Has Your Boss Set You Up To Succeed or Fail?

A reader asked recently (see the archive):

I have a new boss who I don’t trust yet. How can I make sure they’re looking out for me?

The term set up to succeed means a person has been given most of what they need to do their job well. A good boss does more than just set goals and give assignments: they see themselves as responsible for ensuring good work happens (See: Lefferts’ Law of Management).

First, they think through the steps that need to happen for someone to do a project and where the challenges are going to be and discuss them with you. Second, they invest their own time, in coordination with you, clearing a path for those tasks to go more easily, or to become possible at all. A good boss builds a runway for you so that you can smoothly take off and checks in while you’re in the air, making adjustments behind the scenes, so you and your projects will land safely too. But taken too far this becomes micromanagement, which is the inverse way to set up someone to fail because the manager is far too involved. A good manager finds the sweet spot for each person and situation.

You know you’re being set up to fail if you’re assigned a project that:

No one seems to know about
Other people believe is their project or decision
Everyone treats as low priority

When there are major hidden obstacles on the runway, people telling you the runway is theirs and you’re not allowed, or there’s no runway at all, your manager is setting you up to fail. You are being managed poorly.

One exception is that they have clearly warned you about these conditions before you agreed to take them on (perhaps you’re a secret agent), or made clear they themselves have little knowledge of the landscape and part of your task is to map it and report back, they are either incompetent, indifferent or see more benefits in your failure than your success.

The checklist for assessing your situation

Here’s a simple list of questions to discuss with your boss (or at least with yourself) to assess if you are being set up to succeed or not. They can be used to structure a conversation with your boss about what you need and why.

Do I have the right skills? If you’re told to pilot a Boeing 747 but you have never even flown a paper airplane, whose fault is it if you fail? What training and mentoring is provided to help close skill gaps? Does your boss understand what you can and can not do and how that stacks up against what the project requires?
Do I have the right allies? Who has the power you need to do your job and are they on your side? Will they prioritize your requests? Invite you in to decisions early enough to be effective? A good boss will talk to other important people in the organization about your goals and create an agreement for how you all will work together. Or at least call out the roadblocks they can’t resolve so at least you know they are there.
Do I have the right resources (power, budget, staff, time)? You may have the right skills and allies, but if you don’t have enough power, time or money to do the work, you’ll likely fail anyway. The goals of the project might need to change if the available resources can’t.
Are there clear goals (and non-goals)? Clarity on desired outcomes is one of the most important things a leader provides. Does everyone understand and agree on how you’ll know when the work is done and that it was done right? Listing non-goals, things easily assumed to be goals, but are really distractions, can be just as important to discuss.
Are senior management’s goals aligned with the ones you have been given? If not your success will depend on you working against the grain of the organization and you are likely to fail. A good boss has made sure the right senior staff know about your projects and that all the goals line up.
What roadblocks are in your way that you do not have the power or skills to resolve? Who has been made aware of them? Who has the power you need to resolve them? Has your boss worked with you on a plan? Have you warned the right people of what may happen if the roadblock is not cleared? Have they at least agreed you are on a high risk mission and even a small amount of success will be an acceptable win?

Incompetent managers often unintentionally set up their employees to fail. They don’t realize they are giving conflicting goals, poorly allocating resources or that they’re asking people to take on work that is politically sensitive and possibly damaging to their reputation. This means you have to advocate for yourself, first by thinking through the challenges you’re going to face and second by involving your boss in helping you clear them out of your way. If you are continually set up to fail and don’t feel you are getting the proper amount of support, you have a bad manager. You should find a new one if you can.

Of course, depending on the job you have, and how senior your role is, you may be expected to identify and solve many hard problems on your own. It may be possible for you to create your own runway through influence, persuasion, relationship building and negotiation. These are valuable skills and are often necessary even if you have a good manager, but become critical if you are working for a bad one.

Some organizations call this “Dealing with Ambiguity” or “Organizational Agility.” While it’s true more senior staff should be able to handle more challenges on their own, there are limits. The expectation of all good managers is that as the boss they have more responsibility and power for making good work happen and if they fail to use it to help everyone on their team they are simply not doing their job.

What else can someone do to help in these situations? Leave a comment.