How to discuss productivity (and lack thereof) with your boss?

Question

I have recently graduated college and had a fairly dramatic change of lifestyle.

Being that there is never enough time in the day, I used to go to great lengths to minimize my responsibilities and thus (theoretically) maximize the amount of free time I had. Part of this was due to naivety, and part of it was due to laziness.

In the last year or so, I have instead opted to create more time in each day by finding ways to increase my own productivity and spend less time doing unimportant things. I have used myriad sources to help me progress in this area, but perhaps the most beneficial of all of these things has been speaking with and learning from my new boss. He has offered invaluable advice for breaking bad habits and starting new ones, he has lent several books to me from his personal productivity library (a very impressive selection), including David Allen's Getting Things Done among others, and has in general inspired me with his desire to improve.

My question is this: How can I discuss the hurdles I am facing, the lack of progress I sometimes feel I have made, or simply my disappointment after a non-productive period with someone in this "supervisor" role?

I sometimes feel like I am unable to speak freely about my own difficulties with this process because of who I am talking to, and I am concerned I may be wasting some golden opportunities to progress.

Answer 1

Your boss is living two roles. One is the boss and the other is a mentor. This is very common, many bosses do and we should be grateful. However, the double role creates confusion in his mind and also in yours. You both need to be careful. The boss relationship is formal and legal and accordingly must be given higher priority over mentoring. Mentoring is an extra curricula. When you talk to your boss keep in mind that he is your boss before being a mentor.

You may talk to your boss/mentor about the effectiveness of the different methods you learned and applied. You may talk about the progress you made and what you hope to achieve. The discussion would normally be within the context of work but may also cover some personal aspects.

You may not talk about the hurdles you are facing and lack of progress. If you allow yourself to step into the negative area, you will end up, intentionally or unintentionally, whining or at least perceived as whining. Whining is sure killer of any relationship including mentoring and certainly work relationship.

In summary, give the boss-employee relationship higher priority and keep it in your mind during all discussions with the boss.

Answer 2

Most of your interactions (scheduled meetings and otherwise) will probably be in the boss-employee role. Keep that in mind. Ask to set aside a specific time (like a weekly "mentoring meeting") where you discuss only productivity issues. Don't mix the two roles. This will help your boss understand that "productivity frankness" is not the same as employee whining.