How to Help Your Boss Keep You Happy

June 6, 2017

My grandparents had a farm in rural Utah when I was a boy. Whenever I visited, I'd often see the horses and cows at the fence gazing into the next field. My grandfather would say, "The grass must look greener over there." 

Like my grandpa's horses, sometimes we look at outside opportunities and assume the grass is greener there. I know of several colleagues who have jumped ship for "better" opportunities to find they didn't stack up. I've also had more than one colleague who, within a week or two of leaving, shame-facedly reapplied for his or her old job. 

I've been on both sides of this as an employer and an employee. I've also observed that most people don't really quit their job—they quit their boss. So as an employee, it makes sense to invest in that relationship to help your boss help you enjoy a satisfying career. 

With that in mind, here are five things you can do to help your boss help you: 

1. Ask Questions

It's not uncommon for people to fail because expectations were either unrealistic or either left unexplained. For you to be successful, it's important to know what's expected, have an opportunity to discuss those expectations, and have direct input into your goals and objectives.

2. Get Face Time

In big organizations, managers take time frequently (sometimes weekly) to sit face-to-face with their employees. Sometimes this is a very formal meeting with a specific agenda and time frame, but it doesn't have to be. 

It might be easier to approach your boss with the idea of a regular time to touch base to go over your projects and allow him or her to add direction or perspective on what you're doing if you set up a regular time on the calendar. He or she will likely want to talk about what you're doing, but you can give them an opportunity to mentor you and offer you insight into how they would approach your responsibilities. 

It might be uncomfortable to ask how you can improve, but in this type of situation, it doesn't need to be. You'll be demonstrating to your boss that you want to do better, and you're giving them an opportunity to invest in you.

3. Be Communicative, but not Overbearing

Without dialog, it's easy to fall into the trap of feeling underappreciated. I once had the president of the company call me a month or two after I left for another opportunity and say, "We didn't realize everything you were doing to lead your team. We can't get the same level of productivity with them."

It would be easy in that situation to blame him for the lack of communication, but I failed to adequately communicate what I had been doing and why I felt we were seeing the results we were seeing. I thought the team success was an obvious reflection of my leadership, so when I announced that I was pursuing another opportunity, they thought they had it covered. My dissatisfaction with that situation was as much my fault as it was theirs.

4. Don't Be Afraid to Tell Them What Really Motivates You

It's safe to say that your paycheck is a good motivator, but only to a point. People generally need three things to feel positive about their work environment:

  • They Want Autonomy. The people closest to the work tend to understand it best and like to make decisions about the way they do their job and how they do it.
  • They Want to Make Commitments. Most people would prefer to make commitments than be saddled with arbitrary deadlines based upon what your boss thinks rather than what you think you can do.
  • Most People Like a Little Recognition. That's not to say they want a gold star on their forehead every time they show up for work on time, but they want to feel like their boss understands what they're doing and demonstrates appreciation for exceptional efforts.

5.  Don't Be Afraid to Let Them Know What Doesn't Motivate You

Sometimes personality differences allow unintentional de-motivating behaviors to make you (and likely other employees) less productive. If you can't honestly talk to your boss about the things that get in the way of you doing the best job you can, you're not only doing a disservice to yourself, you're doing a disservice to them.

The grass may be greener on the other side, but there's a good chance it's just like the grass everywhere else. If you don't at least try to help your boss help you, it's likely that nobody will be happy in the end.

By: Ty Kiisel is a contributing author focusing on small business financing at OnDeck, a technology company solving small business's biggest challenge: access to capital. With over 25 years of experience in the trenches of small business, Ty shares personal experiences and valuable tips to help small business owners become more financially responsible. OnDeck can also be found on Facebook and Twitter.

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