16 Easy Steps to Make ANY Boss Happy (and Keep Your Soul)


Everyone wants to succeed in their career but you don’t want to be a groupie for your boss, groveling for any scrap of attention. Not only are brownnosers viewed with disdain by their peers but their effort is rarely rewarded in a significant way. They give up their credibility in exchange for minor favors but if they go too far their efforts backfire, the ingratiator’s dilemma.

Follow these 16 steps that will please even the most difficult boss and will not sacrifice your self respect.

1. Remember the First Rule of Employment

Your job is to make your boss more successful in achieving business objectives for your team and your department. The mindset of ‘I’m great but everybody else sucks‘ is prevalent in about half of US workplaces (source) and results in a lone wolf culture. Instead point out the common elements that unite members toward the common business goals in support of your boss.

Understanding your workplace culture is key to maximizing your career opportunities. The book Tribal Leadership by Dave Logan (buy on Amazon) gives excellent insight and is an easy read not just for managers.

In every workforce there is also the group of employees that view work with a cynical ‘us vs them‘ mentality. They believe that the company is always out to exploit workers and only do actions that directly benefit them. A more effective approach is to view work as a long-term relationship. Put in the effort knowing that there is a give and take and have some trust in leadership – at least until they reveal their true character with a pattern of behavior.

2. Communicate, Communicate, COMMUNICATE

Workplace communication styles vary by country and ‘command and control’ approaches continue to lose effectiveness as channels beyond traditional meetings and email take hold (source). Employees are working remotely using technology platforms like Slack, Microsoft Teams, G Suite and Jira/Confluence from Atlassian. Information is more available, but also more susceptible to being outdated, incomplete, and misinterpreted.

Just like the game of telephone, the more times a message is passed along the more it morphs and loses the original intent. Everyone would do well to remember The Plan.

The Plan

In the beginning, there was a plan, 
And then came the assumptions,
And the assumptions were without form, 
And the plan without substance,

And the darkness came upon the face of the workers,
And they spoke among themselves saying,
“It is a crock of shit and it stinketh!”

And the workers went unto their Supervisors and said,
“It is a pile of dung, and we cannot live with the smell.”

And the Supervisors went unto their Managers saying,
“It is a container of excrement, and it is very strong, 
Such that none may abide by it.”

And the Managers went unto their Directors saying,
“It is a vessel of fertilizer, and none may abide by its strength.”

And the Directors spoke among themselves saying to one another,
“It contains that which aids plants growth, and it is very strong.”

And the Directors went to the Vice Presidents saying unto them,
“It promotes growth, and it is very powerful.”

And the Vice Presidents went to the President, saying unto him,
“This new plan will actively promote the growth and vigor 
Of the company With very powerful effects.”

And the President looked upon the Plan 
And saw that it was good,
And the Plan became Policy.

And this, my friend, is how shit happens.

Unknown

The single best action you can take when communicating is to verify understanding. Communication is the exchange of information between individuals and is only effective when the message is both received and understood. For critical items you can not just ‘send it and forget it‘, the email might sit in unread in their inbox or ignored in their messages. Make sure you get a confirmation back either from a response or by speaking with them.

In-person communication has fallen away to the point that people won’t even take a voice call anymore. But there is nothing more effective than speaking with the other person for clear understanding. Tone and urgency are conveyed and there is less delay going back and forth for clarification.

3. Verify Your Work

Mistakes at work are costly in terms of money, time, and your reputation. The mistake is not just a failure, it also leads to mistrust. You can not avoid all mistakes at all times, but double-checking key items will greatly reduce their frequency. Smart people double check their work.

Make a habit of verifying your data is both correct and complete before sending to customers and senior leaders. Proofread your emails to avoid misunderstandings and typos.

Pro Tip: Avoid accidentally sending an email with draft or incomplete content. Leave the To: field blank in your email until after you have composed the content and uploaded your attachments that way there is no way you can accidentally send it before you are ready.

It is easy to go on autopilot for familiar tasks, like when you are driving home and have no memory of the previous 3-4 stoplights. There are practical ways to improve your attention to detail at work – you need to be both thorough and accurate.

  • Break large tasks into smaller pieces, each with a clear deliverable
  • Be present and deliberate in your actions, think about each step
  • Take breaks when you feel your focus wavering
  • Stay active by taking the stairs and going for a walk during your break
  • Minimize distractions with a ‘not to do‘ list, when you feel the urge to check your social media simply write it down instead
  • After an interruption double-check the previous action was fully completed and correct
  • Listen actively by asking questions and recapping important points

4. Take Ownership

Taking ownership is about making sure the business objective is realized. There will be problems, there will be conflicts, you will be short of resources. Instead of getting stopped by these challenges you take initiative to overcome them. You accept responsibility for the quality and timeliness of the deliverable and work with other staff as necessary to get the job done.

