Coaching Up Your Boss: How to Make a Bottom-Up Impact

While it might seem like your boss is out to get you sometimes, most often they are just doing the best they can with what the tools they were given. They are just people and we know, because we see it every day, that they are not perfect. What if you could better equip them? What if you could make them better leaders for you and the rest of the team? You could sharpen the tools in their box and give them a few new ones that would make life so much easier on everyone. That is what coaching up does. Coaching up provides you the opportunity to teach your boss a better way to do their job.

I’m not going to pretend it is easy but it is worth it. Imagine if you were able to make life easier for yourself and your team while getting a better work product? What if you could set better boundaries that reflect your needs? Just think if you could communicate with your boss in a way that saved time, frustration, rework, and delays? It would be worth putting in the effort wouldn’t it? (For a little less reading effort, click here to watch the YouTube video)

Coaching up is not learning how to make your boss like you

It is human nature to want everyone to like you. News flash though, that’s unrealistic and unnecessary. You don’t like everyone and there are probably plenty of people you can work just fine with that wouldn’t be at the top of the list to invite to your birthday party. Fortunately, getting quality work done doesn’t depend on who your best friend is and if they are able to help you on every project. The same is true with your boss.

So we’re not going to focus on being in the right place at the right time, mingling with the higher ups, or any other psychological tactics to get people to like you. Is it helpful if your boss likes you, sure, sometimes. Does it give you credibility if you’re in the rooms of opportunity or seen to be with the more senior leaders, it does. But all of that can be sticky and forced and backfire if it isn’t natural and organic. A better way to be liked by the people with opportunity is to get results and speak objectively to those.

You do want to support and connect with your boss, but only on the issues

Years back I had a manager who was really hard to work with. She spent too much time trying to be friendly with the team but didn’t have our back when we needed her. Any time she got a new request, she’d say to just get it taken care of. Problem was she knew full well the teams were maxed out. She was a yes girl and then we were the ones who needed to deliver. Being the yes girl didn’t really gain her the credibility with her peers and higher-ups that she was hoping for either. It made her look bad. She provided no plans of her own, and just agreed with anything that was pushed to her. Which meant that more and more of the work was pushed to her, and by default, us.

The breaking point

At one point, my team was particularly drowning. We had taken on much more responsibility with no additions to staff. A lot of what came to us had nothing to do with the work our team was intended to do. I worked with the team to ensure we were hitting all of our targets for the work that did belong in our group. Then, I reviewed all of the tasks that didn’t belong there and how they were impacting our ability to execute on our goals. I gave the team a list of the priorities. Work intended for our group came first, naturally. Then came work that likely belonged elsewhere but was assigned to us. Finally work that just didn’t need to be done. I asked the team to focus on work in that order.

Then I sent the list to my boss and said that the workload was becoming unmanageable. We are at risk of dropping things and making critical mistakes. I told her I’d set up a meeting for us to discuss. In the meeting she started with her typical we’re all one big team and we need to help each other out routine. She overshared what was hard in her position and how she really needed us to get the work done and done well.

Then I turned the meeting to a coaching up conversation

I remained focused and objective. I asked my boss if she was prepared to lose critical members of my team. Did she have a plan to account for the work when they weren’t there? Then I explained how I’d had the team prioritize the work because I want them to focus on the priorities.

Had she considered having other leaders review what made sense for their teams, what fits elsewhere, and what should be discontinued. She hadn’t. I explained how empowered my team felt looking for unnecessary processes and workload. We couldn’t get rid of everything they wanted to but putting that power in their hands to identify it helped them focus on what work of theirs supports the vision (if you want to learn more about how to do this click here) and what doesn’t. Finally, I offered to write up our discussion and send it to her so that she could get the other leaders involved. I suggested she could let her boss know that we couldn’t take on any more work until we had this project sorted out.

What will coaching up your boss look like?

Coaching up can look like all sorts of things, but I’ve seen it work best when it looks like this. Did I sit my boss down and address her behavior? No. Did I tell her that she was making a mistake? Not exactly. Instead, I took the lead and asked questions that led us to a better solution and was ready to take more action to make her agreement with the why the easiest decision to make.

While it can be tempting to announce to your boss all the mistakes they’re making, it will very likely not get you anywhere. Imagine if your team, or your kids, did that same thing to you? How would you respond? We like to think we’d be receptive and take the feedback well, but the odds are you’d get defensive. With questions, solutions, and easy yeses we get agreement on the issues. (We maybe even get them to like and appreciate us in the process.)

Get them on your side: Ask better questions – to give better solutions

I’m curious, are you asking questions or are you questioning your boss? This is an important difference to consider. Other leaders in my circumstance asked our boss questions like these. How can you expect us to do all of this? What am I supposed to tell my team? How can anything be a priority if everything is a priority? I asked my boss questions, but they were questions that led in the direction I wanted to go. I had a solution that would take some effort but would produce a better result.

To subtly tilt my boss toward my solution I asked, Have you considered having leaders assess priorities for their team and what work could stop? I knew the answer but I posed it as a question so it was an easy shift (without an ego hit) for her to make. She maybe wouldn’t realize in the moment that she was using my idea but I could help her reflect on that later. Right then, I just needed agreement and action.

Create momentum: Take action quickly – and share the plan

I had already taken a small action when I spoke with her. By aligning my team with my plan I could show that there was success and create a blueprint for her and the rest of the teams to follow. Contrary to belief, it doesn’t really take that long to do that. In one meeting with the top experts on my team I could map out 80% of the work in a simple list. Then in a second meeting (likely a huddle) I could communicate the expectation with the group. I could measure success in one more meeting (again repurposing part of the next huddle). The whole thing could take an additional hour and repurposing of a few minutes of existing meetings.

With that limited extra effort I could demonstrate results and share the outline of a plan. This created the momentum I needed to sway my boss’ agreement and help roll this out to the team. By offering to write up the outline I was further taking the lead on the project which documents that this was my idea (resume booster) and creates a paper trail of her agreement (CYA for the future). It also demonstrates to my team and to my peers that we do have some control. No, they won’t always believe that they can do it too but it does show what is possible.

Reflect and relate: Communicate the why and the results succinctly

So I actually did this twice in this example. First, my meeting with my boss took all of about 15 minutes. I could give just enough detail in the list to satisfy her and keep the time spent on it short and sweet. Then, I did it again in the follow up. The email with the plan was bulleted and brief highlighting why, what, and how we’re going to do this. Keeping things short and to the point, particularly with more senior leaders, helps them digest it and gives another easy way to agree and move on.

Finally, I did circle this back one more time with my boss. Additional coaching up happened when I discussed our progress in my one-on-one later that month. I explained why we needed to make that change and how this plan positively impacted turn over. If I had just said yes every time you asked me to do something, we would drown. It’s our job as leaders to find ways to make it work for the company and for our people. I’m sure you have to give creative solutions to your boss sometimes, right? Can you give me some insight on that?

Final tip: When you’re coaching-up timing is key

I had a basketball coach in high school who said, You never complain about refs when you lose. Only when you win. What he meant was, when you have a problem and you’re not succeeding it sounds like whining and people don’t take you seriously. If you are succeeding and can point out a gap, its crystal clear you want to make things better. This is an amazing concept but oh so tough to do because it means you often have to wait. You have to hold your tongue when you want to yell. You have to watch your face when you want to roll your eyes. You’ll have come up with a solution, implement it, and see some results before you can point out the flaws in the status quo. I know it’s hard but, you’ve got this. Remember, if you want help in your specific situation, I can help. Click here to learn more about the coaching program.