From Founder/Builder to Manager/Leader

From Founder/Builder to Manager/Leader

After I spoke at the Startup2Startup event last month, one of the people who sat with me at dinner emailed me and asked:

I was curious–how did you make the transition from CEO of a startup to manager of a medium-sized business? I’m great at just doing the work myself and interacting with clients, and it’s easy for me to delegate tasks, but it’s hard to have the vision and ability to develop my two employees into greater capacity…

I’d be interested in reading a blog post on what helped you make that transition from founder/builder to manager/leader

It feels like the answer to this question is about a mile long, but I thought I’d at least start with five suggestions.

1. Hire Up!  The place where I see most founders fumble the transition is in not hiring the best people for the critical roles in the organization.  Sometimes this is for cash flow reasons, but more often it is either due to subconscious fear (“will I still be able to control the organization if this person is in it?”) or due to bravado (“I can do engineering way better than that guy”).  Lose that attitude and hire up for key positions.  Even if you COULD do every role better than anyone you’d ever hire, you only have so many hours in the day.
2. Learn the magic of delegation and empowerment.  You can never get as much work done on your own as you can if you get work done THROUGH others.  Get comfortable delegating work by setting clear expectations up front in terms of timing and quality of deliverables and giving your high level input.  And never be a bottleneck.  If people are waiting on you for decisions or comments, that means they’re not working…or at least that they’re not working on the highest value or most urgent things they could be working on.
3. Don’t fear some elements of larger organizations.  Larger organizations require some process so they don’t fall apart.  Make sure you pick your battles and accept that some changes, even if they feel bureaucratic, are critical to ensure success going forward.  I still get a queasy feeling in my stomach half of the times I see a new form or procedure or a suggestion from a lawyer, but as long as they are lightweight and constantly reviewed to make sure they’re having their intended impact AND ONLY their intended impact, some are inevitable.
4. At the same time, don’t lose the founder/builder mentality.  Your company may have grown larger, but if you’re still running it, people will naturally look to you and other founders for much of the energy, vision, and drive in the business.  You will also likely be more inclined to be scrappy and entrepreneurial, which are good traits for any business.  Don’t lose those qualities, even as you modify them or add others.
5. Look to the outside for help.  In my case, I’ve consistently done three things over the years to learn from others and to prevent myopia.  First, I have worked on and off with a fantastic executive coach, Marc Maltz from Triad Group. Second, I have always had one or two “CEO mentors,” e.g., guys who have built larger businesses than Return Path, on my Board, at all times, as resources.  Finally, I do a lot of CEO peer networking, some informal (breakfasts, drinks meetings), and some more formal (a CEO Forum group that I established) to make sure I’m consistently sharing information and best practices with others in comparable situations.

Any other entrepreneurs who have made the leap have other advice to offer?