It is easy to take responsibility when outcomes meet the expectations of your boss, but your true character is revealed when mistakes are made. The single best thing you can do to earn trust is to call attention to your mistakes, accept responsibility for your actions, and then take steps to ensure you and your team will not repeat the same error in the future. This is the foundation of continuous improvement and how teams get better. Making excuses or shirking responsibility is a mark of immaturity in business.

5. Go Beyond Your Job Description

There are few statements that managers dislike more than ‘that’s not my job‘. The modern reality is that nearly every job description includes the phrase ‘and other responsibilities as assigned‘, which means your responsibilities will change based on business needs and what your boss needs done.

Help other staff find the answers and assistance they need, you don’t need to help them do the work but point them in the right direction and introduce them to the right people. Your professional network is one of your most valuable career assets so treat them accordingly. Be the coworker that you want to work with.

6. Show Initiative

Ask questions when getting new project assignments and don’t expect handholding. The most infantile response you can offer is ‘nobody told me‘ when asked why something didn’t get done or was done improperly. Don’t expect to be led through all of the uncertainties, your boss doesn’t want to spoon feed their staff or baby sit every activity. Solve your own little problems. Don’t waste your time with your boss on trivial items, save it for matters when you actually need your boss to get involved and drive actions with other leaders in the company.

Try to solve problems on your own and engage with your peers to find a way forward. Don’t let yourself get stuck however, if you are not making progress then you can bring it to your boss as a coaching moment ‘can I pick your brain on this item‘ just make sure it is clear that you are not trying to hand off the problem to them.

Take the Lead. Don’t knowingly overstep your scope of responsibility but when your boss delegates to you then run with it. Call the stakeholders together, set the meeting agenda, and get things done without your boss even having to ask. One of the best ways to stop a micromanager is to clearly demonstrate that they have no reason to be concerned. The narcissistic powermonger boss is rare, most micromanagers are simply insecure and feel they need to followup on every little item.

7. Be Proactive Instead of Reactive

Be Proactive is such a cliche because it rarely comes with practical guidance on how to be proactive. It really comes down to two concepts: don’t wait for someone to tell you do something (go do it) and follow Murphy’s Law.

Anything that can go wrong will, and at the worst possible moment.

Murphy’s Law

I am constantly surprised by how many people respond passively when something goes wrong at work. They make statements like ‘somebody needs to do something‘ but don’t take action themselves. I most situations the initial steps really are quite obvious, so get started. At a minimum confirm the basic facts with the stakeholders and start thinking of an action plan to resolve the issue.

Murphy’s Law is an adage that proves itself year after year, so you have no excuse to be surprised, especially when the problems are frequent fliers. If a department has been late with their deliverables consistently over the previous weeks then you should expect they will continue to struggle in the near future. Anticipate likely problems and prepare contingency plans earlier rather than scrambling to come up with something in the moment. Every workplace has their challenges, and many of them repeat, so learn to adapt and overcome.

8. Volunteer for Difficult Work

Now you don’t need to fall on your sword and volunteer for every unwanted job or last-minute request, but by the same token you don’t want to be the person that never volunteers. The fact of the matter is that when crap work needs to get done everyone will get their share. Your boss also dreads handing out work that nobody wants to do and will appreciate someone stepping up to the challenge.

Pick your opportunity wisely, when you volunteer for the job nobody wants you can also shape how it gets done. Ask for the resources and support needed to get it done right. You probably won’t get everything you want, but even if everything is denied you have also set the foundation for why there may be difficulties down the road.

9. Arrive On-Time and Prepared

Rushing into a meeting at the last moment is sometime unavoidable, but your target should be to arrive a few minutes early for meetings and for work. Be ready to go, have your laptop charged or a pen and paper for taking notes.

5 Minutes Early Is On Time; On Time Is LateLate Is Unacceptable

Eric Jerome Dickey

Being prompt is not about you, it is about your respect for other people’s time. Everyone has schedule challenges, figure out how to handle yours so that it doesn’t impact other negatively.

10. Never Say ‘At My Previous Company

Not invented here (NIH) syndrome is real and very strong at many companies. Whether it is a genuine effort to avoid infringing on the intellectual property of others, or simple corporate arrogance, few statements will torpedo an idea quicker than introducing it with the phrase ‘at my previous company‘. Instead of giving credibility as you intend, the phrase immediately tarnishes the idea and has negative connotations.

