You can’t be successful reporting to two managers

I attended a great breakfast session with former Mayor Michael Bloomberg, put on by TechNYC, and it was a great reminder of the title of this post. During breakfast he talked about the MTA, and the governance of the system. If you have been following things at home you know it is a mess and has been for quite some time. Between the city of New York getting the brunt of commuter complaints, the governors actual responsibility, and the federal governments meek involvement – this trifecta has not gotten things done.

This reminded me of early stage teams that make reporting decisions based on small size and flat reporting structures. Many choose to “have a dotted line” dual reporting structure or “two managers for now” mentality. Sometimes this is a temporary solution and founders think they are doing their team a favor for “cross comminication” and “team dynamics”.

I struggle to think of a single case where someone with two managers was successful. I have made this mistake and vowed not to repeat it. The 1:1s are setup for failure from the start, there is a lack of leadership and mentoring that happens, and responsibility is shirked. In my case the decision was made based on fast moving parts and thinking about “coping for now” – in hindsight a poor decision for the manager and their team member. It’s unfair to all parties involved.

Our former mayor also talked about delegation and responsibility – two key components of a manager to convey. With two managers I always ask (because folks end up doing it anyways) “who has the final decision here?” Since nobody knows the answer when there are two bosses you can solve things faster.

Leadership and management is hard. You have to work at it like any other relationship. If you don’t have a clear manager, it’s hard to communicate what is working and what is not – let alone building your career.

If you find yourself about to green light a dual reporting strategy think twice. If you find yourself reporting to two people, change things up or move on.

I hesitate to be so direct, but if all else fails let the New York City subway be your example; no clear decision maker and owner leads to failure.