How to Get What You Need From Your Boss

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When was the last time you needed something from your boss?

I bet it was not that long ago.

And I’ll also bet that it wasn’t as straightforward as you’d like it to be.

You may need a decision, approval, or discuss priorities. And to make matters worse, most project managers have two bosses. Their line manager, and the sponsor of the current project they’re working on.

A recipe for disaster. Unless you manage it.

And that’s what we’re digging into today. Managing up.

Not a listicle with 20 random tips that sound great in theory, but practical guidelines to help you get what you need, when you need it.

Your boss should clear bottlenecks, not be one!

But for them to clear bottlenecks, you need a functioning relationship and a clear request. That’s why we’ll break this newsletter up into two parts:

1. Part one focuses on building & managing the relationship

2. Part two is all about how to make that tricky request

Let’s dig in!

Set the playing field

As soon as you start working with a new sponsor or manager, you have a window of opportunity. Are you “another one of those”, or will you take charge of the relationship?

Needless to say, I suggest you do the latter. Go beyond the regular “nice to meet you” and dig into how you’ll work together.

This starts by defining both of your roles and getting on the same side of the table. Yes, your “role” is given on paper. And so is theirs. But what can you expect from each other?

Establish a common goal to align incentives. They’ll look good to their boss if they meet their targets. And to meet their targets, your project needs to succeed.

If you win, they win. So let’s win together.

Make a communication plan

Once you’ve established the relationship and how you can help each other succeed, you need to establish how you’ll communicate.

Executives are busy people. What’s full-time for you may be one of 20 things on their plate. Ask them how you’ll fit into their priorities & schedule.

Ask them what they prefer. Slack? A quick call? Email? The options are endless. You can also ask someone who’s worked with the person before, and see what worked best for them.

Your best bet is to overcommunicate a little in the beginning, and then slowly scale down and find your sweet spot.

Schedule regular 1:1s

One piece of the communication plan is so important that I’ll mention it separately. A regular meeting is crucial to maintain the relationship. Schedule it months in advance, and own the agenda.

This is your moment to shine and report. Where are you against the plan, and why are you where you are? Don’t spend hours on it, but they deserve to know what’s happening.

It’s also the moment for you to share some wins and losses. Highlight a top performer in the team, or raise a point of friction. To take these meetings to the next level, send a quick email a day before the meeting that outlines the above.

Own it

Everyone and their dog comes to a manager with their issues. The fastest way to stand out is to take full ownership of your project, your challenges, and the relationship.

Don't think that you'll solve something quickly and won't need to tell them. Be upfront and transparent about what's going on in the project. This highlights another crucial piece of your communication plan: how much does your manager want to know?

Owning issues and showing some vulnerability is a great way to earn respect and show that you’re on top of things (and when you’re not!). And last but not least: executives lead all day. They’ll be happy to be led in one of their relationships. Don’t be afraid to take charge.

You have to realize that this is a relationship. This is about giving and taking. Don’t be that needy kid that asks for something every time they come in.

Lead with value, show you’re in control, and be selective with your asks.

You’ve built a relationship. Now you need it.

In any project, it’s a matter of time until sh*t hits the fan. Something will go wrong, and you now need an answer or decision. And you need it quickly.

So how do you make that tough and urgent request?

The first thing most people will do is wonder what may go wrong if they ask.

Please, don’t be most people.

Instead, focus on what will go wrong if you don’t get that approval or decision. The cost of waiting or inaction is usually underestimated, but it’s all too easy to come up with 100 reasons not to reach out.

That said ‘n done, to make the actual request I lean heavily on a framework I learned while working with McKinsey:

Situation, complication, resolution.

And in our case, the resolution contains a request. Here’s how it works:

1. Lead with the situation

You’ve kept your manager up to date in your regular meetings, so they should know what’s coming. That being said, executives have dozens of balls in the air and are task-switching for you. They’re probably reading your note between meetings (or during one).

Start by sketching the current situation. Keep it brief and recent, and stick to what your manager knows and accepts as facts.

2. Explain the complication

Next, explain to them why the situation requires action.

Why can’t you continue like this? What is the new change request from the client? What happened to that team member?

And most importantly, explain why it matters and what the consequences are.

3. Suggest a resolution

This is your moment to shine. Don’t just bring up a challenge or opportunity, but come up with a (potential) solution. Show the options you’ve explored, and make a clear recommendation for how you think you should move forward.

Share your criteria, your assumptions, and who & what you’ve included in your analysis.

Explain the impact of the suggested resolution, how you’ll deal with that, and what the next steps are. The keywords here are clear, respectful, and firm.

You own the issue. You’ve done your homework. But you give them control over the decision.

4. Plot twist: turn it around

Now here’s the plot twist of the week. The above framework works best when you turn it upside down.

Lead with the action you want your manager to take.

Then take the time to explain the situation, complication, and resolution that leads to the request you just made.

Why?

Your manager probably reads 100s of emails a day, and you want to make sure the required action is the first thing that grabs their attention. Don’t bury it halfway down the page.

The same goes for a quick chat or call. You hook them in by making a request upfront. If you start by explaining the situation and they get another call, you’re toast.

How much context is enough?

You know the relationship with your manager. You know what they know, because you’ve kept them up to date. Think back to rule nr 1 of stakeholder management: no surprises!

That being said, here are my rules of thumb. You can share less context when:

• You have relevant experience with this kind of decision, and your manager knows that.

• It’s top of mind for your manager

• The decision is inexpensive, reversible, or otherwise low impact

And you have to provide more context when the opposite is true:

• You’re making this decision for the first time

• It’s expensive, irreversible, or otherwise has a high impact

• Or, god forbid, it’s a complete surprise

Putting it all together

The stronger the relationship between you and your manager, the easier it will be to get things done. And getting things done is what builds trust, which leads to a stronger relationship.

Get my point? This is crucial. You owe it to yourself, your team, and your project to take the lead from day one.

The biggest thing to remember in this relationship is that you’re being paid to get things done. You’re not paid to bring them problems, but to solve them.

The recipe for getting what you need:

• Clear and concise request

• A well-maintained relationship

• Own the issue and take the lead

Yes, they might be the boss. But if you show them that you’re in control and that you’re both working towards the same goal, they’ll be happy to support you.

Before we sign off…

There’s some exciting news to share with you: I am finally building a project management course.

And you can be part of creating it.

In the course, you’ll learn the fundamentals and first principles of Project Management. And we’ll put it to work. We’ll build a project plan together.

You’ll get my ideas PLUS the execution. No theoretical stuff.

I’m looking for 10 people to develop and test the curriculum with me. You’ll get a unique look behind the scenes and steer the direction of the Projectleaders platform.

This is a unique opportunity to work learn and work with me 1:1, as I’ll never teach this material in such a small group again.

Are you in? Reply “course” and I’ll get back to you with the details.

And on that bombshell… Until next Tuesday!

Cheers,
Jasper