Instead, simply state the your idea independently of the source. You can be confident in your suggestion because you know that it has worked in similar circumstances. Others will see the merit and give their support. Of course, you need to respect your confidentiality agreements and not infringe on the intellectual property of previous employers. Always operate with integrity – you can get another job, but your reputation endures.

11. Voice Your Objections in Private

When your boss is rolling out a new program or policy, don’t be the person that challenges them in public. Have you ever witnessed this approach be successful? Instead bring up your most pointed concerns in private with your boss. In the public forum take a balanced approach ‘I see this change will help address this area, we will need to make sure xyz doesn’t suffer as a result‘.

When you do have concerns or objections be sure to maintain a solutions-oriented approach. Don’t think of yourself as just saying no to your boss – think about what is needed for you to say yes by modifying the original situation or by suggesting an alternative. Finally, recognize that there is a time for debate and a time to get on board. Even if you don’t agree you can’t keep arguing your case and fighting.

Disagree and commit.

Jeff Bezos

If the business waits for full consensus it will never get anywhere, but a good boss will be open to input on issues under their control. Even when you disagree, once the decision is made you must do your best to make it successful.

12. Challenge Yourself with Stretch Goals

Leaders know that they can teach their staff hard skills like technology, budgeting, and project management, but soft skills are more difficult. Employees that are internally motivated will outperform members that are motivated simply by compensation nearly every time.

Shoot for the moon, even if you fail, you’ll land among the stars.

Norman Vincent Peale, The Power of Positive Thinking (buy on Amazon)

Learn what aspects your boss values and challenge yourself to improve in those areas. Be realistic, but if your boss gives you a target to meet then set a stretch goal that is beyond that target. You may just find that you can hit the stretch target, but you will certainly be better positioned to meet your boss’s target because inevitably some plans will fall short of expectations or be delayed.

13. Be a Pleasant Person

Greet people by name, a simple ‘Good morning Kate‘ said with a smile as you walk by is a small thing that many people simply skip. When your boss sees you being friendly and helpful with your coworkers they know that you improve everyone around you.

Use your manners, never forget please and thank you even when stressed and under time constraints. The flip side of this is that on the rare circumstance that you forget people will notice and go out of their way to ask if you are ok.

14. Celebrate Success

When you or coworkers have a great result be sure to take a moment and recognize it. It can be as spontaneous as passing someone in the hallway and giving them a fist bump ‘Great job on the customer pitch this morning Robert‘. Nothing happens on its own at work, everything is the result of someone putting in effort so when something goes smoothly show appreciation to the members involved and let them know you recognize their work.

15. Give Credit

Don’t hog the spotlight and be sure to recognize contributions from other members. Give credit when it is due to key contributors. Many of us tend to self-deprecate when receiving recognition, especially for a team project ‘Oh thank you boss, but I just coordinated the work, it was really Emily and John that did the heavy lifting‘. There is no reason to step back and it appears timid to others. Own it instead and pull others into the spotlight with you ‘Thank you, I enjoyed working on this project with Emily and John‘.

16. Dress Like a Boss

We don’t mean to copy your boss’s outfit, we mean to dress for the job you want. Look around your workplace at how people dress one or two levels above you, then upgrade your wardrobe in stages. Introduce a new item once each week and phase out the worst items you own at the same time. Don’t combine new shoes, pants, and shirt until you’ve worn them separately at least a couple of times. You want it to look like a natural progression and not a transformation.

Many guys don’t even think about their wardrobe but it has a big impact on how other perceive you at work. When your clothes are put together your work is seen as more polished – image matters. You don’t need to overdo your work outfit, you just want to ensure your business attire doesn’t get in the way. When you know you look good you will act with more confidence and company leaders will notice. They will start to see you in the role you want.

Final Thoughts

Praising your boss directly will not go over well with your coworkers, they will see your actions as trying to ingratiate yourself with your boss. Instead comment about the idea, project, or business result – your boss will appreciate your comments just the same.

You don’t need to apply all of these tips all of the time, but if you apply them consistently you will do more than just manage how your boss perceives you – you will also perform better overall. Be true to your character at all times, you will be happier at work and your coworkers and your boss will respect you for it.

Dan Sawyer

Founding editor and head writer of ExpertEmployee.com. Dan is a job interview and career expert, with more than 20 years of experience in senior roles at high tech leaders Space Exploration Technologies and Samsung Austin Semiconductor.

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