Entrepreneurship to Leadership

Working with both the CEOs of large companies and fast-rising, local entrepreneurs, I’ve gained a unique perspective about the enormous challenges that an entrepreneur faces in becoming an effective leader of a successful organization.

Below is a list of some the challenges that I see entrepreneurs face as they grow their teams and become true leaders.

Get Comfortable with Feedback: Feedback is not necessarily insubordination, even though it can feel that way. What can you do to create a level of trust that lets your people know that they can approach you with bad news or constructive feedback? If you tend to take things personally, be upfront about this with yourself and learn to manage your emotions. You may think you know what is going on in your team, but you’d be surprised what they don’t want to tell the boss. Handle pushback appropriately, and be willing to explain how important certain tasks are to the health of your company.

Know Yourself: This is critical in managing others. Whatever neuroses you have can become contagious and will have a strong effect on your team. Do you do everything at the last minute? Do you avoid confrontation? Are you overtly aggressive? Do you people-please? Are you a perfectionist?

These will permeate your business and lead to bigger issues as time passes and your team grows. Awareness is the critical element, as we all have blind spots. Do not deny them and challenge yourself to get out of your comfort zone, then lead by example in relationships as much as tasks.

Learn to Confront: To be clear, this is not to create conflict. It is very easy with new personalities to avoid confrontation, which can lead to a lack of standards and expectations, which leads to misunderstandings and mutual frustration. Become skilled at assertiveness, without becoming aggressive or passive-aggressive with your demands. Demonstrate how much you value an individual, yet be authentic about their growth opportunities. Be emotionally intelligent, always express confidence in the person you are confronting, and be gentle but direct.

Give up Control: Delegation is a behavioral way of saying this, but the control you seize can manifest beyond that. Control can also be unnecessary oversight, perfectionism and an autocratic style of managing. These kill creativity, hinder the inspiration of your vision and hurt buy-in. Excessive control is a sign your self-esteem is entirely staked in your business’ success. Stay mindful of your values within and outside your business. Although the fear of losing a client and customer can be enormous and sometimes individually motivating, fear is not an effective way to lead others. Remember to give people the space to do the work you hired them for, then verify it’s being executed to your company’s values and expectations.

Balance Tasks and Relationships: Learn to balance holding people accountable and establishing strong, personal rapport. Get to know your people. What they are passionate about? What motivates them? What aspirations outside of work they have for themselves? Building rapport and trust in regular one-on-one meetings lets your team members know that you are as invested in them as they are you. The key word is balance. Do not get so close to your employees that it makes it difficult for you to hold them accountable or confront them.

Create Clear Expectations: In rapidly growing companies, the tendency is to hire the smartest and most talented person you can find to quickly fulfill a need. Often, clear job descriptions aren’t created and expectations aren’t set beyond the initial need at hiring. Over time, the business will evolve and people can get left behind, unsure of what role they are to take in the ongoing change. Expectations and goals that are clearly communicated and annually revisited, sets your team up for success and creates a forecast of what may be in store for their role in the future.

Use Sounding-Boards: I once had an entrepreneur tell me that he makes sure to fit whatever problem he is thinking about into every conversation he can each day. Learn to be truly vulnerable about your shortcomings with people outside your business whom you trust. Mentors, coaches and industry colleagues are great resources to get an objective point of view, to call you out on your blind spots, and to offer alternative ways of thinking through your problems.

From engineers to physicians to creatives, everyone I’ve worked with has faced these kind of interpersonal and awareness challenges. None of us can be perfect entrepreneurs or leaders. We are all flawed, but by accepting our growth edges and leaning into uncomfortable conversations, we can foster that much more creativity and problem-solving, both for ourselves and those who we lead.

– Dan Stover