The authenticity trap:

for executives, keeping it real can be really hard to do


Published on: July 2021

Written by: Elizabeth Freedman

A CEO client was describing an initiative at his company that encouraged employees to bring their whole selves to work.

I asked him, “What does this look like, in practice?” He was silent and finally said, “I’ll need to think about that.” Shifting gears, I asked, “Well, tell me what you personally would do to demonstrate this.” Again, silence. Finally, I said, “Can we admit we really don’t really know what this means?” His reply: “We can admit that.”

Authenticity is having a moment, and that’s a good thing, right? In the spirit of authenticity, I have mixed feelings. Depending on how you define it, authenticity champions transparency, being genuine, keeping it real. It asks us to be vulnerable, to bring our whole selves to work. It also encourages us to speak up, to challenge authority for a purpose, and to behave and act in ways that support an inclusive, diverse environment – all important ideas that hold real value in order to create the kinds of work environments where we – and our teams – can thrive.

The problem comes down to this. The gap between the concept of authenticity and practicing it is wide and confusing. It’s why so many of my C-level clients ask: How do you actually do this? Ironically, this type of question is usually raised behind closed doors because for some, the idea sounds a little too good to be true. As one leader put it: “It feels like a trap. Show too much authenticity, you’re unprofessional or oversharing. Not enough authenticity, you’re seen as hard to read or lacking transparency. It’s tough to figure this out.” No wonder many leaders feel they are navigating a tricky high wire act when it comes to showing up authentically.

So how do you actually practice authenticity? For senior leaders, here are a few tips.

Start with your own authenticity.

Over the past year, I have worked with a number of leaders who have tested positive for COVID. In more than one case, the leader fell ill to the point of hospitalization and missed days of work. Nearly all chose to keep the matter extremely private, only telling one or two close colleagues. To be sure, there are plenty of reasons why a leader may not want to disclose matters related to health, but let’s face it. We often stay quiet because we fear we may be seen as weak or not up for the task of leadership. We wonder if people will question whether we have what it takes. We may worry about the impact on numbers if investors or the board caught wind of what was happening.

The challenge with that approach, fair or not, is that the fewer people you pull under the tent, the more likely it raises questions and causes churn, as colleagues wonder why you’re not acting like your usual self, why you’ve missed the weekly meeting, and so on. It also puts an incredibly tough burden on the leader, who is valiantly trying to work through it all, despite real health issues. And by the way, it goes without saying that good leaders would certainly want to know if a member of their own team had fallen ill or was struggling with a health issue. The point is clear. It always starts at the top. Leaders can’t expect employees to be open and authentic if they aren’t willing to do so themselves.

Be authentic, but don’t self-destruct.

It’s not easy to be authentic at work, because the risks that come with it are real. Consider a recent example from one Business President, who was meeting with his CEO. “Why do I even pay you?” was the response he got from the boss after the leader shared his concerns about the unrealistic goals felt he was given to meet. Nobody likes to disappoint, but even the most thick-skinned leaders have little appetite to engage in conversations like these, particularly when nobody holds the big boss accountable.

So, what to do? For starters, don’t confuse being authentic with saying something you’ll regret. Do not self-destruct because you can’t hold your tongue. The key is to become excellent at being discerning and applying good judgment about what to say and share, and when. And herein lies one of the most important ideas about ‘showing up with your full self.’ It isn’t just something most of us intuitively know how to do. It is a skill, it is a habit, it is a behavior. Knowing when to speak up, when to let a situation go, when to take a risk, and when to simply keep quiet are all part of the package. To ask employees to be authentic, without also helping them develop the skills to navigate the risks that come along with it, is doing them a disservice.

Translate ‘authentic’ into tangible actions and behaviors.

Advice to ‘speak up more in meetings’ or ‘keep it real’ may be well-intended, but it often leaves leaders wondering how. This is where practice, preparation, and a roll-up-your-sleeves approach works wonders. To do that, get very concrete and specific about where you could apply a new action or behavior. For instance:

  • You won’t dance around giving tough feedback to an employee.
  • You’ll make a point to tell someone how you really feel this week when asked how you’re doing.
  • You’ll bring up money in a sales conversation sooner rather than later.
  • You’ll tell a personal story about your life to your team.

Organizations and leaders are taking positive action to shift their cultures into something that goes beyond the lip service of ‘authentic leadership,’ to create thriving, inclusive environments for employees. It’s the right thing to do, but messages that only talk the talk without holding leaders accountable aren’t enough and asking leaders to be authentic without a practical roadmap can be tricky to navigate. The good news is, it isn’t that complicated to be more authentic. As author Simon Sinek writes: “Authenticity is when you say and do the things you actually believe.” Now, it’s up to us to do it.

Interested to read more on authenticity and leadership? Check out this post.

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