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Leadership Mistakes Most People Make

CEO. Founder. Co-Founder. Entrepreneur. President. Having those words in your title does not mean you’re a leader. Starting a company does not make you a leader. Being “the boss” doesn’t make you a leader. Being a leader makes you a leader. That’s just the simple truth. Leadership skills are honed over a lifetime and forged through experience. That said, if you just launched a startup – you better learn how to lead, and you better do it fast, because when leadership fails, companies fail. And you can’t build a successful company alone. Like almost everything in life, it’s just as important (maybe even more important) to know what not to do as it is to know what to do. In my experience, here are the top leadership mistakes most people make – and how to avoid them.

The top 5 leadership mistakes most people make:

1. Trying to avoid risk.

People confuse being strategic with avoiding risk. You cannot eliminate risk and you can’t avoid making mistakes. As someone who’s been fired from a company they founded, I can tell you that for an absolute fact. And guess what? That’s a good thing. Failure teaches you more than success ever will and a hell of a lot faster. I took what I learned from that experience and founded myMatrixx, my pharmacy benefits company that I grew to one of the largest privately-held companies in Tampa Bay and exited for $250mm. The risk of failure is ever-present. Embrace it. Use it as a motivator. Trying to avoid risk keeps you small. It paints you in a corner, making it hard to make the big, creative, strategic, and visionary choices that leaders need to make. 

It’s no secret that I’m an adrenaline junkie. Jump out of a helicopter on skis? Yes. Free dive to spearfish? Absolutely. Climb to an altitude where one misstep will send you plummeting 1000’ down an ice sheet to your death? I can’t honestly say why, but: definitely. Here’s the secret: when you’ve actually put yourself in a life-or-death situation and survived, those everyday, oxygen-rich problems stop seeming quite so dire. You realize every problem can be solved if you just continue to work calmly and systematically toward resolution. Risk and failure are your greatest teachers. Invite them into your life and work.

2. Being a shitty communicator. 

Listen. Don’t talk. That’s the profound secret behind good communication. When people hear “communicate,” they instantly open their mouths. A culture of communication starts with empathetic listening, followed by more listening, and followed by listening again. It’s how you optimize your process. It’s how you benefit from customer feedback. It’s how you make your people feel heard and thereby empowered. Approach conflict and challenge with curiosity and an open mind. When you come in with preconceptions or already have a solution in the barrel, you’re wrong 99% of the time. Don’t fall victim to the temptation to solve what physicians refer to as the “presenting problem.” While your team may be discussing one “symptom” there may be greater dysfunction at heart or a completely separate issue that’s really what’s disrupting progress – or not. Given the space, your team can create optimizations and solutions without you interfering and bogging things down. There’s a big difference between being proactive and being reactive, and a lot can be said for waiting for the right moment to react. 

You’d be surprised how many communication problems can be solved by learning to shut up a little bit.  

3. Not considering your team an investment.

It continues to shock and amaze me how many people make this mistake. What other investment would you take on and then completely ignore? Building your team is one of the most critical investments you make and, as an angel investor, the quality of your team may even carry more weight in my decision to fund your startup than my belief in you as the founder. If I sense internal culture struggles, misalignment, drama…I’m out.

Like any investment, you need to evaluate and support your team with measurable data, strategic planning, and focus. At my companies, I’ve used SMART (Specific, Measurable, Achievable, Relevant, and Timely) goals. As a leader, it’s your job to create the right objectives and determine how best to measure employee performance against those metrics without (this is the important part) beating the joy and passion out of them. 

Read that last part again. Identify what people are good at and position them for success. Don’t give them a bunch of random tasks outside their roles. Don’t pigeonhole them into something they’re terrible at just because you need someone to do it or the job description typically covers it. Find what your employees excel at and feed that hunger. Let them shine. It doesn’t hurt to share equity, too. 

A leader creates leaders. Not managers. 

4. Being set in your ways.

Bend, don’t break. Focus on the outcome, not the process. For your company to evolve, you need to evolve with it. That means looking at employees as individuals. Allowing mentors to guide you and actually listening to what they have to say (see? Listening again). 

Be consistent. Be steady. You can’t flex for one team and not the other. You can’t be the person that everyone comes to when they want a “yes.” Building and growing a startup is a high-test and emotional journey. As a leader, you must provide a centering counter to the fever-pitch highs and the devastating lows. Your team needs to trust that, no matter what else is happening, you’ve got the steady hand they can rely on to steer them forward, together. 

Process is not a one-day event. It’s a journey. It’s iteration. It’s forever. Get used to it. Get inside it. Get uncomfortable.

5. Not having core values.

Okay, so there are exceptions to every rule. Yes, you should be flexible and agile most of the time. But, this is where you don’t flex. Never compromise your values. Clearly define them and don’t deviate. Your values are a totem, a touchpoint you can come back to when faced with a tough decision and know you’re choosing the right path – even, especially, if it’s the harder one. At Macdonald Ventures, we live by our values. if a proposed change or process goes against them, it’s a non-starter.

Defining core values is a critical component of creating a resilient company culture from day one. They should be clearly defined, integrated into every aspect of your company process from hiring to retention, and they should evolve with you as you grow and scale. 

A lot of successful leadership is getting out of your own way. 

I get asked how I define leadership. Leadership, to me, is igniting the motivation people don’t even know they have and fueling that intensity for as long as they remain in your circle of influence. It’s why I purposefully mentor and guide the people behind my investments. It’s why I prefer angel investing to traditional VC funding. It’s why I try to help others benefit from the lessons I’ve learned and the mistakes I’ve made, inspire them, and help them grow and succeed. At the end of the day, there’s only one person who controls your destiny: you. Be the leader your people need, and walk alongside them toward your success.  And don’t forget, this is supposed to be fun, too.

Enjoy the ride.