My Boss is Holding Me Back, What Do I Do? (Ask Christa! S6E68)

Introduction

Hi everyone and welcome to Ask Christa! where I answer listener questions about business challenges and workplace issues. I’m Christa Dhimo, and first—a quick reminder! My show is a free resource to help people get through common day to day issues at work. I keep it going because of the questions I receive and my listeners, but it helps if you like and subscribe wherever you’re watching or listening—and I THANK YOU for the support.

This is episode 68 in Season SIX. In this season we’re focused on bad bosses, and since most people aren’t prepared to be a manager, any problem you’re having with YOUR boss is probably the same kind of problems they’re having with THEIR boss, and that keeps the bad-boss cycle going.

Today’s episode is about what to do when you feel like your manager is holding you back, which can feel like a hopeless or helpless situation since there is a known and inherent power dynamic between you and your boss. If your boss wants to hold you back, they can… until you leave or they leave. But there are things you can do in the meantime, and that’s what we’ll talk about.

Listener Question

Here’s the listener question, “My manager is planning to retire in two years. He’s been my manager for the last three years, and I like him as a person and as a boss. He’s always given me good feedback and coaching, everyone on the team respects him, and he makes sure we get his individual attention and commitment for development. He gives us good exposure to his peers and senior leaders, too. Our company takes management and leadership seriously, which is good. But over the last six months as we talk about my development plan, I’m hearing my boss say things I’ve never heard him say before, like, “I really need you to stay put for now; you can move on after I retire,” and “Slow down a bit, no need to rush your development, you have plenty of time to develop your career.” 

It’s not just frustrating, but really disappointing, too. I thought he stood for the exact opposite. That he wanted to develop us. That he was ready to walk the steps with us and get us moving in the right direction. These days I feel like he’s more focused on holding me back until he retires. What do I do?”

Employee Development is a Competitive Advantage (and a productivity booster!)

Lots of layers here. Our listener conveys their frustration and disappointment, but there’s so much else going on, and I wouldn’t be surprised if some of it feels heartbreaking and grievous, too. Our listener’s boss has consistently cared about and taken positive action around our listener’s development, and suddenly, it seems, he’s putting on the breaks. Slowing things down. Creating drag. 

So… a couple things to mention: we don’t know if he’s doing this with other teammates, we don’t know the context of what’s behind the drag, and we don’t know the context around what our listener is asking about. 

But we DO know that our listener feels this is a shift in how their manager has typically managed development discussions and actions, and we also know this is really hard for our listener, and I get that. It IS hard. Part of that is because employee enrichment and development is ALWAYS in the top portion of what drives employee engagement, or the desire to go above and beyond because employees feel so connected to a mission and their workplace, that they’re ALL IN. 

When Employees See a Successful Future, So Does the Business

Managers who place an emphasis on their employee’s development usually had a manager who did the same for them, OR it’s part of what is expected and even measured in an organization, especially if the organization is competitive enough to understand the value you get out of your good humans when you invest in their development.

And employees who report to a manager who places such an emphasis on development tend to feel more secure, more steady, and more able to do their best work even on tough days. They also tend to be more open with their manager AND they often report feeling they can plan ahead and think about what they can do long term for the organization as part of their value instead of thinking only about the job they presently have.

This not only increases effectiveness and productivity, but also enables various growth opportunities for the organization, not just the employees. Your good humans will be thinking about ways to innovate, take ownership, help each other out, find efficiencies, and take the initiative to make the workplace as good as possible in part because they FEEL so good while in it.

Employees who do not have managers focused on their development often translates into managers who aren’t invested in an employee’s future, and while that might seem irrelevant if you’re showing up each day to do a job, it’s not. For anything in life, if you’re able to talk about the future opportunities with someone else, then layout a roadmap for how that future might be realized, then receive some level of support, you’re essentially enabling a future someone can look forward to. 

So it’s fine if an organization takes a position that an employee’s future isn’t their priority. Just know that it won’t be the employee’s priority, either, and they’ll either move on so they can develop a future they want somewhere else, or maybe worse: they’ll never leave and only do the same things day in and day out. 

Development matters only so far as whether an organization wants to develop, too.

Focusing on Development – Collaboration vs Negotiation

For our listener, they have experienced the benefits of having a manager plugged into and invested in their future. Putting aside the context we don’t have that I’ve already mentioned, it’s hard to get over feeling like you’re able to run at a pace that suits you, then told by a beloved boss that you have to slow down. 

And because of the power dynamics of a boss to employee—and no matter what kind of boss you have, there will always be a dynamic there, by design—an employee’s first response might be, “Well, I guess that’s that. He’s decided, and it’s just not going to happen.”

But there are still things you can do, starting with talking to your boss, and I bring this up because our listener shared that they like their boss and has historically talked about various development opportunities—at least until recently.

So, number 1: approach your boss and address this new dynamic of “slow down” after you’ve felt for so long you could control your own development pace. There may be reasons behind it that become a development opportunity. For example, maybe you want to get a promotion and you’re not ready for it, but your boss also isn’t ready to have that discussion with you yet. Approach and be prepared to help your boss along.  It could sound like this, “Hi, manager. Thank you for meeting with me. I’ve enjoyed various enrichment and development opportunities here, and I’m looking forward to keeping that going. Can we focus on how you’re feeling about my ongoing development? I’m not used to hearing you say I should stay put or slow down developing my career. I’m also not built to do that, as you know from these last three years. I’d like to figure ways to keep up the pace of development I’ve had all along. What do you think?” See what happens.

