Leadership Challenges for Entrepreneurs

Not everyone is a natural leader. But, leadership, fundamentally, is a skill. It is something that can be worked on. 

Because of this, it is easy and sometimes even convenient to allow complacency to set in. This can be particularly detrimental when your skills as a leader were poor to begin with. 

As an entrepreneur, you may find yourself encountering challenges as a leader that you’ve never faced before. While this can be worrisome and even overwhelming, there is nothing that can’t be addressed and resolved.

As entrepreneurs, especially during the solopreneur stage, we are used to making decisions for our business on our own. We are everything to the business from the marketer to the accountant to the strategist.

This is a necessary start to our development but as our business grows we need the support of a team to facilitate the growth with us before we inevitably burn out.

Control is a difficult responsibility for many of us to release. We have been in control for so long and understand what works for us. So, it becomes difficult to allow someone else to take the reins.

A good way to start getting comfortable with relinquishing control is by brainstorming with your team – when you start to allow your team into your decision-making process they start taking ownership of the business more. 

They feel more confident that they are actively involved in the business’ growth and want the same goal as you. This will help you release some of your work when understanding that your team is with you in this.

The more regular meetings you have with your team, the more you will get to know them and trust that they are the right people for the job you have hired them for.

This is a big challenge for many of us. Building trust between ourselves and our team is the foundation of the working relationship. 

This should be treated as a two-way street. 

If a team member feels like their leader is trusting in them, then they are more likely to perform highly. As a consequence of this success, the leader will then trust the team member more – leading to a positive cycle of performance. 

However, in a destructive cycle, whereby the leader is not trusting of their team, this will contribute to low team performance. Thus, the leader becomes less and less trusting as the cycle continues.

In order to break this cycle, either the leader or the team member must respond. The leader may choose to delegate more responsibility to the team member with the intention of creating a positive cycle.

On the other hand, the team member may choose to respond to the lack of trust by demonstrating an increase in productivity. Displaying to the leader they are in fact worthy of their trust.

Until a party decides to break the destructive cycle, it will continue indefinitely.

It’s important for you as an entrepreneur to be able to trust the people you are bringing into your sacred business space. But, it is just as important, if not more important for your team to feel like they can trust you.

This allows for open and honest conversations to take place where challenging questions are invited and received with the understanding that you all want the same thing; the growth of the business and the individuals within it too.

Your team needs to see this unwavering stoicism from their leader. Not only does this build trust that their leader is there for nothing more than the progress of the business, but it allows for freedom of action. 

Knowing that they can (and inevitably will) make a mistake that will only be met with a stoic and rational response, they realise that they can in fact take more risk. The fear of repercussions is gone. 

You want your team to be able to take risks – everything that has ever been and will ever be innovative, has been a risk.

Nothing is more humbling and frightening than the realisation that others not only depend on you financially, but emotionally too. 

Or at least, it should be. 

As an entrepreneur, to varying degrees our egos will have played a role in our decision to go it alone. But, those of us cursed with a fragile ego, for whatever reason, will often struggle with the responsibility of leadership.

This is because of your responsibility as a leader. When things go wrong, in any aspect, you are the sole person who must take ownership of the situation and its consequences. 

This can manifest in an abundance of forms, and it may not be instinctual to you at first to take ownership of wrongs. In some cases, the very thought of taking blame for others’ laziness or neglectful behaviour may even feel illogical. 

But, that is simply ego. Everything that goes wrong, from an unsent email to the total liquidation of your business, is your fault. 

Without an entity in which blame may be put upon, the team has no choice but to either: 

• Blame each other (finger pointing);
• Dwell on the failure or,
• Not learn from the failure.

Sometimes, team members simply need reassurance that everything is going to be okay. For someone to be there to say:

• This is what went wrong;
• This is why it went wrong;
• These are the consequences (the fallout); 
• Here’s what we can do better next time… 
• This is my fault because… 

Extreme ownership allows for quick and constructive evaluations of failures – ensuring the team (and yourself) learns from it.

As both a leader and business owner, you are particularly invested in the outcome(s) of your work.

This will inevitably manifest emotionally. However, you can not allow for your mood to correlate to current success metrics of your team or business.

By all means, celebrate your successes with your team and give appropriate praise when due. Console and rectify failures, but neither should affect your overall emotional wellbeing. 

Accept success without arrogance, and let failure go with indifference.

Our internal values and beliefs will influence the way in which we choose to see the world, and consequently the way in which we interact with that world. 

Our biases (particularly those unchallenged) can even manifest in our communication subconsciously.

A very common example of this is when we climb what is known as the ladder of inference: the mental pathway of rising abstraction which results in misguided beliefs, which we may even interpret as fact.

This phenomenon is so common in fact, that you’ve likely done this without even realising.

Let’s look at a case study of this occurring. 

You are giving a presentation to a potential investor for your startup – we’ll call him Keith. While giving the presentation, you realise that Keith is completely disengaged. He is on his phone, texting, and down right not listening.

When you finish the talk, and open the floor to questions, his only comment is to ask you for a detailed report of your presentation sent to him via email.

Your initial thought is that all the information that is needed was in the presentation. Plus, even if you did create a detailed report, would he even actually read it?

As you come to this claim, you remember similar experiences you’ve had with past presentations like this with other investors. All of which have had poor results.

Clearly, Keith doesn’t know what he’s doing and is undeserving of your extra work he requested. So, you’re not going to do it, because he is just unpleasant.

And, given he wasn’t even paying attention to your presentation, you can just send him that.

This whole thought process takes place in a matter of seconds. But, can you see how quickly this escalated?

While some of this reasoning is fair (the observable fact that Keith was not listening and on his phone), you also added in your own beliefs: that he is just like the other disinterested investors and that he is generally unpleasant.

You have let your beliefs influence the factual; observable data.

What’s more, is that this creates a reflexive loop. The more you believe him to be unpleasant and uninterested, the more behaviour of his you will notice and attribute to such.

This will also create the same for him. He will react to your behaviour just as you have done his. This can cause a destructive cycle of trust and performance as discussed previously. Before long, it will be near impossible to work with Keith.

When you find yourself in this scenario, try to give the benefit of the doubt. Maybe he was dealing with an emergency at the time (work or personal). Could you ask for feedback on the presentation? Initiate some sort of dialogue in order to really understand why his behaviour was poor.

In the name of communication, try to become aware of subconscious biases and their manifestations.

There will be many more challenges you face as a leader. The goal is to be as prepared to face these challenges as you can. And do so with grace and humility. 

Fundamentally, your degree of influence and skill within leadership will come down to how well you know yourself. 

From your ability to delegate your tasks optimally, to deep psychological biases that you need to take control of – everything you think, feel and do will impact others. This is an immense responsibility. Thus, it is your duty to ensure you are (or at least, on track to become) the best possible version of yourself.

You develop yourself and your skills in order to adequately serve the people who follow you.

The key to this is introspection, dedication and humility.