Everyone lies to leaders

The day I became brilliant

It was a proud day for me, but I remember it for the bizarre twist it took.

My boss had just given a heartfelt, remarkable speech to the whole product organization, praising my work and announcing my promotion to Senior Director. Throughout the day, I received congratulations from everyone around me. I was walking on a cloud, just feeling great.

It began in my first meeting after the promotion. Person after person would go out of their way to say why my suggestion was the “right approach”. All of a sudden, my ideas were BRILLIANT.

This persisted throughout the rest of my day. All of a sudden, I was a different person, a Very Important Person. By the end of the day, the initial excitement of the promotion had worn off, and I found myself wondering, “what the hell just happened?”

This day marked the beginning of the time I really started paying attention to how power shapes the relationships and effectiveness of leaders. People treat you differently, and you start to operate in a different bubble. These dynamics can warp the environment around you and stunt your effectiveness as a leader.

I start by sharing some rules of power, each of which makes you less effective. And then I share some habits and patterns you can apply to be a better leader:

Rules of power

Rule 1: leaders don’t know what is going on even when they think they do

A lot of the struggles of leadership are around getting good information, and creating a management structure that gives you enough signals to make good decisions throughout the organization. Yet power directly counters your attempts to get good signals from your organization. Here’s the paradox:

The higher you go in an organization, the less you know what is going on. Yet, the higher you go in an organization, the more you’re responsible for fixing what’s going on.

Leaders often know enough about a situation to pass plausible judgement on the situation, but usually aren’t close enough to the details to know all the implications of their assessment, or to really get it right.

I’ve frequently seen leaders make a gut call on a situation based on the information they have and what feels right, and seen whole departments scurry to follow their direction. Sometimes this can destroy companies (I have seen that more than once). Leaders do this because they are encouraged to “make tough calls” in ambiguous situations all the time, and they are praised no matter what direction they choose. It is a trap!

Rule 2: people lie to leaders

The higher you go in an organization, the less likely people will give you the truth about what’s going on. Why? You have power over them.

Think about the implications of that. The higher you go in an organization, the less accurate the information you receive from people. Dangerous.

People watch leaders carefully. They emulate their behavior: they may dress or talk like their leaders. You’ll see this in meetings — watch how people look around the room, and see how they treat the people who have the biggest titles in the company. If you don’t know who the leader of a group is, you can just watch people, and see where they look.

People don’t lie to leaders to be malicious, they hide things that are problems or downplay things because it’s often not safe for them to bring it up.

Even if the leader claims to want to hear it (they usually do), people know based on your actions if you really mean it. Many people fetishize straight communication and feedback but don’t understand what it takes to actually build a culture where it is safe (for everyone) to do that.

The more tenuous your role, the less you will feel comfortable bringing up problems. So many white male CEOs have no clue what is going on for their employees from underrepresented groups, because those employees are in a more tenuous situation and don’t feel comfortable bringing up hard problems. Why should they?

Rule 3: leaders are overconfident

Humans are hierarchical creatures. Like other apes, we naturally think of ourselves in hierarchy. Leaders are constantly deferred to. They have their ideas validated as brilliant. In meeting after meeting, they see signs that their ideas are taken seriously. This reinforces confidence in leaders.

I’ve seen this spiral out of control, where leaders become aggressively confident, and dismissive of other people’s ideas. Other leaders emulate the behavior of the person on top, and the whole culture tilts towards risky behavior, and aggression. I imagine Uber was like this as a company.

Think about the danger of being overconfident, with poor information on the state of the organization. Confidence is a valuable skill in a leader — overconfidence is a distorting trait in one.

Rule 4: leaders naturally get the credit

One of the weirder parts of our ape psychology is that the leader naturally gets the credit for the accomplishments of their organization.

The team that did all the hard work building something — who coordinated, designed, problem-solved, and figured out how to make something hard work — they don’t get the praise at the all company meeting. Instead, the leader of that organization does.

Getting the credit has a pernicious effect on a leader’s psychology. They may have contributed to the direction or made suggestions that really did improve the trajectory of the project. But it reinforces the exceptionalist mentality that just reinforces the ego of the leader. This is definitely something to be wary of!