Number 2: Focus on your need to continue a plan that develops and enriches you. Here’s where a collaboration mindset versus a negotiation mindset will probably work best because you already have a good relationship with your boss. A collaboration mindset means you will both talk about a shared goal and then determine how you’ll work together (collaborate) to achieve that shared goal. For example, if you’re looking to get a promotion maybe you need to work on your presentation skills in front of a room or your meeting management to develop gravitas and engage with others. In those cases, your boss might be with you as a sponsor of your development: maybe he determines ways you can gain access to or start working with different team members and conduct cross-functional meetings where new meeting management skills will be used and practiced. A collaborative goal focuses on how you work together to achieve the goal. There will be an understanding of how you’ll track progress and determine when you’re ready for a promotion, which could mean an up-level in your current team or a move to a different team where there is a promotional opportunity if not in your team.

 A negotiation mindset is different, and that’s usually needed if you and your boss do not have a shared interest in your development. A negotiation often means you give a little to get a little, then your boss gives a little to get a little. In the example of a promotion, it might be that you participate in formal training to upskill, then you take on some extra work to practice and prove you are ready for a new role. The negotiation would likely be what you’ll need to give up so that you’re not too far over capacity. Your manager would agree and support your participation in formal training to upskill, and then support your extra work to prove your promotion readiness while also supporting what will be offloaded so you aren’t too far over capacity. Here again, there’s a give and a take. Ultimately, there will need to be some level of confidence that going through all of that will more than likely result in a promotion, so just be sure you have everything documented. It’s an example of what a negotiation mindset for development looks like, though. 

Either way, working with your boss collaboratively or as a negotiation, the focus starts on your need to continue your development and enrichment. And check out Season 5, which is focused on Career Growth. Episode 53 focuses on how to manage your growth if your boss is stuck, and Episode 57 focuses on how to talk about promotions with your manager.

Reporting to a Manager with Retirement on the Horizon

There is one unique aspect to our listener’s question that’s an important one: it’s that their manager is retiring in two years. No matter how someone feels about retirement, if they really love what they do and who they work with, it’s going to feel like a loss. It’s going to BE a loss.

And based on what our listener has shared, it sounds like their manager is not just satisfied with being a manager, but feels fulfilled, too. I can’t put myself in the mind of our listener’s manager, but retirement can feel very final to some people—like a resignation they need to make, and even if they WANT to retire, there’s a process of transitioning from one way of life that may be a really long time to a new way of life. Even when someone doesn’t like their job, if they’ve been in it long enough, any kind of transition out of it feels uncomfortable.

And so, to our listener, I want to thank you for sending in your question because although this ISN’T a situation of a bad boss, it IS a situation where your boss may be exhibiting bad boss habits in the face of a big transition ahead of him, and maybe that’s what is behind the slow down for you.

Or not.

But either way, there IS a big transition coming up for him, so every now and then, ask him how he’s feeling about retirement. See where he’s coming from. Become curious about his life and legacy as a manager. Show a mutuality for committing to HIS development, too, because these days, retirement is usually a transition and a shift more than a stop and walk away.

Additional Resources

For your resources, located in the show notes, I’ve included a great article to start called “Is your favorite boss leaving? Seven ways to cope.” It’s written by the Forbes Coaches Council, and I’m offering it because my guess is this team might need it. This season showcases how rare it is to have a great boss, and in fact I could probably argue that ALL seasons showcase how rare it is to have a great boss. When a boss is gearing up for retirement, it’s easy for us to think how life will go on, but you may be surprised how much YOU grieve the retirement of your boss, especially if they’re a good one. 

The article starts with how good leaders, and I quote, “…provide an example of good ways to approach problems, as well as help shelter their team from outside conflicts. They call for hard work — both from themselves and from others — without losing their empathy, and move people to follow their lead, rather than command it. So when you get a great boss — one who not only makes your work easier but opens up new paths for your own growth — it can be hard to say goodbye.”

Indeed so.

Next up, and for those dealing with a boss slowing them down who ISN’T as great as our listener’s boss, I’ve included an article in Psychology Today written by Lynn Taylor, called “Manage Up with Ingenuity for Faster Response Time.” This article focuses on how to keep your boss on pace, and that can easily be transferred to a boss who isn’t keeping pace with your development goals.

Last, I am also providing Lynn Taylors Tame Your Terrible Office Tyrant section in Psychology Today because after finding and reading her article about keeping a manager on pace, I also found a wonderful library of other articles that will FOR SURE help you with common workplace issues.

Wrap Up & Submitting Your Question

And that’s a wrap for Episode 68 from season six focused on Dealing with Bad Bosses. Like and subscribe here, but also go to my site and send in YOUR question. It’s AskChrista.com, that’s Christa with a C-H. You’ll also see answers to other questions, listed by category and season, and every season has a theme. As always, thank you for your support. And remember, if you have a business challenge or a workplace issue—Ask Christa!