don’t outshine the boss: working with an insecure leader

Welcome to the No Bullsh!t Leadership podcast. In a world where knowledge has become a commodity, this podcast is designed to give you something more; access to the experience of a successful CEO who has already walked the path. So join your host, Martin Moore, who will unlock and bring to life your own leadership experiences and accelerate your journey to leadership excellence.

Hi there, and welcome to Episode 13 of the No Bullsh!t Leadership podcast. This episode, Don't Outshine the Boss a.k.a Working with an insecure leader.

Now we spoke last month in the Q&A episode about giving your boss some feedback. As this subject comes up again and again in our feedback, this week I've expanded on the topic. And I'll frame it around one of the best questions from our listeners, thank you Jordan. The question is:

"I'm finding it difficult determining the boundaries between demonstrating a proactive approach to leadership and work whilst also making sure I don't overstep my current job title. I believe I have the support of my peers; however, I don't wish to upset the balance by overthrowing my current senior somehow. What's the best way of dealing with this? Or is it just something that'll run its own course if I just keep working hard?"

It’s a fantastic question. So first we're going to discuss how to work out what type of boss you actually have. We're going to talk about what all bosses think they want. And then we're going to talk about what competent leaders actually do want that incompetent leaders don't. And of course, we're going to talk about working out what types of behaviours work almost universally, and finishing up with the tips that I have, five rules of thumb for stepping up and out of your current role. So, let's get into it.

Now the first step is to work out what type of boss you're actually dealing with. What type of culture does your boss create? And the culture isn't determined by what the boss talks about, but how she actually drives the culture. What behaviours she elicits from the people around her. And remember, culture is simply the way we do things around here, nothing more than that.

So does your boss create respectful challenge in the environment? Does the boss bring out and listen to the diverse views of the team? Or is the boss authoritarian? Does he micromanage? Is credit passed down to the right level when something goes right? Or does the boss always preserve the credit for himself?

What happens when something goes wrong, does the boss fold or fire up under pressure? You can tell a lot about a person by how they behave and perform when the going gets tough.

Does the boss play favourites? Or does he run a merit-based organisation? Is the boss a kiss-up, kick-down kind of leader, so the one that's all smiles and niceties to their seniors, but angry and oppressive to their workforce.

And does the boss have her finger on the pulse? Does she actually know what's going on, and does she keep close to what's happening?

There are probably another 20 or 30 observations we could make or questions we could ask to try and determine what sort of a boss you have. But it's really important to know what you're dealing with, and I think most of us already do. We know what we can get away with and what we can't. We know what's expected and what's not. And we know the things that are going to be on our boss's shortlist for things they don't like.

But regardless of how they behave, and the messages they send, all bosses actually think they want some certain things. And what almost all bosses tell you they want are things like independent, hard-working self-starters. They'll say they want challenging and innovative people, people who take accountability for getting things done. Leaders of others, who can rally the troops to victory. They want people who challenge everyone around them to be better. And of course they want people with high moral and ethical standards.

Now if you actually have a conversation with your boss it doesn't matter how they actually behave, they're going to tell you things like this that they want. But you know as well as I do that sometimes that's simply not the case. Now, competent leaders actually do want these things, but incompetent leaders don't.

But I don't want you to confuse incompetent leaders with incompetent people. As I'm sure you've worked out, senior management ranks are absolutely brimming with extraordinarily competent people, and talented individuals, who are not competent or capable of leading others because they've never paid any attention to that side of their role.

More often than not, these are not bad people. They're just driven by deep emotional and psychological issues that they have not managed to identify and deal with. And let's face it, we all have these things, which is why self-awareness is so vital. And then once you understand what makes you tick, being able to work with that, and to improve on that, for the people around you, is what good leaders do.

So let's talk about some of the characteristics that you're going to see in incompetent leaders and leaders with deep insecurities. The first thing is, that some of them are afraid of being outshone by their team. And so whereas they might articulate the fact that they want really competent, challenging, innovative self-starters, they don't actually want that. And they're conflicted about great ideas that aren't theirs. So when you actually have an idea, you have to make your boss think that they actually thought of it. Has anyone ever done that? And weirdly, I've even seen situations where the boss can end up in competition with their people for attention from above. And that's just crazy.

