There is a fine line between telling a boss too much and telling them too little. I say the line should be before iguanas start falling from trees.

In Miami, when it gets cold (by Florida standards), 50 degrees is getting near frigid and 40 degrees is a near disaster, plant and reptile life cycles are interrupted. It also means iguanas get so cold that they lose their grip and quite literally start falling from trees. It doesn’t happen often, but it happened in 2008, 2010 and this past year (as told to me by my son’s special friend Merrill who is a senior at the University of Miami and familiar with various life forms in Southern Florida).

Back to telling the boss too much or too little; if you wait too long and a disaster unfolds, and the boss is caught off guard (iguanas falling from trees), this will cost you not only your current job, but a future referral and your current boss’s job as well.

If you tell them too much, taking them into the weeds, it doesn’t serve the position well and they might as well do your job for you.

As elected officials, you come to rely heavily upon your staff. You trust their judgment, their ability to collect and weed through information, their resourcefulness, and if they are a really good staffer – their ability to process all the information they collect and apply it to your overall objective.

That over-reliance can also lead to paralysis.

The extreme of something is never a good thing. Case in point, I knew one long time Senator in Passaic County who ALWAYS had his chief of staff in every meeting and making every decision. I remember asking for a candid, one-on-one, meeting with this Senator and was taken aback when the three of us had that intimate meeting. At that meeting, everything I was saying required historical context for the Senator because only the chief knew what I was talking about. That level of disengagement from the pulse of the action surprised me. That level of reliance upon his chief to make all the decisions, because only she knew all the history, baffled me. Here was a Senator, who put his name on the ballot, worked hard to get to where he was, and then he handed the reigns over completely to someone else.

The extreme of something is never a good thing.

Related-unrelated: In my 2007 primary race, I had one moment when my then chief of staff (volunteering at night as my campaign manager) had to decide whether to tell me OR not to tell me just how much money I had left in my campaign account. I had a budget of a little over 400K to spend, I asked my running mates to chip in 30K and I would make up the rest. My chief/campaign manager, already wary of my spending habits during the campaign, was concerned that I’d find another way (I say creative) to spend every nickel we had. We already laid out a 20-piece mail plan, two different TV spots, over 300 paid walkers, but I wanted more – who doesn’t? Our polling indicated that we had a double-digit victory coming but I wanted to run like we were 5 points behind.

With one week to go, I called in my trusty advisor and asked how much do we have in the account (which I did daily)? He said, “I don’t know, how much more did you spend last night?” An apparent reference to my penchant for dreaming up new mail pieces (usually “contrast” pieces) that would be shipped to one of four consultants by 4 am. Ignore his blatant snark, I asked again, “how much is in the account” and annoyingly he said, “I don’t know, how much did you spend last night?”

BOOM

I responded, some might say in anger, “How can you not know?!? Either you are incompetent or lying to me. Figure it out and tell me.” (At this point our call was disconnected, I think I was in a bad cell spot. For the record: he knew to the penny how much we had. If I could time travel, I would take back those words. Dominick was simply trying to protect me from myself, from overspending or doing something over the top – for some reason I was dubbed “Senator Overkill” after that election. I have since apologized 100 times and we laugh about it now.

My point is, use your judgement and always remember that as a staffer you are entrusted to filter through the bs and report up ONLY the relevant details. There is a fine line between telling too much or too little, hint: do it before the iguanas start falling from the trees.

Former 40th District Senator Kevin O’Toole is the chairman of the Port Authority of New York and New Jersey.