Just Because You’re the Leader Doesn’t Mean You Wear an “S” on Your Chest

Starting a company and building a team takes tremendous effort. Most entrepreneurs are pretty dang talented and the successful one’s are great at getting things done. Once you get the company moving, revenues are growing, you’re hiring more people, suddenly the talent and skills that got you here are no longer the skill sets to get you where you want to go. This is the awesome part of being an entrepreneur and it’s also the double edged sword. It’s awesome because every successful entrepreneur has an insatiable appetite for learning and hopefully you learn what you need to know really fast.

Let go to grow

Michael Brown, CEO of Affirma Consulting, says:

“Often businesses start when a talented practitioner of a specific skill set decides to break off and start a company.  I believe this scenario is one of the most difficult for the founder to let go and scale their business.  So much of their self-worth and confidence is tied to that skill set and not to scaling a business, so naturally focusing on that skill set becomes a distraction to growth.  Getting over the ‘no one can do this better than me’ effect and building confidence and value in working on the business instead of in it is critical.  It is also very uncomfortable at first, but holds great rewards if you make it through to the other side.”

I think Michael is dead-on. Quite honestly, this is the part that probably stops most entrepreneurs from growing their business. Also, when an entrepreneur has everything riding on their company it’s hard to let go and trust that someone else will be as committed to it as yourself. Over the last month, I have been stepping aside on a lot of things within my company and let’s just say it hasn’t been without incidence. Trust is a big part of this, relying on another person puts you in a vulnerable position and employee loyalty can become a question mark. It’s probably hard for people that don’t run their own company to understand this but for entrepreneurs it’s a pretty common thought. This last week I finally handed off the control of the website redesign and because it’s been my baby for three years it wasn’t exactly easy. My skills and “self-worth” are somewhat tied to the technology aspects and when I let go of something like that it makes me feel very uncomfortable. The thing that an entrepreneur has to understand is that you have to major in majors and not major in minors. There are a number of other things that I’ve started to release my grip on and it’s because I know that I have to let go to grow.

Take comfort in being uncomfortable about being comfortable

One of my previous managers when I worked for a big company always told me that you want to work yourself out of a job. In order to grow your career you have to get to the point of being uncomfortable. There’s a saying “Take comfort in being uncomfortable about being comfortable.” So as you work yourself out of a job, you work yourself into a new role. Yes, it’s going be uncomfortable because you’re going to be stepping into an area that you are not as skilled in and your self-confidence is probably not going to be as strong as it was in the areas where you started your business.

Just because you’re the leader doesn’t mean you wear an “S” on your chest

Get the support of your team. Similar to how you provide support and encouragement to your team for them to build confidence, they can also provide some support and encouragement too. Teams are always stronger than individuals. One thing that I have been doing over the last month is verbally expressing my appreciation for each team member. Once a week during our daily huddle I’ve been openly telling each person in front of the whole team what I appreciate about them — normally I find something that stands out to me which they have done that week. I do this to firstly show appreciation for their effort (I’d like to build a culture of appreciation) and secondly to build their confidence in what they are doing. An area that I lack the self-confidence in is public speaking. Since college, I’ve always thought of that as my weakness, I even went so far as to take a Drama course at UW to address it. The crazy thing is that over the last few weeks I’ve been asked to speak in public at three different events. I’m a bit nervous about this and I’m looking at my team to provide me some moral support!

Find a mentoring community

Find mentors that are willing to provide some guidance and close the knowledge gaps.

  • Entrepreneur Organization (EO). This organization has been absolutely invaluable to me. Being surrounded by successful entrepreneurs who have been there and done it before plus are willing to share their experiences can help build a ton of confidence. Knowing that the EO members have my back is quite empowering.
  • Founder Institute: Another organization that has a strong mentorship program is the Founders Institute.
  • Advisory Board: Find three or four really smart people that want nothing more that to see you be successful.
  • A Collaborative Community: Find a coworking or shared office environment <– Come ask me about this one, I just might have a recommendation! ;)

Being an entrepreneur can be a lonely place. Where no else really understands what you’re going through except other entrepreneurs. That’s why it’s so important to surround yourself with other entrepreneurs. What are some of the things that you do to build a support network?

