This is based on some emails and conversations with a successful client who had grown his business but was afraid to take a vacation because he was not delegating very effectively to his team.
Q: I Am Afraid to Take a Vacation
This conversation has been adapted from a set of emails and conversations with a client several years ago.
Q: I founded my startup about two years ago and have bootstrapped it to where we have about 30 paying customers and another 60 in the pipeline at some level of product evaluation. Our product is on-premises software that, depending upon configuration, costs between $25,000 and $75,000 a year to license. What with some smaller deals we did when we started and two larger customers, we are doing about a million dollars a year in revenue with five full-time and three part-time employees.
My problem is that I am afraid to take a vacation because I don’t trust the decision-making capability of my team. I feel tremendous pressure to make our revenue targets so that we can continue to meet payroll.
A: First of all, congratulations bootstrapping to a million dollar run rate. I understand the pressure to meet payroll. It sounds like you have built a flat organization where everyone effectively reports to you.
Q: Yes, but I have been considering to either promoting one or two folks to a managerial role or recruiting a solid second in command.
It can be hard to trust folks who may care less about the business than you do–although they may certainly care enough to do good work. You have to allow for an “error budget” that enables your team to learn. Noel Tichy wrote a great book called the “The Leadership Engine” that summarized his efforts and lessons learned at GE, helping them to grow a leadership development capability. In his model, leaders need two things:
- Edge: the ability to triage and make decisions that focus on areas where action makes a difference.
A coachable point of view: the ability to define an operating philosophy and communicate it so that everyone in the organization understands how to make the right decisions.
How do you feel you stack up on these two aspects of leadership?
Q: I have “edge.” I am very realistic about setting goals and managing resources. Without going into detail, we have had to improvise quite a bit in the last two years, to deal with setbacks and seize opportunities. I have a coachable point of view: I react consistently to situations–I rarely dither– and provide guidance to the team. But I have find it easier to provide verbal instruction or short emails than codifying policies and procedure. I would like to hire some more experienced folks but I cannot afford them and I don’t want to let anyone go to add someone new in the hope they will perform better.
A: One approach I have seen work is to ask people to document what they believe are the guidelines they should follow based on your past direction. You can also try delegating decisions that fall within specific categories or parameters (e.g. dollar amount for expenses or bug severity). If you truly don’t trust someone’s judgment and cannot develop them, you should consider letting them go. While you can move fast in a very small team without documenting your decisions and process checklists, at some size, and eight people is certainly close to or above the limit, you need to put more things into writing.
Q: I have always heard that when you agree to “Let’s document the decisions we’re making so that we don’t lose track,” all it means is that things start to slow down.
Letting your team know what you want them to accomplish and allowing them to choose their own methods will free up a lot of your time and probably allow you to take a vacation. Once the lag between when a decision is made and when you can judge whether it’s been effective starts to stretch to even a few weeks, you will want to keep a decision record as your memory can fool you, and you and your team will end up learning more slowly.
You must let your people make some mistakes so that they can take ownership and develop their own “edge.” Unfortunately, you have to trust your people if you want to grow–or even take time off.
Related Blog Posts
- Delegating Enables Growth: A Solo Founder’s Experience
- Combine Clear Goals with Delegation Based on Expertise for High Impact
- Newsletter: Effective Delegation
- Delegation Needed For Growth
- Podcast with Pete Tormey: Bootstrapper’s Delegation Checklist
- Recognizing and Developing Expertise
- Time to Market: Making Tough Decisions as Founders