Some bosses don't like to be challenged at all, as it messes with their deep insecurities. They want their people to nod and smile and tell them how clever they are. And they're more comfortable around people who confirm their greatness, rather than bringing any constructive challenge. Now unfortunately, there are many employees, I'll just call them suck-ups, who will all too happily play into that culture and perpetuate it.

Some bosses like to hoard the limelight and protect their high level relationships. But they want your ideas and your work products. They just expect you to give them up without any credit, because that's what they think you're paid to do. Maybe it's what their boss before them did.

Some bosses are a little more straightforward. They just like to have the last say on everything. So don't expect any of your ideas to get legs, and eventually you'll stop offering ideas.

Some bosses who are quite controlling like to overrule their people on decisions that aren't theirs and mess with the accountability model. They just want you to be submissive, and to capitulate on almost any issue that can arise. And we know what that does to a culture.

Some bosses are just plain erratic and inconsistent. You just never know what to expect, and you spend your days walking around on eggshells.

Now my sincere hope for you is that you're not currently working for a boss that exhibits these types of characteristics. But even if you are, we're going to talk about some behaviours that you can exhibit that almost universally will work despite your boss's incompetence.

Regardless of how hard to read, how insecure, or how controlling your boss is, there are some behaviours that'll always stand you in good stead and not only that, they'll make you a great leader for your people.

So, let's start with the basic principle. It essentially boils down to the fact that you've got to make your boss look good. You have to understand their priorities and work to make them come true. You need to over deliver, and don't let the boss make a mistake, more than anything else. If you can see them just about to step on a landmine, you've got to reel them back from that. You'll be able to establish intrinsic value with any boss if this is how you behave.

So the first thing is, make sure they understand what you're dealing with, because that flows through to the risks that they're dealing with. So keep them informed, but don't invite them into your knitting, and this can be a little bit tricky. You don't want to give them too much detail, if they feel as though you're asking them to solve your problems for you. And it's doesn't require a blow by blow description of everything you're doing. I call it headlines and punchlines. Just give them the CliffsNotes version of what's going on so they understand the environment you're dealing with.

Make sure they know about anything that may turn up on their radar that's important. Say for example, a potential staff bullying issue, or anything that might garner media attention. Just make sure they know what's potentially coming, even though it may not happen, so that they can react accordingly.

The next thing is, be a really straight shooter. But you've got to do this in a diplomatic and respectful way. So here's a couple of suggestions for how you can actually talk to your boss and approach these subjects without being disrespectful.

Try this one. "Look, this is just a suggestion, but what if we tried X?" Or something like, "It appears to me that the data's telling us X." A very nice self-effacing way to start a sentence is, "Look, I could well be wrong, but I think X." Or something a little bit more questioning and creative: "I wonder what would happen if we tried this approach." Or perhaps even being more direct and saying to your boss, "Would you like me to explore this option?"

Now this stuff is deceptively powerful, because it shows us how we can actually have a very, very straight and direct conversation, but doing it in a way that isn't threatening even to the most insecure boss. And if you can actually work out how to play this, your life's going to be a hell of a lot easier, regardless of whether your boss changes or not.

The next thing is, feed the boss insights and observations that they can't access for themselves. You are by definition a level closer to the action than your boss is. And if you can pick up on stuff that's going on at that level, and turn that into insight for your boss, so that you can give them information they couldn't otherwise access, that's going to be really valuable to them. And they're going to have more comfort around what you're doing and what's going on below them if they can actually feel as though they're informed.

The next thing is, respect your boss's confidence. If you want to become a trusted advisor, it's not just about you being able to give them good information and good insight, but it's also about them knowing that they can trust you, that when they talk to you it's not going to go outside of that room. And that you're going to ultimately be supportive of them no matter what.

And finally, keep your values and ethics at the highest possible level. And all of us all the time are working on this, I know. But every issue has to somehow come back to the good of the team and the good of the organisation, and if you keep that frame firmly in your mind, the boss will start to get that too.

