I was reminded the other day of a struggle that all founders face…justifying why they can’t delegate.

For anyone that hasn’t been a founder this sounds like a trivial issue that just needs a little leadership training. It’s not. It’s actually a big issue that needs a lot of attention.

To the founder, a lack of delegation is the end result of a mental struggle that runs deep. On one hand they are afraid that if they delegate the team will fail, as if they are incapable of delivering more. On the other hand the founder is clearly drowning in responsibilities, frustrated that the team isn’t moving faster or working harder.

Trying to balance short term survival with long term success, the founder gets stuck in a terrible cycle of justifying ‘why now’ isn’t the time for the team to step up. Like the a vacation that never happens, they keep kicking the can down the road until ‘right now’ becomes the permanent state of the company.

This denial dramatically impacts the probability that their company will be successful. By carrying the workload, the founder neglects their most important priorities while building a culture that is not empowered or motivated to win.

I struggled with this a lot in building Contour. I didn’t understand why people went home at 5pm everyday. My solution to this problem was to pick up the pencil on their behalf to finish the work. This resulted in me getting too involved in almost every aspect of the business. Although it sounded good in my head, this leadership strategy wasn’t affective.

I ended up spending time on the wrong priorities, which ultimately built a business that was undercapitalized with a disjointed culture that didn’t know how to win.

It turns out that my lack of ability to enable was rooted in my own limitations as a leader. Now in building Moment I’ve tried to build a culture that is empowered, which alleviates the trust issues in delegating.

1. The Team Has To Decide It Wants To Win
There is a built in assumption by founders that everyone who joins the company shares their same passion for winning and therefore everyone is willing to work tirelessly to succeed.

This just isn’t true.

Winning is first a personal commitment and second a learned behavior. You can’t force this desire upon someone just like you can’t assume they want it. Everyone on the team actually has to make the personal decision that winning is what they want.

If they do, it fundamentally changes the relationship of the founder from a player to a coach. Now they can push the team to get better every day, providing constant feedback and clear expectations. Hearing a team make this commitment removes the self doubt the founder faces after 5pm when everyone has gone home.

2. Clearly Define The Destination And Who Is In Charge
Being clear about the company’s definition of success is important. But being crystal clear to the team about the next milestone is even more important. This clarity enables the team to work backwards in building a realistic plan.

Once the team knows where they are going, make sure they understand who is responsible for what. Every major, day to day responsibility should be covered by someone on the team other than the founder. Even if the team is small this transition is critical for creating an empowered culture.

Keep in mind, the team will fuck it up, but they will also get stronger through their own mistakes.

3. Don’t Underestimate People.
A lot of incredibly successful companies are started by founders that approach a problem without any preconceived notions. Their naivety is what gives them a competitive advantage over the incumbents. But at some point their own naivety gives way to knowledge and they forget their own previous ignorance. This translates into underestimating what their own, inexperienced team can deliver.

Constantly remind yourself that inexperience and ignorance are a strength for startups. That naivety is what enables fuels people to work harder, learn faster, and find new solutions to the problems you face. Give people more responsibility and then get out of the way.

4. Maintain The Right Priorities
Hardest of all, the founder should be focused everyday on ensuring that the company has enough capital, the right people, and the correct priorities. Doing this day in and day out is a lot harder than most founders realize mainly because it takes them away from what they naturally love to do…create new things.

It may feel like eating your vegetables first but if you approach every day in this order you will realize there isn’t enough time to also be in the weeds. Always take the hardest, most terrifying problems first.

*Image Credit: Washington State Department Of Transportation via Creative Commons