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Scott Berkun


Has Your Boss Set You Up to Succeed or Fail?

Six questions to ask before wading into a project

Published: Thursday, March 14, 2019 - 12:02

The term “set up to succeed” means people have been given most of what they need to do their job well.

Good bosses do more than just set goals and give assignments; they should see themselves as responsible for ensuring that 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. Second, they invest their own time clearing a path for those tasks to go more easily (so higher levels of performance are possible). A good boss builds a runway for you so that you can smoothly take off. Alternatively, you know you’re being set up to fail if you’re assigned a project with impossible odds, conflicting goals, or a fraction of the resources required. When there are major obstacles on the runway, or no runway at all, your manager isn’t doing his job.

Here’s a simple list of questions you can ask to see how well set up you are to succeed (or fail). 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’t do as well as what the project requires?
Do I have the right resources (budget, staff)? You may have the right skills, but if you don’t have enough time or money to do the work, you’ll fail anyway. The goals of the project might need to change if the available resources can’t.
Are there clear goals (and nongoals)? 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? A nongoal is something that’s easily assumed to be a goal but should be avoided.
Do the people you depend on have the motivation to help you? You may need several people to get work done before you can do yours. Will they prioritize your requests? Will they help to make sure you have what you need? A good boss will have talked to other staff in the organization about your tasks and created an agreement for how you all will work together.
Are senior management’s goals aligned with the ones you have been given? Your odds of success are much higher if your individual goals line up with those around and above you. If they don’t, you’ll be working against the grain of your organization. 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 don’t 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?

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.

Of course, depending on the job you have, and how senior your role is, you may be expected to identify and solve many problems on your own. Some organizations call this “dealing with ambiguity” or “organizational agility” and think of it as a skill. It’s true that stronger employees can handle more challenges on their own. However, the reason why managers are paid more is that they have more responsibility and power for making good work happen. If they do nothing to help their staff succeed, they’re simply not doing their job.

What other ways have you seen managers set up their employees to succeed or fail?

First published on Scott Berkun’s website.


About The Author

Scott Berkun’s picture

Scott Berkun

Scott Berkun is a bestselling author of five books and a speaker known for his work on creativity, management, and philosophy. His work has appeared in The New York Times, The Washington Post, Forbes, The Wall Street Journal, The Economist, The Guardian, Wired magazine, USA Today, Fast Company, and other media. His latest book, The Year Without Pants: WordPress.com & The Future of Work (Jossey-Bass, 2013) was named an Amazon.com best book of the year.