How I Kept My Boss Happy Without Working Hard At It

There are many questions and concerns that new Project Managers have come to me with over the years. Some of them are highly technical and can stretch my Project Management experience. But my favourite ones are those which aren’t really Project Management problems at all. They are general management or workplace problems, for which Project skills give you an advantage. And none is a better example of this than the question: ‘How can I keep my boss happy?’

How can I Keep My Boss Happy?

On the face of it, this is simple: do what your boss wants. But even that presents problems…

‘I don’t know what my boss wants.’

Oops – that’s looking tricky. If you don’t know what someone wants, how can you be sure to give it to them?

The Easy Way to Keep My Boss Happy

How I Kept My Boss Happy

So for this article, I am going to go back on my own experience. As a Project Manager, I have had many bosses. Two have vied for the title ‘worst boss ever’ and, even with hindsight, it’s hard to pick a winner. Equally, two have been in the running for best boss too. Most of the time, my boss of the week has been somewhere in between. But the same three steps have worked well for every boss I have had. Put simply, they are to:

1. Get the basics right, and give my boss what they want
2. Sharpen it up and make sure I communicate really well with my boss
3. Go the extra distance and make life easy for my boss

Let’s look at each one in turn

Step 1: Give My Boss what They Want

This is the basic thing I needed to do to keep my boss happy. So how did I find out what they wanted? Luckily, as a Project manager, I was usually safe in assuming that one thing my boss would want was a successful Project. So, your first priority is to get a clear definition of your Project and what success means. Critically, your boss needs to be at the centre of your discussions and you need to engage them in finalising your project definition, and signing it off.

Project-related Priorities

The framework for creating a Clear Project Brief will help you here, especially if your boss feels a sense of ownership over your project, with a job title like Project Sponsor, Project Director, or Project Owner. For me there was an added complication. You may have it too.

I was a Project Management consultant. This meant that on any project, I would typically have at least two bosses. First, there was my boss, the client. Tis was usually the Project Sponsor or Project owner. Then, I had my boss, the partner or director within my own organization. So my first priority was to find points of common interest so I could easily keep them both happy at the same time. The Time-Cost-Quality triangle is your friend here. Use this to help your bosses figure out what success means.

Personal Priorities

There are some basics that will keep any boss happy. More important, if you get these wrong, you will swiftly find you have a very unhappy boss indeed. The three big things that I always worked on were these:

Diligence

One thing I am sure my boss will want is for me to me to get my work done. This is not about serving long hours for the sake of it. Instead, it is about focusing on the work at hand and getting on with your job. Take your role seriously, think carefully about what it involves, and deliver on the things that matter. This should come naturally to you, as a Project Manager.

Trust

With diligence comes trust. Your boss needs to know that they can trust you, so being trust-worthy at all times is bound to make your boss happy. The number one behaviour that will create trust is to take your commitments seriously, and to always deliver on them.

Loyalty

The trickiest thing I found, as a consultant, was loyalty. If you have two bosses, and they have differing priorities, it is hard to be loyal to both. So what I learned as a Project Manager was to place my loyalty to the project ahead of my loyalty to an individual boss. This way, if I could reflect the priorities of each boss in the way we defined the project, I could show them both loyalty at the same time, through my care for their project. In a more operational role, this translates into a loyalty to the business or the operating unit.

Understanding Your Boss

We cannot help but come full circle. Each boss is different and you do need to understand yours. I have prepared a worksheet to help you build a profile of your boss, and what they want.

Step 2: Excellent Communication with My Boss

If you want a simple boost to how happy your boss is, make good communication your next priority. Because it is not enough to give them what they want, if they don’t know what you have done. By the time your boss comes to ask you what you have done, it is too late. They are already starting to worry. As a result, your standing in their eyes as started to diminish.

So, timing is vital. Each time I got a new boss, I found out their preferences. First, I’d ask my boss what information they needed from me. And secondly, Id ask when and how they wanted me to brief them. If the results didn’t seem to be working, I’d quickly ask them what changes they wanted.

