[Land of Spin] The Job Hunt: Five Things to Look for in the New Boss

Land O’Spin is an occasional set of writings focused on best practices in coaching and assessment: how do take what you observe, know what it means, and draw conclusions about what outcomes will occur in the future.

As I’ve noted before, the ideal goal of any job hunt should be to find a right job at the right place with the right people . While sometimes you simply need to take any job, if you want it to have some legs and last (e.g. – you don’t bolt it at the first chance because you hate it), then you’re looking for something that hits close to those three “rights”.

One of the keys – though not the key – to right people, is your supervisor. An awful boss can make a good job turn to hell on earth– an OK supervisor has little impact on that same job. And a great supervisor can generally make up for a job that has some elements you’d just as soon 86.

With some caveats (below) aside, here are the three questions I’d makes sure I had good answers for, and five things I’d look for if I chose a job based solely on the supervisor:


  1. How do people who work for you, and have worked for you, describe what it’s like to work for you?
  2. What three or four things do they say are your strengths?
  3. What three or four things do they say they wish you would do better?

Five Key Qualities:

Honest, effective communications: Whether you’re in an entry job or a CEO reading signals from your board, having a clear sense of where you’re expected to take things, some specifics on any deliverables, and knowing anything unusual that’s out bounds is a formula for better performance. Truth helps as well: supervisors who are honest and don’t pull punches are people who enable their subordinates, rather than disabling them. Timing – a part of effective communication – helps as well – as does giving people adequate lead time. Listening, and integrating what’s been said, is important as well.

Decent leadership skills: not all managers are good leaders, and conversely, not all good leaders are good managers, so if I have my choice I’ll take both qualities. See Warren Bennis’ thoughts on what makes a good leader here . And I’d agree with Bennis’ belief that leaders – and managers – are made, not born: it’s the reason a large part of my work is coaching execs – and would-be-execs – to increase their skills and effectiveness.

The ability to attract, develop and promote employees : whether you’re almost fully developed or a work in progress, it helps to have a supervisor who can give good, specific, timely feedback (including options and alternatives), and by their actions clearly demonstrate that developing and promoting people is a key part of their job. In terms of the attraction part, it helps to have a supervisor who is able to bring in bright, talented co-workers, a clear case of a rising (talent) tide helping lift all ships. Last, supervisors who can develop and promote employees are typically folks who easily share credit since part of work of getting people promoted is giving them a chance to shine.

Flexibility and understanding: good supervisors end up pushing people to deliver on their potential, but in doing so understand what it is that you can deliver, and that sometimes that potential varies by the different parts of a job, and what else is going on in your world. Flexibility should not imply a lack of consistency or discipline – ensuring compliance to team agreements and values is a key part of the supervisor’s role – but it also means you know what’s appropriate to flex and what’s not.

Demonstrated trust in their employees to do their job well: Not so surprising, people with requisite skills perform up the level of expectations. Supervisors who trust their employees to perform usually get what they expect. Sups who don’t trust their employees, either by cynicism or behaviors like micromanaging, get what they expect as well – sub optimal performance from employees they’ve partially disabled.

Two caveats to this advice: The first is that even when you’re choosing a job based on a supervisor there is little to no guarantee that the person will remain your supervisor. Promotions, life changes, political shake-ups, restructurings, etc. are all things that mean your good boss is here today and maybe gone tomorrow. When I took a job at Chiron in the mid-1990’s it was in part to work with Barbara Kerr, then the head of Human Resources. 3 months later it was clear that Barbara would be moving on to other things, and I’d be picking up a new boss.

The second is that sometimes the supervisor really doesn’t matter very much: you’re taking the job simply to get your ticket punched with sector and domain experience, and plan to move on after a short period of time to something else. When I worked with Barclays earlier this decade I wanted to get added financial services experience and planned to stay 2-3 years. 2 ½ years later I was on my way to taking my consulting practice full-time.

Last, as you might expect, I would suggest spending time with the would-be-bosses current and former direct reports asking them the same questions that I’ve posed above. If you get the qualities outlined above, sounds like a winner. If they come up in the "wish they would improve category", you may want to rethink your options if you can.