Trust Issues (a tale of two bosses)

Currently, I am working for 2 bosses. I have 2 different clients that I work for as the Communications and Social Media Manager. Unlike the resume writing business which is a solopreneur endeavor, I don’t call the shots here, I’m a hired gun. In these roles, I take orders and must deliver results. It’s been more than 6 years since I have had to take orders and I will say it is an adjustment. It’s fair to say that all three of us (the 2 bosses and I) are alpha personalities. They want things their way, and I want things my way. As an HR guy, I know all about proper treatment of employees and the effects on employee engagement, retention, reputation, productivity and team motivation. And after being the boss of me for so long and now being the one bossed, it’s clear to me that the bosses’ words really do hold weight.


I like both of these folks. I really do, BUT, I prefer the leadership style of one over the other.  Again, these are both good people doing very interesting work and there is no personality conflict because I know how to self-manage so when one boss says something I do not like, I just ignore it. Which is easy for me to do for several reasons; number 1, I have a full-time job, my resume writing business; number 2, I don’t take it personally – it’s just the way he is; number 3, I know I am right.

To be specific one boss will say things like, “I trust your judgement on this” while the other will say “I don’t trust anyone” or “My trust is earned.” If I am being diplomatic, I understand what he is really saying, he means “show me something and I will trust you.” I get that, but two things here; number 1, I have already shown him on a few occasions that I know my shit. Number 2, he approached me to work with him, I did not audition, apply, or beg for a job. Sometimes I am tempted to say, “You came to me motherfu*ker!”

Obviously, when you have someone who says “I trust your judgement” you tend to appreciate those words and work harder for them than the person that says “I don’t trust anyone” (at least I do). However,  since I have nothing to lose in this situation (meaning if he fires me, I’m fine, I still have several irons in the fire (gotta love multiple revenue streams)) I really don’t take his words personally…okay maybe a little or I wouldn’t be writing about it. But I don’t take them as hard as I would if I didn’t have the other my own business or the other boss, for which I do the same sort of work, telling me what a great job I am going and how truly awesome I am.


If you think that I am the type of person that needs a pat on the back you would be wrong. I am used to not getting the credit I deserve – so much so that when someone recognizes my accomplishments, I feel a little uncomfortable because in my mind, I am just doing my job. BUT, I do want and expect that if you hire me to do any job (resume, write content for you, manager your social or anything else) that you get out of the way and let me do my job. You don’t trust me, fine! But respect me (or at least my expertise) enough to give me the freedom to operate. I suspect many people feel this way too.

The reason I felt it was important to write this article is because from a HR perspective, I find the duality of the two bosses interesting and just like the millions of articles suggest, when bosses instill trust in their employees they get more out of them. In my situation, I already know I will be working with one of these guys for the foreseeable future and other…well, not so much. If he decides to let me go or if I decide to end the relationship it doesn’t matter, I already know at some point it will end much sooner than the other and it’s mainly because of trust issues.