What do you do if a friend asks you to work for them? Is it a good idea? Will it work? Is your friendship going to be at risk? Can you be successful in both a personal and work relationship? Do you have to set social boundaries?

A few years ago, a client of mine confided that he was approached by one of his customers to come and work for him. The customer was president of the company and they had a long standing friendship.

John went down to talk to the president to discuss the role, VP Marketing and Sales, and became enamored with the scope of responsibility and freedom in a smaller company to create a new team in a product segment he understood intimately.

While he was in the discussion stages, John called me to talk about the career opportunity and ask my opinion.

Should he give up his current position in a large organization where he was close to retirement to go and run his own show? He knew he had about a 5-7 year window and was tempted by the new career challenge and the ability to relocate to where he wanted to retire.

John was very confident that that he had an “in” with the president because of their friendship and that he would be successful.

The conversation that people often ignore is what happens if you are not successful or there is a difference of opinion in strategy or execution. How is that handled when the friendship is a factor?

Knowing John as I do, he is probably the first person to put an issue on the table, however, it is equally important to see if the president is able t0 initiate an uncomfortable discussion.

Would the president avoid conflict and let things percolate to the point where the friendship and work relationship was unrepairable? It is easy to say that the situation will never happen, but faced with it, having the difficult conversation takes being a courageous leader.

The questions I told John to pose were:

  • What are the boundaries with our working and personal relationship? Are those relationship boundaries in the best interest of the employees and our customers?
  • Have you had a performance discussion with a friend who worked for you before? How did that conversation go? What ultimately happened?
  • Can you and would you fire me?
  • What would it take for you to fire me?

When you ask the tough questions before you are hired, you are confirming that your boss is ready to treat you like any other employee and together you establish the parameters for acceptable management behavior. It is important that the president or your boss’s primary responsibility is to the customers and employees above any personal friendship.

If you believe a personal relationship with your boss will cloud their judgment to run the business effectively or to talk to you openly about your performance, my recommendation is to forgo working together and keep your personal relationship or friendship separate and on a positive note.