When an old boss offers you a position at his or her new company it is often very tempting to accept it.  After all, such an offer wouldn’t be made unless the old boss thinks highly of you and believes you had a good working relationship before.  This temptation can be stronger if things haven’t been working out as well at your current company after the departure of your old boss.

Clearly the person you work for is a big issue in overall career satisfaction.  Ideally it should be a boss who believes in you and supports your efforts.    But two other elements also come into play 1- The particular company for which you work   2 – Your job functions and responsibility level.   One reason why things may have gone well for you and your former boss in the past is that he/she had the authority to give you the kind of responsibilities and support you needed.  This may or may not be true at the old boss’ new company.  Which is why it’s always critical to ask:  would this new job and organization be a good fit and move for you even if your former boss was not there?

In order to answer that question, here are some key issues to consider:

1 – What is the status and direction of the new company?    If the new company has a major wave of new senior management this can be exciting but also quite risky.  Expectations can be high, perhaps even too high, for the new team.   Does this new organization have the reputation and resources to pull off the expected changes?  Is it financially sound enough to withstand changes in the market?  What exactly are the challenges for the company and how prepared are they to meet them?  This is not to say seemingly risky new ventures can’t be rewarding.  Those who joined old bosses who recruited them to Amazon or Google ten years ago are very glad they took the plunge.  But those are exceptional organizations.  Understanding both opportunities and risks is key.   Companies without adequate resources can end up having severe layoffs or get acquired which changes the whole game.

2 – How much authority does your old boss have at the new company? This is where some decisions to join an old boss can turn out badly.   Initially, your star is hitched to your old boss as you are one of “his or her people”.   Both your former boss and you face the prospect of entrenched people who will resent newcomers.  This lack of co-operation can be a serious detriment to your old boss and/or you adapting well to the new surroundings.  Especially if an old boss does not yet have the authority at the new company to resolve a problem you may be having with a peer, another department head or even a subordinate.   Your former boss may be put in the uncomfortable position of undermining his/her own standing within the new organization in order to support you.  Which is why it’s important to interview with all the people who affect your success in the new role and ask the right questions as well as read between the lines.  Starting with the person your old boss reports to.    How much control your old boss has to maneuver reflects how well you can navigate the obstacles you might encounter…

3 – How secure would you be if your old boss leaves his or new company?     Ultimately you and your boss are different people even though you’ve worked well in the past.  So while your old bosses’ success in the new culture clearly affects your success, things can change.  He/she could depart but you could thrive if you adapt well to the other players involved.  Again, interviewing as many people as possible is one way to determine the factors that will help you either succeed or not in the new organization irrespective of what happens to your old boss.

 4 – Does this new job enhance your career prospects?   No doubt that by following an old boss, you help that boss immensely.  Your former boss can now rely on you instead of people he/she hasn’t learned to trust yet.   But it may or may not advance your learning, expertise or responsibility levels.  If you wouldn’t accept the same sort of lateral move offer from an unfamiliar boss then why accept a lateral move offer from an old boss?  Unless the new job affords better growth prospects in the longer run.   Accepting a role for comfort reasons isn’t enough.  However, if the new job involves new challenges and helps build your resume, it may be worth the risk.

 5 – What growth prospects do you leave behind in joining an old boss?    Sometimes you may be in line to get your old boss’ job at the current company.  But even if you don’t get an immediate promotion from your old boss leaving, opportunities may exist to expand your current responsibilities.  Plus, you have built credibility and political capital in your current organization that ultimately could benefit you more by staying put.   It may be that a “caretaker” or someone relatively temporary has taken over your bosses’ former job and there will be opportunities for you in the next 12-18 months.

6 – Has your current company become either intolerable or dead-end since your old bosses’ departure?   Sometimes people experience the “double whammy’ of not only an old, trusted boss leaving but having a new boss at the current company bring in his or her “own people” which usurps and/or blocks any opportunities you might have. Or it may simply be that your old boss left because things got too stagnant or frustrating at the current company and you are now experiencing that as well.  Clearly, either of these possibilities makes any offer from an old boss that much more attractive.    But this should not mean an automatic “yes” to such a move if the other factors noted above do not mesh.

What that means is you should be looking at other jobs that may fit your career needs alongside the one offered by your old boss.  You should try to master your own career destiny as much as possible. Asking the same questions as noted above about a former boss’ offer as you would from an unfamiliar boss will help make a career decision much better.