Site icon Preston Smalley

Why Should Leadership Replace Our Personality?

Queen Elizabeth struggled to find her authentic self in her early years (Claire Foy in Netflix's "The Crown")

What is a leader suppose to look like?

How do they act? How do they dress? What shows are they watching? Do they watch TV? What’s their workout routine? Beard or no?

Am I meditating hard enough???

Having the opportunity to lead within an organization is a privilege, but that privilege can be accompanied by uncomfortable pressures and expectations – real or imagined. Some of these pressures and expectations are concrete, while some are obscure. Some expectations should certainly be met, while some would be better challenged, and others even ignored altogether. The key is learning to sort through the pressures and discern which ones are coming from external agents, and which ones we’re placing on ourselves, unnecessarily.

While there may be some universal, “best-practices” in leadership, there’s no one-single best way to lead people. We each have different characters and styles, and should take advantage of these aspectsrather than try and hide them in some misguided attempt to be “what a leader should be”.

Be the kind of leader you should be.

Be proud of your personal quirks and oddities, even (and especially) in the face of the surmounting pressures and expectations that come with leadership. Staying true to who you are, and what you believe in, will make you a better leader. One that inspires and elevates their team members and colleagues.

Collected here are a few tips and reflections from my time so far as a leader in business and tech. 

Tip 1: Don’t hide your personal life at work.

Early in my career, I was hesitant to open up much about my life outside the office. When I’d go on vacation I’d leave a cryptic OOO message in my email. Part of me felt guilty for taking off time. Divulging any details of what could possibly pull me away from the office felt like a confession of disloyalty.

“OOO” leaves room for interpretation… Out of office could mean I’m attending a conference. Out to an important meeting. Sent by the company on a secret mission to establish partnerships in China.

But, somehow, I think people just usually assumed I was taking my PTO like a normal person.

Eventually I realized that small, furtive behaviors like this one were really just missed opportunities to share who I was with my team.

Pardon the cliche, but the truth really does set you free. It’s a relieving weight off your back to not feel like you have to switch into different modes in every environment. It can feel incredibly liberating to be open about who you are as a person, and show how that has contributed to your professional path.

I now use my out of office message to give a glimpse into what I’m up to: “Gone Backpacking”, “Skiing Monday”, etc. I feel more authentic by this simple adjustment, and I also think that, as a leader, it’s good let my team members know that I support them finding ways to relax and enjoy these other areas of life, too.

[Auto-Reply] I’ll be out Monday skiing with my wife

Much of what can be accomplished within a company is based on trust. Can you do what you say you’re gonna do? Are you being candid with me? And if there’s a rapport, both parties are more likely to help each other succeed.

By sharing your whole self at work, I’ve found that I’ve been able to more quickly establish trust. And as I’ve done more of it myself, I’ve also found the opposite true. Those that are heavily guarded and private raise questions to me about whether they are also hiding work-related info.

Me as “Madison Bumble-garner” for Halloween at Work (Oct 2014)

Tip 2: Don’t always assume management is right.

Aside from those fields where instant decision-making is the difference between life and death, most organizations provide a means for their leaders to push back and challenge the decisions of management.

Other times you may need to take it into your own hands. Either way, being able to effectively say no to your boss is an important part of leadership.

As you lead others and move up the ranks, it’s easy to lose sight of who you are and become the instrument of an organization. There may be times when you need to dig deep, and keep what’s important to you in sight.

In the end, it’s important to own your actions, and stand firmly behind your team’s approaches.

Tip 3: Listen to your gut.

Some situations feel out of your control. Set in stone. Like when you’re ordered to deliver the message from a higher up authority that someone needs to be let go.  

Even in these situations, be mindful of the process. If the words don’t feel right, find truer ones to employ. If you can’t, perhaps there’s something wrong about the whole situation that needs to be challenged.

On a few occasions over my career, I’ve had to lay people off. More often than not it’s for one of two reasons: (A) a larger restructuring of the company, or (B) a team member simply isn’t a fit for the role they’re in.

In both of these situations, I’ve found that I’ve had to look inward to maintain who I am, and not just act as the management function I’m serving at the time. It’s easy to get lost and resort to corporate non-speak.

Fight this.

I try to own the wording of the messages I carry. And if I don’t like the words coming out, I push up the management chain to come up with a better solution.

When delivering the message of a layoff for reason (B) above, it’s critical that you separate the person from the role. If you think the person could ultimately succeed, help them. Give honest feedback. Provide course correction. Reflect feedback you hear from others (360 reviews are extremely valuable here).

Be a manager.

However, if that’s not working after a reasonable effort, perhaps this person is just in the wrong role at the moment. I’ve found there really are no “poor performers”, just people in the wrong roles. Or the person may have once been fine in this role, but the company requires a different style at this point in time, for whatever reason. In this case, the person would benefit from finding a new role, perhaps even within the same company.

It’s good to think about how you’d want to be treated if you were in the other chair in these situations, and be genuine about it.

“The reality is that no one can be authentic by trying to be like someone else. There is no doubt you can learn from their experiences, but there is no way you can be successful trying to be like them. People trust you when you are genuine and authentic, not an imitation.”

— Bill George, True North

Tip 4: Stay Balanced

While working at eBay for a leadership class that was part of my MBA curriculum,  I had the chance to interview our company’s president John Donahoe. John told me about a story back when he was consulting at Bain and Co. His wife had taken a role clerking for a federal judge, and he had to find a way to bring his kids to school a few days a week. John and his managing director were able to agree with their client that John would arrive on-site at ten o’clock, every morning. To his amazement, the clients actually appreciated his family-oriented choices, and he did some of his best work during that time.

This story really stuck with me. At a time when I was balancing my own work while earning an MBA, and carving out as much time with my family as I could, my wife and I having just had our first child. I continue to take a proactive approach with my schedule today, and make adjustments when necessary. I now work from home one to two days a week, and leave early on one other day so I can help coach baseball teams or simply be present after school and home for family dinner.

Me with my crew one afternoon dying Easter eggs being silly

Albeit I still find ways to make up the work in other ways. Staying late at the office a couple times a week along with a fair amount of travel. But in almost every case I can think of, these “tradeoffs” have enhanced the overall experience of my daily life at work, and at home. And I think it’s led to me being able to find more authenticity in my leadership.

Tip 5: Don’t Take Yourself Too Seriously

At the end of the day, regardless of your role at work, you’re still your mother’s child. You may be a sibling. A parent. A spouse. Friend. Goofball. We all share something in common with billions of other people on the planet. I go on dates with my wife. We make plans with friends. And even just playing with my kids seems to go a long way in grounding me.

There’s nothing quite as humbling than your own kids pointing out your various shortcomings (for me it’s usually my cooking).

These lessons have helped me in my career, and perhaps they can help an aspect of your own. I’m always on the look for tips and secrets that others have found true, and encourage anyone to share them with myself and with others.


Preston Smalley produced in collaboration with Mark Mizera.

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