A client showed me his ambitious plan for professional development. It showed he had developed a lot, learned his values, learned what he was capable of, set high standards, and listed many SMART goals.

He also said it would entail more than an hour a day every day for the rest of the year--237 days at the time, since he included weekends. I know almost no one who added 237 hours of work on 237 consecutive days just out of the blue (though my posting on my blog daily for over five years and going and doing burpees every day for over four years qualifies).

I want him to succeed. My job as a coach is to help. I asked him if he imagined any problems that could prevent him from finishing and how he might handle them. He's progressed so much so far that I was surprised he answered

I have to work every day for the rest of the year (will not be a problem)


Hurdles... Me being lazy (will not happen)

That's it. No allowances for sickness, etc. I like the intensity of his enthusiasm, but it can't last 237 days. He may do everything he plans, and I will help maximize the chances of it, but it won't be sheer enthusiasm that gets him over the line.

See the guy in the picture above, powering through the mud? Before taking on a challenge, everyone envisions themselves powering through anything. But, like most gyms that are full in January and empty after Valentines Day, most plans end up on shelves.

I applauded my client's initiative in searching himself and creating the plan. Or starting it, because without answering the two questions I asked, I know the plan will end up on a shelf.

In entrepreneurship we say "Ideas are cheap. Execution creates value." Actually, experienced people say that. Inexperienced ones overvalue ideas and underestimate execution.

The same follows in leadership. My client hasn't put himself through enough transitions to realize what undermines execution.

The plan was for himself, but the following would apply for a plan for a team or organization.

What do you think undermines execution?

If you think execution gets undermined by lack of resources or unforeseen circumstances, you misunderstand how any but the most trivial projects work.

There are always unforeseen circumstances, resource issues, and so on. You can't plan how to handle what you can't predict in detail, but you can expect that they will happen.

If you blame outside circumstances for what your team can handle if effectively led, you're devaluing your team and misunderstanding your role as a leader. When unforeseen circumstances threaten success, leaders who deliver reorient the team to handle those circumstances and still deliver.

As a leader, if you don't take responsibility for leading your team through what discourages it, either it won't happen or someone else will become leader. Occasionally you'll get lucky and the team will get through it despite a lack of leadership. Do you want to rely on luck?

Two questions

So after creating your plan and before executing it, asking these question prepares you to handle the human, emotional issues that will arise.

  1. What hurdles might discourage you from finishing it?
  2. How will you face and overcome those hurdles?

Note the word discourage. When you lose sight of how to finish a project, people look to the immediate reasons--lack of money, an accident in the factory, etc--as the problem.

Those external things are only issues if your team thinks it can't handle them. Then they feel discouraged. Those internal issues--discouragement, futility, blaming others, etc--are what actually undermine projects. These questions are designed to prepare you for them.

These questions focus on you, your people, and your abilities to overcome what will come your way.

A bonus third question to make sure you answered the first two

If you think you've answered the first two questions, ask yourself:

Would you put your money where your mouth is?

My client and I have a friendly relationship, so I asked him in a more familiar way than I would with most:

Are you sure about that? How much money would you be willing to bet on yourself that you would deliver 237 days in a row?

How about these odds: would you bet every penny you have and all your future earnings against $10 from me? If there was really no problem, you would say yes to the free money from me.

His response:

Haha.. Ok point taken. Well let me put it this way..

And he followed up with a plan with some leeway for unforeseen problems and a list of problems that might come up.

I'll still coach him to hit his original goal, but this way, if something prevents him from it, I expect he'll still finish the plan and not shelve it.