As an aside, one of the more unfair things I’ve noticed of leaders is that if you’re a white cisgender male, it’s easy to ride on the success of your organization and learn from the failures. If you’re not a white cisgender male, you may get credit for the success of your organization, but you also get blamed for the failures of your organization. There is a lot less latitude and the problems get more tied to you. Frankly I wouldn’t be where I am today if I had been held to the standards I’ve seen some of my colleagues be judged by.

Habits to be effective and humane as a leader

Over the years, I’ve seen a couple of things that seem to help counter some of the downsides of power.

Ask for the best argument against your idea

Leaders often expect the people around them to “push back” against their ideas if there are problems with the idea. But they don’t make explicit space for people to do so, so it doesn’t happen.

The easiest way to make space for other people’s thinking is to be very explicit in looking for it. Instead of saying, “I think this is what we should do. Anyone think different?” say it like this: “It is starting to look like this is what we should do, but I’m not sure it’s really the best course. What are the best arguments against doing it this way.” With this move, you’re inviting everyone to critique the idea together. Instead of them feeling like they’re critiquing YOUR idea, they’re invited to provide tradeoffs. You’ll be surprised what you hear when you make space for it.

There are a lot of variants of this. You might ask, “what problems do you forsee with this approach we might need to watch out for?”, for example. But the basic idea is to explicitly ask people to tell you why something might be a bad idea. Use the people around you to critique your thinking.

Some leaders might be insecure with this approach, because they feel like it’s opening themselves up to look “weaker”. I’ve found the contrary is true: if you’re able to show that you are bigger than your ideas, you earn a lot of trust and your team will see you as a stronger leader.

Propose things that are dumb

This might be a controversial approach, but it’s especially useful when combined with asking people to critique your ideas.

People can often get stuck analyzing a situation, and having an idea to start from can be an effective way of problem-solving. It also helps model the behavior you are looking for — if the team can critique your ideas, they will be more likely to work together to improve each other’s ideas as well.

I’ve found a very effective pattern is to put together my best thinking on a topic, even if it is incomplete. I write it down, and then share it with the people around me. I ask them to improve the plan, and invite them to critique it. “What’s missing in the plan?” “How would you do this differently?”

Proposing incomplete direction, and allowing people to shift it creates trust in the people around you. They’ll see you change your mind, making them more likely to offer their opinion in the future.

Proposing an obviously bad idea can be manipulative. One way to approach this was covered by one of the most interesting talks I’ve seen. Dave Rensin warned the people around he would mix good and bad proposals with people, to make sure they were correcting his thinking. He was explicitly testing how well the decision-making system around him was, and making it okay for people to disagree with him.

You can be explicit that an approach is a bad one. You can say for example, “unless we come up with a better idea, let’s do . What are some ideas for a better way to approach it?”. This makes the bad idea the default, and again aligns all the people in the room towards an impartial discussion of what would be better than the terrible idea you’ve suggested.

This is an approach that takes some guts. You have to be willing to be seen as foolish or be associated with bad ideas. Most likely, you’ve got some political capital you’ve built up, so you can use it to help strengthen your team around you.

Side note: make space for real analysis

Although acting on incomplete information can often be effective, like I outlined above, some situations call for real analysis and information gathering. This trick is to figure out which situations call for what.

Urgency in a situation often results in decisions being made from the gut rather than through analysis. This can result in decisions that miss the mark, or don’t solve things in a complete or lasting way. If you see a pattern of frantic decision-making, this is often a sign to slow down and solve things more thoroughly and completely.

Build relationships throughout your organization

One trap leaders get into is selecting a narrow subset of the organization, building close working relationships with them, and doing all their work through those people.

You can think of the network of people around you as a communication system, and the depth of your relationship with those people is how well information moves between you and them. If you invest in a skeletal structure of strong communication, you’ll have a group of people who are more likely to share problems with you.

