Meditation on power and insecurity

Watching the train wreck of Donald Trump and looking for something to learn from it, I started thinking about power and the way folks change when they get it. I’m not making any excuses for anyone, but folks with power — investors, CEOs, influencers etc — can look in the mirror and learn to catch themselves in small ways by watching the president continue off the rails in his own special way.

Imagine being responsible to tell Trump he lost…how much would that meeting suck? It would be so painful to present facts and logical conclusions and be met with confusion, anger, dismissal, demeaning insults, questions of your integrity, doubts of your loyalty…

Now, in your leadership role at your company, think of times when you could not hear someone or see their point of view. What was the situation? Why was it hard for you to understand where someone else was coming from or what they were trying to say? What were you afraid you would hear? What was it about their point of view that was unacceptable to you?

Usually, if you are really honest with yourself, you will find some way that their world view triggered a fear you harbor and was in conflict with the narrative you have created about yourself — for yourself.

It has been shown that power causes brain damage. It makes you more self-absorbed. For many, this fight against imposter syndrome and the work to convince yourself you belong or deserve to be where you are can be all consuming — and severely limit your capacity for empathy. You become more impulsive, less risk-aware and find it impossible to see things from other people’s point of view. Trump is an extreme example, but start up leaders can fall victim to this same thing and certainly VCs are far from immune.

Powerful people tend to disregard social norms in general and, maybe because they think they have crossed over from asking for help to commanding action, tend to be less considerate, less kind and less conscientious of their teammates. In my own arguments with powerful people, I have struggled to have a conversation when the only point of view they can understand is their own — and if you’ve held these relationships over time, you may note “the power paradox” that the most impaired capacity is often the thing that was foundational to their success in the first place — the ability to pursue something bigger than themselves, to listen, to advance the needs of others, to show respect etc.

The best leaders know who they are — these folks know that their identity does not depend on their role or their power in the organization, but on the value they create for others, the credit they give away.

But for most of us, insecurity about identity and our value can push us toward defining ourselves through performance in a role. When you push to perform at a high level driven by ego — likely an impossible level of perfection to achieve anywhere outside your own head — you stop seeing yourself (and the world) through anyone’s eyes but your own. When you do this as a leader, you make it impossible for those around you to contribute.

When founders fall into this insecurity trap, I see it start to show up in five specific ways:

1. Fear of failure —The risk of failure is a constant in a startup, but when insecurity rises up, you can fall into the trap of focusing on results rather than rewarding good risks. You focus on what works, you make marginal improvements to it and work very hard not to fail. When you think like this, your team loses the ability to identify and take worthwhile risk and you can never achieve outlier success.
2. Size of your slice (vs. size of the pie)—When you feel insecure, you start finding ways to take as much of the credit as you can vs. do everything you can to make the win bigger for the team. This shift from giving credit away to a narrative where you are the star can be subtle, and often emerges as a shift from “we” to “me” when you report to the board or otherwise summarize success for an audience that did not “do the work” or contribute to the win directly. Listen for this red flag and, when you notice it, take the time to reflect on why you are feeling insecure and how you can get your head right.
3. I’ll do it (so that it is done right) — You find that you are taking on everything that needs to be done. It’s a lot of work, but at first you are energized by your capacity to execute. You rationalize this with the reality that startups are so complex, the CEO is often the only one to have information on all parts of the company. This makes it hard for you to agree with the perspective of a team lead because you literally know something they don’t. In this mode of thinking, management tends to shift from collaborative modalities that leverage the strengths of others to command and control that eliminates any sense of agency or autonomy (and responsibility) for the team. The danger lies in the cultural mandate that if anything good is going to happen, you are the one who must make it happen and the explicit lack of trust this conveys to your team. This mindset is often rooted in the fear that you are the only one who knows enough to make the right decision, the voices in your head warning that if you listen too much, your judgement will get worse. If left unchecked, you will spend all your energy working to be right and burnout. Course correct by finding the confidence not to carry the whole load, to liberate yourself and empower others. You will be most successful when you focus on what you are best at and arm the team with the information they need to do the same.
4. Fear of chaos (need for control) — One way to be in control is to limit surprises. This is impossible at a startup, so if you find yourself making a great effort to organize and orchestrate so that no messiness bubbles up, step back and identify the fear behind this work. Warning signs here are rigidity of rules and procedures that seem over built for the scale of your company. For your team, these requirements are imprisoning not empowering. You think you are creating efficiency and reducing uncertainty, but you’re just taking the soul out of everything. As a leader, you’ll spend all your energy to keep folks in their lane as you have defined it and lose the fluidity required in a startup (and desired by the very best employees). The fear of uncertainty makes you forget that mess is required for creativity. When you hand down too many rules, too much judgement, everyone freezes. In the extreme, nothing happens and no matter how much talent you have, the company fails to execute.
5. Refusal to fail (ego over objectives) — It is great to be passionate, but be careful if you become attached to a project, the novelty of the idea or its early success. When this happens, your identity merges with the initiative and you quickly fall into denial that all things must die at some point. When you are victim to this way of thinking, you put too much of yourself in the thing to be able to kill it without destroying a piece of your identity. You tax the team and keep prioritizing things that are no longer vital or alive. Because you don’t want anything to die on your watch or don’t have the confidence to kill something you created, you force others to manage projects with life support level resources and no amount of data or logical argument can move you from this position. Data is often the go to fix here, but this is often too late. Instead, be aware of your emotional attachment and work to be more open to killing the things you love the most — as hard as it is, listen most closely when your team tells you why your baby is ugly.

As awful as it may be to watch the president these days, I think he provides a monstrous version of insecurity that any leader can learn to see early and address before it limits the scale of the opportunity in front of you or your ability to deliver for your team.