The Basics of Good Communication

The basics of good communication are just as true for your boss as for any other stakeholder. Here is my top 5:

1. Timing.
   The right message at the wrong time can be very annoying, so just as with telling a joke… timing is crucial. Ba-boom.
2. Courtesy.
   I don’t mean obsequiousness. Be sure to understand the social norms on your project – especially if you are not working in your own culture Project Managers often need to work with diverse teams, often away from their home ground. If you find yourself working in a new organization, or even a new country, be sure to find out the rules of respectful, courteous behavior. With multi-cultural teams, your work here just doubled!
3. Assertiveness.
   In some cultures, balancing this with courtesy can be hard. But remember that the difference between being assertive and aggressive is respect. Aggressive behavior arises when you do not offer the other person sufficient respect. Passive behavior, by the way, comes from not having enough respect for your own needs.
4. Listening.
   If in doubt, increase the proportion of time you spend listening. If you take care to listen, you will often find out what your boss needs, to keep them happy.
5. Structure.
   Most of the bosses I have had, have been in a hurry. Consequently, I have found ways to deliver my message clearly and concisely. And the secret to this is to structure your message. The simplest and often most effective approaches are often two-, three-, or four-part structures.

Here are Four Examples of Structures:

Example 1
“Here’s what happened…
“This is what it means…
“Here are our principal options…
“This is my recommendation, which I’d like you to endorse…”

Example 2
“This is what I’d like to do…
“These are the implications if we do it…
“And these are the implications if we don’t…
“Here is what I need, to get started…”

Example 3
“These are the problems we are having…
“Here is the solution I have discovered…
“This is what I need from you…”

Example 4
“This is what we have achieved since I last briefed you…”
“And here’s what we are working on for next time…”

Framing

How you frame your message can have an impact on how your boss responds. During a project, you can frame it about:

• The Project
• The Organization
• The Stakeholders
• The Products/Outcomes
• Your Team
• Yourself
• Your Boss

Take a quick guess at which frame will have the biggest impact! The more serious point, is that I always tried listen to what my boss said and how they talked about things, to try to discern where their primary concerns lay at any point in the project. This would a therefore allow me to frame my messages to match their concerns.

Step 3: Make Life Easy for My Boss

The last step is to make life as easy as you can for your boss.

Always take responsibility. Nothing is more likely to annoy your boss than the feeling that you are trying to wriggle out of a problem. And, if your boss should really take responsibility for the issue, by offering to take it yourself, you are showing loyalty and building trust. Yes, it is true that some bosses will abuse this. I had one who often did. But the boss you resect will be very grateful.

Take the initiative where appropriate. If your boss tries to delegate a task, take it gladly, if it will not compromise your primary tasks. But if you can jump in and predict what they will need to delegate, and take it on before being asked, you will gain that awesome reputation as someone who can read a situation and fix a problem before it arises.

Most of all, accept any feedback that your boss gives you and thank them for it. The most successful Project Managers are those with greatest self-control. Therefore, take the tough feedback as a valuable lesson, and reflect on it. Getting upset or angry will tell your boss that you haven’t really learned and are not ready for the next level of responsibility. At one appraisal session, my boss at the time gave me feedback that I was argumentative! ‘Robust in testing ideas’ was how I’d have put it. But I decided this was not the time to challenge their perception. I changed what could probably have turned into an argument (and proved her point) into a chance to show I was prepared to learn.

Some Final Tips

I’ll end with some of my favourite tips that I used to keep my boss happy from time to time. Some worked well with one boss and not with another. So take a few out and try them

1. Find a chance to thank your boss for what they do for you and to give them feedback on what they do that you find most helpful.

2. Take on more than you are asked to, if you want your boss to see you as a promotable star performer. But don’t take on too much: you will only be promoted if you have the time to do things to the highest standards.

3. The more often you can initiate meetings with your boss, the more you can control the agenda. This will relieve them of an unwanted job, allow you to get what you need, and show your boss that you are in control of your own work.

4. From time-to-time, ask your boss for advice, or solicit their opinion. Show them that you value their insight and experience. Not only will this flatter them, but you can learn a lot from it too.

What are Your Tips for How You Keep Your Boss Happy

Share your tips in the comments below. We’d love to hear them and will read every one.