development team has a friction-filled relationship with your dev-ops team, resulting in political fireworks from your manager’s standpoint.

If you are aware of this dilemma, you could actually take the initiative to build a helpful personal network over in the dev-ops team, or perhaps automate away some technical issues that might be increasing the hard feelings between the teams.  This sort of work will reflect positively on you, and quite possibly your manager as well.  Another benefit: this is a free way to grow your own organizational network!

Become Great at Selling….Your Ideas

There is a quote allegedly from Teddy Roosevelt: “Complaining about a problem without posing a solution is called whining.”  Problems and challenges come with the territory in management life.  It is often a breath of fresh air when someone comes in with a problem coupled with some well-reasoned suggestions for addressing it. 

Understanding how your manager views problems and solutions can help you craft better ways to convince him or her to let you take a shot at solving them.  This skill comes in awfully handy when you want to pitch your own ideas.  When I initiate a conversation like this, I normally like to have two alternate solutions ready for discussion, or better yet, a working demo of a potential solution.  This shows initiative and makes it easy to convince a manager that I should be involved in implementing the solution.


By now, I hope you are getting the idea that understanding your manager’s viewpoint can add a new dimension to what you thought was the value of your own contribution.  I have personally used the approaches above in a variety of situations that otherwise would have resulted in very negative outcomes.

There are some cynical people in the software world that view this sort of skill in a less than favorable light, so I will clarify here.  I’m not trying to make a case that you become the manager’s pet, babysit their children, or kiss the posterior of each and every manager in your career.  I am suggesting that one should make efforts to understand how one’s own value is measured from management’s perspective, and use that understanding to discover new opportunities to improve and develop of one’s own skills.  It does not mean a compromise in principles, or “selling out.”

There is the added incentive that the most cynical of these aforementioned people have probably been sitting in the same cubicle at the same company, or in the same position, for a very long time.  Think about what happens if you don’t adopt some of these skills.  You assume that whatever you happen to be working on will meet with your manager’s approval in that once-a-year performance review.  You assume that the manager will ask you when he or she needs a status.  You will wait to be handed work to do.  While there is nothing inherently wrong with this, it is not a philosophy that lends itself taking command of one’s own destiny.

Think about these things the next time you feel that wholesome, well-intentioned eagerness to stampede off to the keyboard and throw down your next piece of legacy code.  Perhaps there are more ways for you to inject value into your organization.