How to Manage Up with Your Boss: 5 Tips From a Manager

If you get stressed all the time dealing with your boss, then this article is for you. In it, I’m going to be sharing with you five strategies that I’ve used to help manage up effectively two different tech CEOs. And I’ll also be sharing my own personal experiences, having been a manager of managees of what works and what doesn’t.

By the end of this article, you’re going to have a few strategies that you can start using to feel less stressed when it comes to interactions with your boss and hopefully be more efficient in your work.

Tip #1: Set regular syncs and bookend your meetings

The first tip that I can give you when it comes to managing up to your boss is to set regular syncs up and to bookend your meetings. Typically, I’ve found it most helpful to have weekly syncs with your manager. That said if your organization doesn’t support that for whatever reason, you might want to try to have them on a bi-weekly or a monthly basis. What you definitely don’t want though, is a situation where you’re only sinking up with your direct manager once a quarter or on a semi-regular basis.

Before you had these meetings, it’s helpful for you to recap what happened in your last sync up and the progress that has happened before you head into this latest sync up. In other words, don’t have a lot of time in your actual sync up discussing status updates that could have been read in some sort of pre-read document.

When I talk about bookending your meetings, what I mean here is to set aside five to 10 minutes at the end of your meeting to make it super clear what everybody’s next steps are. You should have a clear understanding of what’s expected from you from your boss as well as your boss should know what they need to do to set you up for success in this next sprint before you meet up again for your next sync.

In general, it’s super helpful in these meetings to have an agenda up front. That way you can stick to that agenda throughout your sync meeting with your boss. In the case where things get off topic with the agenda, you can give your boss a friendly reminder that it’s not on the agenda and get things back on track. Don’t be afraid to give some pushback here because it keeps everybody on the same page and make sure that we are focusing on the things that matter most for the business or whatever it is that you are working on.

In the case where the topic that your boss brought up is still important, you can always mention to him or her how the two of you can set aside a later time to discuss that topic, but it’s not on the agenda for today.

Tip #2: Communicate your needs from your manager

The second big tip I can give you when it comes to managing up to your boss is to communicate your needs with your manager. Too often, I find that employees don’t like to be vulnerable with their bosses. And as a result, they hold things back in the sync-up meetings.

As a result, both sides get frustrated because the employee doesn’t have what he or she needs for success. And the manager or boss doesn’t know what he or she needs to do to set up the employee for success. So what I found to be super effective is to set aside some space in my agenda document that outlined some of the challenges that I’m facing that need to be addressed.

What I’ll also do in this section of the agenda is I’ll share what I’ve already tried to try to solve my own problem. The reason why this is super important is because it demonstrates to your boss that you are being solutions oriented and that you’re not just waiting for his or her direction as to what you should do next in your dilemma.

If you’re not demonstrating to your boss that you’re trying your hardest at solving the challenges that are preventing you from getting the outcomes that you are hired to do, then it’s going to be a lot harder for your boss to empathize with you, and also feel like they want to support you in whatever it is that you are facing challenges.

It’s really important that you normalize this sort of vulnerability and sharing the challenges that you’re facing with your boss earlier on in your relationship, than waiting a few years to make this clear to your boss. The faster that the two of you can get on the same page as to what both of you guys need from each other, the faster you both will be able to achieve awesome results.

In the case where you have been working with your boss for a while, you can always reset expectations with a script like this, “Hey boss, I’m trying to be more open about what I’m struggling to tackle certain projects. To do this, I’d like to try communicating more of my blockers with you. Would that be okay with you? If so, would be the best way to do this with you.”

The reason why this works is because it shows that you’re serious about wanting to improve in your role. And also it demonstrates to your boss that you want to loop him or her in as part of the solution to the challenge that you’re facing

Tip #3: Follow up in between meetings

The third tip I can give to you when it comes to managing up to your boss effectively is to follow up in between your meetings. The best way to do this can be either through Slack or email, depending on the main ways that you communicate with your boss when you are not speaking to them in a meeting. There are a couple of different ways that I’ve tested this, and it really depends on the employee and boss relationship. From my experience of both being a boss and having a boss, I found it effective to boil things down to either a beginning of week, middle of week or end of week update.

It really depends though, on your relationship with your boss. So try to figure out what gels well, for both of you. In these updates, you might also find it helpful to include one or two questions that could potentially help you out further in making more progress before your next sync meeting with your boss.

Tip #4: Document progress regularly

The fourth tip I can give you when it comes to managing up effectively with your boss is to document your progress regularly. To do this. I found it helpful to create a shared document with my boss, where I share things like how we’re pacing in terms of our spending on our annual budget, overall key performance indicators, as well as our progress towards OKRs, as well as any challenges or questions that I may have for my boss to answer ahead of the meeting and during the meeting.

This document becomes really helpful because it helps both of you guys recall things that may have slipped through the cracks between your sync ups. It also helps you on a personal level because when it comes time for that six or 12 month review, you can use this sink of documents or reference some of the achievements that you’ve had since your last review, which will help you get that pay bump or that promotion that you had been seeking.

Tip #5: Set clear boundaries

The final tip I can give you when it comes to managing up with your boss is to make boundaries super clear with your boss. And what I mean by that is if you’re ever in a situation where your boss has made you uncomfortable, you want to express to your boss that this has happened and that it is not acceptable or that it doesn’t work for you going forward for this sort of thing to happen again.

Sometimes bosses can cross the line. So it’s really clear that you set these boundaries clearly so that you can maintain a professional and working relationship with your boss. This advice applies for deadlines as well. If your boss gives you a deadline that seems completely unrealistic no matter how you try to finagle it, then it makes sense for you to communicate this with your boss earlier, rather than later.

Decent bosses will typically have some sort of range when it comes to the amount of time they think it’ll take for something to get done, so it’s on the employee to manage those expectations with their boss and come up with some sort of compromise that works for both sides.

Big takeaways

There are two things I want you to remember from this article:

  1. The first one is that communication is key when it comes to healthy working relationships. So if you’re not already regularly communicating with your boss in both written and in verbal format, then you want to work on that first.
  2. The second thing I want you to remember though, is that documentation is almost just as important as communication when it comes to your relationship with your boss. Keeping things well documented is super important for both sides, because it makes it clear what you’re working on, as well as it keeps an audit log that both of you guys can reference in your future sync up meetings when you are communicating face to face.

If you found this article helpful, be sure to check out my YouTube channel to get new videos every single week. I’ll help take you from zero to self-starter as you grow your business, get more customers, and hone your business acumen. Also, feel free to share this with anybody that you think might also benefit from learning how to manage up with your boss effectively.

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