11 replies
  1. shandel
    shandel says:

    Peter – thank you for sharing this for other leaders to read and glean wisdom from.  Yes, it is lonely at the top and yet I find that we are leaders set ourselves up for not getting appreciation because of our mask of confidence and drive looking like we have it all together.  It doesn’t look like we need the verbal affirmation because we try so hard to look like we have needs.  Maybe as a culture we have trained employees not to appreciate the leaders.  So I like the way you are changing that in your organization.  I am very passionate about leaders doing so and hope that you find that this encouragement comes back at you as you continue to change your culture.  GOOD FOR YOU!  :)

    Reply
    • Peter Chee
      Peter Chee says:

      Shandel, thank you so much for reading this. When it comes to leadership coaching you’re one of the best out there. You totally get it and also help me stretch beyond my limits.

      There’s a lot of people and CEO’s that seem to put that weird front up that they got it all together and it’s almost to the point of ridiculous that anyone has it together like that all the time. Pretending to not have problems is a sign of weakness… act too strong and really you’re probably weak (just like in poker). I love EO’s motto “leave your ego checked at the door” which helps keep it real.

      I could probably write an entire blog post on your statement: “Maybe as a culture we have trained employees not to appreciate the leaders”. It’s certainly not a Gen-Y issue as I look back through my career and think about how people show verbal appreciation. You wait until it’s your annual review or you have to leave your job and then suddenly all these people show up and want to show you how they appreciated you over the last 10 years. For CEO’s it’s worse, who’s doing our annual review?

      So, yes, I’m determined and on a mission… but please do keep checking in on me once in a while!

      Reply
    • Peter Chee
      Peter Chee says:

      Shandel, thank you so much for reading this. When it comes to leadership coaching you’re one of the best out there. You totally get it and also help me stretch beyond my limits.

      There’s a lot of people and CEO’s that seem to put that weird front up that they got it all together and it’s almost to the point of ridiculous that anyone has it together like that all the time. Pretending to not have problems is a sign of weakness… act too strong and really you’re probably weak (just like in poker). I love EO’s motto “leave your ego checked at the door” which helps keep it real.

      I could probably write an entire blog post on your statement: “Maybe as a culture we have trained employees not to appreciate the leaders”. It’s certainly not a Gen-Y issue as I look back through my career and think about how people show verbal appreciation. You wait until it’s your annual review or you have to leave your job and then suddenly all these people show up and want to show you how they appreciated you over the last 10 years. For CEO’s it’s worse, who’s doing our annual review?

      So, yes, I’m determined and on a mission… but please do keep checking in on me once in a while!

      Reply
  2. Barry
    Barry says:

    Great comments, Peter.  As you state, an entrepreneur may find it lonely at the top.  In some cases this may be somewhat self-imposed, as you and Michael Brown point out.  My experience shows that Mr. Brown’s comments are spot on.  As a vendor that provides a variety of outsourced services (payroll, human resources, risk management, benefits) to our clients, I sometimes interact with owners who have a difficult time letting go of the transactional or non-core portions of their businesses to the detriment of their businesses.  They prefer to keep their hands around the throat of their businesses as opposed to empowering others, either within their organization or outside of it, to manage those portions of their businesses that they are ill equipped to manage.  Trust is a big component of their decision; as is their ability to effectively discern where to put their energies.  It seems simple enough to state “I’m an engineer.  I’ve started an engineering firm.  I need to go secure engineering clients.”  What many owners find is that, as in your case, other facets of their business can distract them from their primary focus: the web page may need updating, or personnel issues eat up their time or any of a hundred other things take their focus away from their core competency.  An owner surrounding themselves with personnel they can trust, vendors who have earned their trust and colleagues who struggle with the same challenges as they have, can certainly help them to let go of the minors and major on the majors.

    Reply
    • Peter Chee
      Peter Chee says:

      Barry, thanks for coming to our blog and leaving a comment. I appreciate you sharing your experience and validating what we’ve expressed. It sounds like you’ve been able to figure out ways to “let go” in your business! – Peter

      Reply

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