All right, so let's get back to answering the original question, which is how do we actually up and beyond our role without upsetting the balance by overthrowing the current boss somehow? Now I've got five rules of thumb here, but don't forget every situation is different, so you've got to apply these to your unique situation to make it work.

The first of these is that if you do actually choose to go beyond your remit, and you have the respect of the people around you, there's one thing you have to be really, really careful of, and that's over-functioning for others.

Now let me explain what I mean. The right way to do this, if you're actually going to step up and out and become first amongst equals as we call it, is that you're actually rallying the people around you to get more out of them, and to lead your peers. And that's a really good thing to do. But you don't want to do is to over-function for them, and what I mean by that is, if you see that one of your peers is actually not doing their job, and not actually delivering the things that they need to deliver, for you to actually step in and take de facto accountability for doing their job for them. That's what I call over-functioning for other people, and that can only end in disaster.

What happens in that situation, is that you let them off the hook. They will stand back, and they'll let you step into their accountability. If something goes wrong, it's not because they haven't done their job, it's because of your interference, and you haven't got a leg to stand on with your boss.

The other thing is that while you're happily away trying to do someone else's job for them, guess what? You can't be doing your own effectively. And so that's not stepping up and out, that's just interference.

Now generally this only happens with the best of intentions. A really high quality, well intentioned leader sees that something isn't happening, and they step in for the good of the organisation. But this breaks the accountability model, and what should actually happen is that the leader, your boss, should be stepping in and holding the person to account for doing their job, not having you step in to try and do it for them.

So the second rule of thumb is, don't go beyond your own remit without telling your boss what you're doing. You've got to make it clear what you're up to. And like anything else, be really clear about what you're accountable for, and let your boss have input. Because if they don't think it's the best way for you to use your time, then they need to be able to tell you that early. Just as importantly, you'll avoid any retrospective backlash. So if something goes wrong, and you do actually end up stepping on a landmine, your boss can't come back and say, "I didn't know you were doing that. If I'd known I would've had you do something else." So this is actually just a very sensible protection mechanism on your way into a situation like this.

So the third rule of thumb is, seek the boss's opinion regularly, and keep them informed. You've got to make sure you don't get called off the reservation. Your boss won't support you, and nor should they, if you're out of bounds without the appropriate authority. So talking to them regularly, letting them know what you're up to, and giving them the opportunity to redirect you, is a really important thing to keep doing.

The fourth rule of thumb is to stay focused on your day job, and ensure that any scope creep doesn't detract from your ability to deliver on your own accountabilities. Now we spoke about this a little bit in rule of thumb number one about over-functioning for others. But you've ultimately got to make sure that you're doing the things that you're going to be judged on first and foremost. And those things are you delivering on your job description. That's what you're being paid to do.

So deliver this first, and then worry about the broader objectives. Because I've seen a lot of people drop the ball when they get distracted with stuff that's outside of their brief, for all the right reasons, and then they don't deliver their own core portfolio function.

And finally, and this is rule of thumb number five, and this is probably more just a caution. You've got to expect to come in for some fire. Not everyone is going to be happy about you demonstrating this first amongst equals leadership. And you're definitely going to piss some people off. So depending on the political environment in your organisation, this can actually end up being quite debilitating for you.

So for you personally, you've got to be robust. You've got to know that this comes with the territory. And then not be discouraged at the first sign of political backlash.

The good news is though, if you can actually pull this off, you'll be establishing yourself as a high potential leader of the future. And this is going to be noticed up the line from you.

Okay, so that brings us to the end of Episode 13. To pick up the free downloadable, "Five Rules of Thumb for Stepping Beyond Your Remit," go to

Thanks so much for joining us and remember, at Your CEO Mentor our purpose is to improve the quality of leaders globally. So if you liked this episode, please share it with your leadership network so that we can reach even more leaders.

I look forward to next week's episode, entitled "Don't Cross the Line." And this is all about appropriate leader relationships.

So until then, I know you take every opportunity you can to be a no bullsh!t leader.