Taking The Easy Road Can Kill Your Business

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By Jonah Midanik

Every founder must step outside their comfort zone to be successful. I’ve never met a founder for whom that isn’t true—but it’s hard. We all have insecurities, bringing a certain level of imposter syndrome to the table. Those deeply personal struggles can cause us to gravitate to what we’re good at, what we know, and what feels safe—even when it’s not what our businesses need at that time.

So, how can leaders get out of that box? It’s not about gaining competency, although that is an undeniably important step. It’s about understanding where, how, and why they’re avoiding what’s uncomfortable. Self-discovery is the beginning of the journey to success.

Getting there is almost never easy. But with better self-awareness can come deliberate habit-breaking, which helps your business strategy and your effectiveness as a leader.

Related: Why Self-Reflection and Self-Awareness Are Vital Skills for Any Entrepreneur

Your First Instinct Is Often Wrong

In times of crisis, we revert to what we’re great at. The founder who’s great at fundraising says, “I’m going to raise more money.” The founder who’s great at engineering says, “I’m going to release a new feature.” But often, collapsing into default isn’t helpful. The odds of your superpower being the optimal next step at any given time are low.

I know a founder who’s unbelievably good at sales. His default is to go out and sell because more sales means increased revenue. But as issues at his company arose, more revenue wasn’t the answer—the product just wasn’t good enough.

He had to analyze data on what was actually happening and consider the relationship that existed after the sale was made. He realized the best thing for his business was to temporarily stop selling. That was uncomfortable for him because it halted momentum, forcing him to learn new skills. But it allowed the team to fix the underlying problems, which put them on track to build a sustainable business.

All founders must look at their business and themselves objectively. Even though founders have to be good at many different things, nobody is good at everything. In the same way that leaders plan company strategy, they need to plan personal strategy. If leaders aren’t methodical, they end up doing only what they’re good at, plus random tasks that come across their desks each day.

Founders have to manage the business they have, not the business they want. You'll inevitably have objectives that aren’t in your wheelhouse, but you must face those tasks to succeed. Part of good management requires leaders to acknowledge their management style—and understand where and when that needs to evolve. I tend to be a raw, demonstrative, talkative person. Sometimes, that works. But there are times when I need to find a style that doesn’t feel as natural but is necessary to build the partnership.

Creating an Environment That Encourages Change

If founders want to push their teams to get outside of their comfort zones, they must lead by example. It’s about encouraging people to be deliberate. What do they need to do today? What resources are necessary for those things to happen? An eat-the-frog mentality is helpful here: If people spend the first 30 minutes of their day doing what makes them uncomfortable, they get a positive feedback loop from knowing they accomplished the worst of it and can spend the rest of their day on tasks they enjoy.

Getting 360-degree feedback matters, too. People will tell leaders if they’re stuck. They can help founders get to the root of why they’re uncomfortable with specific tasks. Open communication will improve leadership accountability so founders don’t slip back into old habits. But leaders have to give their team space to be open. Otherwise, people won’t feel like they can bring anything new to the conversation.

Related: 3 Reasons You Should Have Difficult Conversations Now

A System of Personal Growth

Most founders set aside time to conduct performance reviews. But they typically don’t set aside time to evaluate themselves as humans on the job. Founders need to intentionally allocate time to evaluate what the business needs their ever-changing job to be.

Founders need to authentically look at their performance to find what they’re avoiding and how to start facing it. Start by asking your direct reports and board members: “What do you think makes me uncomfortable? What are three things I’m avoiding?” It is a tough conversation because the answer is deeply personal and often isn’t a work issue but one that will help you in business and life.

Leaders can ask themselves questions to evaluate themselves during the time they’ve set aside:

• Did I do my best to set and make progress toward clear goals?
• Is what I’m supposed to be doing matching what I’m really doing?
• What am I doing more of than I should?
• Did I do my best to find meaning?
• Did I do my best to cultivate relationships?

Clear goals shape the questions leaders will ask themselves. They also keep leaders from drifting. More than aptitude, the ability to not drift is a primary difference between high-performers and those who merely do okay.

Lastly, although everyone can have a stellar day, no one will be able to put 100 percent of themselves into everything. That’s why leaders should frame their questions like “Did I do my best.” It’s impossible to be perfect, so the goal should be to do the best they can with what they’ve got. Work on improving, but be gentle with yourself. Founder life is hard enough.

Embracing Discomfort Is a Challenge, but the Rewards Are Excellent

Founders usually feel uneasy when they step outside of their comfort zone. But failing to face what they’re avoiding can restrict the feedback they need and give them a false sense of what’s going on. That false sense can have a massive negative impact on virtually everything, including employees and vendors.

We need discomfort to grow as entrepreneurs. So, if founders find themselves feeling uneasy but don’t run, it’s a good sign they have what it takes to excel. With consistent self-awareness and bravery, they'll lead themselves and their teams to an inevitable win.

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