I view this as a two way street:

• They help you understand what’s going on, and help you be less clueless and in touch with what’s happening in the organization. They provide a sounding board for you to float ideas and observations with. They help you see patterns you wouldn’t see ordinarily.
• You in turn, have to act on problems they share with you, and show that you’re making their work life better. You can provide mentorship, and be on the lookout for opportunities for them.

Doing this requires genuine vulnerability. People can see through insincerity, so you have to be willing to show your humanity, and approach them as one human being to another. I can’t claim to be the best at this, but what I do is show curiosity about their work experience. For example, I ask junior employees to tell me how well they’re being supported, and what it’s like to work with their coworkers. I’ll ask new employees to share what their initial weeks have been like, so we can improve it for other employees. I’ll also ask them what they see as surprising about the company, both good and bad. Anything they wish had been better? All of these things are useful information that will make you a better leader. But you’re also building relationships that will help you support your organization and the people in it more effectively.

The most common way to do this is with Skip Level 1-1s. Nowadays, I like to use Donut to set up a “skip level 1-1” room in Slack, and that automates setting up the invites and making sure it works for both people’s calendars.

As an Interim VP of Engineering, I once decided to skip building relationships within the company I was working at. I didn’t have a lot of time to invest in building relationships when I was going to be a temporary leader. I found to my chagrin that this ended up causing a lot of problems — a manager quit and mentioned me not building a relationship with them, and I discovered that some of my thinking wasn’t as well developed as it should have been. After correcting for that, I was amazed how much more effective we were as a leadership team. I had wasted a few months, and contributed to a manager leaving the company. It was a hard lesson.

Consistently show appreciation for feedback and opposing points of view

To get people to share feedback and opposing points of view with you, you have to reduce the risk they perceive in offering you hard feedback or opposing your ideas. One way to show that things are less risky is by going out of your way to show appreciation for feedback people offer that makes you look bad. And to show in public that you are open to criticism and alternative ideas.

Market leaders as servants

One of my leadership mentors is Bjorn Freeman-Benson. When he built the engineering organization at New Relic, he had a number of ways he “marketed” leadership within his organization, which helped reinforce the type of organization he wanted to build:

Invisible leaders: Bjorn encouraged his whole management chain to think of themselves as invisible leaders: “The team should get credit for their work. Try to fade into the background whenever there is a success, and recognize the people who did the work.”

Inverted org charts: Bjorn created his own take on an org chart, with the leaders on the bottom, supporting the rest of the organization. It was a dramatic way to make a point that he expected the leaders to support the organization, and it made the managers within engineering reconsider the way they approached their role.

Use whatever opportunities you have to reinforce that leaders serve the organization.

Use a coach

Some of the best companies provide executive coaches for their leadership group. For myself, some of the most rapid growth of my professional career was driven by the advice, council, and mentorship of executive coach Robert Goldmann.

A good executive coach should help you see the world more accurately, and guide you in developing your skills. They can help you overcome some of the leadership traps here.

Many leaders stop developing their skills once they become leaders. An executive coach ideally has been in your shoes before, and can be a sounding board for you to better yourself.

Release your plans like you release software: incrementally and to get feedback

Since your plans may be based on poor information, and the people on the ground will have better information, it’s often good to roll out your plans incrementally. Involve people who have the most direct knowledge of the problem (or better yet, have the manager in that part of the organization solve it). But when you’re rolling out almost anything, roll it out like software: do previews to a wider and wider set of “customers”, and get feedback from them on the plan. See if they can improve on it, or if they can see problems with it. As you roll it out to each wider group of people, encourage them to offer feedback on the plan. You should have increased confidence in the plan as you proceed, because you’ll be hearing all the concerns and feedback as you expand its audience.

Let me know your feedback

So those are some of the things I’ve observed and patterns I’ve seen to help leaders serve their organizations. I’d love to hear your thoughts on this topic. You can reply to this thread on Twitter, or this post on LinkedIn. What’s your biggest critique or response to this post? :)

Thank you to Marco Rogers for teaching me about the pattern of leaders not making space for deep analysis.

Image by OpenClipart-Vectors from Pixabay