5 Obstacles to Great Leadership & How to Address Them

What is your Achilles heel - your weak point - as a leader? Is it delegation? A short temper? Maybe it’s statistics and analytical analysis. Whatever your weaknesses are, you are probably much acquainted with them by this point in your career. You’ve probably found work-arounds that help you function on a daily basis that prevent your shortcomings from affecting your work.

But work-arounds only work for so long, and eventually, you’ll experience an obstacle directly related to your Achilles heel. That’s why it’s so important to address them. Without trying to improve those shortcomings, you fail to reach your full potential, or you may even encounter failure that is even harder to reverse.

All executives and leaders have a weakness, and many of them assume they are “innate” features of their personality; something that they can’t fix. But that’s a false perception.

There are four weaknesses common among many executives and leaders. Below, we discuss how they can affect you, and what you need to know to address them:

1. Fear. It comes in many forms, but true fear is the innate knowledge that something or someone could potentially bring you harm. Fear is natural, but it becomes an issue when you allow yourself to be so fearful of a potential risk that you do everything to avoid it. This is called “risk aversion,” and can be very detrimental to a leader.

It’s your job to take calculated risks in an effort to reap long-term benefits, so in order to address and overcome fear, Forbes recommends that you:

  • Accept it as part of the job. Know that risk is a natural part of your day; simply think of it as part of the job description.

  • Thoroughly examine the market. Research will help you see what your customers want or how promising an opportunity really is, which helps prevent costly mistakes (this also helps executives get over their statistics/analytics slump).

  • Protect yourself. Depending on the level of associated risk, you should always protect yourself and the company. Do not take risks or make decisions that have consequences greater than you’re willing to pay.

2. Insecurity. Insecurity is different from fear. Fear is externally sourced, while an insecurity comes from within. In the case of a leader or executive, it usually stems from an incident or long-term situation that made a person feel less than capable.

Barbara Corcoran recently admitted she experiences insecurity in an interview. When asked how she overcame it, she said: “... If you have something like [insecurity] inside of you, wrap your arms around it and make it your friend. Find a way to use it. Insecurity makes you run. What’s wrong with that?”

Try to embrace your insecurity by letting it fuel your self-improvement, instead of trying to hide from it.

3. Lack of trust. Trust is earned but for some executives, trust doesn’t come easy. If you don’t have trust in your employees or peers, it’s difficult to even let them do their jobs. This often leads executives to take everything onto their own shoulders, which leads to fewer results and more frustration.

Trust will only come when you actively work on it and allow it to grow. To build your “trust muscle,” try:

  • Assigning work to an employee or team member. Don’t interfere with the work; let them do it their own way.
  • Asking for help. You do a lot in a day. Someone on your team can help take some tasks off your plate.
  • Open a discussion with the team. Part of assuaging your distrust is working to make sure everyone is on the same page. When you discuss a new idea or project, you can involve the whole team while also assuring yourself that they are capable of the work.

4. Personal involvement. The title of a recent article in Fox Business reads: “Every Leader’s Achilles Heel.” The subject? Allowing oneself to get too involved in projects and/or with your employees. It happens! Your leadership comes with passion; giving anything less than 120% just doesn’t cut it. When things don’t go as planned, it’s difficult for many senior executives to cut the strings and make a clear distinction between themselves and the goal.

Start by establishing clear lines for yourself and ask others to hold you accountable. Try something like, “If this project doesn’t work out by X date, I will let it go,” or “If [employee name] doesn’t improve sales by the end of this quarter, I will put them on probation.” This removes the chance that you’ll become emotionally involved down the road.

5. Hubris. Hubris, or extreme pride, is a personality element that many people assume executives “just have.” The author of the Fox Business article above says, “Success... makes us think we’re infallible. And we somehow forget the age-old adage that past performance is no indication of future results.” It’s hard to not be confident when things have gone your way for so long, but too much confidence can cause you to overlook potential risks, neglect major relationships, and more. 

To ensure that your hubris doesn’t override your logic, it helps to have someone close. Someone who you trust to call you out on bad habits and encourage the good. As one of my former clients who sold his company for North of $750m said in an Inc magazine interview: "Only you can control self-indulgence. The more successful you become, people won't necessarily call you out on your shit. So, I hired a professional coach because then you're hiring someone to tell you you're an idiot."

Continue to Grow

The key to all of these personal shortcomings is to work on them - constantly. Nobody is perfect, but that doesn’t mean you should give up on improvement. Hopefully, these tools help you become a better executive and leader so that you can give your team and your business the best of you.